Rabeprazole

Structural formula
	1: 1 mixture of ( S ) -form (top) and ( R ) -form (bottom)
General
Non-proprietary name	Rabeprazole
other names	IUPAC : 2 - {[4- (3-methoxypropoxy) -3-methylpyridin-2-yl] methanesulfinyl} -1 H -1,3-benzodiazole;
Molecular formula	C 18 H 21 N 3 O 3 S (rabeprazole) ; C 18 H 20 N 3 NaO 3 S (rabeprazole sodium salt ) ;
Brief description	colorless crystals (rabeprazole) ; colorless crystals (rabeprazole sodium salt) ;
External identifiers / databases
EC number	601-501-2
ECHA InfoCard	100.123.408
PubChem	5029
ChemSpider	4853
DrugBank	DB01129
Wikidata	Q3515
Drug information
ATC code	A02 BC04
Drug class	Proton pump inhibitor ulcer therapeutic
Mechanism of action	Inhibitor of the proton-potassium pump
properties
Molar mass	359.44 g · mol -1 (rabeprazole) ; 381.42 g · mol -1 (· rabeprazole sodium salt) ;
Melting point	99-100 ° C (rabeprazole) ; 140–141 ° C (rabeprazole sodium salt) ;
solubility	Easily soluble in methanol and in water, soluble in ethanol, chloroform and ethyl acetate, insoluble in n -hexane and ether (rabeprazole sodium salt)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Rabeprazole is a drug from the group of proton pump inhibitors that is used to treat gastric and duodenal ulcers as well as reflux esophagitis .

application areas

Treatment and prophylaxis of peptic gastric and duodenal ulcers
Reflux esophagitis
Eradication of Helicobacter pylori (along with two suitable antibiotics )
Zollinger-Ellison Syndrome

Mechanism of action

Rabeprazole acts as an H ⁺ / K ⁺ -ATPase inhibitor . This leads to a reduction in the production of hydrochloric acid in the stomach and the pH of the gastric juice increases. This leads to a lessening of the aggressiveness of the gastric juice and thus to accelerated healing of gastric wall injuries (such as mucosal erosions or ulcers ).

Side effects

Like the other proton pump inhibitors , rabeprazole is considered relatively safe and is largely well tolerated. Common side effects are diarrhea, dizziness, tiredness and headache.

Chemical synthesis and stereoisomerism

The multi-step synthesis of rabeprazole - starting from 2,3-dimethylpyridine - is described in the literature.

Rabeprazole has a stereocenter on the sulfur atom, so it is chiral . The drug is a racemate , i.e. it consists of a 1: 1 mixture of the ( R ) form and the mirror image ( S ) form.

Trade names

Pariet (D, A, CH), Aciphex (USA)

Individual evidence

↑ ^a ^b ^c ^d ^e The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition. 2006, ISBN 0-911910-00-X , p. 1392.
↑ ^a ^b data sheet Rabeprazole sodium, ≥98% (HPLC) from Sigma-Aldrich , accessed on May 9, 2017 ( PDF ).
^ Axel Kleemann , Jürgen Engel, Bernd Kutscher, Dieter Reichert: Pharmaceutical Substances. 5th edition. Thieme-Verlag Stuttgart 2009, ISBN 978-3-13-558405-8 , pp. 1178-1179; also online with biannual additions and updates.

[MerckIndex-1] The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition. 2006, ISBN 0-911910-00-X , p. 1392.

[Sigma-2] ta sheet Rabeprazole sodium, ≥98% (HPLC) from Sigma-Aldrich , accessed on May 9, 2017 ( PDF ).

[Kleemann-3] Axel Kleemann , Jürgen Engel, Bernd Kutscher, Dieter Reichert: Pharmaceutical Substances. 5th edition. Thieme-Verlag Stuttgart 2009, ISBN 978-3-13-558405-8 , pp. 1178-1179; also online with biannual additions and updates.