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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:03 UTC

HMDB ID

HMDB0015606

Secondary Accession Numbers

HMDB15606

Metabolite Identification

Common Name

Lofexidine

Description

Lofexidine, also known as britlofex, belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it. Based on a literature review a significant number of articles have been published on Lofexidine.

Structure

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


  Mrv0541 02231218022D          

 16 17  0  0  1  0            999 V2000
    4.5080   -0.8410    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8410    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.0160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1261    1.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4610    1.7065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2060    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.0160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.2535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 13  1  0  0  0  0
  3  6  1  0  0  0  0
  3 11  1  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  7  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  8  9  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015606

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12Cl2N2O/c1-7(11-14-5-6-15-11)16-10-8(12)3-2-4-9(10)13/h2-4,7H,5-6H2,1H3,(H,14,15)

> <INCHI_KEY>
KSMAGQUYOIHWFS-UHFFFAOYSA-N

> <FORMULA>
C11H12Cl2N2O

> <MOLECULAR_WEIGHT>
259.132

> <EXACT_MASS>
258.03266843

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.111456986145203

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
2.663057541333333

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.667410695432359

> <JCHEM_POLAR_SURFACE_AREA>
33.62

> <JCHEM_REFRACTIVITY>
64.41300000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lofexidine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       8.415  -1.570   0.000  0.00  0.00          Cl+0
HETATM    2 Cl   UNK     0       3.080  -1.570   0.000  0.00  0.00          Cl+0
HETATM    3  O   UNK     0       5.748  -0.030   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       5.835   3.185   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       8.327   3.185   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.081   0.740   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.081   2.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.311   4.650   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.851   4.650   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415  -0.030   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -1.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -2.340   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414  -2.340   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -3.880   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414  -3.880   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.748  -4.650   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3    6   11                                                       
CONECT    4    7    8                                                       
CONECT    5    7    9                                                       
CONECT    6    3    7   10                                                  
CONECT    7    4    5    6                                                  
CONECT    8    4    9                                                       
CONECT    9    5    8                                                       
CONECT   10    6                                                            
CONECT   11    3   12   13                                                  
CONECT   12    1   11   14                                                  
CONECT   13    2   11   15                                                  
CONECT   14   12   16                                                       
CONECT   15   13   16                                                       
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0015606
HETATM    1  C1  UNL     1       0.819   1.816   1.153  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.475   0.569   0.369  1.00  0.00           C  
HETATM    3  O1  UNL     1      -0.471   0.782  -0.623  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.760   0.330  -0.655  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.742   1.122  -0.102  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -2.368   2.675   0.630  1.00  0.00          CL  
HETATM    7  C5  UNL     1      -4.078   0.718  -0.102  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.425  -0.489  -0.663  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.439  -1.272  -1.212  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.117  -0.875  -1.212  1.00  0.00           C  
HETATM   11 CL2  UNL     1      -0.885  -1.932  -1.939  1.00  0.00          CL  
HETATM   12  C9  UNL     1       1.695  -0.121  -0.115  1.00  0.00           C  
HETATM   13  N1  UNL     1       2.035  -0.332  -1.358  1.00  0.00           N  
HETATM   14  C10 UNL     1       3.297  -1.039  -1.436  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.885  -0.804  -0.074  1.00  0.00           C  
HETATM   16  N2  UNL     1       2.699  -0.660   0.742  1.00  0.00           N  
HETATM   17  H1  UNL     1       1.909   1.798   1.375  1.00  0.00           H  
HETATM   18  H2  UNL     1       0.198   1.965   2.040  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.666   2.690   0.482  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.006  -0.123   1.129  1.00  0.00           H  
HETATM   21  H5  UNL     1      -4.845   1.348   0.335  1.00  0.00           H  
HETATM   22  H6  UNL     1      -5.465  -0.821  -0.672  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.662  -2.234  -1.666  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.959  -0.659  -2.231  1.00  0.00           H  
HETATM   25  H9  UNL     1       3.100  -2.129  -1.559  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.551  -1.619   0.262  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.380   0.190  -0.091  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.582  -0.896   1.747  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   12   20
CONECT    3    4
CONECT    4    5    5   10
CONECT    5    6    7
CONECT    7    8    8   21
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   11
CONECT   12   13   13   16
CONECT   13   14
CONECT   14   15   24   25
CONECT   15   16   26   27
CONECT   16   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(alpha-(2,6-Dichlorophenoxy)ethyl)2-imidazoline	ChEBI
Lofexidina	ChEBI
Lofexidinum	ChEBI
2-(a-(2,6-Dichlorophenoxy)ethyl)2-imidazoline	Generator
2-(Α-(2,6-dichlorophenoxy)ethyl)2-imidazoline	Generator
2-(1-(2,6-Dichlorophenoxy)ethyl)-4,5-dihydro-1H-imidazole	HMDB
BritLofex	HMDB
2-(alpha-(2,6-Dichlorophenoxy)ethyl) delta-2-imidazoline	HMDB
Lofexidine mono-hydrochloride	HMDB
Lofexidine, (+-)-isomer	HMDB
Lofexidine hydrochloride	HMDB
Lofexidine monohydrochloride	HMDB

Chemical Formula

C₁₁H₁₂Cl₂N₂O

Average Molecular Weight

259.132

Monoisotopic Molecular Weight

258.03266843

IUPAC Name

2-[1-(2,6-dichlorophenoxy)ethyl]-4,5-dihydro-1H-imidazole

Traditional Name

lofexidine

CAS Registry Number

31036-80-3

SMILES

CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1

InChI Identifier

InChI=1S/C11H12Cl2N2O/c1-7(11-14-5-6-15-11)16-10-8(12)3-2-4-9(10)13/h2-4,7H,5-6H2,1H3,(H,14,15)

InChI Key

KSMAGQUYOIHWFS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dichlorobenzenes. Dichlorobenzenes are compounds containing a benzene with exactly two chlorine atoms attached to it.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Halobenzenes

Direct Parent

Dichlorobenzenes

Alternative Parents

Substituents

Phenoxy compound
1,3-dichlorobenzene
Phenol ether
Alkyl aryl ether
Aryl chloride
Aryl halide
Imidolactam
2-imidazoline
Amidine
Carboxylic acid amidine
Ether
Azacycle
Organoheterocyclic compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organic oxygen compound
Organohalogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:51368 )
imidazoles (CHEBI:51368 )
carboxamidine (CHEBI:51368 )
dichlorobenzene (CHEBI:51368 )

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

Membrane (HMDB: HMDB0015606)

Source

Exogenous

Exogenous (HMDB: HMDB0015606)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	127 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.15 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.15 g/L	ALOGPS
logP	3.31	ALOGPS
logP	2.66	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	7.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	33.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	64.41 m³·mol⁻¹	ChemAxon
Polarizability	25.11 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
DeepCCS	[M+H]+	146.455	30932474
DeepCCS	[M-H]-	144.097	30932474
DeepCCS	[M-2H]-	178.069	30932474
DeepCCS	[M+Na]+	152.806	30932474
AllCCS	[M+H]+	154.7	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	158.2	32859911
AllCCS	[M+Na]+	159.2	32859911
AllCCS	[M-H]-	153.4	32859911
AllCCS	[M+Na-2H]-	153.7	32859911
AllCCS	[M+HCOO]-	154.0	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.	2.96 minutes	32390414
Predicted by Siyang on May 30, 2022	12.9851 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.81 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1478.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	393.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	147.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	244.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	136.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	482.0 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	530.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	982.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	429.6 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	1389.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	369.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	159.8 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	13.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lofexidine	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1	2917.0	Standard polar	33892256
Lofexidine	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1	1951.0	Standard non polar	33892256
Lofexidine	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1	1914.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lofexidine,1TMS,isomer #1	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1[Si](C)(C)C	2180.1	Semi standard non polar	33892256
Lofexidine,1TMS,isomer #1	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1[Si](C)(C)C	2039.8	Standard non polar	33892256
Lofexidine,1TMS,isomer #1	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1[Si](C)(C)C	3243.7	Standard polar	33892256
Lofexidine,1TBDMS,isomer #1	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1[Si](C)(C)C(C)(C)C	2402.3	Semi standard non polar	33892256
Lofexidine,1TBDMS,isomer #1	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1[Si](C)(C)C(C)(C)C	2240.3	Standard non polar	33892256
Lofexidine,1TBDMS,isomer #1	CC(OC1=C(Cl)C=CC=C1Cl)C1=NCCN1[Si](C)(C)C(C)(C)C	3287.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lofexidine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0459-8910000000-1ef99e126c03b06d18c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lofexidine 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 - Lofexidine LC-ESI-qTof , Positive-QTOF	splash10-0bta-5090000000-966c69c881b261c7d39d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lofexidine , positive-QTOF	splash10-0bta-5090000000-966c69c881b261c7d39d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Lofexidine 35V, Positive-QTOF	splash10-0002-9000000000-050254002a602761b8da	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 10V, Positive-QTOF	splash10-0a4i-1090000000-8e8a68e1e0da6f2db6c0	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 20V, Positive-QTOF	splash10-0002-9320000000-7faea52073b41d21462b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 40V, Positive-QTOF	splash10-0006-9200000000-3304f31e8314347b14f6	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 10V, Negative-QTOF	splash10-0a4i-1190000000-551a9882c5776e075589	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 20V, Negative-QTOF	splash10-0bt9-1590000000-6c7abe970b6a82a66fb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 40V, Negative-QTOF	splash10-03k9-5900000000-6009a76b4783970c379f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 10V, Positive-QTOF	splash10-0a4i-1090000000-87c678178e712eefd851	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 20V, Positive-QTOF	splash10-0a4i-3090000000-3ccfbdb674335f23cfcb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 40V, Positive-QTOF	splash10-02ml-9340000000-d5dbe0cad228bd86fdc3	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 10V, Negative-QTOF	splash10-0a4i-0090000000-2325e327fe9b11ee6616	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 20V, Negative-QTOF	splash10-06si-9850000000-535a4993c6fd9fc54d5c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lofexidine 40V, Negative-QTOF	splash10-001i-9110000000-93a31f1cd12ec1e55b8d	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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 DB04948	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04948	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04948

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28460

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Lofexidine

METLIN ID

Not Available

PubChem Compound

30668

PDB ID

Not Available

ChEBI ID

51368

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

Walsh SL, Strain EC, Bigelow GE: Evaluation of the effects of lofexidine and clonidine on naloxone-precipitated withdrawal in opioid-dependent humans. Addiction. 2003 Apr;98(4):427-39. [PubMed:12653813 ]
Manufacturer Website [Link]

Enzymes

Enzyme Details

1. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Jin Y, Verstappen A, Elko E, Cammarata P, Yorio T: Effects of lofexidine, an alpha 2-adrenoreceptor agonist, on ocular blood flow and ion transport of rabbit iris-ciliary body. J Ocul Pharmacol. 1992 Spring;8(1):23-33. [PubMed:1357064 ]
Strang J, Bearn J, Gossop M: Lofexidine for opiate detoxification: review of recent randomised and open controlled trials. Am J Addict. 1999 Fall;8(4):337-48. [PubMed:10598217 ]
Erb S, Hitchcott PK, Rajabi H, Mueller D, Shaham Y, Stewart J: Alpha-2 adrenergic receptor agonists block stress-induced reinstatement of cocaine seeking. Neuropsychopharmacology. 2000 Aug;23(2):138-50. [PubMed:10882840 ]

Showing metabocard for Lofexidine (HMDB0015606)

MOL for HMDB0015606 (Lofexidine)

3D MOL for HMDB0015606 (Lofexidine)

3D SDF for HMDB0015606 (Lofexidine)

3D-SDF for HMDB0015606 (Lofexidine)

PDB for HMDB0015606 (Lofexidine)

3D PDB for HMDB0015606 (Lofexidine)

SMILES for HMDB0015606 (Lofexidine)

INCHI for HMDB0015606 (Lofexidine)

Structure for HMDB0015606 (Lofexidine)

3D Structure for HMDB0015606 (Lofexidine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References