Rifabutin

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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	J04 AB04
PubChem	6323490
DrugBank	APRD00094
Chemical data
Formula	C₄₆H₆₂N₄O₁₁
Mol. weight	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.

1 History
2 Other indications
3 Supply
4 External links

[edit] 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.

[edit] Other indications

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

[edit] Supply

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

[edit] External links

U.S. Patent 3,150,046 to Achifar.

Antimycobacterials (J04) edit
Tuberculosis:	Aminosalicylic acid, Calcium aminosalicylate, Capreomycin, Cycloserine, Ethambutol, Ethionamide, Isoniazid, Morinamide, Protionamide, Pyrazinamide, Rifabutin, Rifampicin, Rifamycin, Rifapentin, Sodium aminosalicylate, Terizidone, Tiocarlide
Leprosy:	Aldesulfone sodium, Clofazimine, Dapsone