Pantoprazole

from Wikipedia, the free encyclopedia
Structural formula
Pantoprazole enantiomers
( R ) shape (top) and ( S ) shape (bottom)
General
Non-proprietary name Pantoprazole
other names
  • ( RS ) -5- (difluoromethoxy) -2 - [(3,4-dimethoxy-2-pyridyl) methylsulfinyl] benzimidazole ( IUPAC )
  • (±) -5- (Difluoromethoxy) -2 - [(3,4-dimethoxy-2-pyridyl) methylsulfinyl] benzimidazole
Molecular formula
  • C 16 H 15 F 2 N 3 O 4 S (pantoprazole)
  • C 16 H 14 F 2 N 3 NaO 4 S (pantoprazole sodium salt )
Brief description

colorless crystalline powder (pantoprazole sodium salt)

External identifiers / databases
CAS number
  • 102625-70-7 (pantoprazole)
  • 138786-67-1 (pantoprazole sodium salt)
  • 164579-32-2 (pantoprazole sodium sesquihydrate)
EC number 600-331-6
ECHA InfoCard 100.111.005
PubChem 4679
ChemSpider 4517
DrugBank DB00213
Wikidata Q286846
Drug information
ATC code

A02 BC02

Drug class

Proton pump inhibitor ulcer therapeutic

Mechanism of action

Inhibitor of the proton-potassium pump

properties
Molar mass
  • 383.37 g · mol -1 (pantoprazole)
  • 405.35 g · mol -1 (· pantoprazole sodium salt)
Physical state

firmly

Melting point

139–140 ° C (pantoprazole)

solubility

Easily soluble in ethanol , soluble in water, poorly in n -hexane

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances

Sodium sesquihydrate

07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

1000 mg kg −1 ( LD 50 ,  mouse ,  oral , sodium salt)

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

Mechanism of action

Pantoprazole works in the parietal cells of the gastric mucosa, where it acts as an irreversible inhibitor of H + / K + -ATPase . This leads to a decrease in the production of hydrochloric acid in the stomach and the pH of the gastric juice increases. This leads to less aggressive gastric juice, which in turn promotes the accelerated healing of gastric wall injuries (e.g. mucosal erosions or gastric ulcers).

Clinical information

application areas

Side effects

Like the other proton pump inhibitors , pantoprazole is considered relatively safe and is largely well tolerated. Rarely occurring side effects include diarrhea, dizziness, tiredness and headache. Occasionally, nausea and vomiting, abdominal pain and allergic skin reactions can occur. A higher number of patients who experienced muscle pain were observed compared to omeprazole .

Thrombocytopenia is very rarely observed. To what extent these are causally caused by the drug has not yet been proven.

A 2013 study found that long-term medication significantly increases the risk of vitamin B 12 deficiency.

According to a 2016 study in Bonn, older people who take pantoprazole or omeprazole for a long time have an increased risk of dementia. "Whether there is a causal relationship or whether it is a matter of random statistical significance remains unclear. The suspicion of a causal relationship exists in any case, according to the researchers clinically verified. " Another objection concerns the different patient characteristics. "Affected patients had an increased number of comorbidities such as depression, stroke and ischemic heart disease, and they took other medication more often. An analysis by the Women's Health Initiative has shown, according to Kuller, that PPI users are more likely to be in poor health and more likely to be obese. "

Like other proton pump inhibitors, pantoprazole is suspected of promoting the development of food allergies .

Interactions

Pantoprazole can cause a false positive result for THC in rapid urine tests .

Stereochemistry

Pantoprazole 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.

Analytics

For the reliable qualitative and quantitative determination of pantoprazole, the coupling of the HPLC with the mass spectrometry is used after sufficient sample preparation .

Development and marketing

Pantoprazole was patented by Byk Gulden (now Takeda ) in 1986 . In 2009 it was released from the prescription requirement in Germany.

Veterinary medicine

It is not allowed to be used in food-producing animals because it is not listed in any appendix to Regulation (EEC) No. 2377/90 on maximum levels for veterinary drug residues in food .

Trade names

Monopreparations

Azidex (A), Azidosan (A), Gastroloc (A), Gastrozol (D, A), Panprabene (A), Panprax (CH), Pantip (A), Pantoloc (A), Pantozol (D, CH), Prazopant (A), Rifun (D), Zurcal (A, CH), Controloc (PL), numerous generics (D, A, CH), Protonix (USA)

Combination preparations

Zacpac (D)

Web links

Individual evidence

  1. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. 2006, ISBN 0-911910-00-X , pp. 1209-1210.
  2. ↑ a b c Entry on pantoprazole. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
  3. ↑ Data sheet PANTOPRAZOLE SODIUM SESQUIHYDRATE CRS (PDF) at EDQM , accessed on June 12, 2009.
  4. ↑ a b Datasheet Pantoprazole sodium hydrate from Sigma-Aldrich , accessed on October 22, 2016 ( PDF ).
  5. ↑ E. Schönig, D. Taubert: Gastrointestinal diseases. In: B. Lemmer , K. Brune (eds.): Pharmakotherapie - Klinische Pharmakologie. 13th edition. Heidelberg 2007, p. 325.
  6. ↑ Package insert PANTOPRAZOLE NYC 40MG , last seen on February 3, 2017.
  7. ↑ J. Labenz, K. Petersen, W. Rösch, H. Koelz: Selection of proton pump inhibitors. In: Deutsches Ärzteblatt. Vol. 99, Issue 37, September 13, 2002, pp. 2425-2429.
  8. ↑ TD Watson, JE Stark, KS Vesta: Pantoprazole-induced thrombocytopenia. In: Ann Pharmacother . 40 (4), Apr 2006, pp. 758-761. PMID 16569810 .
  9. ^ E. Dotan, R. Katz, J. Bratcher, C. Wasserman, M. Liebman et al: The prevalence of pantoprozole associated thrombocytopenia in a community hospital. In: Expert Opin Pharmacother . 8 (13), Sep 2007, pp. 2025-2028. PMID 17714057 .
  10. ↑ Jameson R. Lam, Jennifer L. Schneider, Wei Zhao, Douglas A. Corley: Proton Pump Inhibitor and Histamine 2 Receptor Antagonist Use and Vitamin B12 Deficiency. In: Journal of the American Medical Association . Vol 310, No. December 22, 2013. doi: 10.1001 / jama.2013.280490
  11. ^ Gomm W, von Holt K, Thomé F, Broich K, Maier W, Fink A, Doblhammer G, Haenisch B: Association of Proton Pump Inhibitors With Risk of Dementia: A Pharmacoepidemiological Claims Data Analysis. , JAMA Neurol. 2016 Apr; 73 (4): 410-6, PMID 26882076
  12. ↑ a b pharmacy Adhoc (ed.): Dementia by omeprazole . February 18, 2016 ( apotheke-adhoc.de [accessed October 9, 2017]).
  13. ↑ Deutscher Ärzteverlag GmbH, editorial office of the Deutsches Ärzteblatt: Do proton pump inhibitors increase the risk of dementia? February 16, 2016, accessed February 13, 2020 .
  14. ↑ Susanne C. Diesner, Isabella Pali-Schöll, Erika Jensen-Jarolim, Eva Untersmayr: Mechanisms and risk factors for type 1 food allergies: the role of gastric digestion . In: Wiener Medical Wochenschrift . tape 162 , no. 23 , December 1, 2012, ISSN  1563-258X , p. 513-518 , doi : 10.1007 / s10354-012-0154-4 .
  15. ^ Labeling.pfizer.com
  16. ↑ Jiao H, Li Y, Sun L, Zhang H, Yu L, Yu L, Yuan Z, Xie L, Chen J, Wang Y: A chiral LC-MS / MS method for the enantioselective determination of R - (+) - and S - (-) - pantoprazole in human plasma and its application to a pharmacokinetic study of S - (-) - pantoprazole sodium injection. , Biomed Chromatogr. 2017 Oct; 31 (10), PMID 28370240
  17. ↑ Zhao P, Deng M, Huang P, Yu J, Guo X, Zhao L. Solid-phase extraction combined with dispersive liquid-liquid microextraction and chiral liquid chromatography-tandem mass spectrometry for the simultaneous enantioselective determination of representative proton-pump inhibitors in water samples. , Anal Bioanal Chem. 2016 Sep; 408 (23): 6381-92, PMID 27449644
  18. ↑ Chen M, Xia Y, Ma Z, Li L, Zhong D, Chen X: Validation of a chiral liquid chromatography-tandem mass spectrometry method for the determination of pantoprazole in dog plasma. , J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Oct 1; 906: 85-90, PMID 22959824
  19. ↑ Red List online, as of October 2009.
  20. ↑ AM comp. d. Switzerland, as of October 2009.
  21. ↑ AGES-PharmMed, as of October 2009.