RIFAMPIN

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 Search

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	No
Defined Stereocenters	9 / 9
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050420s075,050627s014lbl.pdf
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/rifadin-drug.htm http://www.wikidoc.org/index.php/Rifampin_(oral)

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

Targets

Primary Target	Pharmacology	Potency
DNA-directed RNA polymerase subunit beta 5 Target ID: P0A8V2 Gene ID: 948488.0 Gene Symbol: rpoB Target Organism: Escherichia coli (strain K12) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15805525 \| https://www.ncbi.nlm.nih.gov/pubmed/11290327	Inhibitor 8504
Cytochrome P450 3A4 127 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16176562	Inhibitor 8504	18.5 µM [Ki]
Cytochrome P450 2C8 18 Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16176562	Inhibitor 8504	30.2 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050420s075,050627s014lbl.pdf	Primary		Approved 8583	RIFADIN Approved Use In the treatment of both tuberculosis and the meningococcal carrier state, the small number of resistant cells present within large populations of susceptible cells can rapidly become the predominant type. Bacteriologic cultures should be obtained before the start of therapy to confirm the susceptibility of the organism to rifampin and they should be repeated throughout therapy to monitor the response to treatment. Since resistance can emerge rapidly, susceptibility tests should be performed in the event of persistent positive cultures during the course of treatment. If test results show resistance to rifampin and the patient is not responding to therapy, the drug regimen should be modified. Tuberculosis Rifampin is indicated in the treatment of all forms of tuberculosis. A three-drug regimen consisting of rifampin, isoniazid, and pyrazinamide (e.g., RIFATER®) is recommended in the initial phase of short-course therapy which is usually continued for 2 months. The Advisory Council for the Elimination of Tuberculosis, the American Thoracic Society, and Centers for Disease Control and Prevention recommend that either streptomycin or ethambutol be added as a fourth drug in a regimen containing isoniazid (INH), rifampin, and pyrazinamide for initial treatment of tuberculosis unless the likelihood of INH resistance is very low. The need for a fourth drug should be reassessed when the results of susceptibility testing are known. If community rates of INH resistance are currently less than 4%, an initial treatment regimen with less than four drugs may be considered. Following the initial phase, treatment should be continued with rifampin and isoniazid (e.g., RIFAMATE®) for at least 4 months. Treatment should be continued for longer if the patient is still sputum or culture positive, if resistant organisms are present, or if the patient is HIV positive. RIFADIN IV is indicated for the initial treatment and retreatment of tuberculosis when the drug cannot be taken by mouth. Meningococcal Carriers Rifampin is indicated for the treatment of asymptomatic carriers of Neisseria meningitidis to eliminate meningococci from the nasopharynx. Rifampin is not indicated for the treatment of meningococcal infection because of the possibility of the rapid emergence of resistant organisms. (See WARNINGS.) Rifampin should not be used indiscriminately, and therefore, diagnostic laboratory procedures, including serotyping and susceptibility testing, should be performed for establishment of the carrier state and the correct treatment. So that the usefulness of rifampin in the treatment of asymptomatic meningococcal carriers is preserved, the drug should be used only when the risk of meningococcal disease is high. To reduce the development of drug-resistant bacteria and maintain the effectiveness of rifampin and other antibacterial drugs, rifampin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1971
Asymptomatic meningococcal infection 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050420s075,050627s014lbl.pdf	Curative		Approved 8583	RIFADIN Approved Use In the treatment of both tuberculosis and the meningococcal carrier state, the small number of resistant cells present within large populations of susceptible cells can rapidly become the predominant type. Bacteriologic cultures should be obtained before the start of therapy to confirm the susceptibility of the organism to rifampin and they should be repeated throughout therapy to monitor the response to treatment. Since resistance can emerge rapidly, susceptibility tests should be performed in the event of persistent positive cultures during the course of treatment. If test results show resistance to rifampin and the patient is not responding to therapy, the drug regimen should be modified. Tuberculosis Rifampin is indicated in the treatment of all forms of tuberculosis. A three-drug regimen consisting of rifampin, isoniazid, and pyrazinamide (e.g., RIFATER®) is recommended in the initial phase of short-course therapy which is usually continued for 2 months. The Advisory Council for the Elimination of Tuberculosis, the American Thoracic Society, and Centers for Disease Control and Prevention recommend that either streptomycin or ethambutol be added as a fourth drug in a regimen containing isoniazid (INH), rifampin, and pyrazinamide for initial treatment of tuberculosis unless the likelihood of INH resistance is very low. The need for a fourth drug should be reassessed when the results of susceptibility testing are known. If community rates of INH resistance are currently less than 4%, an initial treatment regimen with less than four drugs may be considered. Following the initial phase, treatment should be continued with rifampin and isoniazid (e.g., RIFAMATE®) for at least 4 months. Treatment should be continued for longer if the patient is still sputum or culture positive, if resistant organisms are present, or if the patient is HIV positive. RIFADIN IV is indicated for the initial treatment and retreatment of tuberculosis when the drug cannot be taken by mouth. Meningococcal Carriers Rifampin is indicated for the treatment of asymptomatic carriers of Neisseria meningitidis to eliminate meningococci from the nasopharynx. Rifampin is not indicated for the treatment of meningococcal infection because of the possibility of the rapid emergence of resistant organisms. (See WARNINGS.) Rifampin should not be used indiscriminately, and therefore, diagnostic laboratory procedures, including serotyping and susceptibility testing, should be performed for establishment of the carrier state and the correct treatment. So that the usefulness of rifampin in the treatment of asymptomatic meningococcal carriers is preserved, the drug should be used only when the risk of meningococcal disease is high. To reduce the development of drug-resistant bacteria and maintain the effectiveness of rifampin and other antibacterial drugs, rifampin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1971

C_max

Value	Dose	Co-administered	Analyte	Population
6.3 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22330931/	10 mg/kg 1 times / day steady-state, oral dose: 10 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
3.3 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22330931/	10 mg/kg 1 times / day steady-state, oral dose: 10 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered:		RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.4 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	10 mg/kg 1 times / day steady-state, oral dose: 10 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
21.6 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	20 mg/kg 1 times / day steady-state, oral dose: 20 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
25.1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	25 mg/kg 1 times / day steady-state, oral dose: 25 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
33.1 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	30 mg/kg 1 times / day steady-state, oral dose: 30 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
35.2 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	35 mg/kg 1 times / day steady-state, oral dose: 35 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
26.3 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	10 mg/kg 1 times / day steady-state, oral dose: 10 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
113 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	20 mg/kg 1 times / day steady-state, oral dose: 20 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
135 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	25 mg/kg 1 times / day steady-state, oral dose: 25 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
190 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	30 mg/kg 1 times / day steady-state, oral dose: 30 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
235 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25654354/	35 mg/kg 1 times / day steady-state, oral dose: 35 mg/kg route of administration: Oral experiment type: STEADY-STATE co-administered: ISONIAZID	ISONIAZID	RIFAMPIN serum	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
325 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9773393/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		RIFAMPIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
16.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9773393/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		RIFAMPIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN
17.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9773393/	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		25-DESACETYLRIFAMPIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
60 g single, oral Overdose Dose: 60 g Route: oral Route: single Dose: 60 g Sources: https://pubmed.ncbi.nlm.nih.gov/702755	unknown, 26 years Health Status: unknown Age Group: 26 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/702755	Other AEs: Pruritus... Other AEs: Pruritus (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/702755
1200 mg 1 times / day multiple, oral Highest studied dose Dose: 1200 mg, 1 times / day Route: oral Route: multiple Dose: 1200 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2319517	unhealthy, adult Health Status: unhealthy Age Group: adult Sources: https://pubmed.ncbi.nlm.nih.gov/2319517	Sources: https://pubmed.ncbi.nlm.nih.gov/2319517
1200 mg single, intravenous Highest studied dose Dose: 1200 mg Route: intravenous Route: single Dose: 1200 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6473487	unknown, adult Health Status: unknown Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/6473487	Sources: https://pubmed.ncbi.nlm.nih.gov/6473487

AEs

AE	Significance	Dose	Population
Pruritus	grade 5, 1 patient	60 g single, oral Overdose Dose: 60 g Route: oral Route: single Dose: 60 g Sources: https://pubmed.ncbi.nlm.nih.gov/702755	unknown, 26 years Health Status: unknown Age Group: 26 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/702755

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252	inducer 440	inducer 109

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057 OCT1 620		CYP2C19 329 CYP2A6 86 CYP2B6 669 CYP2C8 198 CYP2E1 131 CYP4A11 4 UGT1A9 9 UGT2B7 14

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C8 1117	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
CYP2C9 2497	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/; https://link.springer.com/article/10.2165/00003088-200342090-00003	no
CYP2D6 2546	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
CYP2E1 1146	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
CYP4A11 25	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/21456052/	yes [IC50 79.1 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/j.1742-7843.2005.pto_157.x	yes [Ki 18.5 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/j.1742-7843.2005.pto_157.x	yes [Ki 30.2 uM]
CYP2A6 911	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	yes
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	yes
CYP2C19 2141	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	yes
UGT2B7 210	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/30170758/	yes
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050420s084,050627s027lbl.pdf#page=12; https://link.springer.com/article/10.2165/00003088-200342090-00003 Page: 12.0	yes	yes (co-administration study) Comment: induced levels of CYP1C19 apoprotein to 330% of control; coadministration with simvastatin: decrease exposure of simvastatin; coadministration with irinotecan: decrease irinotecan and active metabolite exposure; rifampicin reduced AUC of repaglinide by 57%; Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/; https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050420s084,050627s027lbl.pdf#page=12; https://link.springer.com/article/10.2165/00003088-200342090-00003 Page: 12.0
UGT1A9 155	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/30170758/	yes	yes (co-administration study) Comment: Coadministration of ertugliflozin with rifampin decreased ertugliflozin AUC0-∞ and Cmax by 39% and 15%, respectively Sources: https://pubmed.ncbi.nlm.nih.gov/30170758/

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P0039O7
A2B Chem	AB51703
AA Blocks	AA00394R
AbovChem LLC	HY-B0272
AK Scientific	J10110
Ambeed	A146981
Apollo Scientific	BIR0146
AstaTech	40034
BLD Pharm	BD31770
BOC Sciences	13292-46-1
Bosche Scientific	R2263
Capot Chemical	35984
Cayman Chemical	14423
Chem-Impex International	260
Chem Scene	CS-2261
eMolecules	114312711
eMolecules	206905303
eMolecules	308482568
eMolecules	313078805
eMolecules	48856455
Enamine	Z2786051605
eNovation Chemicals	D388951
Hairui	HR122701
Hangzhou Yuhao Chemical Technology	LX2948
IBScreen	Bio-0621
KeyOrganics	AS-13687
Lab Network	465
mcule	MCULE-4811185911
mcule	MCULE-5418259954
mcule	MCULE-8210589684
MedChem Express	HY-B0272
Molnova	M11310
MolPort	MolPort-000-767-051
MolPort	MolPort-002-513-586
MolPort	MolPort-006-395-891
MolPort	MolPort-023-277-070
MolPort	MolPort-046-594-156
NCI Plated 2007	113926
Pharmeks	PHAR098427
PI Chemicals	PI-14752
Selleck Chemicals	S1764
Sigma Aldrich	1604009
Sigma Aldrich	46713
Sigma Aldrich	83907
Sigma Aldrich	PHR1806
Sigma Aldrich	R8883
TargetMol	T0681
TimTec	ST057531
Tocris	4121
Vitas-M Laboratory	STK080143
W&J PharmaChem	50A588536
ZINC	ZINC000253979247	http://zinc15.docking.org/substances/ZINC000253979247
ZINC	ZINC000253979253	http://zinc15.docking.org/substances/ZINC000253979253
ZINC	ZINC000331353658	http://zinc15.docking.org/substances/ZINC000331353658
ZINC	ZINC000334138289	http://zinc15.docking.org/substances/ZINC000334138289
ZINC	ZINC001307311638	http://zinc15.docking.org/substances/ZINC001307311638

PubMed

Title	Date	PubMed
Glucocorticoid receptor enhancement of pregnane X receptor-mediated CYP2B6 regulation in primary human hepatocytes.	2003-05	12695351
Regulation of CYP3A4 expression in human hepatocytes by pharmaceuticals and natural products.	2003-05	12695340
A novel distal enhancer module regulated by pregnane X receptor/constitutive androstane receptor is essential for the maximal induction of CYP2B6 gene expression.	2003-04-18	12571232
Induction of CYP3As in HepG2 cells by several drugs. Association between induction of CYP3A4 and expression of glucocorticoid receptor.	2003-04	12673034
Synergic activity of fluoroquinolones and linezolid against Mycobacterium tuberculosis.	2003-04	12672583
Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition.	2003-04	12642470
Induction of cytochrome P450 enzymes in cultured precision-cut human liver slices.	2003-03	12584154
Molecular basis of rifampicin-induced inhibition of anti-CD95-induced apoptosis of peripheral blood T lymphocytes: the role of CD95 ligand and FLIPs.	2003-01	12645856
Activities of moxifloxacin alone and in combination with other antimicrobial agents against multidrug-resistant Mycobacterium tuberculosis infection in BALB/c mice.	2003-01	12499213
Receptor-dependent regulation of the CYP3A4 gene.	2002-12-27	12505310
PXR-dependent induction of human CYP3A4 gene expression by organochlorine pesticides.	2002-11-15	12417264
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.	2002-11	12407118
Regulation of a xenobiotic sulfonation cascade by nuclear pregnane X receptor (PXR).	2002-10-15	12370413
Endocarditis caused by methicillin-resistant Staphylococcus aureus: treatment failure with linezolid.	2002-10-15	12355391
Acute renal failure due to rifampicin: a study of 25 patients.	2002-10	12324902
A cell-based reporter gene assay for determining induction of CYP3A4 in a high-volume system.	2002-10	12235278
Simple fibroblast-based assay for screening of new antimicrobial drugs against Mycobacterium tuberculosis.	2002-08	12121929
Functional analysis of the rat bile salt export pump gene promoter.	2002-07	12135489
CYP3A4 induction by drugs: correlation between a pregnane X receptor reporter gene assay and CYP3A4 expression in human hepatocytes.	2002-07	12065438
[Specific features of acute renal failure in patients treated with rifampicin].	2002-06-05	12043271
Paraquat detoxicative system in the mouse liver postmitochondrial fraction.	2002-06-01	12051692
Diffuse glomerulonephritis associated with rifampicin treatment for tuberculosis.	2002-06	12109797
Evaluation of gene induction of drug-metabolizing enzymes and transporters in primary culture of human hepatocytes using high-sensitivity real-time reverse transcription PCR.	2002-05	12040753
Death associated with rifampin and pyrazinamide 2-month treatment of latent mycobacterium tuberculosis.	2002-05	12006469
[Post-rifampicin acute renal failure--serious, but seldom recognized complication of the anti-tuberculosis treatment].	2002-04-30	11977498
Limitations in the use of rifampicin-gelatin grafts against virulent organisms.	2002-04	11932679
Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression.	2002-02-28	11836020
Comparative inhibitory effects of different compounds on rat oatpl (slc21a1)- and Oatp2 (Slc21a5)-mediated transport.	2002-02	11883641
In vitro activity of 11 antimicrobial agents, including gatifloxacin and GAR936, tested against clinical isolates of Mycobacterium marinum.	2002-02	11858912
Antimicrobial activities of clarithromycin, gatifloxacin and sitafloxacin, in combination with various antimycobacterial drugs against extracellular and intramacrophage Mycobacterium avium complex.	2002-02	11850167
Rifampicin inhibits CD95-mediated apoptosis of Jurkat T cells via glucocorticoid receptors by modifying the expression of molecules regulating apoptosis.	2002-01	11958592
Rapidly progressive glomerulonephritis due to rifampicin therapy.	2002-01	11744817
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin.	2002-01	11744607
The drug efflux pump MRP2: regulation of expression in physiopathological situations and by endogenous and exogenous compounds.	2002	12206135
Bactericidal activities of commonly used antiseptics against multidrug-resistant mycobacterium tuberculosis.	2002	12011515
Postantibiotic effects of antituberculosis agents alone and in combination.	2001-12	11709357
Acute renal failure caused by rifampicin re-exposure with 10-year of interval.	2001-11	11820654
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001-11	11792017
Antimycobacterial plant terpenoids.	2001-11	11731906
Rifampicin-induced erythema nodosum leprosum-like eruption in borderline lepromatous leprosy.	2001-10-03	11579653
Bisphenol-A, an environmental estrogen, activates the human orphan nuclear receptor, steroid and xenobiotic receptor-mediated transcription.	2001-10	11581012
Acute renal failure complicating rifampicin therapy.	2001-09	11837753
Optic neuropathy after treatment with anti-tuberculous drugs in a subject with Leber's hereditary optic neuropathy mutation.	2001-09	11596792
[Clinico-pathological features and possible pathogenesis of rifampicin-induced acute renal failure].	2001-06	11798598
CYP3A inductive potential of the rifamycins, rifabutin and rifampin, in the rabbit.	2001-05	11745918
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.	2001	11706922
Rifampin-induced methadone withdrawal.	1976-05-13	1256526
[Tolerance of rifampicin in long-term treatment of patients with pulmonary tuberculosis].	1976-02	1264980
[A new case of acute renal failure, with high hemolysis, after rifampicin (author's transl)].	1975-11-01	1232790
[Letter: Acute renal failure caused by rifampicin].	1975-04-19	1161475

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: Other

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 `Wed Apr 02 06:52:05 GMT 2025` Edited by `admin` on `Wed Apr 02 06:52:05 GMT 2025`
Record UNII	VJT6J7R4TR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RIFAMPICIN

Preferred Name

English

RIFAMPIN

Official Name

English

RIFALDAZINE

Common Name

English

RIFAMPICIN [JAN]

Common Name

English

BA-41166/E

Code

English

RIMACTAN

Brand Name

English

RIFATER COMPONENT RIFAMPIN

Common Name

English

NSC-113926

Code

English

BA-41166E

Code

English

RIMACTANE

Brand Name

English

RIFAMPICIN [EP IMPURITY]

Common 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 [MI]

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 [WHO-DD]

Common Name

English

EREMFAT

Brand Name

English

RIFADIN

Brand Name

English

RIFAMPIN [USP MONOGRAPH]

Common Name

English

RIFAMPICIN [EP MONOGRAPH]

Common Name

English

RIFAMPIN [HSDB]

Common Name

English

RIFALDIN

Brand Name

English

RIFAMPIN [VANDF]

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

6585