CAS 131959-78-9|CAS 73590-58-6|CAS 161796-78-7|5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazole|antra|5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanes...

General Information

Structure

Molecular Formula

C₁₇H₁₉N₃O₃S

Molecular Mass

345.41606

Exact Mass

345.11471248

Charge

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

Canonic Smiles

COc1ccc2c(c1)[nH]c(n2)S(=O)Cc1ncc(c(c1C)OC)C

Isomeric Smiles

S(=O)(Cc1ncc(c(OC)c1C)C)c1[nH]c2c(n1)ccc(OC)c2

Calculated Properties

JChem

LogD (pH = 7.4)

2.43

LogD (pH = 5.5)

2.36

Log P

2.43

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.68

Polar Surface Area

77.10

Polarizability

37.43

Molar Refractivity

93.66

LOG S

-3.51

Data Source

Names and Identifiers

Synonyms

5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1H-benzo[d]imidazoleZegeridPrilosecPrilosec OTCOmeprazoleOmeprazoleLosec5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazoleAntra6-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazoleMepralZoltumGastrogardMopral(±)-OmeprazoleOmepralGastrolocOMEPomeprazoleEsomeprazole SodiumesomeprazoleOmeprazolum [INN-Latin]OMZOmeprazol [INN-Spanish]EsomeprazoleOmeprazole magnesiumOMPEsomperazole5-methoxy-2-((4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl)-3h-benzoimidazole5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazoleParizacOmaprenAudazolBelmazolLogastricOmeprazen5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole

IUPAC Traditional name

antra 5-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]-3H-1,3-benzodiazole omeprazole

IUPAC name

5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

Brand Name

LensorPrysmaPeptilcerEmeprotonLosecDizprazolGastrimutPepticusOmidPaprazolGastrolocUltopZoltumBelmazolElgamUlcozolMiolSecrepinaOmaprenMiracidPepticumOmeprazonOmezolUlzolOmegastPrazolitInhipumpNopraminAntraNexiumNilsecGibancerTedec UlceralOmpanytOmisecOmepralAulcerUlsenInhibitronDesecUlceralMepralUlcesepAudazolOmesekZimorOcidPrilosecDanloxLomacOsirenMopralOmeprolRegulacidParizacEpirazoleRamezolZefxonNexiamNexium IVOrtanolGasecOzokenOmizacResultUlcometionIndurganLogastricVictrixMoreconCeprandalProcelacZegeridOmebeta 20OmezolanSanamidolOlexinProclorOmedDemeprazolErbolinZepralDudencerExterUlcsepPrazidecPrazentolLucenEsopralAxagon

API Name

Omeprazole

Names and Identifiers

Registration numbers

CAS Number

131959-78-973590-58-6161796-78-7

MDL Number

MFCD00002233MFCD00083192

PubChem CID

4594

PubChem SID

2489787046509065160963685223442771

DrugBank ID

DB00338

CHEMBL

CHEMBL1503

ACToR Database

73590-58-6119141-89-8131959-78-9

NMRShiftDB Database

2003265410018799

VirtualMetabolicHuman Database

KEGG DRUG Database

CHEBI ID

CompTox Database

SABIO-RK Database

SureChEMBL Database

KEGG ID

BKMS React Database

BRENDA Ligand Database

14574

Registration numbers

Properties

Product Information

Pharmacology Properties

Target

adrenergic receptor

Gene Information

human ... ABCB1(5243), CYP1A2(1544)

Mechanism of Action

Proton pump inhibitor

Inhibits gastric acid secretion

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00338

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]

DB00736

Drug Groups

approved; investigational

Description

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

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

Biochem/physiol Actions
Binds covalently to proton pump; inhibits gastric secretion.
Caution
Hygroscopic, photosensitive

TRC

O635000

Binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative.

ChEBI

CHEBI:77260

A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.

Molecule Details

References

PubChem Literature

From Data Sources

• 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

• http://en.wikipedia.org/wiki/Omeprazole

• Muller, P., et al.: Arzneimittel-Forsch., 33, 1685 (1983)

• Wallmark, B., et al.: Biochim. Biophys. Acta., 778, 549 (1983)

• Morii, M., et al.: J. Biol. chem., 268, 21553 (1983)

• Ritter, M., et al.: Br. J. Pharmacol., 124, 627 (1998)

• Creutzfeldt, W., Drug Saf., 1994, 10, 66, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5818, (synonyms)

• Brndstrom, A. et al., Acta Chem. Scand., 1989, 43, 536; 549; 569; 577; 587; 595, (props, bibl)

• Hetzel, D.J., Digestion, Suppl. 1, 1992, 51, 35, (clin trials, rev)

• Ferner, R.E. et al., Human Exp. Toxicol., 1993, 12, 541, (tox, human)

• Yeomans, N.D., Adverse Drug React. Toxicol. Rev., 1994, 13, 145, (tox, rev)

• Maton, P.N., N. Engl. J. Med., 1991, 324, 965, (rev)

• Adams, M.H. et al., Clin. Pharm., 1988, 7, 725, (rev)

• Ohishi, H. et al., Acta Cryst. C, 1989, 45, 1921, (cryst struct)

• Eur. Pat., 1979, Aktiebolag Haessle, 5 129; CA, 92, 198396z, (synth, pharmacol)

• Massoomi, F. et al., Pharmacotherapy (Carlisle, Mass.), 1993, 13, 46, (rev)

• Langtry, H.D. et al., Drugs, 1998, 56, 447-486, (rev)

• Unge, S. et al., Tetrahedron: Asymmetry, 1997, 8, 1967-1970, (bibl, resoln, abs config)

• Wilde, M.I. et al., Drugs, 1994, 48, 91, (rev)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

antra 5-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]-3H-1,3-benzodiazole omeprazole

IUPAC name

5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazole

Brand Name

API Name

Omeprazole

Registration numbers

CAS Number

131959-78-973590-58-6161796-78-7

MDL Number

MFCD00002233MFCD00083192

PubChem CID

4594

PubChem SID

2489787046509065160963685223442771

DrugBank ID

DB00338

CHEMBL

CHEMBL1503

ACToR Database

73590-58-6119141-89-8131959-78-9

NMRShiftDB Database

2003265410018799

VirtualMetabolicHuman Database

KEGG DRUG Database

CHEBI ID

CompTox Database

SABIO-RK Database

SureChEMBL Database

KEGG ID

BKMS React Database

BRENDA Ligand Database

14574

Bioactivity

PubChem BioAssay

Properties

Product Information

Pharmacology Properties

Target

adrenergic receptor

Gene Information

human ... ABCB1(5243), CYP1A2(1544)

Mechanism of Action

Proton pump inhibitor

Inhibits gastric acid secretion

References

PubChem Literature

From Data Sources

• 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

• http://en.wikipedia.org/wiki/Omeprazole

• Muller, P., et al.: Arzneimittel-Forsch., 33, 1685 (1983)

• Wallmark, B., et al.: Biochim. Biophys. Acta., 778, 549 (1983)

• Morii, M., et al.: J. Biol. chem., 268, 21553 (1983)

• Ritter, M., et al.: Br. J. Pharmacol., 124, 627 (1998)

• Creutzfeldt, W., Drug Saf., 1994, 10, 66, (rev)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 5818, (synonyms)

• Brndstrom, A. et al., Acta Chem. Scand., 1989, 43, 536; 549; 569; 577; 587; 595, (props, bibl)

• Hetzel, D.J., Digestion, Suppl. 1, 1992, 51, 35, (clin trials, rev)

• Ferner, R.E. et al., Human Exp. Toxicol., 1993, 12, 541, (tox, human)

• Yeomans, N.D., Adverse Drug React. Toxicol. Rev., 1994, 13, 145, (tox, rev)

• Maton, P.N., N. Engl. J. Med., 1991, 324, 965, (rev)

• Adams, M.H. et al., Clin. Pharm., 1988, 7, 725, (rev)

• Ohishi, H. et al., Acta Cryst. C, 1989, 45, 1921, (cryst struct)

• Eur. Pat., 1979, Aktiebolag Haessle, 5 129; CA, 92, 198396z, (synth, pharmacol)

• Massoomi, F. et al., Pharmacotherapy (Carlisle, Mass.), 1993, 13, 46, (rev)

• Langtry, H.D. et al., Drugs, 1998, 56, 447-486, (rev)

• Unge, S. et al., Tetrahedron: Asymmetry, 1997, 8, 1967-1970, (bibl, resoln, abs config)

• Wilde, M.I. et al., Drugs, 1994, 48, 91, (rev)

Molecule Details

DrugBank

DB00338

Drug Groups

approved; investigational

Description

Indication

For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.

Pharmacology

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]

DB00736

Drug Groups

approved; investigational

Description

Indication

For the treatment of acid-reflux disorders (GERD), peptic ulcer disease, H. pylori eradication, and prevention of gastroinetestinal bleeds with NSAID use.

Pharmacology

Toxicity

Blurred vision, confusion, drowsiness, dry mouth, flushing headache, nausea, rapid heartbeat, sweating

Affected Organisms

Humans and other mammals

Biotransformation

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

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1389

Sigma Aldrich

O104

Biochem/physiol Actions
Binds covalently to proton pump; inhibits gastric secretion.
Caution
Hygroscopic, photosensitive

TRC

O635000

Binds covalently to proton pump. It inhibits gastric secretion. Used as an anttiulcerative.

ChEBI

CHEBI:77260

A member of the class of benzimidazoles that is 1H-benzimidazole which is substituted by a [4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl group at position 2 and a methoxy group at position 5.

Molecule

ID:222