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Rifabutin



Rifabutin
Systematic (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
Identifiers
CAS number 72559-06-9
ATC code J04AB04
PubChem 6323490
DrugBank APRD00094
Chemical data
Formula C46H62N4O11 
Mol. mass 847.005 g/mol
Pharmacokinetic data
Bioavailability 85%
Protein binding 85%
Metabolism Hepatic
Half life 28 to 62 hours (mean)
Excretion Renal and fecal
Therapeutic considerations
Pregnancy cat.

C (Au), B (U.S.)

Legal status

POM (UK), ℞-only (U.S.)

Routes Oral

Rifabutin is a bactericidal antibiotic drug primarily used in the treatment of tuberculosis. The drug is a semi-synthetic derivative of rifamycin S. Its effect is based on blocking the DNA-dependend RNA-polymerase of the bacteria. It is effective against Gram-positive and some Gram-negative bacteria, but also against the highly resistant Mycobacteria, e.g. Mycobacterium tuberculosis, M. leprae and M. avium intracellulare.

Additional recommended knowledge

History

Scientists at the Italian drug company Achifar discovered rifabutin in 1975. Eventually Archifar became part of Farmitalia Carlo Erba, a unit of the conglomerate Montedison. This company's Adria Laboratories subsidiary filed for Food and Drug Administration (FDA) approval of rifabutin under the brand name Mycobutin® in the early 1990s. The drug gained FDA approval in December 1992.

Other indications

Rifabutin is used in the treatment of mycobacterium avium complex disease, a bacterial infection most commonly encountered in late-stage AIDS patients.

Rifabutin is well tolerated in patients with HIV-related tuberculosis (TB), but patients with low CD4 cell counts have a high risk of treatment failure or relapse due to acquired rifamycin resistance, a new study found.

Since patients co-infected with TB and HIV / AIDS are likely to get TB treated first, doctors and patients should be aware of a possible rifamycin resistance issue, if the CD4 is so suppressed at the time TB treatment is to begin.

Supply

Rifabutin is now sold in the U.S. market by Pfizer.


 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Rifabutin". A list of authors is available in Wikipedia.
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