Rifapentine

Rifapentine
Clinical data
Trade namesPriftin
Other names3{[(4-cyclopentyl-1-piperazinyl)imino]methyl}rifamycin
AHFS/Drugs.comMonograph
MedlinePlusa616011
License data
Routes of
administration		By mouth
Drug classMacrolactam
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityincreases when administered with food
Identifiers
  • (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
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.057.021 Edit this at Wikidata
Chemical and physical data
FormulaC47H64N4O12
Molar mass877.045 g·mol−1
3D model (JSmol)
Melting point179 to 180 °C (354 to 356 °F)
  • 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=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 checkY
  • Key:WDZCUPBHRAEYDL-GZAUEHORSA-N checkY
  (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 Clostridium 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] In many areas of the world it is not easy to get as of 2015.[5]

  1. ^ "Rifapentine (Priftin) Use During Pregnancy". Drugs.com. 2 December 2019. Retrieved 16 March 2020.
  2. ^ a b c d e "Priftin- rifapentine tablet, film coated". DailyMed. 22 October 2019. Retrieved 6 November 2020.
  3. ^ a b c d "Rifapentine". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  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.
  5. ^ Nieburg P, Dubovi T, Angelo S (2015). Tuberculosis—A Complex Health Threat: A Policy Primer of Global TB Challenges. Rowman & Littlefield. p. 15. ISBN 9781442240957. Archived from the original on 2016-12-20.