Back Rifampisien Afrikaans ريفامبيسين Arabic ریفامپین AZB রিফামপিসিন Bengali/Bangla Rifampicina Catalan ڕیفامپین CKB Rifampicin Czech Rifampicin Danish Rifampicin German Ριφαμπικίνη Greek

Rifampicin

Rifampicin
Clinical data
Pronunciation/rɪˈfæmpəsɪn/
Trade namesRifadin, others
Other namesRifampin (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa682403
License data
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, Intravenous therapy
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability90 to 95% (by mouth)
Protein binding80%
MetabolismLiver and intestinal wall
Elimination half-life3–4 hours
ExcretionUrine (~30%), faeces (60–65%)
Identifiers
  • (7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-{(E)-[(4-methylpiperazin-1-yl)imino]methyl}-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25(29),26-octaen-13-yl acetate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
NIAID ChemDB
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.032.997 Edit this at Wikidata
Chemical and physical data
FormulaC43H58N4O12
Molar mass822.953 g·mol−1
3D model (JSmol)
Melting point183 to 188 °C (361 to 370 °F)
Boiling point937 °C (1,719 °F) [2]
  • CN1CCN(CC1)/N=C/c2c(O)c3c5C(=O)[C@@]4(C)O/C=C/[C@H](OC)[C@@H](C)[C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(\C)C(=O)Nc2c(O)c3c(O)c(C)c5O4
  • InChI=1S/C43H58N4O12/c1-21-12-11-13-22(2)42(55)45-33-28(20-44-47-17-15-46(9)16-18-47)37(52)30-31(38(33)53)36(51)26(6)40-32(30)41(54)43(8,59-40)57-19-14-29(56-10)23(3)39(58-27(7)48)25(5)35(50)24(4)34(21)49/h11-14,19-21,23-25,29,34-35,39,49-53H,15-18H2,1-10H3,(H,45,55)/b12-11+,19-14+,22-13-,44-20+/t21-,23+,24+,25+,29-,34-,35+,39+,43-/m0/s1 checkY
  • Key:JQXXHWHPUNPDRT-WLSIYKJHSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Rifampicin, also known as rifampin, is an ansamycin antibiotic used to treat several types of bacterial infections, including tuberculosis (TB), Mycobacterium avium complex, leprosy, and Legionnaires' disease.[3] It is almost always used together with other antibiotics with two notable exceptions: when given as a "preferred treatment that is strongly recommended"[4] for latent TB infection; and when used as post-exposure prophylaxis to prevent Haemophilus influenzae type b and meningococcal disease in people who have been exposed to those bacteria.[3] Before treating a person for a long period of time, measurements of liver enzymes and blood counts are recommended.[3] Rifampicin may be given either by mouth or intravenously.[3]

Common side effects include nausea, vomiting, diarrhea, and loss of appetite.[3] It often turns urine, sweat, and tears a red or orange color.[3] Liver problems or allergic reactions may occur.[3] It is part of the recommended treatment of active tuberculosis during pregnancy, though its safety in pregnancy is not known.[3] Rifampicin is of the rifamycin group of antibiotics.[3] It works by decreasing the production of RNA by bacteria.[3]

Rifampicin was discovered in 1965, marketed in Italy in 1968, and approved in the United States in 1971.[5][6][7] It is on the World Health Organization's List of Essential Medicines.[8] The World Health Organization classifies rifampicin as critically important for human medicine.[9] It is available as a generic medication.[3] Rifampicin is made by the soil bacterium Amycolatopsis rifamycinica.[7]

  1. ^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
  2. ^ "Rifampicin (CAS 13292-46-1)". Santa Cruz Biotechnology Product Block. Santa Cruz Biotechnology. Archived from the original on 27 November 2014. Retrieved 14 November 2014.
  3. ^ a b c d e f g h i j k "Rifampin". The American Society of Health-System Pharmacists. Archived from the original on 2015-09-07. Retrieved Aug 1, 2015.
  4. ^ Sterling TR, Njie G, Zenner D, Cohn DL, Reves R, Ahmed A, et al. (February 2020). "Guidelines for the Treatment of Latent Tuberculosis Infection: Recommendations from the National Tuberculosis Controllers Association and CDC, 2020". MMWR. Recommendations and Reports. 69 (1). Centers for Disease Control, Atlanta, GA, USA: 1–11. doi:10.15585/mmwr.rr6901a1. PMC 7041302. PMID 32053584.
  5. ^ Sensi P (1983). "History of the development of rifampin". Reviews of Infectious Diseases. 5 (Suppl 3): S402 – S406. doi:10.1093/clinids/5.supplement_3.s402. JSTOR 4453138. PMID 6635432.
  6. ^ Oxford Handbook of Infectious Diseases and Microbiology. OUP Oxford. 2009. p. 56. ISBN 978-0-19-103962-1. Archived from the original on 2015-11-24.
  7. ^ a b McHugh TD (2011). Tuberculosis: diagnosis and treatment. Wallingford, Oxfordshire: CAB International. p. 219. ISBN 978-1-84593-807-9.
  8. ^ 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.
  9. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.
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