Rifapentine
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| Systematic (IUPAC) name | |
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(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
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| Clinical data | |
| AHFS/Drugs.com | monograph |
| MedlinePlus | a602026 |
| Pharmacokinetic data | |
| Bioavailability | increases when administered with food |
| Identifiers | |
| CAS Number | 61379-65-5  |
| ATC code | J04AB05 (WHO) |
| PubChem | CID: 5462354 |
| DrugBank | DB01201 |
| ChemSpider | 10482075 |
| UNII | XJM390A33U |
| KEGG | D00879 |
| ChEBI | CHEBI:45304 |
| ChEMBL | CHEMBL1660 |
| NIAID ChemDB | 007686 |
| Synonyms | 3{[(4-cyclopentyl-1-piperazinyl)imino]methyl}rifamycin |
| Chemical data | |
| Formula | C47H64N4O12 |
| Molecular mass | 877.031 g/mol |
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Rifapentine (INN, marketed under the brand name Priftin by Sanofi-Aventis) is an antibiotic drug used in the treatment of tuberculosis.
It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.[1]
Contents
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. [2]
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. [3]
Adverse effects
Common side effects are hyperuricemia, pyuria, hematuria, urinary tract infection, proteinuria, neutropenia, anemia, and hypoglycemia. [3]
Contraindications
Rifapentine should be avoided in patients with an allergy to the rifamycin class of drugs. [3] This drug class includes rifampin and rifabutin. [4]
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.[3]
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
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- ↑ 3.0 3.1 3.2 3.3 Sanofi-Aventis. (2010) Priftin (rifapentine): Highlights of Prescribing Information. Retrieved from http://products.sanofi.us/priftin/Priftin.pdf.
- ↑ CDC. (2013) Core Curriculum on Tuberculosis: What the Clinician Should Know. Retrieved from http://www.cdc.gov/TB/education/corecurr/default.htm.
