Product Name

Rifabutin

CAS Number

72559-06-09

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Product Name:
Rifabutin
CAS Number:
72559-06-09
Indication:
For the prevention of disseminated Mycobacterium avium complex (MAC) disease in patients with advanced HIV infection.
Mode of Action:

Rifabutin acts via the inhibition of DNA-dependent RNA polymerase in gram-positive and some gram-negative bacteria, leading to a suppression of RNA synthesis and cell death.

Pharmacodynamics:

Rifabutin is an antibiotic that inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. It is bactericidal and has a very broad spectrum of activity against most gram-positive and gram-negative organisms (including Pseudomonas aeruginosa) and specifically Mycobacterium tuberculosis. Because of rapid emergence of resistant bacteria, use is restricted to treatment of mycobacterial infections and a few other indications. Rifabutin is well absorbed when taken orally and is distributed widely in body tissues and fluids, including the CSF. It is metabolized in the liver and eliminated in bile and, to a much lesser extent, in urine, but dose adjustments are unnecessary with renal insufficiency.

Metabolism:

Hepatic. Of the five metabolites that have been identified, 25-O-desacetyl and 31-hydroxy are the most predominant. The former metabolite has an activity equal to the parent drug and contributes up to 10% to the total antimicrobial activity.

Toxicity:

LD50 = 4.8 g/kg (mouse, male)

ATC:
J04AB04
PubChem:
6323490
DrugBank:
DB00615 (APRD00094)
Formula:
C22H21Cl3N4O
Molecular Mass:
847.0047
Synonyms:
Ansatipin Ansatipine Antibiotic LM 427 RBT Rifabutina [Spanish] Rifabutine [French] Rifabutinum [Latin]
SMILES:
CO[C@H]1C=CO[C@@]2(C)OC3=C(C2=O)C2=C(C(O)=C3C)C(=O)C(NC(=O)C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)=C1NC3(CCN(CC3)CC(C)C)N=C21
AHFS Code:
08:16.0
InChi:
ATEBXHFBFRCZMA-VXTBVIBXSA-N

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