ChemFOnt: Showing chemical card for (S)-Esomeprazole (CFc000009207)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:16 UTC

Chemfont ID

CFc000009207

Molecule Identification

Common Name

(S)-Esomeprazole

Definition

Esomeprazole is only found in individuals that have used or taken this drug. It is a highly effective inhibitor of gastric acid secretion used in the therapy of stomach ulcers and Zollinger-Ellison syndrome. The drug inhibits the H(+)-K(+)-ATPase (H(+)-K(+)-exchanging ATPase) in the proton pump of gastric parietal cells. [PubChem]Esomeprazole is a proton pump inhibitor that suppresses gastric acid secretion by specific inhibition of the H⁺/K⁺-ATPase in the gastric parietal cell. By acting specifically on the proton pump, Esomeprazole blocks the final step in acid production, thus reducing gastric acidity.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Omeprazole	ChEBI
(S)-(-)-Omeprazole	ChEBI
(S)-Omeprazole	ChEBI
Alenia	ChEBI
Escz	ChEBI
Esofag	ChEBI
Esomeprazol	ChEBI
Esomeprazolum	ChEBI
Inexium paranova	ChEBI
(S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole	HMDB
(S)-5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole	HMDB
Esomeprazole strontium anhydrous	HMDB
Strontium, esomeprazole	HMDB
Esomeprazole sodium	HMDB
Esomeprazole strontium	HMDB
Nexium	HMDB
AstraZeneca brand OF esomeprazole magnesium	HMDB
Esomeprazole magnesium	HMDB
Esomeprazole potassium	HMDB

Chemical Formula

C₁₇H₁₉N₃O₃S

Average Molecular Weight

345.416

Monoisotopic Molecular Weight

345.114712179

IUPAC Name

5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

Traditional Name

5-methoxy-2-[(S)-(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

CAS Registry Number

161796-78-7

SMILES

COC1=CC2=C(NC(=N2)[S@@](=O)CC2=NC=C(C)C(OC)=C2C)C=C1

InChI Identifier

InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)/t24-/m0/s1

InChI Key

SUBDBMMJDZJVOS-DEOSSOPVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sulfinylbenzimidazoles. These are polycyclic aromatic compounds containing a sulfinyl group attached at the position 2 of a benzimidazole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzimidazoles

Sub Class

Sulfinylbenzimidazoles

Direct Parent

Sulfinylbenzimidazoles

Alternative Parents

Substituents

Sulfinylbenzimidazole
Anisole
Alkyl aryl ether
Methylpyridine
Pyridine
Benzenoid
Azole
Imidazole
Heteroaromatic compound
Sulfoxide
Azacycle
Ether
Sulfinyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

5-methoxy-2-\{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl\}-1H-benzimidazole (CHEBI:50275 )

Functional Ontology

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014874)
Cell membrane (HMDB: HMDB0014874)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0014874)

Source

Exogenous

Exogenous (HMDB: HMDB0014874)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Esomeprazole Action Pathway (HMDB: HMDB0014874)
Esomeprazole Action Pathway (PathBank: SMP0000225)

Metabolic pathway

Esomeprazole Metabolism Pathway (HMDB: HMDB0014874)
Esomeprazole Metabolism Pathway (PathBank: SMP0000612)

Role

Industrial application

Pharmaceutical industry

Anti-histamine (HMDB: HMDB0014874)

Enzyme Inhibitor (HMDB: HMDB0014874)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.35 g/L	ALOGPS
logP	1.66	ALOGPS
logP	2.43	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	4.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	77.1 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	93.66 m³·mol⁻¹	ChemAxon
Polarizability	35.81 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon