Details of the Drug

General Information of Drug (ID: DM5DSFZ)

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
Disease Entry ICD 11 Status REF
Non-insulin dependent diabetes 5A11 Approved [1]
Pulmonary tuberculosis 1B10.Z Approved [2]
Affected Organisms
MycobacteriaVarious gram-negative and gram-positive eubacteriaMycobacterium tuberculosis
ATC Code
J04AB02: Rifampicin
J04AB: Antibiotics
J04A: DRUGS FOR TREATMENT OF TUBERCULOSIS
J04: ANTIMYCOBACTERIALS
J: ANTIINFECTIVES FOR SYSTEMIC USE
J04AB02: Rifampicin
J04AB: Antibiotics
J04A: DRUGS FOR TREATMENT OF TUBERCULOSIS
J04: ANTIMYCOBACTERIALS
J: ANTIINFECTIVES FOR SYSTEMIC USE
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 822.9
Logarithm of the Partition Coefficient (xlogp) 4.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 6
Hydrogen Bond Acceptor Count (hbondacc) 15
Chemical Identifiers
Formula
C43H58N4O12
IUPAC Name
[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate
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
JQXXHWHPUNPDRT-WLSIYKJHSA-N
InChIKey
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
Cross-matching ID
PubChem CID
135398735
ChEBI ID
CHEBI:27470
CAS Number
13292-46-1
UNII
VJT6J7R4TR
DrugBank ID
DB01045
INTEDE ID
DR1420
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [3]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [4]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [5]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [6]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [7]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [8]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [9]
Rifampicin monooxygenase (rox) DE6PKFB ROX_NOCFA Substrate [10]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
1,25-dihydroxyvitamin D(3) 24-hydroxylase, mitochondrial (CYP24A1) OTG2T749 CP24A_HUMAN Gene/Protein Processing [11]
28 kDa heat- and acid-stable phosphoprotein (PDAP1) OTJSWMOD HAP28_HUMAN Gene/Protein Processing [12]
3',5'-cyclic-AMP phosphodiesterase 4D (PDE4D) OT1RWFV0 PDE4D_HUMAN Gene/Protein Processing [12]
5' exonuclease Apollo (DCLRE1B) OT2LFW7A DCR1B_HUMAN Gene/Protein Processing [12]
5-aminolevulinate synthase, non-specific, mitochondrial (ALAS1) OTQY6ZSF HEM1_HUMAN Gene/Protein Processing [13]
ABC-type organic anion transporter ABCA8 (ABCA8) OTCWLX6N ABCA8_HUMAN Gene/Protein Processing [14]
ABI gene family member 3 (ABI3) OTQTDSHP ABI3_HUMAN Gene/Protein Processing [12]
Actin-related protein 10 (ACTR10) OTRF3E58 ARP10_HUMAN Gene/Protein Processing [12]
Adenosine receptor A2a (ADORA2A) OTVRBZ0I AA2AR_HUMAN Gene/Protein Processing [12]
Alanine aminotransferase 1 (GPT) OTOXOA0Q ALAT1_HUMAN Gene/Protein Processing [15]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Inhibitors can arrest the membrane activity of human islet amyloid polypeptide independently of amyloid formation. FEBS Lett. 2001 Oct 26;507(2):200-4.
2 Xpert MTB/RIF Ultra assay for tuberculosis disease and rifampicin resistance in children. Cochrane Database Syst Rev. 2022 Sep 6;9(9):CD013359.
3 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.
4 Protective effect of rifampicin against acute liver injury induced by carbon tetrachloride in mice. Jpn J Pharmacol. 1995 Dec;69(4):325-34.
5 Xenobiotic-metabolizing cytochromes p450 in human white adipose tissue: expression and induction. Drug Metab Dispos. 2010 Apr;38(4):679-86.
6 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.
7 Rifampin markedly decreases plasma concentrations of praziquantel in healthy volunteers. Clin Pharmacol Ther. 2002 Nov;72(5):505-13.
8 Effects of prototypical microsomal enzyme inducers on cytochrome P450 expression in cultured human hepatocytes. Drug Metab Dispos. 2003 Apr;31(4):421-31.
9 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.
10 Mechanism of rifampicin inactivation in Nocardia farcinica. PLoS One. 2016 Oct 5;11(10):e0162578.
11 Possible involvement of pregnane X receptor-enhanced CYP24 expression in drug-induced osteomalacia. J Clin Invest. 2005 Jan;115(1):177-86.
12 Integrated analysis of rifampicin-induced microRNA and gene expression changes in human hepatocytes. Drug Metab Pharmacokinet. 2014;29(4):333-40.
13 No activation of human pregnane X receptor by hyperforin-related phloroglucinols. J Pharmacol Exp Ther. 2014 Mar;348(3):393-400.
14 Rifampin Regulation of Drug Transporters Gene Expression and the Association of MicroRNAs in Human Hepatocytes. Front Pharmacol. 2016 Apr 26;7:111.
15 Rifampicin-induced injury in L02 cells is alleviated by 4-PBA via inhibition of the PERK-ATF4-CHOP pathway. Toxicol In Vitro. 2016 Oct;36:186-196. doi: 10.1016/j.tiv.2016.07.017. Epub 2016 Jul 26.