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Substance Name: Rifabutin [USAN:USP:INN:BAN:JAN]
RN: 72559-06-9
UNII: 1W306TDA6S
InChIKey: ATEBXHFBFRCZMA-VXTBVIBXSA-N

Note

  • A broad-spectrum antibiotic that is being used as prophylaxis against disseminated Mycobacterium avium complex infection in HIV-positive patients.

Molecular Formula

  • C46-H62-N4-O11

Molecular Weight

  • 847.013
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Antibacterial (Antimycobacterial)
  • Antibiotics, Antitubercular
  • Antimycobacterial
  • Antitubercular Agents
  • Drug / Therapeutic Agent
  • Human Data

Names and Synonyms

Name of Substance

  • Rifabutin
  • Rifabutin [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Rifabutin

Synonyms

  • (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-6-16,18,20-Tetrahydroxy-1'-isobutyl-14-methoxy-7,9,15,17,19,21,25-heptamethylspiro(9,4-(epoxypentadeca(1,11,13)trienimino)-2H-furo(2',3':7,8)naphth(1,2-d)imidazole-2,4'-piperidine)-5,10,26(3H,9H)-trione,16-acetate
  • 1,4-Dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl)-1-oxorifamycin XIV
  • 4-Deoxo-3,4-(2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo)-rifamycin S
  • 4-N-isobutylspiropiperidylrifamycin S
  • Alfacid
  • Ansamycin
  • Ansatipin
  • Ansatipine
  • Antibiotic LM 427
  • BRN 3584778
  • DRG-0085
  • HSDB 3577
  • LM 427
  • LM-427
  • Mycobutin
  • Rifabutin
  • Rifabutina
  • Rifabutina [Spanish]
  • Rifabutine
  • Rifabutine [French]
  • Rifabutinum
  • Rifabutinum [Latin]
  • UNII-1W306TDA6S

Systematic Names

  • (9S,12E,14S,15R,16S,17R,18R,19R,20S,21S,22E,24Z)-6-16,18,20-Tetrahydroxy-1'-isobutyl-14-methoxy-7,9,15,17,19,21,25-heptamethylspiro(9,4-(epoxypentadeca(1,11,13)trienimino)-2H-furo(2',3':7,8)naphth(1,2-d)imidazole-2,4'-piperidine)-5,10,26(3H,9H)-trione,16-acetate
  • Ansamycin
  • Rifamycin XIV, 1',4-didehydro-1-deoxy-1,4-dihydro-5'-(2-methylpropyl)-1-oxo-
  • Rifamycin XIV, 1,4-dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl)-1-oxo-

Registry Numbers

CAS Registry Number

  • 72559-06-9

FDA UNII

  • 1W306TDA6S

System Generated Number

  • 0072559069

Structure Descriptors

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

InChIKey

ATEBXHFBFRCZMA-VXTBVIBXSA-N

Smiles

N1C2(N=C3c4c5C(=O)C(NC(C(=CC=C[C@H](C)[C@@H]([C@@H](C)[C@H]([C@@H](C)[C@H](OC(=O)C)[C@@H]([C@H](C=CO[C@@]6(C)Oc(c4C6=O)c(C)c5O)OC)C)O)O)C)=O)=C13)CCN(CC2)CC(C)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 2gm/kg (2000mg/kg)   Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
man TDLo unreported 60mg/kg/14D-I (60mg/kg) BLOOD: AGRANULOCYTOSIS Lancet. Vol. 348, Pg. 685, 1996.
monkey LD oral > 4gm/kg (4000mg/kg)   Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
mouse LD50 intravenous 266mg/kg (266mg/kg) BEHAVIORAL: ATAXIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
mouse LD50 oral 3322mg/kg (3322mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
rat LD50 intravenous 51mg/kg (51mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
rat LD50 oral > 5gm/kg (5000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Experimental and Toxicologic Pathology. Vol. 47, Pg. 1, 1995.
women TDLo unreported 84mg/kg/14D-I (84mg/kg) BLOOD: AGRANULOCYTOSIS Lancet. Vol. 348, Pg. 685, 1996.