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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H58N4O12
Molecular Weight 822.9402
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of RIFAMPIN

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C2=O)C4=C(O)C(\C=N\N5CCN(C)CC5)=C(NC(=O)C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)C(O)=C4C(O)=C3C

InChI

InChIKey=JQXXHWHPUNPDRT-WLSIYKJHSA-N
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

HIDE SMILES / InChI

Molecular Formula C43H58N4O12
Molecular Weight 822.9402
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 9 / 9
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Rifampin is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. It is FDA approved for the treatment of tuberculosis, meningococcal carrier state. Healthy subjects who received rifampin 600 mg once daily concomitantly with saquinavir 1000 mg/ritonavir 100 mg twice daily (ritonavir-boosted saquinavir) developed severe hepatocellular toxicity. Rifampin has been reported to substantially decrease the plasma concentrations of the following antiviral drugs: atazanavir, darunavir, fosamprenavir, saquinavir, and tipranavir. These antiviral drugs must not be co-administered with rifampin. Common adverse reactions include heartburn, epigastric distress, anorexia, nausea, vomiting, jaundice, flatulence, cramps.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
[Letter: Acute renal failure caused by rifampicin].
1975 Apr 19
[A new case of acute renal failure, with high hemolysis, after rifampicin (author's transl)].
1975 Nov-Dec
[Tolerance of rifampicin in long-term treatment of patients with pulmonary tuberculosis].
1976 Feb
Rifampin-induced methadone withdrawal.
1976 May 13
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.
2001
Rifampicin-induced erythema nodosum leprosum-like eruption in borderline lepromatous leprosy.
2001 Apr-Jun
Postantibiotic effects of antituberculosis agents alone and in combination.
2001 Dec
[Clinico-pathological features and possible pathogenesis of rifampicin-induced acute renal failure].
2001 Jun
CYP3A inductive potential of the rifamycins, rifabutin and rifampin, in the rabbit.
2001 May
Acute renal failure caused by rifampicin re-exposure with 10-year of interval.
2001 Nov
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Antimycobacterial plant terpenoids.
2001 Nov
Bisphenol-A, an environmental estrogen, activates the human orphan nuclear receptor, steroid and xenobiotic receptor-mediated transcription.
2001 Oct
[Post-rifampicin acute renal failure--serious, but seldom recognized complication of the anti-tuberculosis treatment].
2001 Oct-Dec
Acute renal failure complicating rifampicin therapy.
2001 Sep
Optic neuropathy after treatment with anti-tuberculous drugs in a subject with Leber's hereditary optic neuropathy mutation.
2001 Sep
The drug efflux pump MRP2: regulation of expression in physiopathological situations and by endogenous and exogenous compounds.
2002
Bactericidal activities of commonly used antiseptics against multidrug-resistant mycobacterium tuberculosis.
2002
Limitations in the use of rifampicin-gelatin grafts against virulent organisms.
2002 Apr
Simple fibroblast-based assay for screening of new antimicrobial drugs against Mycobacterium tuberculosis.
2002 Aug
Receptor-dependent regulation of the CYP3A4 gene.
2002 Dec 27
Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport.
2002 Feb
In vitro activity of 11 antimicrobial agents, including gatifloxacin and GAR936, tested against clinical isolates of Mycobacterium marinum.
2002 Feb
Antimicrobial activities of clarithromycin, gatifloxacin and sitafloxacin, in combination with various antimycobacterial drugs against extracellular and intramacrophage Mycobacterium avium complex.
2002 Feb
Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression.
2002 Feb 28
Rifampicin inhibits CD95-mediated apoptosis of Jurkat T cells via glucocorticoid receptors by modifying the expression of molecules regulating apoptosis.
2002 Jan
Rapidly progressive glomerulonephritis due to rifampicin therapy.
2002 Jan
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin.
2002 Jan
[Specific features of acute renal failure in patients treated with rifampicin].
2002 Jan-Mar
Functional analysis of the rat bile salt export pump gene promoter.
2002 Jul
CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes.
2002 Jul
Diffuse glomerulonephritis associated with rifampicin treatment for tuberculosis.
2002 Jun
Paraquat detoxicative system in the mouse liver postmitochondrial fraction.
2002 Jun 1
Evaluation of gene induction of drug-metabolizing enzymes and transporters in primary culture of human hepatocytes using high-sensitivity real-time reverse transcription PCR.
2002 May
Death associated with rifampin and pyrazinamide 2-month treatment of latent mycobacterium tuberculosis.
2002 May
3-[4'-bromo-(1,1'-biphenyl)-4-yl]-N, N-dimethyl-3-(2-thienyl)-2-propen-1-amine: synthesis, cytotoxicity, and leishmanicidal, trypanocidal and antimycobacterial activities.
2002 Nov
PXR-dependent induction of human CYP3A4 gene expression by organochlorine pesticides.
2002 Nov 15
Acute renal failure due to rifampicin: a study of 25 patients.
2002 Oct
A cell-based reporter gene assay for determining induction of CYP3A4 in a high-volume system.
2002 Oct
Regulation of a xenobiotic sulfonation cascade by nuclear pregnane X receptor (PXR).
2002 Oct 15
Endocarditis caused by methicillin-resistant Staphylococcus aureus: treatment failure with linezolid.
2002 Oct 15
Induction of CYP3As in HepG2 cells by several drugs. Association between induction of CYP3A4 and expression of glucocorticoid receptor.
2003 Apr
Synergic activity of fluoroquinolones and linezolid against Mycobacterium tuberculosis.
2003 Apr
Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition.
2003 Apr
A novel distal enhancer module regulated by pregnane X receptor/constitutive androstane receptor is essential for the maximal induction of CYP2B6 gene expression.
2003 Apr 18
Molecular basis of rifampicin-induced inhibition of anti-CD95-induced apoptosis of peripheral blood T lymphocytes: the role of CD95 ligand and FLIPs.
2003 Jan
Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.
2003 Jan
Induction of cytochrome P450 enzymes in cultured precision-cut human liver slices.
2003 Mar
Glucocorticoid receptor enhancement of pregnane X receptor-mediated CYP2B6 regulation in primary human hepatocytes.
2003 May
Regulation of CYP3A4 expression in human hepatocytes by pharmaceuticals and natural products.
2003 May
Patents

Sample Use Guides

In Vivo Use Guide
Tuberculosis: 10 mg/kg, in a single daily administration, not to exceed 600 mg/day, oral or intravenous. It is recommended that oral rifampin be administered once daily, either 1 hour before or 2 hours after a meal with a full glass of water. Meningococcal Carriers: it is recommended that 600 mg rifampin be administered twice daily for two days.
Route of Administration: Oral; Intravenous
In Vitro Use Guide
By the absolute concentration method, the MIC50 and MIC90 of rifampicin were 0.5-1 mg/L
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:47:20 UTC 2019
Edited
by admin
on Mon Oct 21 19:47:20 UTC 2019
Record UNII
VJT6J7R4TR
Record Status Validated (UNII)
Record Version
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Name Type Language
RIFAMPIN
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
RIFALDAZINE
Common Name English
RIFAMPIN [USP]
Common Name English
RIFAMPICIN [JAN]
Common Name English
BA-41166/E
Code English
RIMACTAN
Brand Name English
RIFATER COMPONENT RIFAMPIN
Common Name English
RIFAMPIN COMPONENT OF RIFATER
Common Name English
NSC-113926
Code English
RIFAMPICIN
EP   INN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
BA-41166E
Code English
RIMACTANE
Brand Name English
RIFADINE
Brand Name English
NIH-10782
Code English
RIFAMYCIN AMP
Common Name English
3-(((4-METHYL-1-PIPERAZINYL)IMINO)METHYL)RIFAMYCIN
Systematic Name English
RIFA
Brand Name English
RIFAMPICIN [IARC]
Common Name English
RIFAMPIN COMPONENT OF RIFAMATE
Common Name English
RIFAMPIN [MI]
Common Name English
RIFAMPIN [USP-RS]
Common Name English
RIFAMPICINUM [WHO-IP LATIN]
Common Name English
L-5103 LEPETIT
Code English
RIFAPRODIN
Brand Name English
RIFAMYCIN, 3-(((4-METHYL-1-PIPERAZINYL)IMINO)METHYL)-
Common Name English
RIFAMPICIN [MART.]
Common Name English
BA 41166/E
Code English
RIFOLDIN
Brand Name English
RIFAMPICIN [WHO-IP]
Common Name English
RIFAPIAM
Brand Name English
RIFAMPIN [USAN]
Common Name English
RIFAMYCIN AMP [MI]
Common Name English
L-5103
Code English
RIFAMPICIN [INN]
Common Name English
L-5103-LEPETIT
Code English
RIFAMATE COMPONENT RIFAMPIN
Common Name English
RIFAMPIN [ORANGE BOOK]
Common Name English
R/AMP
Common Name English
5,6,9,17,19,21-HEXAHYDROXY-23-METHOXY-2,4,12,16,18,20,22-HEPTAMETHYL-8-(N-(4-METHYL-1-PIPERAZINYL)FORMIMIDOYL)-2,7-(EPOXYPENTADECA(1,11,13)TRIENIMINO)NAPHTHO(2,1-B)FURAN-1,11(2H)-DIONE 21-ACETATE
Systematic Name English
ABRIFAM
Brand Name English
RIFAMPICIN [EP]
Common Name English
EREMFAT
Brand Name English
RIFADIN
Brand Name English
RIFAMPIN [HSDB]
Common Name English
RIFALDIN
Brand Name English
RIFAMPIN [VANDF]
Common Name English
RIFAMPICIN [WHO-DD]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 6585
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.4 (ETH/ISO/PYR/RIF)
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
NDF-RT N0000175500
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.4 (ISO/RIF)
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.4 (ISO/PYR/RIF)
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
FDA ORPHAN DRUG 7685
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.3
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-VATC QJ04AM05
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ATC J04AB02
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ATC J04AM07
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ATC J04AM02
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ATC J04AM05
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
NCI_THESAURUS C280
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-VATC QJ04AB02
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-VATC QJ04AM02
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ATC J04AM06
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.4 (ETH/ISO/RIF)
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-VATC QJ04AM06
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
NCI_THESAURUS C25995
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
WHO-VATC QJ54AB02
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
LIVERTOX 845
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL374478
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
LactMed
13292-46-1
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
WIKIPEDIA
RIFAMPICIN
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
RIFAMPIN
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY Description: A brick red to red-brown, crystalline powder. Solubility: Very slightly to slightly soluble in water; soluble in methanol R; slightly soluble in acetone R, ethanol (~750 g/l) TS, and ether R. Category: Antileprosy drug; antituberculosis drug. Storage: Rifampicin should be kept in a tightly closed container or in an atmosphere of nitrogen, protected from light. Additional information: Rifampicin exhibits polymorphism. Definition: Rifampicin contains not less than 97.0% and not more than 102.0% of C43H58N4O12, calculated with reference to the dried substance.
EPA CompTox
13292-46-1
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
RXCUI
9384
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY RxNorm
INN
2323
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
HSDB
13292-46-1
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
CAS
845504-52-1
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
ALTERNATIVE
MESH
D012293
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
IUPHAR
2765
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
ECHA (EC/EINECS)
236-312-0
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
NCI_THESAURUS
C811
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
EVMPD
SUB10309MIG
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
MERCK INDEX
M9611
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY Merck Index
DRUG BANK
DB01045
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
CAS
13292-46-1
Created by admin on Mon Oct 21 19:47:20 UTC 2019 , Edited by admin on Mon Oct 21 19:47:20 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INDUCER
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> INDUCER
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
METABOLIC ENZYME -> INDUCER
POTENT
METABOLIC ENZYME -> INDUCER
POTENT
METABOLIC ENZYME -> INDUCER
METABOLIC ENZYME -> INDUCER
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> INHIBITOR
CAN BE USED FOR IN-VIVO STUDIES OF TRANSPORTER
IN-VIVO
METABOLIC ENZYME -> INDUCER
TARGET -> INHIBITOR
METABOLIC ENZYME -> INDUCER
TRANSPORTER -> INHIBITOR
SUBSTRATE USED: Bromsulphthalein (BSP)
Related Record Type Details
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Duration of Action PHARMACOKINETIC ROUTE OF ADMINISTRATION: ORAL

MIC BIOLOGICAL SUSCEPTIBILITY: RESISTANT

PATHOGEN: N. MENINGIDITIS

Biological Half-life PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC POPULATION: END-STAGE RENAL DISEASE

Tmax PHARMACOKINETIC POPULATION: PEDIATRICS

ROUTE OF ADMINISTRATION: ORAL

Cmax PHARMACOKINETIC POPULATION: PEDIATRICS

ROUTE OF ADMINISTRATION: ORAL

Biological Half-life PHARMACOKINETIC ROUTE OF ADMINISTRATION: ORAL

POPULATION: PEDIATRICS

Biological Half-life PHARMACOKINETIC POPULATION: HEPATIC IMPAIRMENT

Biological Half-life PHARMACOKINETIC ROUTE OF ADMINISTRATION: IV

POPULATION: PEDIATRICS

Cmax PHARMACOKINETIC POPULATION: PEDIATRICS

ROUTE OF ADMINISTRATION: IV

MIC BIOLOGICAL PATHOGEN: N. MENINGIDITIS

SUSCEPTIBILITY: SUSCEPTIBLE

Tmax PHARMACOKINETIC ROUTE OF ADMINISTRATION: ORAL

MIC BIOLOGICAL PATHOGEN: N. MENINGIDITIS

SUSCEPTIBILITY: INTERMEDIATE