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| CAS No.: | 73590-58-6 |
|---|---|
| Name: | Omeprazole |
| Molecular Structure: | |
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| Formula: | C17H19N3O3S |
| Molecular Weight: | 345.422 |
| Synonyms: | Pepticus;Zoltum;Lensor;Pepticum;Indurgan;1H-Benzimidazole,5-methoxy-2-[[(4-methoxy- 3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-;Prilosec (TN);Omerprazole;Omisec;Gibancer;Prazidec;Ulzol;Omezolan;Ulsen;Ortanol;Victrix;Omeprazon;Omapren;Zimor;Procelac;Dudencer;5-Methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl)benzimidazole;Proclor;Antra;Omesek;Omeprol;Mopral;Gasec;Peptilcer;Nopramin;Tedec Ulceral;Omid;Zegerid;Result;Ulcesep;Gastroloc;Losec;Ompanyt;2-(((3,5-Dimethyl-4-methoxy-2-pyridyl)methyl)sulfinyl)-5-methoxy-1H-benzimidazole;Omed;Prilosec OTC;Antra MUPS;Omeprazolum [INN-Latin];Omebeta 20;Omizac;Zepral;Demeprazol;Ozoken;Omegast;Zefxon;Omeprazol [INN-Spanish];Danlox;Ceprandal;Olexin;Belmazol;Ulcometion;Erbolin;Miracid;Osiren;Prazolit;Ulcozol;Inhipump;Nilsec;Exter;Regulacid; |
| EINECS: | 201-212-8 |
| Density: | 1.371 g/cm3 |
| Melting Point: | 156 °C |
| Boiling Point: | 599.991 °C at 760 mmHg |
| Flash Point: | 316.663 °C |
| Solubility: | Easily soluble in dichloromethane, chloroform and methanol |
| Appearance: | white crystalline solid |
| Hazard Symbols: |
 Xi
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| Risk Codes: | 36/37/38 |
| Safety: | 26-36-37/39 |
| PSA: | 96.31000 |
| LogP: | 3.76540 |
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- 97730-31-9(S)-4'-(2-Methylbutyl)Biphenyl-4-Carbonitrile
- 86604-75-3
2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride
- 37052-78-1
6-methoxy-1H-benzoimidazole-2-thiol
- 73590-58-6
omeprazole
| Conditions | Yield |
|---|---|
| Stage #1: 6-methoxy-1H-benzoimidazole-2-thiol With sodium hydroxide In ethanol; water at 70 - 90℃; Stage #2: 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride With hydrogenchloride In ethanol; water at -10 - 30℃; for 4h; Reflux; | 96% |
- 73590-85-9
omeprazole sulfide
- 73590-58-6
omeprazole
| Conditions | Yield |
|---|---|
| With dihydrogen peroxide; molybdenyl acetylacetonate In methanol; water at 0 - 5℃; for 3h; | 91% |
| With dihydrogen peroxide; sodium carbonate; sodium tungstate In methanol; water at 20℃; for 0.666667h; Product distribution / selectivity; | 91% |
| With sodium hydroxide; dihydrogen peroxide; sodium tungstate In methanol; water at 20℃; for 0.666667h; Product distribution / selectivity; | 88% |
- 1080503-61-2
(-)-menthyl 5-methoxy-2-benzimidazolylsulphinate
- 109371-19-9
2,3,5-trimethyl-4-methoxypyridine
- 73590-58-6
omeprazole
| Conditions | Yield |
|---|---|
| Stage #1: 4-methoxy-2,3,5-trimethylpyridine With n-butyllithium In tetrahydrofuran at -90 - -80℃; for 0.5h; Stage #2: (-)-menthyl 5-methoxy-2-benzimidazolylsulphinate In tetrahydrofuran at -80 - -20℃; Stage #3: With water In tetrahydrofuran at -20℃; | 86% |
- 85-44-9
phthalic anhydride
- 73590-58-6
omeprazole
| Conditions | Yield |
|---|---|
| With sodium hydroxide; dihydrogen peroxide; sodium carbonate In water; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran | 85.9% |
| Conditions | Yield |
|---|---|
| With oxone; sodium hydrogencarbonate; bis(acetylacetonate)oxovanadium In methanol; water at -2 - 0℃; for 5.5h; | A 84% B n/a |
| With oxone; sodium hydrogencarbonate In methanol; water at 0℃; for 5.5h; | A 84% B 0.15% |
| With oxone; sodium hydrogencarbonate In methanol; tetrabutylammomium bromide; water at -2 - 3℃; for 7.5h; Product distribution / selectivity; | A 84% B n/a |
| Conditions | Yield |
|---|---|
| Stage #1: (chloromethyl)-4-methoxy-3,5-dimethylpyridine With [Mg(anthracene)(THF)3] In tetrahydrofuran at -5 - 0℃; Inert atmosphere; Stage #2: C10H12N2O3S In tetrahydrofuran at -5 - 30℃; for 4h; Inert atmosphere; | A n/a B 30% |
- 73590-85-9
omeprazole sulfide
A
- 73590-58-6
omeprazole
| Conditions | Yield |
|---|---|
| With potassium sulfate; potassium hydrogensulfate; potassium peroxomonosulfate In ethanol; acetate buffer at -5℃; pH=5.0; Oxidation; cyclization; |
- 142885-92-5
5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl-1-oxide)methyl]sulfanyl]-1H-benzimidazole
- 73590-58-6
omeprazole
| Conditions | Yield |
|---|---|
| With iodobenzene; silver(I) acetate; Ru(III)(N,N'-bis(salicylidene)-o-phenylenediamine)(triphenylphosphine)Cl In dichloromethane Heating / reflux; | |
| With iodobenzene; silver(I) acetate; Ru(III)(salen)(PPh3)Cl In dichloromethane Heating / reflux; |
- 73590-85-9
omeprazole sulfide
- 73590-58-6
omeprazole
| Conditions | Yield |
|---|---|
| With tert.-butylhydroperoxide; VO(acac)2 In toluene |
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Specification
The Omeprazole, with the CAS registry number 73590-58-6, is also known as 2-(((3,5-Dimethyl-4-methoxy-2-pyridyl)methyl)sulfinyl)-5-methoxy-1H-benzimidazole. It belongs to the product categories of Drug bulk; Active Pharmaceutical Ingredients; Omeprazole; Intermediates & Fine Chemicals; Pharmaceuticals; API's; ATPase. Its EINECS number is 200-636-0. This chemical's molecular formula is C17H19N3O3S and molecular weight is 345.42. What's more, its systematic name is 6-Methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl}-1H-benzimidazole. Its classification codes are: (1)Anti-ulcer agents; (2)Depressant [gastric acid secretory]; (3)Drug / Therapeutic Agent; (4)Enzyme inhibitors; (5)Gastrointestinal Agents; (6)Human Data; (7)Mutation data; (8)Reproductive Effect. This chemical 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. Omeprazole is one of the most widely prescribed drugs internationally and is available over the counter in some countries. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides.
Physical properties of Omeprazole are: (1)ACD/LogP: 2.452; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.39; (4)ACD/LogD (pH 7.4): 2.44; (5)ACD/BCF (pH 5.5): 37.10; (6)ACD/BCF (pH 7.4): 41.57; (7)ACD/KOC (pH 5.5): 443.46; (8)ACD/KOC (pH 7.4): 496.87; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 96.31 Å2; (13)Index of Refraction: 1.669; (14)Molar Refractivity: 94.021 cm3; (15)Molar Volume: 251.869 cm3; (16)Polarizability: 37.273×10-24cm3; (17)Surface Tension: 75.2 dyne/cm; (18)Density: 1.371 g/cm3; (19)Flash Point: 316.663 °C; (20)Enthalpy of Vaporization: 89.315 kJ/mol; (21)Boiling Point: 599.991 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection.
Mechanism of action of Omeprazole: it 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, omeprazole blocks the final step in acid production, thus reducing gastric acidity.
Pharmacokinetics of Omeprazole: The absorption of omeprazole takes place in the small intestine and is usually completed within 3–6 hours. The systemic bioavailability of omeprazole after repeated dose is about 60%. Omeprazole bioavailability is significantly impaired by the presence of food and, therefore, patients should be advised to take omeprazole with a glass of water on an empty stomach (i.e., fast for at least 60 minutes before taking omeprazole). Additionally, most sources recommend that after taking omeprazole at least 30 minutes should be allowed to elapse before eating (at least 60 minutes for immediate-release omeprazole plus sodium bicarbonate products, such as Zegerid), though some sources say that with delayed-release forms of omeprazole it is not necessary to wait before eating after taking the medication. Plasma protein binding is about 95%. Omeprazole is completely metabolized by the cytochrome P450 system, mainly in the liver. Identified metabolites are the sulfone, the sulfide and hydroxy-omeprazole, which exert no significant effect on acid secretion. About 80% of an orally given dose is excreted as metabolites in the urine and the remainder is found in the feces, primarily originating from bile secretion.
You can still convert the following datas into molecular structure:
(1)SMILES: O=S(c2nc1ccc(OC)cc1n2)Cc3ncc(c(OC)c3C)C
(2)Std. 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)
(3)Std. InChIKey: SUBDBMMJDZJVOS-UHFFFAOYSA-N
The toxicity data is as follows:
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD50 | unreported | > 600mg/kg (600mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 33, Pg. 782, 1991. | |
| man | TDLo | oral | 4mg/kg/2W-I (4mg/kg) | MUSCULOSKELETAL: JOINTS | Lancet. Vol. 345, Pg. 461, 1995. |
| mouse | LD50 | intraperitoneal | > 100mg/kg (100mg/kg) | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. | |
| mouse | LD50 | intraperitoneal | > 100mg/kg (100mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. |
| mouse | LD50 | intravenous | 82800ug/kg (82.8mg/kg) | Scandinavian Journal of Gastroenterology, Supplement. Vol. 108, Pg. 53, 1985. | |
| mouse | LD50 | oral | > 4gm/kg (4000mg/kg) | BEHAVIORAL: ATAXIA LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. |
| mouse | LD50 | subcutaneous | > 100mg/kg (100mg/kg) | SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. |
| rat | LD50 | intraperitoneal | > 100mg/kg (100mg/kg) | LUNGS, THORAX, OR RESPIRATION: DYSPNEA SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. |
| rat | LD50 | intravenous | > 50mg/kg (50mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" LUNGS, THORAX, OR RESPIRATION: DYSPNEA SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. |
| rat | LD50 | oral | 2210mg/kg (2210mg/kg) | BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. |
| rat | LD50 | subcutaneous | > 100mg/kg (100mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | Oyo Yakuri. Pharmacometrics. Vol. 36, Pg. 369, 1988. |
| women | TDLo | oral | 800ug/kg/2D-I (.8mg/kg) | LUNGS, THORAX, OR RESPIRATION: COUGH LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION | Pharmacotherapy Vol. 14, Pg. 119, 1993. |
| women | TDLo | oral | 4400ug/kg/11D (4.4mg/kg) | KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED" | American Journal of Gastroenterology. Vol. 94, Pg. 1119, 1999. |
| women | TDLo | oral | 24mg/kg/60D-I (24mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BLOOD: NORMOCYTIC ANEMIA | Postgraduate Medical Journal. Vol. 74, Pg. 416, 1998. |
| women | TDLo | oral | 30mg/kg/10W-I (30mg/kg) | BLOOD: EOSINOPHILIA SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS | American Journal of Medicine. Vol. 95, Pg. 248, 1993. |
| women | TDLo | oral | 36400ug/kg/13 (36.4mg/kg) | BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | Journal of Clinical Gastroenterology. Vol. 25, Pg. 718, 1997. |