Structure via PubChem · Public domain (PubChem)
rifabutin
Sign in to saveAlso known as LM-427, Ansamicin, 4-N-Isobutylspiropiperidylrifamycin S, Mycobutin (tn), 1,4-Dihydro-1-deoxy-1',4-didehydro-5'-(2-methylpropyl)-1-oxorifamycin xiv, Ansamycin, 4-Deoxo-3,4-(2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo)-rifamycin S, Mycobutin
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.
Chemical data
- Formula
- C46H62N4O11
- Molecular weight
- 847 g/mol
- IUPAC name
- [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-1'-(2-methylpropyl)-6,23,32-trioxospiro[8,33-dioxa-24,27,29-triazapentacyclo[23.6.1.14,7.05,31.026,30]tritriaconta-1(31),2,4,9,19,21,25,29-octaene-28,4'-piperidine]-13-yl] acetate
- SMILES
- C[C@H]1/C=C/C=C(\C(=O)NC2=C3C(=NC4(N3)CCN(CC4)CC(C)C)C5=C(C2=O)C(=C(C6=C5C(=O)[C@](O6)(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)O)/C
- InChIKey
- ATEBXHFBFRCZMA-VXTBVIBXSA-N
- XLogP
- 6.3
- Polar surface area
- 206 Ų
- H-bond donors
- 5
- H-bond acceptors
- 14
- Formal charge
- 0
via PubChem
~2 min read
Encyclopedic overview
4 sectionsContents
- Medical uses
- Adverse effects
- History
- References
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 was approved for medical use in the United States in 1992. It is on the World Health Organization's List of Essential Medicines.
Excerpted from Wikipedia’s “rifabutin” article, available under the CC BY-SA 4.0 licence.