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| Clinical data | |
|---|---|
| Trade names | Priftin |
| Other names | 3{[(4-cyclopentyl-1-piperazinyl)imino]methyl}rifamycin |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a616011 |
| License data | |
| Routes of administration | By mouth |
| Drug class | Macrolactam |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | increases when administered with food |
| Identifiers | |
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| CAS Number | |
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| DrugBank |
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| UNII | |
| KEGG | |
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| ChEMBL | |
| NIAID ChemDB | |
| PDB ligand | |
| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.057.021 |
| Chemical and physical data | |
| Formula | C47H64N4O12 |
| Molar mass | 877.045 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 179 to 180 °C (354 to 356 °F) |
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Rifapentine, sold under the brand namePriftin, is anantibiotic used in the treatment oftuberculosis.[2] In active tuberculosis it is used together with otherantituberculosis medications.[2] In latent tuberculosis it is typically used withisoniazid.[2] It is taken by mouth.[2]
Common side effects includelow neutrophil counts in the blood,elevated liver enzymes, andwhite blood cells in the urine.[3] Serious side effects may includeliver problems orClostridioides difficile associated diarrhea.[3] It is unclear if use duringpregnancy is safe.[3] Rifapentine is in therifamycin family of medication and works by blockingDNA-dependent RNA polymerase.[3]
Rifapentine was approved for medical use in the United States in 1998.[2] It is on theWorld Health Organization's List of Essential Medicines.[4]
A systematic review of 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 three months was as effective as a daily, self-administered regimen of isoniazid for nine months. The three-month rifapentine-isoniazid regimen had higher rates of treatment completion and lower rates of hepatotoxicity. However, the rate of treatment-limiting adverse events was higher in the rifapentine-isoniazid regimen compared to the nine-month isoniazid regimen.[5]
Common side effects includeallergic reaction,anemia,neutropenia,elevated transaminases,[2] andpyuria.[3] Overdoses have been associated withhematuria andhyperuricemia.[2]
Rifapentine in pregnant women has not been studied, but animal reproduction studies have resulted in fetal harm and were teratogenic.[2]
Rifapentine should be avoided in patients with an allergy to therifamycin class of drugs.[2] This drug class includesrifampicin andrifabutin.[6]
Rifapentine induces metabolism by CYP3A4, CYP2C8 and CYP2C9 enzymes. It may be necessary to adjust the dosage of drugs metabolized by these enzymes if they are taken with rifapentine. Examples of drugs that may be affected by rifapentine includewarfarin,propranolol,digoxin,protease inhibitors andbirth control pills.[2]
The chemical structure of rifapentine is similar to that ofrifampicin, with the notable substitution of a methyl group for acyclopentane (C5H9) group.
Rifapentine was first synthesized in 1965, by the same company that producedrifampicin.[citation needed] The drug was approved by the U.S.Food and Drug Administration (FDA) in June 1998.[7][8] It is made from rifampicin.[medical citation needed]
Rifapentine was grantedorphan drug designation by the FDA in June 1995,[9] and by the European Commission in June 2010.[10]
In August 2020, the U.S.Food and Drug Administration (FDA) became aware of nitrosamine impurities in certain samples of rifapentine.[11] The FDA and manufacturers are investigating the origin of these impurities in rifapentine, and the agency is developing testing methods for regulators and industry to detect the 1-cyclopentyl-4-nitrosopiperazine (CPNP).[11] CPNP belongs to the nitrosamine class of compounds, some of which are classified as probable or possible human carcinogens (substances that could cause cancer), based on laboratory tests such as rodent carcinogenicity studies.[11] Although there are no data available to directly evaluate the carcinogenic potential of CPNP, information available on closely related nitrosamine compounds was used to calculate lifetime exposure limits for CPNP.[11]
As of January 2021, the FDA continues to investigate the presence of 1-methyl-4-nitrosopiperazine (MNP) in rifampin or 1-cyclopentyl-4-nitrosopiperazine (CPNP) in rifapentine approved for sale in the US.[12]
This article incorporates text from this source, which is in thepublic domain. This article incorporates text from this source, which is in thepublic domain.
