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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015137

Secondary Accession Numbers

HMDB15137

Metabolite Identification

Common Name

Levobupivacaine

Description

Levobupivacaine is an amino-amide local anaesthetic drug belonging to the family of n-alkylsubstituted. pipecoloxylidide. It is the S-enantiomer of bupivacaine. Levobupivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Chirocaine. Compared to bupivacaine, levobupivacaine is associated with less vasodilation and has a longer duration of action. It is approximately 13 per cent less potent (by molarity) than racemic bupivacaine.Levobupivacaine is indicated for local anaesthesia including infiltration, nerve block, ophthalmic, epidural and intrathecal anaesthesia in adults; and infiltration analgesia in children. Adverse drug reactions (ADRs) are rare when it is administered correctly. Most ADRs relate to administration technique (resulting in systemic exposure) or pharmacological effects of anesthesia, however allergic reactions can rarely occur. [Wikipedia ]

Structure

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

HMDB0015137
     RDKit          3D
Levobupivacaine
 49 50  0  0  0  0  0  0  0  0999 V2000
    3.5348    1.7813   -1.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045    0.7024   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7230    0.8003    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149    0.6183    0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781   -0.6585    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -1.7672    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235   -2.9959   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.2740   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857   -2.3073   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -0.8713   -0.3828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4669    0.0086    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    0.8915    1.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973   -0.1168   -0.3076 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802    0.6846    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6198    0.2777    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -1.0016    1.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    1.0155    1.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    2.2119    1.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813    2.6164   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    1.8656   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    2.3573   -1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734    2.6222   -1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325    2.2339   -2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    1.3641   -2.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.3062   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    0.9178   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815    0.1452    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    1.8556    0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897    0.7616    1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    1.4214   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320   -1.6456    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089   -2.0335    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1926   -2.7007   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218   -3.8930    0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -4.3166   -0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -3.1622   -1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858   -2.4238   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -2.4850    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848   -0.7185   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0311   -0.8338   -1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0772   -1.8152    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.8925    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -1.3518    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524    0.6974    2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495    2.8037    1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    3.5444   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    3.0344   -2.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2232    1.4649   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074    2.8733   -1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10  5  1  0
 20 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  6
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
M  END

1002
  Mrv0541 02231215102D          

 21 22  0  0  1  0            999 V2000
    5.9370   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9370    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  1  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015137

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1

> <INCHI_KEY>
LEBVLXFERQHONN-INIZCTEOSA-N

> <FORMULA>
C18H28N2O

> <MOLECULAR_WEIGHT>
288.4277

> <EXACT_MASS>
288.220163528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.448141268605326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
4.515518884333334

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.623539229353206

> <JCHEM_PKA_STRONGEST_BASIC>
8.003403055870814

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
90.19330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-bupivacaine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015137
     RDKit          3D
Levobupivacaine
 49 50  0  0  0  0  0  0  0  0999 V2000
    3.5348    1.7813   -1.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045    0.7024   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7230    0.8003    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149    0.6183    0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781   -0.6585    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -1.7672    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235   -2.9959   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.2740   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857   -2.3073   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -0.8713   -0.3828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4669    0.0086    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    0.8915    1.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973   -0.1168   -0.3076 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802    0.6846    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6198    0.2777    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -1.0016    1.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    1.0155    1.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    2.2119    1.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813    2.6164   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    1.8656   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    2.3573   -1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734    2.6222   -1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325    2.2339   -2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    1.3641   -2.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.3062   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    0.9178   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815    0.1452    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    1.8556    0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897    0.7616    1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    1.4214   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320   -1.6456    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089   -2.0335    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1926   -2.7007   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218   -3.8930    0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -4.3166   -0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -3.1622   -1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858   -2.4238   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -2.4850    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848   -0.7185   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0311   -0.8338   -1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0772   -1.8152    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.8925    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -1.3518    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524    0.6974    2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495    2.8037    1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    3.5444   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    3.0344   -2.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2232    1.4649   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074    2.8733   -1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10  5  1  0
 20 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  6
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1002                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082  -0.385   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.415   2.695   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.415  -0.385   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.748   1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.082   2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082   4.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -5.005   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    4    6    9                                                  
CONECT    3   10   13                                                       
CONECT    4    2    5   10                                                  
CONECT    5    4    7                                                       
CONECT    6    2    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    2   11                                                       
CONECT   10    1    3    4                                                  
CONECT   11    9   12                                                       
CONECT   12   11   14                                                       
CONECT   13    3   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13   17   19                                                  
CONECT   16   13   18   20                                                  
CONECT   17   15   21                                                       
CONECT   18   16   21                                                       
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0015137
HETATM    1  C1  UNL     1       3.535   1.781  -1.740  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.205   0.702  -0.919  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.723   0.800   0.504  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.215   0.618   0.603  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.878  -0.658   0.098  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.319  -1.767   0.885  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.424  -2.996  -0.027  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.127  -3.274  -0.725  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.086  -2.307  -0.202  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.566  -0.871  -0.383  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.467   0.009   0.151  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.234   0.892   1.013  1.00  0.00           O  
HETATM   13  N2  UNL     1      -1.797  -0.117  -0.308  1.00  0.00           N  
HETATM   14  C11 UNL     1      -2.880   0.685   0.141  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.620   0.278   1.227  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.264  -1.002   1.914  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.670   1.016   1.694  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.028   2.212   1.080  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.281   2.616  -0.012  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.209   1.866  -0.490  1.00  0.00           C  
HETATM   21  C18 UNL     1      -2.447   2.357  -1.667  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.173   2.622  -1.109  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.232   2.234  -2.493  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.683   1.364  -2.347  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.067  -0.306  -1.331  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.297   0.918  -0.907  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.282   0.145   1.200  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.913   1.856   0.858  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.990   0.762   1.695  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.781   1.421  -0.026  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.332  -1.646   1.321  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.609  -2.034   1.709  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.193  -2.701  -0.790  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.722  -3.893   0.532  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.765  -4.317  -0.556  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.240  -3.162  -1.829  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.786  -2.424  -0.903  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.180  -2.485   0.837  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.585  -0.719  -1.503  1.00  0.00           H  
HETATM   40  H19 UNL     1      -2.031  -0.834  -1.022  1.00  0.00           H  
HETATM   41  H20 UNL     1      -3.077  -1.815   1.167  1.00  0.00           H  
HETATM   42  H21 UNL     1      -2.383  -0.892   2.583  1.00  0.00           H  
HETATM   43  H22 UNL     1      -4.108  -1.352   2.545  1.00  0.00           H  
HETATM   44  H23 UNL     1      -5.252   0.697   2.548  1.00  0.00           H  
HETATM   45  H24 UNL     1      -5.850   2.804   1.435  1.00  0.00           H  
HETATM   46  H25 UNL     1      -4.547   3.544  -0.500  1.00  0.00           H  
HETATM   47  H26 UNL     1      -3.097   3.034  -2.274  1.00  0.00           H  
HETATM   48  H27 UNL     1      -2.223   1.465  -2.298  1.00  0.00           H  
HETATM   49  H28 UNL     1      -1.507   2.873  -1.381  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   10
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39
CONECT   11   12   12   13
CONECT   13   14   40
CONECT   14   15   15   20
CONECT   15   16   17
CONECT   16   41   42   43
CONECT   17   18   18   44
CONECT   18   19   45
CONECT   19   20   20   46
CONECT   20   21
CONECT   21   47   48   49
END

HMDB0015137
     RDKit          3D
Levobupivacaine
 49 50  0  0  0  0  0  0  0  0999 V2000
    3.5348    1.7813   -1.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045    0.7024   -0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7230    0.8003    0.5042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149    0.6183    0.6027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8781   -0.6585    0.0984 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3193   -1.7672    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4235   -2.9959   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -3.2740   -0.7252 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0857   -2.3073   -0.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5658   -0.8713   -0.3828 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4669    0.0086    0.1506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2342    0.8915    1.0134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7973   -0.1168   -0.3076 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802    0.6846    0.1410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6198    0.2777    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2641   -1.0016    1.9139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6701    1.0155    1.6940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0278    2.2119    1.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2813    2.6164   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2095    1.8656   -0.4895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4467    2.3573   -1.6671 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734    2.6222   -1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2325    2.2339   -2.4931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826    1.3641   -2.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0666   -0.3062   -1.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2972    0.9178   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2815    0.1452    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9128    1.8556    0.8577 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9897    0.7616    1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7813    1.4214   -0.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3320   -1.6456    1.3209 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6089   -2.0335    1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1926   -2.7007   -0.7900 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218   -3.8930    0.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651   -4.3166   -0.5562 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2404   -3.1622   -1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858   -2.4238   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1803   -2.4850    0.8368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5848   -0.7185   -1.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0311   -0.8338   -1.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0772   -1.8152    1.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3826   -0.8925    2.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1083   -1.3518    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524    0.6974    2.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8495    2.8037    1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5469    3.5444   -0.4996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0971    3.0344   -2.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2232    1.4649   -2.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5074    2.8733   -1.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10  5  1  0
 20 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  6
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Bupivacaine	ChEBI
(S)-1-Butyl-2',6'-pipecoloxylidide	ChEBI
(S)-Bupivacaine	ChEBI
L-(-)-Bupivacaine	ChEBI
L-(-)-1-Butyl-2',6'-pipecoloxylidide	ChEBI
Novabupi	Kegg
Levobupivacaine hydrochloride	HMDB
Chirocaine	HMDB

Chemical Formula

C₁₈H₂₈N₂O

Average Molecular Weight

288.4277

Monoisotopic Molecular Weight

288.220163528

IUPAC Name

(2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Traditional Name

(-)-bupivacaine

CAS Registry Number

27262-47-1

SMILES

CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C

InChI Identifier

InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)/t16-/m0/s1

InChI Key

LEBVLXFERQHONN-INIZCTEOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidinecarboxamides. Piperidinecarboxamides are compounds containing a piperidine ring substituted with a carboxamide functional group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinecarboxylic acids and derivatives

Direct Parent

Piperidinecarboxamides

Alternative Parents

Substituents

2-piperidinecarboxamide
Piperidinecarboxamide
M-xylene
Xylene
Monocyclic benzene moiety
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Carboximidic acid
Carboximidic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide (CHEBI:6149 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Extracellular (HMDB: HMDB0015137)
Membrane (HMDB: HMDB0015137)

Source

Exogenous

Exogenous (HMDB: HMDB0015137)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Levobupivacaine Pathway (HMDB: HMDB0015137)
Levobupivacaine Action Pathway (PathBank: SMP0000397)

Industrial application

Local anaesthetic (HMDB: HMDB0015137)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anti adrenergic (HMDB: HMDB0015137)

Indirect biological role

Amphiphile (HMDB: HMDB0015137)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.098 g/L	Not Available
LogP	3.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.098 g/L	ALOGPS
logP	3.31	ALOGPS
logP	4.52	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.19 m³·mol⁻¹	ChemAxon
Polarizability	34.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	169.969	31661259
DarkChem	[M-H]-	169.797	31661259
DeepCCS	[M+H]+	175.677	30932474
DeepCCS	[M-H]-	173.319	30932474
DeepCCS	[M-2H]-	206.205	30932474
DeepCCS	[M+Na]+	181.77	30932474
AllCCS	[M+H]+	172.8	32859911
AllCCS	[M+H-H2O]+	169.6	32859911
AllCCS	[M+NH4]+	175.8	32859911
AllCCS	[M+Na]+	176.7	32859911
AllCCS	[M-H]-	174.4	32859911
AllCCS	[M+Na-2H]-	174.9	32859911
AllCCS	[M+HCOO]-	175.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.17 minutes	32390414
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	-1.63 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0135 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.27 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	59.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1626.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	193.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	176.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	165.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	93.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.6 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	493.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	257.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	930.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	382.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1136.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	382.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	316.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	47.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Levobupivacaine	CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C	2737.3	Standard polar	33892256
Levobupivacaine	CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C	2332.1	Standard non polar	33892256
Levobupivacaine	CCCCN1CCCC[C@H]1C(=O)NC1=C(C)C=CC=C1C	2286.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Levobupivacaine,1TMS,isomer #1	CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C	2150.7	Semi standard non polar	33892256
Levobupivacaine,1TMS,isomer #1	CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C	2238.5	Standard non polar	33892256
Levobupivacaine,1TMS,isomer #1	CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C	2871.2	Standard polar	33892256
Levobupivacaine,1TBDMS,isomer #1	CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C	2375.4	Semi standard non polar	33892256
Levobupivacaine,1TBDMS,isomer #1	CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C	2459.3	Standard non polar	33892256
Levobupivacaine,1TBDMS,isomer #1	CCCCN1CCCC[C@H]1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C	2969.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Levobupivacaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-6920000000-20e4e8d5c09a52a31c75	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Levobupivacaine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 10V, Positive-QTOF	splash10-0079-0970000000-e665f05dc8da9fafd8f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 20V, Positive-QTOF	splash10-00dl-2900000000-6396ddc6fc9d5e9b6c64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 40V, Positive-QTOF	splash10-0ac0-9200000000-befeaee90e72918d68b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 10V, Negative-QTOF	splash10-000i-0290000000-e01610a30f93d9c5ec2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 20V, Negative-QTOF	splash10-00ri-0970000000-e26949f880557c6da815	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 40V, Negative-QTOF	splash10-00xr-3900000000-56dfe5d9cd7f629f17e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 10V, Negative-QTOF	splash10-000i-0090000000-e83ab5b70775090159b7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 20V, Negative-QTOF	splash10-000i-0690000000-6ff0193988455d286726	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 40V, Negative-QTOF	splash10-00xr-1920000000-87f1897c4a60793791d5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 10V, Positive-QTOF	splash10-000i-0190000000-23ffc562239624515183	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 20V, Positive-QTOF	splash10-000g-3920000000-6aaf7d8f5f0149cec33e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Levobupivacaine 40V, Positive-QTOF	splash10-0007-8900000000-e62af4b8065c6c1caf01	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Levobupivacaine 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 DB01002	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01002	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01002

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

83289

KEGG Compound ID

C07887

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Levobupivacaine

METLIN ID

Not Available

PubChem Compound

92253

PDB ID

Not Available

ChEBI ID

6149

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

Burlacu CL, Buggy DJ: Update on local anesthetics: focus on levobupivacaine. Ther Clin Risk Manag. 2008 Apr;4(2):381-92. [PubMed:18728849 ]
Leone S, Di Cianni S, Casati A, Fanelli G: Pharmacology, toxicology, and clinical use of new long acting local anesthetics, ropivacaine and levobupivacaine. Acta Biomed. 2008 Aug;79(2):92-105. [PubMed:18788503 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 1A2

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:: CYP1A2
Uniprot ID:: P05177
Molecular weight:: 58406.915

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Sodium channel protein type 10 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:: SCN10A
Uniprot ID:: Q9Y5Y9
Molecular weight:: 220623.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Ueta K, Sugimoto M, Suzuki T, Uchida I, Mashimo T: In vitro antagonism of recombinant ligand-gated ion-channel receptors by stereospecific enantiomers of bupivacaine. Reg Anesth Pain Med. 2006 Jan-Feb;31(1):19-25. [PubMed:16418020 ]
Vladimirov M, Nau C, Mok WM, Strichartz G: Potency of bupivacaine stereoisomers tested in vitro and in vivo: biochemical, electrophysiological, and neurobehavioral studies. Anesthesiology. 2000 Sep;93(3):744-55. [PubMed:10969308 ]
Brau ME, Branitzki P, Olschewski A, Vogel W, Hempelmann G: Block of neuronal tetrodotoxin-resistant Na+ currents by stereoisomers of piperidine local anesthetics. Anesth Analg. 2000 Dec;91(6):1499-505. [PubMed:11094008 ]

Showing metabocard for Levobupivacaine (HMDB0015137)

MOL for HMDB0015137 (Levobupivacaine)

3D MOL for HMDB0015137 (Levobupivacaine)

3D SDF for HMDB0015137 (Levobupivacaine)

3D-SDF for HMDB0015137 (Levobupivacaine)

PDB for HMDB0015137 (Levobupivacaine)

3D PDB for HMDB0015137 (Levobupivacaine)

SMILES for HMDB0015137 (Levobupivacaine)

INCHI for HMDB0015137 (Levobupivacaine)

Structure for HMDB0015137 (Levobupivacaine)

3D Structure for HMDB0015137 (Levobupivacaine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References