Rifabutin

Rifabutin

Clinical data
Trade names	Mycobutin
AHFS/Drugs.com	Monograph
MedlinePlus	a693009
Pregnancy category	AU: C US: B (No risk in non-human studies)
Routes of administration	by mouth (capsules)
ATC code	J04AB04 (WHO)
Legal status
Legal status	UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	85%
Protein binding	85%
Metabolism	liver
Biological half-life	28 to 62 hours (mean)
Excretion	kidney and fecal
Identifiers
IUPAC name (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	72559-06-9 Y
PubChem CID	6323490
DrugBank	DB00615 Y
ChemSpider	10482168 Y
UNII	1W306TDA6S
KEGG	D00424 Y
ChEBI	CHEBI:45367 Y
ChEMBL	CHEMBL444633 Y
ECHA InfoCard	100.133.627
Chemical and physical data
Formula	C46H62N4O11
Molar mass	847.005 g/mol
3D model (Jmol)	Interactive image
SMILES CC(C)CN1CCC2(CC1)/N=C\3/c4c6C(=O)[C@@]5(C)O/C=C/[C@H](OC)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)N\C(=C/3/N2)C(=O)c4c(O)c(C)c6O5
InChI 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

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.

Common side effects include abdominal pain, nausea, rash, headache, and low blood neutrophil levels. Other side effects include muscles pains and uveitis. While no harms have been found during pregnancy it has not been well studied in this population. Rifabutin is in the rifamycin family of medications. Its mechanism of action is not clear.

Rifabutin was approved for medical use in the United States in 1992. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. The wholesale cost in the developing world is about 30 USD a month. In the United States a month of treatment is more than 200 USD.

Rifabutin is now recommended as first-line treatment for tuberculosis, but rifampicin is more widely used because of its cheaper cost.

Rifabutin is used in the treatment of Mycobacterium avium complex disease, a bacterial infection most commonly encountered in late-stage AIDS patients. Its main usefulness lies in the fact that it has lesser drug interactions than rifampicin; therefore HIV infected patients on HAART are usually given rifabutin for treatment of TB.