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enzymes (3) Show 3 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:41 UTC

HMDB ID

HMDB0014632

Secondary Accession Numbers

HMDB14632

Metabolite Identification

Common Name

Sotalol

Description

Sotalol is only found in individuals that have used or taken this drug. It is an adrenergic beta-antagonist that is used in the treatment of life-threatening arrhythmias (PubChem). Sotalol has both beta-adrenoreceptor blocking (Vaughan Williams Class I) and cardiac action potential duration prolongation (Vaughan Williams Class I) antiarrhythmic properties. Sotalol is a racemic mixture of d- and l-sotalol. Both isomers have similar Class I antiarrhythmic effects, while the l-isomer is responsible for virtually all of the beta-blocking activity. Sotalol inhibits response to adrenergic stimuli by competitively blocking β₁-adrenergic receptors within the myocardium and β₂-adrenergic receptors within bronchial and vascular smooth muscle. The electrophysiologic effects of sotalol may be due to its selective inhibition of the rapidly activating component of the potassium channel involved in the repolarization of cardiac cells. The class II electrophysiologic effects are caused by an increase in sinus cycle length (slowed heart rate), decreased AV nodal conduction, and increased AV nodal refractoriness, while the class III electrophysiological effects include prolongation of the atrial and ventricular monophasic action potentials, and effective refractory period prolongation of atrial muscle, ventricular muscle, and atrio-ventricular accessory pathways (where present) in both the anterograde and retrograde directions.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0253916
     RDKit          3D
l-Sotalol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -5.4991    0.0126    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0424    0.3895    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0656    1.5454   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412   -0.7731   -0.2537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -0.6848   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0837   -0.5416    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3338    0.6160    1.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199   -0.5759    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532    0.5239   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    0.4832   -0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9869   -0.6790   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471   -0.7403   -1.1839 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4227    0.5038   -0.7500 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.5157    0.5527    1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.8555   -1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8040    0.2347   -1.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687   -1.8059   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707   -1.7408    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4185   -0.8707    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0515   -0.3124   -0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.8888    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6176    0.7826    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807    1.9973   -0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.2003   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3556    2.3502   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397   -1.3288   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225    0.1001   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -1.6498   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -1.4560    1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2495    1.3762    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    1.4691   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570    1.3657   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648   -1.5523   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.0395    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5538    0.2433    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6839    1.6087    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631   -2.7164   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005   -2.6324    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 13 16  2  0
 11 17  1  0
 17 18  2  0
 18  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
M  END

489
  Mrv0541 02231214432D          

 18 18  0  0  1  0            999 V2000
    4.5080    2.7366    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.3885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9205    2.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    3.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.2135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.3241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.6260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.4991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    3.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  3  2  0  0  0  0
  1  4  2  0  0  0  0
  1  6  1  0  0  0  0
  1 18  1  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 15  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  2  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014632

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H20N2O3S/c1-9(2)13-8-12(15)10-4-6-11(7-5-10)14-18(3,16)17/h4-7,9,12-15H,8H2,1-3H3

> <INCHI_KEY>
ZBMZVLHSJCTVON-UHFFFAOYSA-N

> <FORMULA>
C12H20N2O3S

> <MOLECULAR_WEIGHT>
272.364

> <EXACT_MASS>
272.119463206

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.34074945103318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl)methanesulfonamide

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
-0.3950640027108308

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.100645593387327

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.069402607110716

> <JCHEM_PKA_STRONGEST_BASIC>
9.428215396630177

> <JCHEM_POLAR_SURFACE_AREA>
78.42999999999999

> <JCHEM_REFRACTIVITY>
71.1191

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
sotalol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0253916
     RDKit          3D
l-Sotalol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -5.4991    0.0126    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0424    0.3895    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0656    1.5454   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412   -0.7731   -0.2537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -0.6848   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0837   -0.5416    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3338    0.6160    1.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199   -0.5759    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532    0.5239   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    0.4832   -0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9869   -0.6790   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471   -0.7403   -1.1839 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4227    0.5038   -0.7500 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.5157    0.5527    1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.8555   -1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8040    0.2347   -1.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687   -1.8059   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707   -1.7408    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4185   -0.8707    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0515   -0.3124   -0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.8888    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6176    0.7826    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807    1.9973   -0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.2003   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3556    2.3502   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397   -1.3288   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225    0.1001   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -1.6498   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -1.4560    1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2495    1.3762    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    1.4691   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570    1.3657   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648   -1.5523   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.0395    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5538    0.2433    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6839    1.6087    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631   -2.7164   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005   -2.6324    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 13 16  2  0
 11 17  1  0
 17 18  2  0
 18  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 489                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       8.415   5.108   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       8.415  -2.592   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.185   3.775   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       7.645   6.442   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       5.748  -4.132   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081   4.338   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081  -1.822   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -2.592   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -4.902   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -0.282   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   0.488   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -6.442   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -4.132   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081   2.798   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748   2.028   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.415   2.028   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   5.878   0.000  0.00  0.00           C+0
CONECT    1    3    4    6   18                                             
CONECT    2    7                                                            
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    8    9                                                       
CONECT    6    1   15                                                       
CONECT    7    2    8   10                                                  
CONECT    8    5    7                                                       
CONECT    9    5   13   14                                                  
CONECT   10    7   11   12                                                  
CONECT   11   10   16                                                       
CONECT   12   10   17                                                       
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    6   16   17                                                  
CONECT   16   11   15                                                       
CONECT   17   12   15                                                       
CONECT   18    1                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0014632
HETATM    1  C1  UNL     1      -4.183  -0.377  -0.692  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.035   0.984  -0.099  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.407   1.381   0.487  1.00  0.00           C  
HETATM    4  N1  UNL     1      -3.088   1.178   0.915  1.00  0.00           N  
HETATM    5  C4  UNL     1      -1.702   1.043   0.672  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.263  -0.322   0.410  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.556  -1.177   1.477  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.184  -0.499   0.149  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.084   0.482  -0.056  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.438   0.234  -0.311  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.869  -1.063  -0.355  1.00  0.00           C  
HETATM   12  N2  UNL     1       4.227  -1.374  -0.635  1.00  0.00           N  
HETATM   13  S1  UNL     1       5.594  -0.694   0.102  1.00  0.00           S  
HETATM   14  C10 UNL     1       5.682   1.047  -0.187  1.00  0.00           C  
HETATM   15  O2  UNL     1       5.613  -0.965   1.597  1.00  0.00           O  
HETATM   16  O3  UNL     1       6.845  -1.327  -0.505  1.00  0.00           O  
HETATM   17  C11 UNL     1       1.946  -2.106  -0.144  1.00  0.00           C  
HETATM   18  C12 UNL     1       0.638  -1.799   0.101  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.983  -1.177   0.031  1.00  0.00           H  
HETATM   20  H2  UNL     1      -5.296  -0.510  -0.924  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.722  -0.507  -1.693  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.896   1.718  -0.953  1.00  0.00           H  
HETATM   23  H5  UNL     1      -5.395   1.078   1.552  1.00  0.00           H  
HETATM   24  H6  UNL     1      -6.200   0.777  -0.018  1.00  0.00           H  
HETATM   25  H7  UNL     1      -5.599   2.446   0.312  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.362   2.036   1.469  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.173   1.574   1.497  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.473   1.702  -0.230  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.759  -0.742  -0.480  1.00  0.00           H  
HETATM   30  H12 UNL     1      -1.783  -2.087   1.179  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.751   1.499  -0.021  1.00  0.00           H  
HETATM   32  H14 UNL     1       3.109   1.059  -0.470  1.00  0.00           H  
HETATM   33  H15 UNL     1       4.354  -2.124  -1.401  1.00  0.00           H  
HETATM   34  H16 UNL     1       6.751   1.397  -0.152  1.00  0.00           H  
HETATM   35  H17 UNL     1       5.135   1.636   0.581  1.00  0.00           H  
HETATM   36  H18 UNL     1       5.335   1.333  -1.199  1.00  0.00           H  
HETATM   37  H19 UNL     1       2.355  -3.104  -0.195  1.00  0.00           H  
HETATM   38  H20 UNL     1      -0.032  -2.647   0.258  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   22
CONECT    3   23   24   25
CONECT    4    5   26
CONECT    5    6   27   28
CONECT    6    7    8   29
CONECT    7   30
CONECT    8    9    9   18
CONECT    9   10   31
CONECT   10   11   11   32
CONECT   11   12   17
CONECT   12   13   33
CONECT   13   14   15   15   16
CONECT   13   16
CONECT   14   34   35   36
CONECT   17   18   18   37
CONECT   18   38
END

HMDB0253916
     RDKit          3D
l-Sotalol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -5.4991    0.0126    0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0424    0.3895    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0656    1.5454   -0.7077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4412   -0.7731   -0.2537 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772   -0.6848   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0837   -0.5416    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3338    0.6160    1.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3199   -0.5759    0.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9532    0.5239   -0.5110 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2663    0.4832   -0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9869   -0.6790   -0.7730 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3471   -0.7403   -1.1839 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4227    0.5038   -0.7500 S   0  0  0  0  0  6  0  0  0  0  0  0
    5.5157    0.5527    1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0160    1.8555   -1.2439 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8040    0.2347   -1.2989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3687   -1.8059   -0.2269 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707   -1.7408    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4185   -0.8707    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0515   -0.3124   -0.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9315    0.8888    1.1317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6176    0.7826    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0807    1.9973   -0.6620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    1.2003   -1.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3556    2.3502   -0.4073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0397   -1.3288   -0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9225    0.1001   -1.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8371   -1.6498   -1.1824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2405   -1.4560    1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2495    1.3762    0.5472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4050    1.4691   -0.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7570    1.3657   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6648   -1.5523   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3711   -0.0395    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5538    0.2433    1.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6839    1.6087    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9631   -2.7164   -0.1294 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6005   -2.6324    0.5871 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 13 16  2  0
 11 17  1  0
 17 18  2  0
 18  8  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4'-(1-Hydroxy-2-(isopropylamino)ethyl)methane sulfonanilide	ChEBI
beta-Cardone	ChEBI
Sotalolum	ChEBI
Darob mite	Kegg
4'-(1-Hydroxy-2-(isopropylamino)ethyl)methane sulphonanilide	Generator
b-Cardone	Generator
Β-cardone	Generator
Sotalol HCL	HMDB
Sotalol hydrochloride	MeSH, HMDB
Sotalol monohydrochloride	MeSH, HMDB
Darob	MeSH, HMDB
Knoll pharmaceutical brand OF sotalol	MeSH, HMDB

Chemical Formula

C₁₂H₂₀N₂O₃S

Average Molecular Weight

272.364

Monoisotopic Molecular Weight

272.119463206

IUPAC Name

N-(4-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}phenyl)methanesulfonamide

Traditional Name

sotalol

CAS Registry Number

3930-20-9

SMILES

CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1

InChI Identifier

InChI=1S/C12H20N2O3S/c1-9(2)13-8-12(15)10-4-6-11(7-5-10)14-18(3,16)17/h4-7,9,12-15H,8H2,1-3H3

InChI Key

ZBMZVLHSJCTVON-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Sulfanilides

Direct Parent

Sulfanilides

Alternative Parents

Substituents

Sulfanilide
Aralkylamine
Organic sulfonic acid amide
Organosulfonic acid amide
Aminosulfonyl compound
Sulfonyl
Organic sulfonic acid or derivatives
Organosulfonic acid or derivatives
Secondary alcohol
1,2-aminoalcohol
Secondary aliphatic amine
Secondary amine
Organopnictogen compound
Alcohol
Organic nitrogen compound
Aromatic alcohol
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Amine
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

sulfonamide (CHEBI:63622 )
secondary alcohol (CHEBI:63622 )
secondary amino compound (CHEBI:63622 )
ethanolamines (CHEBI:63622 )

Ontology

Physiological effect

Health effect

Ulcerative colitis (PMID: 33440385)
Atherosclerosis (PMID: 21475195)

Cancer

Breast cancer (PMID: 9468591)
Cervical cancer (PMID: 26566624)

Disposition

Biological location

Cellular substructure

Organelle

endoplasmic reticulum (HMDB: HMDB0285669)

cell membrane (HMDB: HMDB0285669)
golgi apparatus membrane (HMDB: HMDB0285669)

Cell

All cells and tissues (HMDB: HMDB0285669)

Process

Naturally occurring process

Biological process

Cellular process

Apoptosis (PMID: 23350810)
Cell proliferation (PMID: 23350810)

Biochemical pathway

Metabolic pathway

Phosphatidylcholine Biosynthesis (HMDB: HMDB0285669)

Signaling pathway

Apoptosis (PMID: 23350810)

Biochemical process

Lipid transport (PMID: 21979151)

Role

Biological role

Nutrient

Nutrient (PMID: 28411170)

Industrial application

Pharmaceutical industry

Biomarker

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	206.5 - 207 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.78 g/L	Not Available
LogP	1.1	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	167.0	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.78 g/L	ALOGPS
logP	0.85	ALOGPS
logP	-0.4	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	10.07	ChemAxon
pKa (Strongest Basic)	9.43	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	78.43 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.12 m³·mol⁻¹	ChemAxon
Polarizability	29.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.242	31661259
DarkChem	[M-H]-	164.377	31661259
DeepCCS	[M+H]+	168.169	30932474
DeepCCS	[M-H]-	165.811	30932474
DeepCCS	[M-2H]-	198.698	30932474
DeepCCS	[M+Na]+	174.262	30932474
AllCCS	[M+H]+	164.5	32859911
AllCCS	[M+H-H2O]+	161.2	32859911
AllCCS	[M+NH4]+	167.6	32859911
AllCCS	[M+Na]+	168.5	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	163.5	32859911
AllCCS	[M+HCOO]-	164.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sotalol	CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1	3660.1	Standard polar	33892256
Sotalol	CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1	2284.4	Standard non polar	33892256
Sotalol	CC(C)NCC(O)C1=CC=C(NS(C)(=O)=O)C=C1	2287.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sotalol,1TMS,isomer #1	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1	2273.9	Semi standard non polar	33892256
Sotalol,1TMS,isomer #2	CC(C)N(CC(O)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C	2438.2	Semi standard non polar	33892256
Sotalol,1TMS,isomer #3	CC(C)NCC(O)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	2270.9	Semi standard non polar	33892256
Sotalol,2TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C	2427.7	Semi standard non polar	33892256
Sotalol,2TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C	2425.2	Standard non polar	33892256
Sotalol,2TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C	2905.5	Standard polar	33892256
Sotalol,2TMS,isomer #2	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	2162.8	Semi standard non polar	33892256
Sotalol,2TMS,isomer #2	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	2394.4	Standard non polar	33892256
Sotalol,2TMS,isomer #2	CC(C)NCC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1	2796.3	Standard polar	33892256
Sotalol,2TMS,isomer #3	CC(C)N(CC(O)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C	2359.6	Semi standard non polar	33892256
Sotalol,2TMS,isomer #3	CC(C)N(CC(O)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C	2570.3	Standard non polar	33892256
Sotalol,2TMS,isomer #3	CC(C)N(CC(O)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C	2974.7	Standard polar	33892256
Sotalol,3TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C	2358.1	Semi standard non polar	33892256
Sotalol,3TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C	2565.7	Standard non polar	33892256
Sotalol,3TMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C)C1=CC=C(N([Si](C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C	2747.3	Standard polar	33892256
Sotalol,1TBDMS,isomer #1	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1	2523.7	Semi standard non polar	33892256
Sotalol,1TBDMS,isomer #2	CC(C)N(CC(O)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	2716.5	Semi standard non polar	33892256
Sotalol,1TBDMS,isomer #3	CC(C)NCC(O)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	2512.2	Semi standard non polar	33892256
Sotalol,2TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	2962.8	Semi standard non polar	33892256
Sotalol,2TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	2918.7	Standard non polar	33892256
Sotalol,2TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(NS(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	3055.6	Standard polar	33892256
Sotalol,2TBDMS,isomer #2	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	2645.5	Semi standard non polar	33892256
Sotalol,2TBDMS,isomer #2	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	2885.7	Standard non polar	33892256
Sotalol,2TBDMS,isomer #2	CC(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1	2955.0	Standard polar	33892256
Sotalol,2TBDMS,isomer #3	CC(C)N(CC(O)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	2889.5	Semi standard non polar	33892256
Sotalol,2TBDMS,isomer #3	CC(C)N(CC(O)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	3007.0	Standard non polar	33892256
Sotalol,2TBDMS,isomer #3	CC(C)N(CC(O)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	3097.5	Standard polar	33892256
Sotalol,3TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	3109.9	Semi standard non polar	33892256
Sotalol,3TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	3286.4	Standard non polar	33892256
Sotalol,3TBDMS,isomer #1	CC(C)N(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(N([Si](C)(C)C(C)(C)C)S(C)(=O)=O)C=C1)[Si](C)(C)C(C)(C)C	2961.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Sotalol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zn9-9570000000-d4b8eccd09c6d9bdc80c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sotalol GC-MS (1 TMS) - 70eV, Positive	splash10-0uk9-5982000000-a7262c3ec90ea5ecf7a8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sotalol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sotalol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sotalol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sotalol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sotalol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-b3dca1dbda7d2457ee97	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-a29ae691c7c3aac0cd25	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-3826232ebd5c11e1fb09	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-0uk9-0590000000-c1cd421f642943a3e40d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-62e0058eee644436c974	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-00di-0090000000-1c2e1183f392f02dd2f3	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-00di-0900000000-467f723fa9c5b11ac3a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , negative-QTOF	splash10-0udi-0090000000-ec702c0822212cb2e764	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0090000000-3fe820b16cdb741dfa3e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-0ab9-0090000000-ba1b9c76db4e9239d8ff	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0090000000-9855a87a9a317eccb37e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-03e9-0690000000-0c5b752605586d60828a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-001i-0910000000-399c8ea4647bc5a24781	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-001i-0900000000-f44d2d18cd4dfd9b2756	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-053r-0900000000-422f178f83cadcda84d7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-0ab9-0090000000-06e3079747baad9d6087	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-0a4i-0090000000-69df046b345e5e50d742	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-03e9-0690000000-94ba050da9e6a24f29b1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Sotalol LC-ESI-ITFT , positive-QTOF	splash10-001i-0910000000-0ef0a4777ff5e99c8462	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sotalol 10V, Positive-QTOF	splash10-0adi-0590000000-09098535885ecdd33e06	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sotalol 20V, Positive-QTOF	splash10-01t9-0910000000-fe5e3cea1910aa494493	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sotalol 40V, Positive-QTOF	splash10-0079-4900000000-f69c1721a736a690e1f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sotalol 10V, Negative-QTOF	splash10-00fr-7090000000-8f2d5c2fc4cd2a32e84e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sotalol 20V, Negative-QTOF	splash10-004i-9120000000-51d630654bc798397a72	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sotalol 40V, Negative-QTOF	splash10-004i-9000000000-c9c1175194f72014c120	2016-08-03	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Sotalol Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00489	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00489	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00489

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5063

KEGG Compound ID

C07309

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sotalol

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

63622

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Waldo AL, Camm AJ, deRuyter H, Friedman PL, MacNeil DJ, Pauls JF, Pitt B, Pratt CM, Schwartz PJ, Veltri EP: Effect of d-sotalol on mortality in patients with left ventricular dysfunction after recent and remote myocardial infarction. The SWORD Investigators. Survival With Oral d-Sotalol. Lancet. 1996 Jul 6;348(9019):7-12. [PubMed:8691967 ]

Enzymes

Enzyme Details

1. Beta-1 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:: ADRB1
Uniprot ID:: P08588
Molecular weight:: 51322.1

References

Lowe MD, Lynham JA, Grace AA, Kaumann AJ: Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium. Br J Pharmacol. 2002 Jan;135(2):451-61. [PubMed:11815381 ]
Joseph SS, Lynham JA, Colledge WH, Kaumann AJ: Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):525-32. Epub 2004 Apr 2. [PubMed:15060759 ]
Yalcin I, Choucair-Jaafar N, Benbouzid M, Tessier LH, Muller A, Hein L, Freund-Mercier MJ, Barrot M: beta(2)-adrenoceptors are critical for antidepressant treatment of neuropathic pain. Ann Neurol. 2009 Feb;65(2):218-25. doi: 10.1002/ana.21542. [PubMed:19259968 ]
Doggrell SA: The effects of (+/-)-, (+)-, and (-)-atenolol, sotalol, and amosulalol on the rat left atria and portal vein. Chirality. 1993;5(1):8-14. [PubMed:8095397 ]
Juberg EN, Minneman KP, Abel PW: Beta 1- and beta 2-adrenoceptor binding and functional response in right and left atria of rat heart. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):193-202. [PubMed:2865685 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

2. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Lowe MD, Lynham JA, Grace AA, Kaumann AJ: Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium. Br J Pharmacol. 2002 Jan;135(2):451-61. [PubMed:11815381 ]
Joseph SS, Lynham JA, Colledge WH, Kaumann AJ: Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers. Naunyn Schmiedebergs Arch Pharmacol. 2004 May;369(5):525-32. Epub 2004 Apr 2. [PubMed:15060759 ]
Yalcin I, Choucair-Jaafar N, Benbouzid M, Tessier LH, Muller A, Hein L, Freund-Mercier MJ, Barrot M: beta(2)-adrenoceptors are critical for antidepressant treatment of neuropathic pain. Ann Neurol. 2009 Feb;65(2):218-25. doi: 10.1002/ana.21542. [PubMed:19259968 ]
Doggrell SA: The effects of (+/-)-, (+)-, and (-)-atenolol, sotalol, and amosulalol on the rat left atria and portal vein. Chirality. 1993;5(1):8-14. [PubMed:8095397 ]
Juberg EN, Minneman KP, Abel PW: Beta 1- and beta 2-adrenoceptor binding and functional response in right and left atria of rat heart. Naunyn Schmiedebergs Arch Pharmacol. 1985 Sep;330(3):193-202. [PubMed:2865685 ]

Enzyme Details

3. Potassium voltage-gated channel subfamily H member 2

General function:: Involved in ion channel activity
Specific function:: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the delayed rectifying potassium current in heart (IKr). Isoform 3 has no channel activity by itself, but modulates channel characteristics when associated with isoform 1
Gene Name:: KCNH2
Uniprot ID:: Q12809
Molecular weight:: 126653.5

References

Shimizu W, Antzelevitch C: Effects of a K(+) channel opener to reduce transmural dispersion of repolarization and prevent torsade de pointes in LQT1, LQT2, and LQT3 models of the long-QT syndrome. Circulation. 2000 Aug 8;102(6):706-12. [PubMed:10931813 ]
Numaguchi H, Mullins FM, Johnson JP Jr, Johns DC, Po SS, Yang IC, Tomaselli GF, Balser JR: Probing the interaction between inactivation gating and Dd-sotalol block of HERG. Circ Res. 2000 Nov 24;87(11):1012-8. [PubMed:11090546 ]
Wolpert C, Schimpf R, Giustetto C, Antzelevitch C, Cordeiro J, Dumaine R, Brugada R, Hong K, Bauersfeld U, Gaita F, Borggrefe M: Further insights into the effect of quinidine in short QT syndrome caused by a mutation in HERG. J Cardiovasc Electrophysiol. 2005 Jan;16(1):54-8. [PubMed:15673388 ]
Wolpert C, Schimpf R, Veltmann C, Giustetto C, Gaita F, Borggrefe M: Clinical characteristics and treatment of short QT syndrome. Expert Rev Cardiovasc Ther. 2005 Jul;3(4):611-7. [PubMed:16076272 ]
Fedida D, Orth PM, Hesketh JC, Ezrin AM: The role of late I and antiarrhythmic drugs in EAD formation and termination in Purkinje fibers. J Cardiovasc Electrophysiol. 2006 May;17 Suppl 1:S71-S78. [PubMed:16686685 ]

Showing metabocard for Sotalol (HMDB0014632)

MOL for HMDB0014632 (Sotalol)

3D MOL for HMDB0014632 (Sotalol)

3D SDF for HMDB0014632 (Sotalol)

3D-SDF for HMDB0014632 (Sotalol)

PDB for HMDB0014632 (Sotalol)

3D PDB for HMDB0014632 (Sotalol)

SMILES for HMDB0014632 (Sotalol)

INCHI for HMDB0014632 (Sotalol)

Structure for HMDB0014632 (Sotalol)

3D Structure for HMDB0014632 (Sotalol)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

References

References

References