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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 No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/cdi/rifabutin.html http://www.rxlist.com/mycobutin-drug.htm 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
2588
Curator's Comment: Because of frequent side effects at high doses (e.g., arthralgia, uveitis, and stomatitis), rifabutin has rarely been used to treat CNS infections. https://www.ncbi.nlm.nih.gov/pubmed/20930076

Originator

Approval Year

1992
113
Targets

Targets

Primary TargetPharmacologyConditionPotency
Substrate
661
DNA-directed RNA polymerase subunit beta
5
Target ID: P0A8V2
Gene ID: 948488.0
Gene Symbol: rpoB
Target Organism: Escherichia coli (strain K12)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8583
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

1992
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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
150

inducer
1087

substrate
1946
inhibitor
2438
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP3A
227

CYP2B6
926

CYP2C8
1057

CYP2C19
2057

CYP2E1
1060

UGT1A1
246

UGT1A4
98

UGT1A6
136

UGT1A9
148

UGT2B7
197

UGT2B15
84
AADAC
1
P-gp
301

OATP1B1
29

OATP1B3
8

MRP2
146
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
UGT1A4
100
 likely
CYP1A2
2333
 no
CYP2C19
2141
 no
CYP2E1
1146
 no
MRP2
625
 no
OATP1B1
1095
 no
UGT1A6
171
 no
UGT1A9
155
 no
CYP3A
317
 unlikely [IC50 31.5 uM]
CYP2B6
1160
 unlikely
CYP2C8
1117
 unlikely
CYP2C9
2497
 unlikely
CYP2D6
2546
 unlikely
UGT1A1
303
 unlikely
UGT2B15
84
 unlikely
UGT2B7
210
 unlikely
CYP3A4
2633
 yes
OATP1B3
970
 yes
P-gp
1932
 yes
CYP3A4
2633
 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
1946
 no
AADAC
1
 yes
CYP3A4
1946
 yes
25-O-DEACETYLRIFABUTIN
1
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:45367
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:45367
ChemicalBook
CB0702764
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0702764
eMolecules
29541954
https://www.emolecules.com/cgi-bin/more?vid=29541954
eMolecules
3717994
https://www.emolecules.com/cgi-bin/more?vid=3717994
Selleck Chemicals
Rifabutin(Mycobutin)
http://www.selleckchem.com/products/Rifabutin(Mycobutin).html
ZINC
ZINC000169621215
http://zinc15.docking.org/substances/ZINC000169621215
PubMed

PubMed

TitleDatePubMed
LM 427, a new spiropiperidylrifamycin: in vitro and in vivo studies.
1983 Nov
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.
1987
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
Interaction between rifabutin and human immunodeficiency virus type 1: inhibition of replication, cytopathic effect, and reverse transcriptase in vitro.
1988 May
Comparative in-vitro activity of fleroxacin and other 6-fluoroquinolones against mycobacteria.
1988 Oct
In vitro activities against mycobacteria of two long-acting rifamycins, FCE22807 and CGP40/469A (SPA-S-565).
1990 Jun
[In vivo activities of new rifamycin derivatives against mycobacteria].
1991 Jan
In vitro antimycobacterial activities of newly synthesized benzoxazinorifamycins.
1991 Mar
Oxazolidinones, a new class of synthetic antituberculosis agent. In vitro and in vivo activities of DuP-721 against Mycobacterium tuberculosis.
1991 Nov-Dec
In vivo activities of newer rifamycin analogs against Mycobacterium avium infection.
1991 Oct
Activity of azithromycin against Mycobacterium avium infection in beige mice.
1992 Aug
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Comparative in vivo activities of rifabutin and rifapentine against Mycobacterium avium complex.
1994 Feb
Rifabutin is active in murine models of toxoplasmosis.
1994 Mar
In vitro and in vivo antibacterial activities of KRM-1648 and KRM-1657, new rifamycin derivatives.
1994 May
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
Chemotherapeutic activity of benzoxazinorifamycin, KRM-1648, against Mycobacterium tuberculosis in C57BL/6 mice.
1996 Apr
Rifamycin resistance in mycobacteria.
1996 Jan-Feb
Rifapentine is active in vitro and in vivo against Toxoplasma gondii.
1996 Jun
Rapid drug susceptibility of Mycobacterium avium complex using a fluorescence quenching method.
1997 Aug
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
Activities of eighteen antimicrobial regimens against Mycobacterium avium infection in beige mice.
1999 Fall
In vitro anticryptosporidial activity of ranalexin alone and in combination with other peptides and with hydrophobic antibiotics.
1999 Nov
In-vitro activity of rifabutin and albendazole singly and in combination with other clinically used antimicrobial agents against Pneumocystis carinii.
1999 Nov
Activity of nitazoxanide alone and in combination with azithromycin and rifabutin against Cryptosporidium parvum in cell culture.
2000 Apr
Therapeutic efficacy of liposomal rifabutin in a Mycobacterium avium model of infection.
2000 Sep
Idiosyncratic rifabutin-induced leukopenia and SIADH: case report and review.
2001 Apr
Activity of moxifloxacin by itself and in combination with ethambutol, rifabutin, and azithromycin in vitro and in vivo against Mycobacterium avium.
2001 Jan
CYP3A inductive potential of the rifamycins, rifabutin and rifampin, in the rabbit.
2001 May
In vitro effect of short-term exposure to two synthetic peptides, alone or in combination with clarithromycin or rifabutin, on Cryptosporidium parvum infectivity.
2002 May
New agents active against Mycobacterium avium complex selected by molecular topology: a virtual screening method.
2004 Jan
In-vitro activity of rifabutin against rifampicin-resistant Mycobacterium tuberculosis isolates with known rpoB mutations.
2004 Jul
The activity of grepafloxacin in two murine models of Mycobacterium avium infection.
2004 Jun
Efficacy of rifabutin-loaded microspheres for treatment of Mycobacterium avium-infected macrophages and mice.
2007 Mar
Interference with bile salt export pump function is a susceptibility factor for human liver injury in drug development.
2010 Dec
The pharmacokinetics and pharmacodynamics of pulmonary Mycobacterium avium complex disease treatment.
2012 Sep 15
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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 Mon Mar 31 18:28:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:28:33 GMT 2025
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
TALICIA COMPONENT RIFABUTIN
Preferred 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 [MI]
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
Rifabutin [WHO-DD]
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 [USP MONOGRAPH]
Common Name English
RIFABUTIN [MART.]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ04AB04
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
NCI_THESAURUS C280
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
NDF-RT N0000007911
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
LIVERTOX NBK547975
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
NDF-RT N0000007911
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
NDF-RT N0000007911
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
NDF-RT N0000007911
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
FDA ORPHAN DRUG 41989
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
WHO-ATC J04AB04
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
FDA ORPHAN DRUG 770820
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
NDF-RT N0000175501
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.2.4
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
FDA ORPHAN DRUG 338811
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
FDA ORPHAN DRUG 41889
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
Code System Code Type Description
LACTMED
Rifabutin
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
WIKIPEDIA
RIFABUTIN
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
INN
5668
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
MERCK INDEX
m9608
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY Merck Index
PUBCHEM
6323490
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
RXCUI
55672
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
2376
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
NCI_THESAURUS
C1408
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
MESH
D017828
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
DAILYMED
1W306TDA6S
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
SMS_ID
100000091607
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID0033960
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
EVMPD
SUB10304MIG
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
FDA UNII
1W306TDA6S
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
CHEBI
45367
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
DRUG BANK
DB00615
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
HSDB
3577
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
RS_ITEM_NUM
1603800
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
USAN
FF-8
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
CAS
72559-06-9
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL444633
Created by admin on Mon Mar 31 18:28:33 GMT 2025 , Edited by admin on Mon Mar 31 18:28:33 GMT 2025
PRIMARY
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METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 3A4
METABOLIC ENZYME -> INDUCER
CYTOCHROME P450 3A5
METABOLIC ENZYME -> INDUCER
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Structure of 32-HYDROXY-25-O-DEACETYLRIFABUTIN
METABOLITE -> PARENT
Structure of 31-HYDROXYRIFABUTIN
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Structure of RIFABUTIN N-OXIDE OPEN RING
IMPURITY -> PARENT
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Structure of 3-AMINORIFAMYCIN S
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CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-nitroso-rifabutin
IMPURITY -> PARENT
Structure of 1-ISOBUTYL-4-PIPERIDONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
Structure of RIFABUTIN 14R EPIMER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of RIFABUTIN 21R EPIMER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
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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
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ACTIVE MOIETY
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