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Rifapentine

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Rifapentine Basic information

Product Name:
Rifapentine
CAS:
61379-65-5
MF:
C47H64N4O12
MW:
877.03
EINECS:
262-743-9
Mol File:
61379-65-5.mol
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Rifapentine Chemical Properties

Melting point:
179-1800C
Boiling point:
969.3±65.0 °C(Predicted)
Density 
1.35±0.1 g/cm3(Predicted)
storage temp. 
-20°C Freezer
solubility 
methanol: soluble2mg/mL, clear, red to red-brown
form 
powder
pka
4.81±0.70(Predicted)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26
WGK Germany 
3
RTECS 
JQ0902000
Toxicity
LD50 in mice (mg/kg): >2000 orally; 750 i.p. (Cricchio); LD50 in mice (mg/kg): 3300 orally; 710 i.p. (Aroli)
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Rifapentine Usage And Synthesis

Description

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.

Chemical Properties

Crystalline Solid

Originator

Shanghai No. 5 Factory (China)

Uses

antibacterial (tuberculostatic);'inhibits DNA-dependent RNA polymerase in susceptible strains of Mycobacterium tuberculosis

Uses

PDE5 inhibitor for erectile dysfunction A semisynthetic ansamycin antibiotic, cyclopentyl derivative of Rifamycin. Treatment of pulmonary tuberculosis

Uses

Semi-synthetic rifamycin. Antibacterial (tuberculostatic)

Indications

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.

brand name

Priftin (Sanofi Aventis);Rifampin.

Antimicrobial activity

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.

Hazard

Moderately toxic by ingestion.

Pharmaceutical Applications

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.

Pharmacokinetics

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%
absorption
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.
Distribution
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.
Metabolism
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.
excretion
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.

Clinical Use

Tuberculosis (in combination with other antituberculosis drugs)

Side effects

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).

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RifapentineSupplierMore

Chengdu BoShi Technology Co., Ltd. Gold
Tel:
13982188065
Email:
2983871989@qq.com
J & K SCIENTIFIC LTD.
Tel:
010-82848833- ;010-82848833-
Email:
jkinfo@jkchemical.com;market6@jkchemical.com
Chembest Research Laboratories Limited
Tel:
021-20908456-
Email:
sales@BioChemBest.com
Pure Chemistry Scientific Inc.
Tel:
001-857-928-2050 or 1-888-588-9418
Email:
sales@chemreagents.com
Nanjing Chemlin Chemical Co., Ltd
Tel:
025-83697070
Email:
info@chemlin.com.cn
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