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
Wikidata facts
- Subclass of
- rifamycin
- Mass
- 846.442
- Manufacturer
- Pfizer
- Has use
- medication
Show 10 more facts
- chemical formula
- C₄₆H₆₂N₄O₁₁
- subject has role
- essential medicine
- World Health Organisation international non-proprietary name
- rifabutin
- medical condition treated
- Mycobacterium avium-intracellulare infection
- isomeric SMILES
- 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
- canonical SMILES
- CC1C=CC=C(C(=O)NC2=C3C(=NC4(N3)CCN(CC4)CC(C)C)C5=C6C(=C(C(=C5C2=O)O)C)OC(C6=O)(OC=CC(C(C(C(C(C(C1O)C)O)C)OC(=O)C)C)OC)C)C
- Commons category
- Rifabutin
- defined daily dose
- 0.15
- found in taxon
- Streptomyces
- significant drug interaction
- cobicistat
via Wikidata · CC0
~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.