Rifabutin

Base Information

• Chemical Name: Rifabutin
• CAS No.: 72559-06-9
• Molecular Formula: C46H62N4O11
• Molecular Weight: 847.02
• Hs Code.: 3003.20
• Mol file: 72559-06-9.mol

Synonyms:Rifabutin;4-deoxo-3,4-[2-spiro(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo]-rifamicin S;Ansamycin;RIFABUTINE;Mycobutin;lm427;Rifabatin;antibioticlm427;1',4-didehydro-1-desoxi-1,4-di-hydro-5'-(2-methyl-propyl)-1-oxo-rifamycin;Ansatipine;6,9-dihydro-5,17,19,21-tetrahydroxy-8,9-[2-spiro-(N-isobutyl-4-piperidyl)-2,5-dihydro-1H-imidazo]-23-methoxy-2,4,12,16,18,20,22-heptamethyl-6-oxo-2,7-epoxypentadeca-[1,11,13]-trienimine-2H-furo[2',3',7,8]nafto[1,2-d]imidazolo-2,4'-piperidine-5,10,26. (3H,9H)-trione-16-acetate;

Chemical Property of Rifabutin

Chemical Property:

• Appearance/Colour: Red-brown powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 169-171oC
• Refractive Index: 1.623
• Boiling Point: 969.589 °C at 760 mmHg
• Flash Point: 540.188 °C
• PSA: 205.55000
• Density: 1.339 g/cm³
• LogP: 4.64680
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO: >5mg/mL
• Water Solubility.: 0.19g/L(temperature not stated)

Purity/Quality:

99% ^*data from raw suppliers

Rifabutin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Rifabutin, a rifamycin antibacterial derivative, is the first agent approved and introduced for the prevention of Mycobacterium avium complex (MAC) in AIDS patients. It is also indicated in combination chemotherapy for the prophylaxis and treatment of MAC infections in HIV positive patients and for newly diagnosed and chronic tuberculosis.
• Uses: Semisynthetic derivative of Rifamycin S that inhibits nucleic acid synthesis. An antibacterial (tuberculostatic). Antibiotic;RNA-polymerase inhibitor Rifamycins are antibiotics that inhibit DNA-dependent RNA polymerases and are usually bactericidal against Gram-positive bacteria but bacteriostatic against Gram-negative bacteria. Rifamycins are also effective against Mycobacterium species, including M. tuberculosis. Rifabutin is a broad-spectrum rifamycin antibiotic that has applications against tuberculosis, H. pylori, M. avium complex, Chlamydia, and other bacteria. It is also useful in co-infections with human immunodeficiency virus, including tuberculosis.
• Indications: Rifabutin (Mycobutin), an antibiotic related to rifampin, shares its mechanism of action, that is, inhibition of RNA polymerase. Rifabutin has significant activity in vitro and in vivo against M. avium-intracellular complex (MAC) isolates from both HIV-infected and non–HIV-infected individuals. It has better activity against MAC organisms than rifampin. Rifabutin is active against M. tuberculosis, including some rifampinresistant strains, such as M.leprae and M.fortuitum. It has a spectrum of activity against gram-positive and gramnegative organisms similar to that of rifampin. The molecular basis for resistance to rifabutin is shared by both rifampin and rifabutin; this explains the virtually complete cross-resistance that occurs between these drugs.
• Clinical Use: Rifabutin, the spiroimidazopiperidyl derivative of rifamycin B was approved in the United States for the prophylaxis of disseminated MAC in AIDS patients on the strength of clinical trials establishing its effectiveness. The activity of rifabutin against MAC organisms greatly exceeds that of rifamycin. This rifamycin derivative is not effective, however, as monotherapy for existing disseminated MAC disease. Rifabutin is a very lipophilic compound with a high affinity for tissues. Its elimination is distribution limited, with a half-life averaging 45 hours (range, 16 69 hours). Approximately 50% of an orally administered dose of rifabutin is absorbed, but the absolute oral bioavailability is only about 20%. Extensive first-pass metabolism and significant biliary excretion of the drug occur, with about 35% and 53% of the orally administered dose excreted, largely as metabolites, in the feces and urine, respectively. Despite its greater potency against M. tuberculosis in vitro, rifabutin is considered inferior to rifampin for the short-term therapy of tuberculosis because of its significantly lower plasma concentrations. Although rifabutin is believed to cause less hepatotoxicityand induction of cytochrome P450 enzymes than rifampin,these properties should be borne in mind when the drug is usedprophylactically. Rifabutin and its metabolites are highly coloredcompounds that can discolor skin, urine, tears, feces, etc. Prevention of infections with M. avium complex in AIDS patients Treatment of non-tuberculous mycobacterial disease (in combination with other agents)Rifabutin in combination with other agents has been proposed as a rescue therapy after Helicobacter pylori treatment failures.Although some efficacy has been observed in the treatment of tuberculosis, its use for this condition is not recommended.
• Drug interactions: Potentially hazardous interactions with other drugs Anti-arrhythmics: metabolism of disopyramide, and propafenone accelerated; concentration of dronedarone reduced. Antibacterials: increased risk of side effects with azithromycin; clarithromycin and other macrolides increase concentration of rifabutin, resulting in increased risk of uveitis - reduce rifabutin dose; reduced concentration of dapsone and clarithromycin. Anticoagulants: reduced anticoagulant effect of coumarins. Antidiabetics: reduced antidiabetic effect of tolbutamide; possibly reduced antidiabetic effect with sulphonylureas. Antiepileptics: reduced concentration of fosphenytoin, phenytoin and carbamazepine. Antifungals: fluconazole, triazoles, posaconazole and voriconazole increase the concentration of rifabutin resulting in increased risk of uveitis - reduce rifabutin dose; rifabutin reduces concentration of posaconazole, voriconazole and itraconazole - increase voriconazole dose, avoid with isavuconazole and itraconazole. Antipsychotics: possibly reduced aripiprazole concentration - increase dose of aripiprazole. Antivirals: atazanavir darunavir, fosamprenavir, saquinavir and tipranavir and possibly nevirapine increase concentration of rifabutin - halve or reduce dose of rifabutin; efavirenz reduces the concentration of rifabutin - increase dose of rifabutin; concentration of both drugs reduced with etravirine; indinavir increases rifabutin concentration - avoid; concentration of indinavir reduced - increase indinavir dose; concentration of elvitegravir reduced and active metabolite of rifabutin increased - reduce dose of rifabutin; concentration of rilpivirine reduced - increase rilpivirine dose to 50mg once daily; ritonavir increases the concentration of rifabutin resulting in increased risk of uveitis - reduce rifabutin dose; concentration of saquinavir reduced and concentration of rifabutin increased - reduce rifabutin dose; concentration of daclatasvir and simeprevir possibly reduced - avoid; avoid with ledipasvir, sofosbuvir and telaprevir. Atovaquone: concentration of atovaquone reduced (possible therapeutic failure of atovaquone). Ciclosporin: possibly reduced ciclosporin levels. Cobicistat: concentration of cobicistat reduced - adjust cobicistat dose. Corticosteroids: reduced level of corticosteroids - double steroid dose. Give as twice daily dosage. Cytotoxics: possibly reduced concentration of axitinib (increase axitinib dose), bosutinib, cabazitaxel, ceritinib, crizotinib, lapatinib, olaparib, panobinostat, ponatinib and vemurafenib - avoid. Guanfacine: concentration of guanfacine possibly reduced - increase dose of guanfacine. Hormone antagonists: concentration of abiraterone possibly reduced - avoid. Ivacaftor: concentration of ivacaftor possibly reduced - avoid. Oestrogens and progestogens: reduced contraceptive effect due to increased metabolism. Sirolimus: reduced sirolimus concentration - avoid. Tacrolimus: possibly reduced tacrolimus trough concentration. Ulipristal: possibly reduced contraceptive effect - avoid.