Rifampicin

Structural formula
General
Non-proprietary name	Rifampicin
other names	5,6,9,17,19,21-hexahydroxy-23-methoxy-2,4,12,16,18,20,22-heptamethyl-8- [ N - (4-methyl-1-piperazinyl) formimidoyl] -2,7- (epoxypentadeca- [1,11,13] trienimino) -naphtho [2,1- b ] furan-1,11 (2 H ) -dione-21-acetate ( IUPAC ); Rifampin; RMP;
Molecular formula	C 43 H 58 N 4 O 12
Brief description	red to orange, crystalline powder (from acetone)
External identifiers / databases
EC number	236-312-0
ECHA InfoCard	100.032.997
PubChem	5381226
ChemSpider	10468813
DrugBank	DB01045
Wikidata	Q422652
Drug information
ATC code	J04 AB02
Drug class	antibiotic
Mechanism of action	Transcription inhibitors
properties
Molar mass	822.94 g mol −1
Physical state	firmly
Melting point	183–188 ° C (decomposition)
pK s value	1.7
solubility	Easily soluble in chloroform , dimethyl sulfoxide ; soluble in ethyl acetate , methanol , tetrahydrofuran ; sparingly soluble in water (pH <6), acetone ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335
	P: 261-305 + 351 + 338
Toxicological data	1570 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rifampicin is a bactericidally effective antibiotic from the group of ansamycins . It is semi-synthetically from rifamycin B , isolated from Amycolatopsis rifamycinica , manufactured.

Rifampicin is mainly used in infections with mycobacteria , especially in tuberculosis and leprosy . It is also used in the therapy of methicillin-resistant staphylococci . It will also prophylactically in contacts of patients at Meningococcal - Meningitis recommended. It is also effective against enterococci and Legionella pneumophila and is easily accessible to liquor .

Rifampicin is an ansa compound .

pharmacology

Rifampicin inhibits bacterial DNA- dependent RNA polymerase . In this way, the transcription of the bacteria is specifically inhibited.

Rifampicin is usually combined with at least one other effective antibiotic (such as isoniazid ). Since it is chemically different from almost all other antibiotics, there is no cross-resistance with these active ingredients .

Side effects and contraindications

Liver damage is known to be the most important side effect, so regular monitoring of liver values is necessary, and diseases of the liver are a contraindication. The occurrence of Redman syndrome has been described.

When taken, rifampicin causes body fluids ( saliva , urine , tears , etc.) to turn red-orange .

Teratogenicity has been proven in animal experiments with rifampicin, and pregnancy is accordingly a contraindication.

interaction

Like all drugs that induce enzyme induction in the liver cells (e.g. barbiturates , hydantoin ), rifampicin (induction of the cytochrome P450 isoenzymes 1A2, 2C8 and 3A) also reduces the effectiveness of oral contraceptives (" birth control pills "). It also induces p-glycoprotein , which is important for drugs that are substrates thereof. It also ensures an increased breakdown of L-thyroxine.

Trade names

Monopreparations
Eremfat (D, A), Rifa (D), Rimactan (A, CH), various generics (D, CH)

Combination
preparations Iso-Eremfat (D), Rifater (D, A, CH), Rifinah (D, CH), Rifoldin (A), Rimactazid (CH), Rimstar (CH), Tebesium Duo / -Trio (D)

Individual evidence

↑ ^a ^b ^c ^d ^e ^f The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals . 14th edition. Merck & Co., Whitehouse Station NJ 2009, ISBN 978-0-911910-00-1 .
↑ ^a ^b ^c data sheet rifampicin from Sigma-Aldrich , accessed on December 9, 2015 ( PDF ).
↑ S. Bala, R. Khanna et al. a .: Reclassification of Amycolatopsis mediterranei DSM 46095 as Amycolatopsis rifamycinica sp. nov. In: International journal of systematic and evolutionary microbiology. Volume 54, No. 4, July 2004, pp. 1145-1149, doi: 10.1099 / ijs.0.02901-0 . PMID 15280283 .
↑ ^a ^b ^c ^d Rifampicin-Hefa-N 300mg. Medikamio, January 23, 2012, accessed February 16, 2016 .
↑ Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt , Volume 116, Issue 29 f., July 22, 2019, pp. 508-517, p. 510.
↑ Petra Zagermann-Muncke: When drugs influence transport proteins . In: Pharmaceutical newspaper . No. 50 , 2006 ( online ).
↑ R. Gärtner: Thyroid hormone therapy . In: German Medical Weekly . tape 138 , no. 27 , 2013, p. 1413-1424 , doi : 10.1055 / s-0032-1327385 .
↑ Red List Online, as of August 2009.
↑ AM comp. d. Switzerland, as of August 2009.
↑ AGES-PharmMed, as of August 2009.

[MERCK_Index-1] ↑ ^a ^b ^c ^d ^e ^f The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals . 14th edition. Merck & Co., Whitehouse Station NJ 2009, ISBN 978-0-911910-00-1 .

[Sigma-2] ta sheet rifampicin from Sigma-Aldrich , accessed on December 9, 2015 ( PDF ).

[PMID15280283-3] S. Bala, R. Khanna et al. a .: Reclassification of Amycolatopsis mediterranei DSM 46095 as Amycolatopsis rifamycinica sp. nov. In: International journal of systematic and evolutionary microbiology. Volume 54, No. 4, July 2004, pp. 1145-1149, doi: 10.1099 / ijs.0.02901-0 . PMID 15280283 .

[diagnosia-4] Rifampicin-Hefa-N 300mg. Medikamio, January 23, 2012, accessed February 16, 2016 .

[5] Torsten Kratz, Albert Diefenbacher: Psychopharmacotherapy in old age. Avoidance of drug interactions and polypharmacy. In: Deutsches Ärzteblatt , Volume 116, Issue 29 f., July 22, 2019, pp. 508-517, p. 510.

[pharmZ-6] Petra Zagermann-Muncke: When drugs influence transport proteins . In: Pharmaceutical newspaper . No. 50 , 2006 ( online ).

[Schilddrüse-7] R. Gärtner: Thyroid hormone therapy . In: German Medical Weekly . tape 138 , no. 27 , 2013, p. 1413-1424 , doi : 10.1055 / s-0032-1327385 .

[8] Red List Online, as of August 2009.

[9] AM comp. d. Switzerland, as of August 2009.

[10] AGES-PharmMed, as of August 2009.