Rifapentine

Rifapentine
Clinical data
Trade names	Priftin
Other names	3{[(4-cyclopentyl-1-piperazinyl)imino]methyl}rifamycin
AHFS/Drugs.com	Monograph
MedlinePlus	a616011
License data	US DailyMed: Rifapentine;
Routes of; administration	By mouth
Drug class	Macrolactam
ATC code	J04AB05 (WHO) ;
Legal status
Legal status	CA: Urgent Public Health Need; US: ℞-only;
Pharmacokinetic data
Bioavailability	increases when administered with food
Identifiers
	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;
CAS Number	61379-65-5 ;
PubChem CID	6323497; 135403821;
DrugBank	DB01201 ;
ChemSpider	10482075 ;
UNII	XJM390A33U;
KEGG	D00879 ; C08059 ;
ChEBI	CHEBI:45304 ;
ChEMBL	ChEMBL1660 ;
NIAID ChemDB	007686;
PDB ligand	RPT (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID8041115 ;
ECHA InfoCard	100.057.021
Chemical and physical data
Formula	C47H64N4O12
Molar mass	877.045 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	179 to 180 °C (354 to 356 °F)
	SMILES CC(=O)O[C@H]3[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)Nc6c(/C=N/N1CCN(CC1)C2CCCC2)c(O)c5c4C(=O)[C@@](C)(O/C=C/[C@H](OC)[C@H]3C)Oc4c(C)c(O)c5c6O;
	InChI InChI=1S/C47H64N4O12/c1-24-13-12-14-25(2)46(59)49-37-32(23-48-51-20-18-50(19-21-51)31-15-10-11-16-31)41(56)34-35(42(37)57)40(55)29(6)44-36(34)45(58)47(8,63-44)61-22-17-33(60-9)26(3)43(62-30(7)52)28(5)39(54)27(4)38(24)53/h12-14,17,22-24,26-28,31,33,38-39,43,53-57H,10-11,15-16,18-21H2,1-9H3,(H,49,59)/b13-12+,22-17+,25-14-,48-23+/t24-,26+,27+,28+,33-,38-,39+,43+,47-/m0/s1 ; Key:WDZCUPBHRAEYDL-GZAUEHORSA-N ;
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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.

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.

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