Pantoprazole magnesiumProduct ingredient for Pantoprazole

Name
Pantoprazole magnesium
Drug Entry
Pantoprazole

Pantoprazole is a first-generation proton pump inhibitor (PPI) used for the management of gastroesophageal reflux disease (GERD), for gastric protection to prevent recurrence of stomach ulcers or gastric damage from chronic use of NSAIDs, and for the treatment of pathological hypersecretory conditions including Zollinger-Ellison (ZE) Syndrome. It can also be found in quadruple regimens for the treatment of H. pylori infections along with other antibiotics including amoxicillin, clarithromycin, and metronidazole, for example.1023 Its efficacy is considered similar to other medications within the PPI class including omeprazole, esomeprazole, lansoprazole, dexlansoprazole, and rabeprazole.

Pantoprazole exerts its stomach acid-suppressing effects by preventing the final step in gastric acid production by covalently binding to sulfhydryl groups of cysteines found on the (H+, K+)-ATPase enzyme at the secretory surface of gastric parietal cell. This effect leads to inhibition of both basal and stimulated gastric acid secretion, irrespective of the stimulus. As the binding of pantoprazole to the (H+, K+)-ATPase enzyme is irreversible and new enzyme needs to be expressed in order to resume acid secretion, pantoprazole's duration of antisecretory effect persists longer than 24 hours.Label

Due to their good safety profile and as several PPIs are available over the counter without a prescription, their current use in North America is widespread. Long term use of PPIs such as pantoprazole have been associated with possible adverse effects, however, including increased susceptibility to bacterial infections (including gastrointestinal C. difficile), reduced absorption of micronutrients including iron and B12, and an increased risk of developing hypomagnesemia and hypocalcemia which may contribute to osteoporosis and bone fractures later in life.12

PPIs such as pantoprazole have also been shown to inhibit the activity of dimethylarginine dimethylaminohydrolase (DDAH), an enzyme necessary for cardiovascular health. DDAH inhibition causes a consequent accumulation of the nitric oxide synthase inhibitor asymmetric dimethylarginie (ADMA), which is thought to cause the association of PPIs with increased risk of cardiovascular events in patients with unstable coronary syndromes.14,15

Pantoprazole doses should be slowly lowered, or tapered, before discontinuing as rapid discontinuation of PPIs such as pantoprazole may cause a rebound effect and a short term increase in hypersecretion.13

Accession Number
DBSALT000853
Structure
Thumb
Synonyms
Magnesium pantoprazole / Pantoprazole hemimagnesium
UNII
1AL13B11R4
CAS Number
199387-73-0
Weight
Average: 789.03
Monoisotopic: 788.11965859
Chemical Formula
C32H28F4MgN6O8S2
InChI Key
RDRUTBCDIVCMMX-UHFFFAOYSA-N
InChI
InChI=1S/2C16H14F2N3O4S.Mg/c2*1-23-13-5-6-19-12(14(13)24-2)8-26(22)16-20-10-4-3-9(25-15(17)18)7-11(10)21-16;/h2*3-7,15H,8H2,1-2H3;/q2*-1;+2
IUPAC Name
magnesium(2+) ion bis(6-(difluoromethoxy)-2-[(3,4-dimethoxypyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazol-1-ide)
SMILES
[Mg++].COC1=CC=NC(CS(=O)C2=NC3=CC=C(OC(F)F)C=C3[N-]2)=C1OC.COC1=CC=NC(CS(=O)C2=NC3=CC=C(OC(F)F)C=C3[N-]2)=C1OC
PubChem Compound
71587624
ChemSpider
32700176
Predicted Properties
PropertyValueSource
Water Solubility0.0475 mg/mLALOGPS
logP4.09ALOGPS
logP2.18ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.15ChemAxon
pKa (Strongest Basic)3.55ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area83.43 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity90.66 m3·mol-1ChemAxon
Polarizability36.16 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon