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

General Information of Drug (ID: DR1420)
Drug Name
Rifampicin
Synonyms
Rifadin; Rifadine; Rifagen; Rifaldazin; Rifaldazine; Rifaldin; Rifamor; Rifampicin; Rifampicin SV; Rifampicina; Rifampicina [INN-Spanish]; Rifampicine [French]; Rifampicinum; Rifampicinum [INN-Latin]; Rifamycin AMP; Rifaprodin; Rifcin; Rifinah; Rifobac; Rifoldin; Rifoldine; Riforal; Rimactan; Rimactane; Rimactazid; Rimactizid; Rimazid; Sinerdol; Tubocin; Archidyn; Arficin; Arzide; Benemicin; Dione 21-acetate; Doloresum; Eremfat; Fenampicin; L-5103 Lepetit; rifampin; 13292-46-1; Abrifam; Ba 41166/E; R/AMP; Rifa; Rifam
Indication Osteoporosis [ICD11: FB83] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 822.9 Topological Polar Surface Area 220
Heavy Atom Count 59 Rotatable Bond Count 5
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 15
Cross-matching ID
PubChem CID
135398735
ChEBI ID
CHEBI:27470
CAS Number
13292-46-1
Formula
C43H58N4O12
Canonical SMILES
CC1C=CC=C(C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)C(O4)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)C=NN5CCN(CC5)C)C
InChI
1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1
InChIKey
JQXXHWHPUNPDRT-WLSIYKJHSA-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
25-deacetyl-rifampicin DM016653
135889898
Oxidation - Deacetylation 1 [11]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009531 Rifampicin 25-deacetyl-rifampicin Oxidation - Deacetylation Unclear [11]
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 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[7]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[8]
Rifampicin monooxygenase (rox) DME1294 Nocardia farcinica
ROX_NOCFA
1.14.13.-
[9]
Unclear metabolic mechanism (DME-unclear) DME1279 Methanobrevibacter oralis Not Available Not Available [10]
Unclear metabolic mechanism (DME-unclear) DME1280 Methanobrevibacter smithii Not Available Not Available [10]
Unclear metabolic mechanism (DME-unclear) DME1281 Methanomassiliicoccus luminyensis Not Available Not Available [10]
Unclear metabolic mechanism (DME-unclear) DME1282 Methanosphaera stadtmanae Not Available Not Available [10]
⏷ Show the Full List of 12  DME(s)
References
1 Rifampicin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos. 2003 Apr;31(4):421-31.
3 Cytochrome P450 2B6 activity as measured by bupropion hydroxylation: effect of induction by rifampin and ethnicity. Clin Pharmacol Ther. 2006 Jul;80(1):75-84.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Xenobiotic-metabolizing cytochromes p450 in human white adipose tissue: expression and induction. Drug Metab Dispos. 2010 Apr;38(4):679-86.
6 Protective effect of rifampicin against acute liver injury induced by carbon tetrachloride in mice. Jpn J Pharmacol. 1995 Dec;69(4):325-34.
7 Ketoconazole and rifampin significantly affect the pharmacokinetics, but not the safety or QTc interval, of casopitant, a neurokinin-1 receptor antagonist. J Clin Pharmacol. 2010 Aug;50(8):951-9.
8 Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13.
9 Mechanism of rifampicin inactivation in Nocardia farcinica. PLoS One. 2016 Oct 5;11(10):e0162578.
10 The antimicrobial resistance pattern of cultured human methanogens reflects the unique phylogenetic position of archaea. J Antimicrob Chemother. 2011 Sep;66(9):2038-44.
11 Determination of rifampicin and its main metabolite in plasma and urine in presence of pyrazinamide and isoniazid by HPLC method

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