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 ;
	(verify)

Rifapentine, sold under the brand name Priftin, is an antibiotic used in the treatment of tuberculosis.^[2] In active tuberculosis it is used together with other antituberculosis medications.^[2] In latent tuberculosis it is typically used with isoniazid.^[2] It is taken by mouth.^[2]

Common side effects include low neutrophil counts in the blood, elevated liver enzymes, and white blood cells in the urine.^[3] Serious side effects may include liver problems or Clostridioides difficile associated diarrhea.^[3] It is unclear if use during pregnancy is safe.^[3] Rifapentine is in the rifamycin family of medication and works by blocking DNA-dependent RNA polymerase.^[3]

Rifapentine was approved for medical use in the United States in 1998.^[2] It is on the World Health Organization's List of Essential Medicines.^[4]

^ "List of Drugs for an Urgent Public Health Need". Health Canada. 28 June 2017. Retrieved 2 February 2025.
^ ^a ^b ^c ^d ^e "Priftin- rifapentine tablet, film coated". DailyMed. 22 October 2019. Retrieved 6 November 2020.
^ ^a ^b ^c ^d "Rifapentine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[1] "List of Drugs for an Urgent Public Health Need". Health Canada. 28 June 2017. Retrieved 2 February 2025.

[Priftin_FDA_label-2] "Priftin- rifapentine tablet, film coated". DailyMed. 22 October 2019. Retrieved 6 November 2020.

[AHFS2016-3] "Rifapentine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.

[WHO21st-4] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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