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73590-58-6

73590-58-6 structure

Name: omeprazole
Chemical Name: 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole
CAS Number: 73590-58-6
Molecular Formula: C₁₇H₁₉N₃O₃S
Molecular Weight: 345.416
Catalog: API Digestive system medication Inhibition of gastric acid secretion
Create Date: 2018-02-03 08:00:00
Modify Date: 2024-01-02 00:24:34
Omeprazole(Prilosec) is a proton pump inhibitor used in the treatment of dyspepsia.Target: Proton PumpOmeprazole is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease, gastroesophageal reflux disease, laryngopharyngeal reflux, and Zollinger-Ellison syndrome. Omeprazole virtually eliminated intragastric acidity in all patients: the median 24 hour intragastric pH rose from 1.4 to 5.3 and the mean hourly hydrogen ion activity fell from 38.50 to 1.95 mmol(mEq)/1 (p less than 0.001). This inhibition of 24 hour intragastric acidity is more profound than that previously reported with either cimetidine 1 g daily or ranitidine 300 mg daily [1]. The pharmacokinetics of omeprazole were studied in a group of healthy male subjects after single and repeated oral doses of 30 and 60 mg. Absorption of omeprazole from its enteric-coated formulation was unpredictable. There was a highly significant increase in the area under the plasma concentration time curve (AUC) after repeated dosing. Omeprazole increases its own relative availability following repeated dosing. This may be due to inhibition of gastric acid secretion by omeprazole which is an acid-labile compound [2].Clinical indications: Duodenal ulcer; Endocrine tumor; Esophagitis; Gastroesophageal reflux; Helicobacter pylori infection; Stomach ulcer; Zollinger-Ellison syndromeToxicity: Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.

Name	5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole
Synonyms	5-methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)-methylsulfinyl]benzimidazole 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole Omepral (RS)-5-Methoxy-2-(4-methoxy-3,5-dimethyl-2-pyridylmethylsulphinyl)benzimidazole elgam ANTRA MEPRAL Zoltum 1H-Benzimidazole, 5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulfinyl)- [14C]-Omeprazole PRILOSEC (-)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole zimor Losec Omeprazen Pepticum prysma 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole EINECS 201-212-8 (±)-Omeprazole MFCD00083192 Omeprazole 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulphinyl]-1H-benzimidazole aulcer 6-Methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole 5-Methoxy-2-{[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl}-1H-benzimidazole 1H-Benzimidazole, 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]- sulfonium, hydroxy(6-methoxy-1H-benzimidazol-2-yl)[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-, inner salt ulcsep 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulphinyl]-1H-benzimidazole Miol Gastrogard

Description	Omeprazole(Prilosec) is a proton pump inhibitor used in the treatment of dyspepsia.Target: Proton PumpOmeprazole is a proton pump inhibitor used in the treatment of dyspepsia, peptic ulcer disease, gastroesophageal reflux disease, laryngopharyngeal reflux, and Zollinger-Ellison syndrome. Omeprazole virtually eliminated intragastric acidity in all patients: the median 24 hour intragastric pH rose from 1.4 to 5.3 and the mean hourly hydrogen ion activity fell from 38.50 to 1.95 mmol(mEq)/1 (p less than 0.001). This inhibition of 24 hour intragastric acidity is more profound than that previously reported with either cimetidine 1 g daily or ranitidine 300 mg daily [1]. The pharmacokinetics of omeprazole were studied in a group of healthy male subjects after single and repeated oral doses of 30 and 60 mg. Absorption of omeprazole from its enteric-coated formulation was unpredictable. There was a highly significant increase in the area under the plasma concentration time curve (AUC) after repeated dosing. Omeprazole increases its own relative availability following repeated dosing. This may be due to inhibition of gastric acid secretion by omeprazole which is an acid-labile compound [2].Clinical indications: Duodenal ulcer; Endocrine tumor; Esophagitis; Gastroesophageal reflux; Helicobacter pylori infection; Stomach ulcer; Zollinger-Ellison syndromeToxicity: Symptoms of overdose include confusion, drowsiness, blurred vision, tachycardia, nausea, diaphoresis, flushing, headache, and dry mouth.
Related Catalog	Signaling Pathways >> Autophagy >> Autophagy Signaling Pathways >> Membrane Transporter/Ion Channel >> Proton Pump Research Areas >> Metabolic Disease
References	[1]. Walt, R.P., et al., Effect of daily oral omeprazole on 24 hour intragastric acidity. Br Med J (Clin Res Ed), 1983. 287(6384): p. 12-4. [2]. Howden, C.W., et al., Oral pharmacokinetics of omeprazole. Eur J Clin Pharmacol, 1984. 26(5): p. 641-3.

Density	1.4±0.1 g/cm3
Boiling Point	600.0±60.0 °C at 760 mmHg
Melting Point	156ºC
Molecular Formula	C₁₇H₁₉N₃O₃S
Molecular Weight	345.416
Flash Point	316.7±32.9 °C
Exact Mass	345.114716
PSA	96.31000
LogP	2.17
Vapour Pressure	0.0±1.7 mmHg at 25°C
Index of Refraction	1.669
Storage condition	2-8°C
Stability	Stable, but hygroscopic and photosensitive. Incompatible with strong oxidizing agents. Store in the dark.
Water Solubility	H2O: 0.5 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DD9087000

CHEMICAL NAME :: 1H-Benzimidazole, 5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)met hyl)sulfinyl)-

CAS REGISTRY NUMBER :: 73590-58-6

LAST UPDATED :: 199806

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C17-H19-N3-O3-S

MOLECULAR WEIGHT :: 345.45

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 800 ug/kg/2D-I

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 30 mg/kg/10W-I

TOXIC EFFECTS :: Blood - eosinophilia Kidney, Ureter, Bladder - interstitial nephritis Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 4 mg/kg/2W-I

TOXIC EFFECTS :: Musculoskeletal - joints Biochemical - Metabolism (Intermediary) - effect on inflammation or mediation of inflammation

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2210 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Gastrointestinal - hypermotility, diarrhea Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >50 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Gastrointestinal - hypermotility, diarrhea Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Skin and Appendages - hair Nutritional and Gross Metabolic - body temperature decrease

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >100 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - ptosis Behavioral - altered sleep time (including change in righting reflex) Skin and Appendages - dermatitis, other (after systemic exposure)

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 82800 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 8320 mg/kg

SEX/DURATION :: female 17-20 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 3520 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects

TYPE OF TEST :: DNA damage

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 262,73,1991

Symbol	GHS07
Signal Word	Warning
Hazard Statements	H315-H319-H335
Precautionary Statements	P305 + P351 + P338
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes	Xi:Irritant;
Risk Phrases	R36/37/38
Safety Phrases	S26-S36
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	DD9087000

Precursor 8
73590-85-9 1080503-61-2 109371-19-9 142885-92-5
408332-88-7 13811-71-7 861359-74-2 26787-78-0
DownStream 7
109371-19-9 37052-78-1 60-54-8 119141-89-8
119141-88-7 1227380-90-6 26787-78-0

73590-58-6	119141-89-8
161973-10-0	161796-78-7
119141-88-7	934293-92-2
922731-01-9	161796-77-6
95510-70-6	92340-57-3
1158522-08-7	940364-43-2
134104-43-1	117338-88-2
131615-57-1	6906-52-1
930439-75-1	1018584-77-4
1375289-11-4	849349-65-1