Rifapentine
-
Rifapentine
structure -
-
CAS No:
61379-65-5
-
Formula:
C47H64N4O12
-
Chemical Name:
Rifapentine
-
Synonyms:
Rifamycin,3-[[(4-cyclopentyl-1-piperazinyl)imino]methyl]-;2,7-(Epoxypentadeca[1,11,13]trienimino)naphtho[2,1-b]furan,rifamycin deriv.;3-[[(4-Cyclopentyl-1-piperazinyl)imino]methyl]rifamycin;Rifamycin AF/ACPP;DL 473;Antibiotic DL 473IT;Rifapentine;MDL 473;Cyclopentylrifampicin;R 77-3;KTC 1;Priftin;Rifapentin;Prifitin;71950-35-1;773848-08-1
- Categories:
-
CAS No:
Description
Rifapentine (Priftin; DL 473) is an antibiotic compound used in the treatment of tuberculosis.Target: AntibacterialRifapentine inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme. A review of alternative regimens for prevention of active tuberculosis in HIV-negative individuals with latent TB found that a weekly, directly observed regimen of rifapentine with isoniazid for t
Rifapentine is a N-alkylpiperazine, a N-iminopiperazine and a member of rifamycins. It has a role as an antitubercular agent and a leprostatic drug.|Rifapentine is an antibiotic drug used in the treatment of tuberculosis. It inhibits DNA-dependent RNA polymerase activity in susceptible cells. Specifically, it interacts with bacterial RNA polymerase but does not inhibit the mammalian enzyme.|Rifapentine is a Rifamycin Antimycobacterial.|Rifapentine is a rifamycin antibiotic that is similar in structure and activity to rifampin and rifabutin and that is used in combination with other agents as therapy of tuberculosis, particularly in once or twice weekly regimens. Rifapentine is associated with transient and asymptomatic elevations in serum aminotransferase and is a likely cause of clinically apparent acute liver injury.|Rifapentine is a long-acting, cyclopentyl-substituted derivative of rifamycin used to treat mycobacterium infections.
Rifapentine Basic Attributes
877.03
877.03
262-743-9
XJM390A33U
DTXSID8041115
C66516
J - Antiinfectives for systemic use
2941903000
Characteristics
4
1.4±0.1 g/cm3
179-180 °C
540.0±34.3 °C
1.625
methanol: soluble2mg/mL, clear, red to red-brown
-20°C Freezer
LD50 in mice (mg/kg): >2000 orally; 750 i.p. (Cricchio); LD50 in mice (mg/kg): 3300 orally; 710 i.p. (Aroli)
Safety Information
NONH for all modes of transport
3
36/37/38
26
JQ0902000
Xi
P261-P305 + P351 + P338
H315-H319-H335
|Warning|H315 (97.5%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 40 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Toxicity
Because of its limited use, the effects of rifapentine on the liver have been less well defined than those of rifampin, but they are likely to be similar. Thus, long term therapy with rifapentine is associated with minor, transient elevations in serum aminotransferase levels in 2% to 7% of patients, abnormalities that usually do not require dose adjustment or discontinuation. Clinically apparent liver injury due to rifapentine has not been reported, but it is likely to be similar to rifampin in its potential for causing acute liver injury. Because rifapentine is usually given in combination with isoniazid and/or pyrazinamide, two other known hepatotoxic agents, the cause of the acute liver injury in patients on rifapentine containing regimens may be difficult to relate to a single agent, and some evidence suggests that these combinations are more likely to cause injury than the individual drugs. Typically, the onset of injury due to rifamycins is within 1 to 6 weeks and the serum enzyme pattern is usually hepatocellular at the onset of injury, but can cholestatic and mixed in contrast to isoniazid and pyrazinamide. Extrahepatic manifestations due to rifamycin hepatotoxicity such as fever, rash, arthralgias, edema and eosinophilia are uncommon as is autoantibody formation. This potential for hepatotoxicity has not been specifically demonstrated for rifapentine.
97.7% (bound to plasma proteins)
Drug Information
For the treatment of pulmonary tuberculosis.|FDA Label
Rifapentine is a rifamycin antibiotic that is similar in structure and activity to rifampin and rifabutin and that is used in combination with other agents as therapy of tuberculosis, particularly in once or twice weekly regimens. Rifapentine is associated with transient and asymptomatic elevations in serum aminotransferase and is a likely cause of clinically apparent acute liver injury.
Antituberculosis Agents
Rifapentine 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. Rifampin 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.
Substances obtained from various species of microorganisms that are, alone or in combination with other agents, of use in treating various forms of tuberculosis; most of these agents are merely bacteriostatic, induce resistance in the organisms, and may be toxic. (See all compounds classified as Antibiotics, Antitubercular.)|Substances that suppress Mycobacterium leprae, ameliorate the clinical manifestations of leprosy, and/or reduce the incidence and severity of leprous reactions. (See all compounds classified as Leprostatic Agents.)
Rapidly and well absorbed from the gastrointestinal tract.|Following a single 600 mg oral dose of radiolabeled rifapentine to healthy volunteers (n=4), 87% of the total 14C rifapentine was recovered in the urine (17%) and feces (70%).|70.2 ± 9.1 L|Apparent Oral cl=2.51 +/- 0.14 L/h [Male tuberculosis patients who received 600 mg rifapentine in combination with isoniazid, pyrazinamide and ethambutol]
Hepatic
Rifapentine has shown higher bacteriostatic and bactericidal activities especially against intracellular bacteria growing in human monocyte-derived macrophages. Rifapentine inhibits DNA-dependent RNA polymerase in susceptible strains of M. tuberculosis. Rifapentine acts via the inhibition of DNA-dependent RNA polymerase, leading to a suppression of RNA synthesis and cell death.
3-(((4-cyclopentyl-1-piperazinyl)imino)methyl)rifamycin
Rifapentine Use and Manufacturing
Semi-synthetic rifamycin. Antibacterial (tuberculostatic)
Human drugs -> Rare disease (orphan)|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Computed Properties
Molecular Weight:877.0
XLogP3:6.7
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:6
Exact Mass:876.45207349
Monoisotopic Mass:876.45207349
Topological Polar Surface Area:220
Heavy Atom Count:63
Complexity:1730
Defined Atom Stereocenter Count:9
Defined Bond Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Extract from the above information
Registered Holders
-
MACLEODS PHARMACEUTICALS LTD
Active
India
-
Chongqing Shengkai Pharmaceutical Co., Ltd.
Active
China
-
Sichuan LONG March Pharmaceutical Co., Ltd.
Active
China
Recommended Suppliers of Rifapentine
-
![China]()
CN
5 YRS
Business licensedTrader Supplier of Pharmaceuticals,Peptide,Cosmetics,Nutritional SupplementsInquiryCAS No.: 61379-65-5Grade: Pharmaceutical GradeContent: 99% -
![China]()
CN
5 YRS
Business licensed Certified factoryManufactory Supplier of BBiochemicals,Peptides,Silicones,Pharmaceuticals,Building blocks,Intermediates
Learn More Other Chemicals
-
Rifapentine hydrochloride
127923-87-9
-
25-DESACETYL RIFAPENTINE
79039-56-8
-
Oseltamivir phosphate
204255-11-8
-
Imidazole salicylate Formula
36364-49-5
-
5H-Pyrazolo[1,2-a][1,2,4]triazol-4-ium, 6,7-dihydro-6-mercapto-, chloride (1:1) Formula
153851-71-9
-
Cefminox Formula
75481-73-1
-
Clindamycin Structure
18323-44-9
-
Bacitracin Zinc Structure
1405-89-6
-
What is Spectinomycin hydrochloride
21736-83-4
-
What is Isoconazole nitrate
24168-96-5