Rifampicin

Rifampicin
Clinical data
Pronunciation	/rɪˈfæmpəsɪn/
Trade names	Rifadin, others
Other names	Rifampin (USAN US)
AHFS/Drugs.com	Monograph
MedlinePlus	a682403
License data	US DailyMed: Rifampin;
Pregnancy; category	AU: C; ;
Routes of; administration	By mouth, Intravenous therapy
ATC code	J04AB02 (WHO) QJ54AB02 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	90 to 95% (by mouth)
Protein binding	80%
Metabolism	Liver and intestinal wall
Elimination half-life	3–4 hours
Excretion	Urine (~30%), faeces (60–65%)
Identifiers
	IUPAC name (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	13292-46-1 ;
PubChem CID	5381226;
IUPHAR/BPS	2765;
DrugBank	DB01045 ;
ChemSpider	10468813 ;
UNII	VJT6J7R4TR;
KEGG	D00211 ;
ChEBI	CHEBI:28077 ;
ChEMBL	ChEMBL374478 ;
NIAID ChemDB	007228;
PDB ligand	RFP (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID6021244 ;
ECHA InfoCard	100.032.997
Chemical and physical data
Formula	C43H58N4O12
Molar mass	822.953 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	183 to 188 °C (361 to 370 °F)
Boiling point	937 °C (1,719 °F)
	SMILES 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 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 ; Key:JQXXHWHPUNPDRT-WLSIYKJHSA-N ;
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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]

^ "Drug and medical device highlights 2018: Helping you maintain and improve your health". Health Canada. 14 October 2020. Retrieved 17 April 2024.
^ "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.
^ ^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.
^ 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.
^ 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.
^ 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.
^ ^a ^b McHugh TD (2011). Tuberculosis: diagnosis and treatment. Wallingford, Oxfordshire: CAB International. p. 219. ISBN 978-1-84593-807-9.
^ 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.
^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.

[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.

[AHFS2015-3] ^ ^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.

[CDC2020-4] 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.

[Sensi1983-5] 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.

[Ox2009-6] 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.

[Mc2011-7] McHugh TD (2011). Tuberculosis: diagnosis and treatment. Wallingford, Oxfordshire: CAB International. p. 219. ISBN 978-1-84593-807-9.

[WHO21st-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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