Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0346)
Drug Name
Clofazimine
Synonyms
Chlofazimine; Clofazimina; Clofazimina [INN-Spanish]; Clofaziminum; Clofaziminum [INN-Latin]; Lampren; Lamprene; clofazimine; 2030-63-9; 3-(p-Chloranilino)-10-(p-chlorphenyl)-2,10-dihydro-2-(isopropylimino)-phenazin; 3-(p-Chloroanilino)-10-(p-chlorophenyl)-2,10-dihydro-2-(isopropylimino)phenazine; B 663; B 663 (Pharmaceutical); B 663 (VAN); B-663; C27H22Cl2N4; G 30320; N,5-bis(4-chlorophenyl)-3-propan-2-yliminophenazin-2-amine; NSC-141046; UNII-D959AE5USF
Indication Crohn disease [ICD11: DD70] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 473.4 Topological Polar Surface Area 40
Heavy Atom Count 33 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2794
PubChem SID
9132 ; 426821 ; 602744 ; 627688 ; 855829 ; 4302579 ; 7847344 ; 7978968 ; 8151803 ; 10321645 ; 11112506 ; 11466404 ; 11467524 ; 11486188 ; 14761008 ; 15356285 ; 24714740 ; 24893114 ; 29221949 ; 32963436 ; 46386952 ; 46508174 ; 47275676 ; 47349472 ; 47499671 ; 47795160 ; 48243512 ; 48415799 ; 49681815 ; 49698463 ; 50004010 ; 50100467 ; 50124245 ; 50376246 ; 56314325 ; 57321463 ; 92125497 ; 92308020 ; 92308564 ; 93167165 ; 93619701 ; 96079551 ; 103400985 ; 103755939 ; 103914133 ; 104153270 ; 104301631 ; 118816613 ; 121269827 ; 121363168
ChEBI ID
CHEBI:3749
CAS Number
2030-63-9
TTD Drug ID
D0S5UH
Formula
C27H22Cl2N4
Canonical SMILES
CC(C)N=C1C=C2C(=NC3=CC=CC=C3N2C4=CC=C(C=C4)Cl)C=C1NC5=CC=C(C=C5)Cl
InChI
1S/C27H22Cl2N4/c1-17(2)30-24-16-27-25(15-23(24)31-20-11-7-18(28)8-12-20)32-22-5-3-4-6-26(22)33(27)21-13-9-19(29)10-14-21/h3-17,31H,1-2H3
InChIKey
WDQPAMHFFCXSNU-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Hydrated clofazimine DM006096 N. A. Other reaction - Hydration 1 [2]
Hydrolytic-deaminated clofazimine DM006092 N. A. Hydrolysis - Hydrolytic Deamination 1 [2]
Hydrolytic-dehalogenated clofazimine DM006090 N. A. Other reaction - Hydrolytic Dehalogenation 1 [2]
Hydroxylated clofazimine DM006094 N. A. Oxidation - Hydrolyzationn 1 [2]
Hydrated clofazimine glucuronidation DM006097 N. A. Conjugation - Glucuronidation 2 [2]
Hydrolytic-deaminated clofazimine glucuronide DM006093
133546
Conjugation - Glucuronidation 2 [2]
Hydrolytic-dehalogenated Clofazimine sulfate DM006091 N. A. Conjugation - sulfation 2 [2]
Hydroxylated clofazimine glucuronidation DM006095 N. A. Conjugation - Glucuronidation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006557 Clofazimine Hydrolytic-dehalogenated clofazimine Other reaction - Hydrolytic Dehalogenation CYP1A2 [2]
MR006559 Clofazimine Hydrolytic-deaminated clofazimine Hydrolysis - Hydrolytic Deamination CYP3A4 ... [2]
MR006561 Clofazimine Hydroxylated clofazimine Oxidation - Hydrolyzationn Unclear [2]
MR006563 Clofazimine Hydrated clofazimine Other reaction - Hydration Unclear [2]
MR006564 Hydrated clofazimine Hydrated clofazimine glucuronidation Conjugation - Glucuronidation UGT1A1 ... [2]
MR006560 Hydrolytic-deaminated clofazimine Hydrolytic-deaminated clofazimine glucuronide Conjugation - Glucuronidation UGT1A4 ... [2]
MR006558 Hydrolytic-dehalogenated clofazimine Hydrolytic-dehalogenated Clofazimine sulfate Conjugation - sulfation Unclear [2]
MR006562 Hydroxylated clofazimine Hydroxylated clofazimine glucuronidation Conjugation - Glucuronidation UGT1A1 ... [2]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 8  DME(s)
References
1 Clofazimine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Characterization of Clofazimine Metabolism in Human Liver Microsomal Incubation In Vitro
3 Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448.

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