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Details

Stereochemistry ABSOLUTE
Molecular Formula C46H62N4O11
Molecular Weight 847.0047
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFABUTIN

SMILES

CO[C@H]1\C=C\O[C@@]2(C)OC3=C(C)C(O)=C4C(=O)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)=C5NC6(CCN(CC(C)C)CC6)N=C5C4=C3C2=O

InChI

InChIKey=ATEBXHFBFRCZMA-VXTBVIBXSA-N
InChI=1S/C46H62N4O11/c1-22(2)21-50-18-16-46(17-19-50)48-34-31-32-39(54)28(8)42-33(31)43(56)45(10,61-42)59-20-15-30(58-11)25(5)41(60-29(9)51)27(7)38(53)26(6)37(52)23(3)13-12-14-24(4)44(57)47-36(40(32)55)35(34)49-46/h12-15,20,22-23,25-27,30,37-38,41,49,52-54H,16-19,21H2,1-11H3,(H,47,57)/b13-12+,20-15+,24-14-/t23-,25+,26+,27+,30-,37-,38+,41+,45-/m0/s1

HIDE SMILES / InChI

Molecular Formula C46H62N4O11
Molecular Weight 847.0047
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Rifabutin 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 prophylaxis of disseminated Mycobacterium avium complex (MAC) disease in patients with advanced HIV infection. Multiple dosing of rifabutin has been associated with induction of hepatic metabolic enzymes of the CYP3A subfamily. Rifabutin’s predominant metabolite (25-desacetyl rifabutin: LM565), may also contribute to this effect. Similarly, concomitant medications that competitively inhibit the CYP3A activity may increase plasma concentrations of rifabutin. Common adverse reactions include discoloration of skin, rash, diarrhea, disorder of taste, indigestion, loss of appetite, nausea, vomiting, increased liver aminotransferase level (mild), ocular discoloration, uveitis, abnormal color of body fluid.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Biological activity of a new class of rifamycins. Spiro-piperidyl-rifamycins.
1980 Oct
LM 427, a new spiropiperidylrifamycin: in vitro and in vivo studies.
1983 Nov
Activity of the spiropiperidyl rifamycin LM 427 on rifampicin resistant Mycobacterium tuberculosis.
1984 Sep-Dec
Determination of ansamycin MICs for Mycobacterium avium complex in liquid medium by radiometric and conventional methods.
1985 Oct
Comparative in vitro activities of MDL 473, rifampin, and ansamycin against Mycobacterium intracellulare.
1985 Sep
Determination of in vitro susceptibility of mycobacteria to ansamycin.
1985 Sep
Activity of rifabutin alone or in combination with clofazimine or ethambutol or both against acute and chronic experimental Mycobacterium intracellulare infections.
1987 Aug
In vitro activity of antimicrobial agents against mycobacteria.
1988
New antibacterial drugs for the treatment of mycobacterial disease in man.
1988 Jul
Action of antituberculous and beta-lactam drugs (including imipenem) against extra- and intra-cellularly growing Mycobacterium avium-intracellulare.
1988 Mar-Apr
Qualitative and quantitative drug-susceptibility tests in mycobacteriology.
1988 May
In vitro effectiveness of a combination of zidovudine and ansamycin against human immunodeficiency virus.
1988 Oct
Comparative in-vitro activity of fleroxacin and other 6-fluoroquinolones against mycobacteria.
1988 Oct
Effectiveness of rifampin, rifabutin, and rifapentine for preventive therapy of tuberculosis in mice.
1993 Dec
Synthesis and biological activity of 3'-hydroxy-5'-aminobenzoxazinorifamycin derivatives.
1993 Jan
In vitro antimicrobial activity of benzoxazinorifamycin, KRM-1648, against Mycobacterium avium complex, determined by the radiometric method.
1993 Jan
Azithromycin, rifabutin, and rifapentine for treatment and prophylaxis of Mycobacterium avium complex in rats treated with cyclosporine.
1993 Mar
Anti-Mycobacterium avium activity of quinolones: in vitro activities.
1993 Sep
Comparative in vivo activities of rifabutin and rifapentine against Mycobacterium avium complex.
1994 Feb
Rifabutin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy.
1994 Jun
Rifabutin is active in murine models of toxoplasmosis.
1994 Mar
Rifabutin and sparfloxacin but not azithromycin inhibit binding of Mycobacterium avium complex to HT-29 intestinal mucosal cells.
1994 May
In vitro and in vivo antibacterial activities of KRM-1648 and KRM-1657, new rifamycin derivatives.
1994 May
A bone marrow-derived murine macrophage model for evaluating efficacy of antimycobacterial drugs under relevant physiological conditions.
1994 Nov
Effectiveness of various antimicrobial agents against Mycobacterium avium complex in the beige mouse model.
1994 Nov
[New drugs against tuberculosis and nontuberculous mycobacterial infections: a review].
1994 Nov
In vitro model to assess effect of antimicrobial agents on Encephalitozoon cuniculi.
1994 Oct
Activity of KRM-1648, a new benzoxazinorifamycin, against Mycobacterium tuberculosis in a murine model.
1994 Oct
Clinical experience with rifabutin in the treatment of mycobacterial infections.
1995
[Extra and intracellular activity of dirithromycin against Mycobacterium avium].
1995 Apr
In-vitro and intracellular activity of rifabutin on drug-susceptible and multiple drug-resistant (MDR) tubercle bacilli.
1995 Aug
Mutation position and type of substitution in the beta-subunit of the RNA polymerase influence in-vitro activity of rifamycins in rifampicin-resistant Mycobacterium tuberculosis.
1995 Feb
Activities of rifabutin, clarithromycin, and ethambutol against two virulent strains of Mycobacterium avium in a mouse model.
1995 Mar
Comparison of activities of fluoroquinolones in murine macrophages infected with Mycobacterium tuberculosis.
1995 Mar
In vitro and in vivo activities of the benzoxazinorifamycin KRM-1648 against Mycobacterium tuberculosis.
1995 Oct
Activity of seven antimicrobial agents, alone and in combination, against AIDS-associated isolates of Mycobacterium avium complex.
1995 Sep
New drugs for tuberculosis.
1995 Sep
Chemotherapeutic activity of benzoxazinorifamycin, KRM-1648, against Mycobacterium tuberculosis in C57BL/6 mice.
1996 Apr
Susceptibility testing of Mycobacterium avium complex isolates.
1996 Aug
Low-dose aerosol infection model for testing drugs for efficacy against Mycobacterium tuberculosis.
1996 Dec
How effective is KRM-1648 in treatment of disseminated Mycobacterium avium complex infections in beige mice?
1996 Feb
Rifamycin resistance in mycobacteria.
1996 Jan-Feb
Use of rifabutin in combination with atovaquone, clindamycin, pyrimethamine, or sulfadiazine for treatment of toxoplasmic encephalitis in mice.
1996 May
Comparative activity of azithromycin against clinical isolates of mycobacteria.
1996 Sep
In vitro and in vivo effects of rifabutin alone or combined with atovaquone against Toxoplasma gondii.
1996 Sep
Evaluation of the activities of rifabutin combined with atovaquone or low-dose of cotrimoxazole for prevention of pneumocystosis and toxoplasmosis in a dual infection rat model.
1996 Sep-Oct
New ophthalmic manifestations of presumed rifabutin-related uveitis.
1997 Apr
Clinically used antimicrobial drugs against experimental pneumocystosis, singly and in combination: analysis of drug interactions and efficacies.
1997 Feb
Metabolism of rifabutin in human enterocyte and liver microsomes: kinetic parameters, identification of enzyme systems, and drug interactions with macrolides and antifungal agents.
1997 May
Contribution of rpoB mutations to development of rifamycin cross-resistance in Mycobacterium tuberculosis.
1998 Jul
Patents

Sample Use Guides

In Vivo Use Guide
It is recommended that Rifabutin Capsules be administered at a dose of 300 mg once daily. For those patients with propensity to nausea, vomiting, or other gastrointestinal upset, administration of Rifabutin at doses of 150 mg twice daily taken with food may be useful.
Route of Administration: Oral
In Vitro Use Guide
The IC50 of rifabutin was 26.5 mg/L in a different series of experiments using an enzyme-linked immunoassay and the T. gondii high virulence strain.
Substance Class Chemical
Created
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on Mon Oct 21 19:47:19 UTC 2019
Edited
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on Mon Oct 21 19:47:19 UTC 2019
Record UNII
1W306TDA6S
Record Status Validated (UNII)
Record Version
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Name Type Language
RIFABUTIN
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
RIFABUTIN [EP]
Common Name English
LM-427
Code English
RIFABUTIN [VANDF]
Common Name English
LM 427
Code English
RIFABUTIN [ORANGE BOOK]
Common Name English
MYCOBUTIN
Code English
RIFABUTIN [USP-RS]
Common Name English
ANSAMYCIN
Common Name English
RIFABUTIN [JAN]
Common Name English
RIFABUTIN [USP]
Common Name English
RIFABUTIN [MI]
Common Name English
RIFABUTIN [WHO-DD]
Common Name English
1',4-DIDEHYDRO-1-DEOXY-1,4-DIHYDRO-5'-(2-METHYLPROPYL)-1-OXORIFAMYCIN XIV
Common Name English
RIFABUTIN [INN]
Common Name English
4-DEOXO-3,4-(2-SPIRO-(N-ISOBUTYL-4-PIPERIDYL))-(1H)-IMIDAZO-(2,5-DIHYDRO)RIFAMYCIN S
Common Name English
RIFABUTIN [USAN]
Common Name English
4-N-ISOBUTYLSPIROPIPERIDYLRIFAMYCIN S
Common Name English
RIFABUTIN [HSDB]
Common Name English
RIFABUTIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB04
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
NCI_THESAURUS C280
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
LIVERTOX 844
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
NDF-RT N0000007911
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
FDA ORPHAN DRUG 41989
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
WHO-ATC J04AB04
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
NDF-RT N0000175501
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
FDA ORPHAN DRUG 338811
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
FDA ORPHAN DRUG 41889
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
Code System Code Type Description
WIKIPEDIA
RIFABUTIN
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
INN
5668
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
MERCK INDEX
M9608
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY Merck Index
PUBCHEM
6323490
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
RXCUI
55672
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C1408
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
MESH
D017828
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
EPA CompTox
72559-06-9
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
EVMPD
SUB10304MIG
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
LactMed
72559-06-9
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
DRUG BANK
DB00615
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
HSDB
72559-06-9
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
CAS
72559-06-9
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL444633
Created by admin on Mon Oct 21 19:47:19 UTC 2019 , Edited by admin on Mon Oct 21 19:47:19 UTC 2019
PRIMARY
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