Rifabutin

Rifabutin (Rfb) is an antibiotic used to treat tuberculosis and prevent and treat Mycobacterium avium complex. It is typically only used in those who cannot tolerate rifampin such as people with HIV/AIDS on antiretrovirals. For active tuberculosis it is used with other antimycobacterial medications. For latent tuberculosis it may be used by itself when the exposure was with drug-resistant TB.

Rifabutin
Clinical data
Trade namesMycobutin
AHFS/Drugs.comMonograph
MedlinePlusa693009
Pregnancy
category
  • AU: C
Routes of
administration		By mouth (capsules)
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability85%
Protein binding85%
Metabolismliver
Elimination half-life28 to 62 hours (mean)
Excretionkidney and fecal
Identifiers
  • (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-
    hepta-methyl-spiro[9,4-(epoxypentadeca
    [1,11,13]trienimino)-2H-furo-[2',3':7,8]-naphth
    [1,2-d]imidazol-2,4'-piperidin]-5,10,26-(3H,9H)-
    trione-16-acetate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.133.627
Chemical and physical data
FormulaC46H62N4O11
Molar mass847.019 g·mol−1
3D model (JSmol)
  • C[C@H]1/C=C\C=C(/C(=O)NC2=C3C(=NC4(N3)CCN(CC4)CC(C)C)C5=C6C(=C(C(=C5C2=O)O)C)O[C@@](C6=O)(O/C=C\[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)\C
  • 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 Y
  • Key:ATEBXHFBFRCZMA-VXTBVIBXSA-N Y
  (verify)

Rifabutin was approved for medical use in the United States in 1992. It is on the World Health Organization's List of Essential Medicines.

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