Rifapentine

Overview

Rifapentine, sold under the brand name Priftin, is an antibiotic used in the treatment of tuberculosis. In active tuberculosis it is used together with other antituberculosis medications. In latent tuberculosis it is typically used with isoniazid. It is taken by mouth.[1] WP

Common side effects include low neutrophil counts in the blood, elevated liver enzymes, and white blood cells in the urine. Serious side effects may include liver problems or Clostridioides difficile associated diarrhea. It is unclear if use during pregnancy is safe. Rifapentine is in the rifamycin family of medication and works by blocking DNA-dependent RNA polymerase.[2] WP

Rifapentine was approved for medical use in the United States in 1998. It is on the World Health Organization's List of Essential Medicines.[1][3] WP

Drug class

Macrolactam WP

From the Wikipedia article's infobox.

Uses, dosage and effects

Medical uses

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.[4] WP

Risks and side effects

Adverse effects

Common side effects include allergic reaction, anemia, neutropenia, elevated transaminases, and pyuria. Overdoses have been associated with hematuria and hyperuricemia.[1][2] WP

Pregnancy

Rifapentine in pregnant women has not been studied, but animal reproduction studies have resulted in fetal harm and were teratogenic.[1] WP

Contraindications

Rifapentine should be avoided in patients with an allergy to the rifamycin class of drugs. This drug class includes rifampicin and rifabutin.[1][5] WP

Interactions

Interactions

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 include warfarin, propranolol, digoxin, protease inhibitors and birth control pills.[1] WP

History

History

Rifapentine was first synthesized in 1965, by the same company that produced rifampicin. The drug was approved by the U.S. Food and Drug Administration (FDA) in June 1998. It is made from rifampicin.[6][7] WP⚠ Part of this sentence could not be copied from the source. Open the source to read it in full.⚠ Wikipedia itself has flagged this text: citation needed.

Rifapentine was granted orphan drug designation by the FDA in June 1995, and by the European Commission in June 2010.[8][9] WP

Legal status

Cancer-causing impurities

In August 2020, the U.S. Food and Drug Administration (FDA) became aware of nitrosamine impurities in certain samples of rifapentine. 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). 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. 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.[10] WP

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.[11] WP

Chemistry

Formula

C47H64N4O12 PC

CAS number

61379-65-5 PC

Molar mass (g/mol)

877.0 PC

IUPAC name (computed by PubChem)

[(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-[(E)-(4-cyclopentylpiperazin-1-yl)iminomethyl]-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate PC

SMILES

C[C@H]1/C=C/C=C(\C(=O)NC2=C(C(=C3C(=C2O)C(=C(C4=C3C(=O)[C@](O4)(O/C=C/[C@@H]([C@H]([C@H]([C@@H]([C@@H]([C@@H]([C@H]1O)C)O)C)OC(=O)C)C)OC)C)C)O)O)/C=N/N5CCN(CC5)C6CCCC6)/C PC

InChIKey

WDZCUPBHRAEYDL-GZAUEHORSA-N PC

PubChem CID

135403821

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

User reports

Pop culture

No references added yet.

Sources

1. Journal / agency Priftin- rifapentine tablet, film coated. 22 October 2019
2. Other Rifapentine
3. Other World Health Organization. World Health Organization model list of essential medicines: 21st list 2019. 2019
4. Journal / agency Sharma SK, Sharma A, Kadhiravan T, Tharyan P. Rifamycins (rifampicin, rifabutin and rifapentine) compared to isoniazid for preventing tuberculosis in HIV-negative people at risk of active TB. Cochrane Database of Systematic Reviews. July 2013. doi:10.1002/14651858.CD007545.pub2 · PMID 23828580 · PMC6532682
5. Journal / agency CDC - Core Curriculum: What the Clinician Should Know - TB
6. Journal / agency Drug Approval Package: Priftin/Rifapentine NDA# 21024. 30 March 2001
7. Journal / agency Priftin
8. Journal / agency Rifapentine Orphan Drug Designation and Approval. 24 December 1999
9. Journal / agency EU/3/10/750. 21 June 2010
10. Journal / agency FDA works to mitigate shortages of rifampin and rifapentine. 26 August 2020
11. Journal / agency Laboratory analysis of rifampin/rifapentine products. 28 January 2021

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.