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161796-78-7 molecular structure
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6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

ChemBase ID: 222
Molecular Formular: C17H19N3O3S
Molecular Mass: 345.41606
Monoisotopic Mass: 345.11471248
SMILES and InChIs

SMILES:
S(=O)(Cc1ncc(c(OC)c1C)C)c1[nH]c2c(n1)ccc(OC)c2
Canonical SMILES:
COc1ccc2c(c1)[nH]c(n2)S(=O)Cc1ncc(c(c1C)OC)C
InChI:
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)
InChIKey:
SUBDBMMJDZJVOS-UHFFFAOYSA-N

Cite this record

CBID:222 http://www.chembase.cn/molecule-222.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
IUPAC Traditional name
5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-3H-1,3-benzodiazole
5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
antra
omeprazole
Brand Name
Nexiam
Nexium
Nexium IV
Lucen
Esopral
Axagon
Antra
Audazol
Aulcer
Belmazol
Ceprandal
Danlox
Demeprazol
Desec
Dizprazol
Dudencer
Elgam
Emeproton
Epirazole
Erbolin
Exter
Gasec
Gastrimut
Gastroloc
Gibancer
Indurgan
Inhibitron
Inhipump
Lensor
Logastric
Lomac
Losec
Mepral
Miol
Miracid
Mopral
Morecon
Nilsec
Nopramin
Ocid
Olexin
Omapren
Omebeta 20
Omed
Omegast
Omepral
Omeprazon
Omeprol
Omesek
Omezol
Omezolan
Omid
Omisec
Omizac
Ompanyt
Ortanol
Osiren
Ozoken
Paprazol
Parizac
Pepticum
Pepticus
Peptilcer
Prazentol
Prazidec
Prazolit
Prilosec
Procelac
Proclor
Prysma
Ramezol
Regulacid
Result
Sanamidol
Secrepina
Tedec Ulceral
Ulceral
Ulcesep
Ulcometion
Ulcozol
Ulcsep
Ulsen
Ultop
Ulzol
Victrix
Zefxon
Zegerid
Zepral
Zimor
Zoltum
Synonyms
Esomeprazole Sodium
Esomperazole
esomeprazole
Esomeprazole
6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
(±)-Omeprazole
Gastrogard
Gastroloc
Mepral
Mopral
Omepral
Zoltum
Audazol
Belmazol
Logastric
Omapren
Omeprazen
Parizac
5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole
Omeprazol [INN-Spanish]
Omeprazolum [INN-Latin]
OMEP
OMZ
OMP
Omeprazole magnesium
omeprazole
Omeprazole
Prilosec
Zegerid
Prilosec OTC
5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
Antra
Losec
Omeprazole
5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole
5-methoxy-2-((4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl)-3h-benzoimidazole
CAS Number
161796-78-7
131959-78-9
73590-58-6
MDL Number
MFCD00083192
MFCD00002233
PubChem SID
46509065
24897870
160963685
PubChem CID
4594

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.294158  H Acceptors
H Donor LogD (pH = 5.5) 2.361715 
LogD (pH = 7.4) 2.4276938  Log P 2.433509 
Molar Refractivity 93.6623 cm3 Polarizability 37.349922 Å3
Polar Surface Area 77.1 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.66  LOG S -2.98 
Solubility (Water) 3.59e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
82.3 mg/L expand Show data source
Acetonitrile expand Show data source
DMSO expand Show data source
DMSO: >19 mg/mL expand Show data source
Ethanol expand Show data source
ethanol: soluble4.5 mg/mL expand Show data source
H2O: soluble0.5 mg/mL expand Show data source
Very slightly soluble in water expand Show data source
Apperance
white solid expand Show data source
White to Off-White Solid expand Show data source
Melting Point
148-150°C (dec.) expand Show data source
Hydrophobicity(logP)
0.6 expand Show data source
2.565 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
DD9087000 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
adrenergic receptor expand Show data source
Gene Information
human ... ABCB1(5243), CYP1A2(1544) expand Show data source
Mechanism of Action
Inhibits gastric acid secretion expand Show data source
Proton pump inhibitor expand Show data source
Purity
95% expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antiulcer agent expand Show data source
Pharmacopeia Traceability
traceable to BP 765 expand Show data source
traceable to PhEur O0150000 expand Show data source
traceable to USP 1478505 expand Show data source
Empirical Formula (Hill Notation)
C17H19N3O3S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00338 external link
Item Information
Drug Groups approved; investigational
Description 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]
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacology Omeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Omeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase at the secretory surface of the gastric parietal cell. As a result, it inhibits acid secretion into the gastric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
Toxicity Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic.
Absorption Absorption is rapid, absolute bioavailability (compared to intravenous administration) is about 30-40% at doses of 20-40 mg.
Half Life 0.5-1 hour
Protein Binding 95%
Elimination Urinary excretion is a primary route of excretion of omeprazole metabolites.
Clearance * total body cl=500-600 mL/min [healthy]
* 250 mL/min [Geriatric]
* 70 mL/min [Hepatic Impairment]
* 10 - 62 mL/min/1.73 m2 [Renal Impairment]
References
Yang YX, Lewis JD, Epstein S, Metz DC: Long-term proton pump inhibitor therapy and risk of hip fracture. JAMA. 2006 Dec 27;296(24):2947-53. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
DrugBank - DB00736 external link
Item Information
Drug Groups approved; investigational
Description 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]
Indication For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.
Pharmacology Esomeprazole is a compound that inhibits gastric acid secretion and is indicated in the treatment of gastroesophageal reflux disease (GERD), the healing of erosive esophagitis, and H. pylori eradication to reduce the risk of duodenal ulcer recurrence. Esomeprazole belongs to a new class of antisecretory compounds, the substituted benzimidazoles, that do not exhibit anticholinergic or H2 histamine antagonistic properties, but that suppress gastric acid secretion by specific inhibition of the H+/K+ ATPase at the secretory surface of the gastric parietal cell. By doing so, it inhibits acid secretion into the gsatric lumen. This effect is dose-related and leads to inhibition of both basal and stimulated acid secretion irrespective of the stimulus.
Toxicity Blurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating
Affected Organisms
Humans and other mammals
Biotransformation Mainly hepatic. Esomeprazole is completely metabolized by the cytochrome P450 system via CYP2C19 and CYP3A4. Metabolism produces inactive hydroxy and desmethyl metabolites, which have no effect on gastric acid secretion. Less than 1% of the parent drug is excreted in urine.
Absorption 90%
Half Life 1-1.5 hours
Protein Binding 97%
Elimination Approximately 80% of the administered dose of esomeprazole is excreted as metabolites in urine and the remaining 20% is excreted in feces.
Distribution * 16 L [healthy volunteers]
References
Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1389 external link
Research Area: Gastro-oesophageal reflux
Biological Activity:
Omeprazole(Prilosec) is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease (PUD), gastroesophageal reflux disease (GORD/GERD), laryngopharyngeal reflux (LPR), and Zollinger-Ellison syndrome. [1]
Sigma Aldrich - O104 external link
Biochem/physiol Actions
Binds covalently to proton pump; inhibits gastric secretion.
Caution
Hygroscopic, photosensitive
Toronto Research Chemicals - O635000 external link
Binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Yang YX, Lewis JD, Epstein S, Metz DC: Long-term proton pump inhibitor therapy and risk of hip fracture. JAMA. 2006 Dec 27;296(24):2947-53. Pubmed
  • • Lind T, Rydberg L, Kyleback A, Jonsson A, Andersson T, Hasselgren G, Holmberg J, Rohss K: Esomeprazole provides improved acid control vs. omeprazole In patients with symptoms of gastro-oesophageal reflux disease. Aliment Pharmacol Ther. 2000 Jul;14(7):861-7. Pubmed
  • •  http://en.wikipedia.org/wiki/Omeprazole
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PATENTS

PATENTS

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INTERNET

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