Rifapentine Chemical Properties
- Melting point:
- Boiling point:
- 969.3±65.0 °C(Predicted)
- 1.35±0.1 g/cm3(Predicted)
- storage temp.
- -20°C Freezer
- methanol: soluble2mg/mL, clear, red to red-brown
Rifapentine Usage And Synthesis
Rifapentine is a broad spectrum antibiotic highly active against Gram-positive bacteria and Neisseria gonorrhoea. It is reported to be 10 times more active than the structurally related rifampicin against Mycobacrerim fuberculosis. Unlike rifampicin the bioavailability of rifapentine is significantly increased when administered after a meal.
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antibacterial (tuberculostatic);'inhibits DNA-dependent RNA polymerase in susceptible strains of Mycobacterium tuberculosis
PDE5 inhibitor for erectile dysfunction A semisynthetic ansamycin antibiotic, cyclopentyl derivative of Rifamycin. Treatment of pulmonary tuberculosis
Semi-synthetic rifamycin. Antibacterial (tuberculostatic)
Rifapentine is an analogue of rifampin that is active against M. tuberculosis and M. avium. Rifapentine’s mechanism of action, cross-resistance, hepatic induction of P450 enzymes, drug interactions, and toxic profile are similar to those of rifampin. It has been used in the treatment of tuberculosis caused by rifampinsusceptible strains.
Priftin (Sanofi Aventis);Rifampin.
Activity is similar to that of rifampicin, but it is more active against atypical mycobacteria, especially the M. avium complex (MIC <0.06–0.5 mg/L). It has good activity on staphylococci and streptococci (MIC 0.01–0.5 mg/L), L. monocytogenes and Brucella spp.; less against Enterococcus faecalis (MIC 1–4 mg/L). Bacteroides spp. are inhibited by 0.5–2 mg/L. Gram-negative cocci are susceptible and, although some Gram-negative bacilli are inhibited by 4–32 mg/L, most are resistant.
Moderately toxic by ingestion.
An analog of rifampicin in which a cyclopentyl group is substituted for a methyl group on the piperazine ring. It is available for oral administration.
Oral absorption：c. 70%
Cmax600 mg oral ：12 mg/L after 5 h
Plasma half-life：13 h
Volume of distribution：1.5 L/kg
Plasma protein binding：97%
The absolute oral bioavailability of rifapentine has not been determined. The relative bioavailability of capsules (with an oral solution as reference) is 70%. Food increases absorption: a 600 mg dose taken after a meal gives Cmax and AUC values 44% higher than under fasting conditions. The extended halflife provides therapeutic concentrations for at least 72 h after administration, allowing less frequent dosing.
Animal data suggest that it is well distributed in the body, with tissue concentrations exceeding the plasma concentration, except in bone, testes and brain. The ratio of intracellular:extracellular concentration in macrophages was estimated as 24:1.
The main metabolite is an antimicrobially active 25-desacetyl derivative. Although it induces liver cytochromes it is not an inducer of its own metabolism, which is mediated by an esterase. The peak concentration of 25-desacetyl rifapentine is about one-third of that of the unchanged drug, and is attained after about 11 h.
The main route of elimination is through the bile. In healthy volunteers about 70% of a 600 mg dose of 14C rifapentine was recovered in the feces, and less than 17% in the urine. There is evidence of enterohepatic recycling in humans.
Tuberculosis (in combination with other antituberculosis drugs)
Signs of teratogenic effects and fetal toxicity have been observed when administered during pregnancy to rats and rabbits. Rifapentine should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus.
The most common adverse effect observed in combinations with other antimycobacterial agents was hyperuricemia, most probably due to pyrazinamide. Effects likely to be due to rifapentine were neutropenia (3.7% of patients) and hepatitis (increased transaminases in 1.6% of patients).
- 25-DESACETYL RIFAPENTINE
- RIFAPENTINE HYDROCHLORIDE,3-[[(4-CYCLOPENTYL-1-PIPERAZINYL)-IMINO]METHYL]RIFAMYCIN/RIFAPENTINE HYDROCHLORIDE,RIFAPENTINE
- RIFAMYCIN SV
- Methyl acetate
- Methyl acrylate
- TERT-AMYL METHYL ETHER
- Rifamycin Sodium
- Bensulfuron methyl
- METHYL THIOPHENE-2-CARBOXYLATE
- Methyl bromide
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