Rifapentine

Rifapentine
Systematic (IUPAC) name
(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z,26E)-26-{[(4-cyclopentylpiperazin-1-yl)amino]methylidene}-2,15,17,29-tetrahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27-trioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29)-heptaen-13-yl acetate
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a602026
Pharmacokinetic data
Bioavailability increases when administered with food
Identifiers
61379-65-5 Yes
J04AB05
PubChem CID 5462354
DrugBank DB01201 Yes
ChemSpider 10482075 Yes
UNII XJM390A33U Yes
KEGG D00879 Yes
ChEBI CHEBI:45304 Yes
ChEMBL CHEMBL1660 Yes
NIAID ChemDB 007686
Synonyms 3{[(4-cyclopentyl-1-piperazinyl)imino]methyl}rifamycin
Chemical data
Formula C47H64N4O12
877.031 g/mol
 Yes (what is this?)  (verify)

Rifapentine (INN, marketed under the brand name Priftin by Sanofi-Aventis) is an antibiotic drug used in the treatment of tuberculosis.

Medical uses

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 three months was as effective as a daily, self -administered regimen of isoniazid for nine months. But the 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. [1]

Use in special populations

Pregnancy

Rifapentine has been assigned a Pregnancy Category C by the FDA. Rifapentine in pregnant women has not been studied, but animal reproduction studies have resulted in fetal harm and were teratogenic. If rifapentine and rifampin are used together in pregnancy, coagulation should be monitored due to a possible increased risk of maternal postpartum hemorrhage and infant bleeding. [2]

Adverse effects

Common side effects are hyperuricemia, pyuria, hematuria, urinary tract infection, proteinuria, neutropenia, anemia, and hypoglycemia. [2]

Contraindications

Rifapentine should be avoided in patients with an allergy to the rifamycin class of drugs. [2] This drug class includes rifampin and rifabutin. [3]

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 oral contraceptives.[2]

History

Rifapentine was first synthesized in 1965 by the same company that produced rifampin. The drug was approved by the Food and Drug Administration (FDA) in June 1998. It is synthesized in one step from rifampicine.

See also

References

  1. ↑ Sharma SK et al . (2013). "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 7: CD007545. doi:10.1002/14651858.CD007545.pub2. PMID 23828580.
  2. ↑ 2.0 2.1 2.2 2.3 Sanofi-Aventis. (2010) Priftin (rifapentine): Highlights of Prescribing Information. Retrieved from http://products.sanofi.us/priftin/Priftin.pdf.
  3. ↑ CDC. (2013) Core Curriculum on Tuberculosis: What the Clinician Should Know. Retrieved from http://www.cdc.gov/TB/education/corecurr/default.htm.