U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C46H62N4O11
Molecular Weight 847.0064
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RIFABUTIN

SMILES

CC(C)CN1CCC2(CC1)N=C3c4c5c(c(C)c6c4C(=O)[C@@](C)(O/C(/[H])=C(\[H])/[C@@]([H])([C@@]([H])(C)[C@]([H])([C@]([H])(C)[C@@]([H])([C@]([H])(C)[C@]([H])([C@@]([H])(C)/C(/[H])=C(\[H])/C(/[H])=C(/C)\C(=NC(=C3N2)C5=O)O)O)O)OC(=O)C)OC)O6)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 847.0064
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: http://www.wikidoc.org/index.php/Rifabutin

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

CNS Penetrant
2415
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/20930076

Originator

Approval Year

1992
62
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
609
DNA-directed RNA polymerase subunit beta
5
Target ID: P0A8V2
Gene ID: 948488
Gene Symbol: rpoB
Target Organism: Escherichia coli (strain K12)
Inhibitor
7701
Disseminated Mycobacterium avium complex (MAC) disease
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
DNA-directed RNA polymerase subunit beta
Approved
7997
MYCOBUTIN

Approved Use

MYCOBUTIN Capsules are indicated for the prevention of disseminated Mycobacterium avium complex (MAC) disease in patients with advanced HIV infection.

Launch Date

725068800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
613 ng/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/8785251/
450 mg 1 times / day multiple, oral
dose: 450 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
RIFABUTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
691 ng/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/8785251/
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFABUTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5803 ng × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/8785251/
450 mg 1 times / day multiple, oral
dose: 450 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
RIFABUTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
9287 ng × h/mL
REVIEW
https://pubmed.ncbi.nlm.nih.gov/8785251/
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFABUTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
58 h
REVIEW
https://pubmed.ncbi.nlm.nih.gov/8785251/
450 mg 1 times / day multiple, oral
dose: 450 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
RIFABUTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
45 h
REVIEW
https://pubmed.ncbi.nlm.nih.gov/8785251/
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFABUTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
21.5%
REVIEW
https://pubmed.ncbi.nlm.nih.gov/8785251/
450 mg single, oral
dose: 450 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RIFABUTIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Other AEs: Abdominal pain, Asthenia...
Other AEs:
Abdominal pain (4%)
Asthenia (1%)
Chest pain (1%)
Fever (2%)
Headache (3%)
Pain (1%)
Anorexia (2%)
Diarrhea (3%)
Dyspepsia (3%)
Eructation (3%)
Flatulence (2%)
Nausea (6%)
Nausea and vomiting (3%)
Vomiting (1%)
Myalgia (2%)
Insomnia (1%)
Rash (11%)
Taste perversion (3%)
Urine discoloration (30%)
Alkaline phosphatase increased (<1%)
SGOT increased (7%)
SGPT increased (9%)
Anemia (6%)
Eosinophilia (1%)
Leukopenia (17%)
Neutropenia (25%)
Thrombocytopenia (5%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Asthenia 1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Chest pain 1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Eosinophilia 1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Insomnia 1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Pain 1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Vomiting 1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Rash 11%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Leukopenia 17%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Anorexia 2%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Fever 2%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Flatulence 2%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Myalgia 2%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Neutropenia 25%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Diarrhea 3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Dyspepsia 3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Eructation 3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Headache 3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Nausea and vomiting 3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Taste perversion 3%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Urine discoloration 30%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Abdominal pain 4%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Thrombocytopenia 5%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Anemia 6%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Nausea 6%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
SGOT increased 7%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
SGPT increased 9%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Alkaline phosphatase increased <1%
300 mg 1 times / day multiple, oral
Recommended
Dose: 300 mg, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg, 1 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/050689Orig1s018lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
activator
55

inducer
657

substrate
1470
inhibitor
1318
inhibitor
1421

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1268

CYP3A
175

CYP2B6
679

CYP2C8
761

CYP2C19
1215

CYP2E1
761

UGT1A1
174

UGT1A4
67

UGT1A6
94

UGT1A9
102

UGT2B7
130

UGT2B15
56
AADAC
1
P-gp
225

OATP1B1
23

OATP1B3
6

MRP2
100
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
UGT1A4
70
 likely
CYP1A2
1406
 no
CYP2C19
1277
 no
CYP2E1
841
 no
MRP2
421
 no
OATP1B1
713
 no
UGT1A6
126
 no
UGT1A9
107
 no
CYP3A
244
 unlikely [IC50 31.5 uM]
CYP2B6
845
 unlikely
CYP2C8
810
 unlikely
CYP2C9
1362
 unlikely
CYP2D6
1455
 unlikely
UGT1A1
219
 unlikely
UGT2B15
56
 unlikely
UGT2B7
138
 unlikely
CYP3A4
1462
 yes
OATP1B3
622
 yes
P-gp
1255
 yes
CYP3A4
1462
 yes
yes (co-administration study)
Comment: many DDIs: see https://www.accessdata.fda.gov/drugsatfda_docs/label/2008/050689s016lbl.pdf#page=3
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1470
 no
AADAC
1
 yes
CYP3A4
1470
 yes
25-O-DEACETYLRIFABUTIN
1
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:45367
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45367
ZINC
ZINC000169621215
http://zinc15.docking.org/substances/ZINC000169621215
PubMed

PubMed

TitleDatePubMed
Biological activity of a new class of rifamycins. Spiro-piperidyl-rifamycins.
1980 Oct
In vitro susceptibility of Mycobacterium avium complex and Mycobacterium tuberculosis strains to a spiro-piperidyl rifamycin.
1982 Sep
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
Comparative in vitro activities of MDL 473, rifampin, and ansamycin against Mycobacterium intracellulare.
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 susceptibility of Mycobacterium avium complex to antibacterial agents.
1987 Nov
New antibacterial drugs for the treatment of mycobacterial disease in man.
1988 Jul
Rifabutine: minimal inhibitory and bactericidal concentrations for Mycobacterium tuberculosis.
1988 Mar
Combinations of rifampin or rifabutine plus ethambutol against Mycobacterium avium complex. Bactericidal synergistic, and bacteriostatic additive or synergistic effects.
1988 Mar
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
Interaction between rifabutin and human immunodeficiency virus type 1: inhibition of replication, cytopathic effect, and reverse transcriptase in vitro.
1988 May
Activities of clarithromycin, sulfisoxazole, and rifabutin against Mycobacterium avium complex multiplication within human macrophages.
1990 Aug
Bactericidal activity in vitro of various rifamycins against Mycobacterium avium and Mycobacterium tuberculosis.
1990 Mar
[In vivo activities of new rifamycin derivatives against mycobacteria].
1991 Jan
Oxazolidinones, a new class of synthetic antituberculosis agent. In vitro and in vivo activities of DuP-721 against Mycobacterium tuberculosis.
1991 Nov-Dec
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
Rifabutin. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy.
1994 Jun
Rifabutin and sparfloxacin but not azithromycin inhibit binding of Mycobacterium avium complex to HT-29 intestinal mucosal cells.
1994 May
A bone marrow-derived murine macrophage model for evaluating efficacy of antimycobacterial drugs under relevant physiological conditions.
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
Clinical experience with rifabutin in the treatment of mycobacterial infections.
1995
In-vitro and intracellular activity of rifabutin on drug-susceptible and multiple drug-resistant (MDR) tubercle bacilli.
1995 Aug
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
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
Rifapentine is active in vitro and in vivo against Toxoplasma gondii.
1996 Jun
Activity of rifabutin, clarithromycin, ethambutol, sparfloxacin and amikacin, alone and in combination, against Mycobacterium avium complex in human macrophages.
1996 Mar
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
Rapid drug susceptibility of Mycobacterium avium complex using a fluorescence quenching method.
1997 Aug
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
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997 May
[Therapeutic efficacy of benzoxazinorifamycin KRM-1648 against experimental murine tuberculosis: (1). A study on the efficacy of short course treatment with the intratracheal and intravenous infection model].
1998 Feb
Contribution of rpoB mutations to development of rifamycin cross-resistance in Mycobacterium tuberculosis.
1998 Jul
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010 Dec
Patents

Patents

JP2001500477A
110
JP2002541233A
376
JP2002541255A
1
JP2003515526A
439
JP2005519848A
1
JP2005520795A
22
JP2006520756A
14
JP2007511600A
3
JP2008001720A
3
JP2008024713A
1
JP2008545621A
2
JP2009256388A
1
JP2010516437A
33
JP2010534213A
1
JP2011225614A
2
JP2011511012A
1
JP2012500104A
106
JP3220466B2
11
JP3553083B2
56
JP4689666B2
2
JP4763957B2
80
JP4787165B2
92
JP4808380B2
14
JP5313308B2
1
JPS5653683A
1
JPS61236767A
1

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
by admin
on Fri Jun 25 21:05:16 UTC 2021
Edited
by admin
on Fri Jun 25 21:05:16 UTC 2021
Record UNII
1W306TDA6S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RIFABUTIN
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official 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 [EP MONOGRAPH]
Common Name English
RIFABUTIN COMPONENT OF TALICIA
Brand 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
TALICIA COMPONENT RIFABUTIN
Brand Name English
4-N-ISOBUTYLSPIROPIPERIDYLRIFAMYCIN S
Common Name English
RIFABUTIN [HSDB]
Common Name English
RIFABUTIN [USP MONOGRAPH]
Common Name English
RIFABUTIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB04
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
NCI_THESAURUS C280
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
NDF-RT N0000007911
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
LIVERTOX 844
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
NDF-RT N0000007911
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
NDF-RT N0000007911
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
NDF-RT N0000007911
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
FDA ORPHAN DRUG 41989
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
WHO-ATC J04AB04
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
FDA ORPHAN DRUG 770820
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
NDF-RT N0000175501
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
FDA ORPHAN DRUG 338811
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
FDA ORPHAN DRUG 41889
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
Code System Code Type Description
LACTMED
Rifabutin
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
WIKIPEDIA
RIFABUTIN
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
INN
5668
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
MERCK INDEX
M9608
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY Merck Index
PUBCHEM
6323490
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
RXCUI
55672
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
2376
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
NCI_THESAURUS
C1408
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
MESH
D017828
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
EPA CompTox
72559-06-9
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
EVMPD
SUB10304MIG
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
FDA UNII
1W306TDA6S
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
USP_CATALOG
1603800
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB00615
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
HSDB
3577
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
CAS
72559-06-9
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
ChEMBL
CHEMBL444633
Created by admin on Fri Jun 25 21:05:16 UTC 2021 , Edited by admin on Fri Jun 25 21:05:16 UTC 2021
PRIMARY
Related Record Type Details
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
MRP-2
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A5
METABOLIC ENZYME -> INDUCER
Related Record Type Details
Structure of 25-O-DEACETYLRIFABUTIN
METABOLITE ACTIVE -> PARENT
MAJOR
Structure of 32-HYDROXY-25-O-DEACETYLRIFABUTIN
METABOLITE -> PARENT
Structure of 31-HYDROXYRIFABUTIN
METABOLITE -> PARENT
MAJOR
Related Record Type Details
Structure of RIFABUTIN N-OXIDE OPEN RING
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 3-AMINORIFAMYCIN S
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 1-ISOBUTYL-4-PIPERIDONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
Structure of RIFABUTIN N-OXIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 21,31-DIDEHYDRORIFABUTIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 3-AMINO-4-DEOXO-4-IMINORIFAMYCIN S
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 25-O-DEACETYLRIFABUTIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of RIFABUTIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966