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 8228
Cytochrome P450 3A4 126 Target ID: CHEMBL340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16176562	Inhibitor 8228	18.5 µM [Ki]
Cytochrome P450 2C8 18 Target ID: CHEMBL3721 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16176562	Inhibitor 8228	30.2 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 81 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050420s075,050627s014lbl.pdf	Primary		Approved 8360	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 4.3632001E10
Asymptomatic meningococcal infection 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050420s075,050627s014lbl.pdf	Curative		Approved 8360	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 4.3632001E10

C_max

Value	Dose	Co-administered	Analyte	Population
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
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
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
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

AUC

Value	Dose	Co-administered	Analyte	Population
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
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
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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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
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

Doses

Dose	Population	Adverse events
60 g single, oral (total) Overdose Dose: 60 g Route: oral Route: single Dose: 60 g Sources: https://pubmed.ncbi.nlm.nih.gov/702755	unknown, 26 years n = 1 Health Status: unknown Age Group: 26 years Sex: M Population Size: 1 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 n = 8 Health Status: unhealthy Condition: rheumatoid arthritis Age Group: adult Population Size: 8 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 n = 18 Health Status: unknown Age Group: adult Sex: M Population Size: 18 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 (total) Overdose Dose: 60 g Route: oral Route: single Dose: 60 g Sources: https://pubmed.ncbi.nlm.nih.gov/702755	unknown, 26 years n = 1 Health Status: unknown Age Group: 26 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/702755

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 768 inhibitor 1579	inducer 383	inducer 97

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 901 OCT1 506		CYP2C19 290 CYP2A6 79 CYP2B6 538 CYP2C8 168 CYP2E1 126 CYP4A11 4 UGT1A9 9 UGT2B7 14

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP2C8 955	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
CYP2C9 1803	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/; https://link.springer.com/article/10.2165/00003088-200342090-00003	no
CYP2D6 1875	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
CYP2E1 964	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
CYP4A11 25	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	no
OCT1 523	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/21456052/	yes [IC50 79.1 uM]
CYP3A4 1909	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/j.1742-7843.2005.pto_157.x	yes [Ki 18.5 uM]
CYP2C8 955	inhibitor 3240 Sources: https://onlinelibrary.wiley.com/doi/full/10.1111/j.1742-7843.2005.pto_157.x	yes [Ki 30.2 uM]
CYP2A6 736	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	yes
CYP2B6 985	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	yes
CYP2C19 1537	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/12584154/	yes
UGT2B7 157	inducer 1542 Sources: https://pubmed.ncbi.nlm.nih.gov/30170758/	yes
CYP3A4 1909	inducer 1542 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 121	inducer 1542 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
AK Scientific	J10110
AbovChem LLC	HY-B0272
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 Scene	CS-2261
Chem-Impex International	260
Enamine	Z2786051605
Hairui	HR122701
Hangzhou Yuhao Chemical Technology	LX2948
IBScreen	Bio-0621
KeyOrganics	AS-13687
Lab Network	465
MedChem Express	HY-B0272
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
Molnova	M11310
NCI Plated 2007	113926
PI Chemicals	PI-14752
Pharmeks	PHAR098427
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
eMolecules	114312711
eMolecules	206905303
eMolecules	308482568
eMolecules	313078805
eMolecules	48856455
eNovation Chemicals	D388951
mcule	MCULE-4811185911
mcule	MCULE-5418259954
mcule	MCULE-8210589684

PubMed

Title	Date	PubMed








[Side effects of rifampicin in the treatment of chronic pulmonary tuberculosis by the intermittent method].	1975 Mar 31	1121469
[A new case of acute renal failure, with high hemolysis, after rifampicin (author's transl)].	1975 Nov-Dec	1232790
[Tolerance of rifampicin in long-term treatment of patients with pulmonary tuberculosis].	1976 Feb	1264980
Antituberculosis activity of certain antifungal and antihelmintic drugs.	1999	10707260
Comparative in vitro antimicrobial activities of the newly synthesized quinolone HSR-903, sitafloxacin (DU-6859a), gatifloxacin (AM-1155), and levofloxacin against Mycobacterium tuberculosis and Mycobacterium avium complex.	1999 Dec	10582897
Analysis of rifapentine for preventive therapy in the Cornell mouse model of latent tuberculosis.	1999 Sep	10471552
Antimycobacterial activities of novel levofloxacin analogues.	2000 Aug	10898685
Dexamethasone differentially regulates expression of carboxylesterase genes in humans and rats.	2000 Feb	10640517
Minimal change nephrotic syndrome associated with rifampicin treatment.	2000 Jul	10862648
Measurement of cytochrome P450 gene induction in human hepatocytes using quantitative real-time reverse transcriptase-polymerase chain reaction.	2000 Jul	10859152
Activity of poloxamer CRL-1072 against drug-sensitive and resistant strains of Mycobacterium tuberculosis in macrophages and in mice.	2000 Jun	10856678
A multicentre study of the early bactericidal activity of anti-tuberculosis drugs.	2000 Jun	10837441
Activity of rifapentine and its metabolite 25-O-desacetylrifapentine compared with rifampicin and rifabutin against Mycobacterium tuberculosis, Mycobacterium africanum, Mycobacterium bovis and M. bovis BCG.	2000 Oct	11020253
Intrinsic resistance of Mycobacterium tuberculosis to clarithromycin is effectively reversed by subinhibitory concentrations of cell wall inhibitors.	2000 Sep	10980165
Mutant prevention concentration as a measure of antibiotic potency: studies with clinical isolates of Mycobacterium tuberculosis.	2000 Sep	10952625
Rifampicin-induced erythema nodosum leprosum-like eruption in borderline lepromatous leprosy.	2001 Apr-Jun	11579653
Drug-induced acute interstitial nephritis.	2001 Aug	11473672
Postantibiotic effects of antituberculosis agents alone and in combination.	2001 Dec	11709357
[Clinico-pathological features and possible pathogenesis of rifampicin-induced acute renal failure].	2001 Jun	11798598
Treatment of tuberculosis using a combination of sustained-release rifampin-loaded microspheres and oral dosing with isoniazid.	2001 Jun	11353605
CYP3A inductive potential of the rifamycins, rifabutin and rifampin, in the rabbit.	2001 May	11745918
[Acute renal insufficiency and interstitial nephritis caused by rifampicin. A comment on this subject].	2001 May-Jun	11471316
Acute renal failure caused by rifampicin re-exposure with 10-year of interval.	2001 Nov	11820654
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.	2001 Nov	11792017
Antimycobacterial plant terpenoids.	2001 Nov	11731906
Bisphenol-A, an environmental estrogen, activates the human orphan nuclear receptor, steroid and xenobiotic receptor-mediated transcription.	2001 Oct	11581012
Acute renal failure complicating rifampicin therapy.	2001 Sep	11837753
Rifampicin inhibits CD95-mediated apoptosis of Jurkat T cells via glucocorticoid receptors by modifying the expression of molecules regulating apoptosis.	2002 Jan	11958592
Rapidly progressive glomerulonephritis due to rifampicin therapy.	2002 Jan	11744817
Induction of multidrug resistance-1 and cytochrome P450 mRNAs in human mononuclear cells by rifampin.	2002 Jan	11744607
[Specific features of acute renal failure in patients treated with rifampicin].	2002 Jan-Mar	12043271
Functional analysis of the rat bile salt export pump gene promoter.	2002 Jul	12135489
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	12040753
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	12407118
Endocarditis caused by methicillin-resistant Staphylococcus aureus: treatment failure with linezolid.	2002 Oct 15	12355391
Synergic activity of fluoroquinolones and linezolid against Mycobacterium tuberculosis.	2003 Apr	12672583
Comparative effects of thiazolidinediones on in vitro P450 enzyme induction and inhibition.	2003 Apr	12642470
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	12571232
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	12645856
Induction of cytochrome P450 enzymes in cultured precision-cut human liver slices.	2003 Mar	12584154
Glucocorticoid receptor enhancement of pregnane X receptor-mediated CYP2B6 regulation in primary human hepatocytes.	2003 May	12695351
Regulation of CYP3A4 expression in human hepatocytes by pharmaceuticals and natural products.	2003 May	12695340

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 `Thu Jul 06 21:22:23 UTC 2023` Edited by `admin` on `Thu Jul 06 21:22:23 UTC 2023`
Record UNII	VJT6J7R4TR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

RIFAMPIN COMPONENT OF RIFATER

Common Name

English

NSC-113926

Code

English

RIFAMPICIN

Official Name

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 COMPONENT OF RIFAMATE

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