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

CAS No. 73590-58-6

Formula: C17H19N3O3S
Basic Info

Omeprazole, sold under the brand names Prilosec and Losec among others, is a medication used in the treatment of gastroesophageal reflux disease, peptic ulcer disease, and Zollinger–Ellison syndrome. It is also used to prevent upper gastrointestinal bleeding in people who are at high risk. It can be taken by mouth or injected into a vein.
Common side effects include nausea, vomiting, headaches, and increased intestinal gas. Serious side effects may include Clostridium difficile colitis, an increased risk of pneumonia, an increased risk of bone fractures, and the potential of masking stomach cancer. It is unclear if it is safe for use in pregnancy. Omeprazole is a proton pump inhibitor and as such blocks the release of stomach acid.
Omeprazole was discovered in 1979. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system. It is available as a generic medication. The wholesale cost in the developing world as of 2014 is 0.01 to 0.07 USD per dose. In the United States it costs about 1.00 USD per pill.

Formula
C17H19N3O3S
Molecular Weight
345.416
Exact Mass
345.115
LogP
3.7654
PSA
96.31
Synonyms

ulcsep

MEPRAL

(RS)-5-Methoxy-2-(4-methoxy-3,5-dimethyl-2-pyridylmethylsulphinyl)benzimidazole

5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulphinyl]-1H-benzimidazole

5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

prysma

elgam

miol

ZOLTUM

5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulphinyl]-1H-benzimidazole

Omeprazole

(-)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole

aulcer

ANTRA

[14C]-Omeprazole

zimor

LOSEC

5-methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)-methylsulfinyl]benzimidazole

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Properties
Appearance & Physical State
white solid
Density
1.37 g/cm3
Boiling Point
600ºC at 760 mmHg
Melting Point
156ºC
Flash Point
316.7ºC
Stability
Stable, but hygroscopic and photosensitive. Incompatible with strong oxidizing agents. Store in the dark.
Storage Condition
2-8ºC
Safety Info
Safety Statements
S26-S36
WGK Germany
2
Risk Statements
R36/37/38
Hazard Codes
Spectrum
NMR Spectrum 1H NMR : Predict
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Synthesis Route
Toxicity
ACUTE TOXICITY DATA
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Type of Test
TDLo - Lowest published toxic dose
Exposure Route
Oral
Species Observed
Human - woman
Dose/Duration
800 ug/kg/2D-I
Toxic Effects
Lungs, Thorax, or Respiration--pleural effusion<br>Lungs, Thorax, or Respiration--cough<br>Immunological Including Allergic--other immediate (humoral): urticaria, allergic rhinitis, serum sickness
Reference
Pharmacotherapy (Carlisle, MA). (Pharmacotherapy Pub., Inc., 112 School St., Carlisle, MA 01741) V.1- 1981- Volume(issue)/page/year: 14,119,1993
ACUTE TOXICITY DATA
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Type of Test
TDLo - Lowest published toxic dose
Exposure Route
Oral
Species Observed
Human - woman
Dose/Duration
30 mg/kg/10W-I
Toxic Effects
Blood--eosinophilia<br>Kidney, Ureter, Bladder--interstitial nephritis<br>Skin and Appendages--dermatitis, other (after systemic exposure)
Reference
American Journal of Medicine. (Technical Pub., 875 Third Ave., New York, NY 10022) V.1- 1946- Volume(issue)/page/year: 95,248,1993
ACUTE TOXICITY DATA
expand collapse
Type of Test
TDLo - Lowest published toxic dose
Exposure Route
Oral
Species Observed
Human - man
Dose/Duration
4 mg/kg/2W-I
Toxic Effects
Musculoskeletal--joints<br>Biochemical-Metabolism (Intermediary)-effect on inflammation or mediation of inflammation
Reference
Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 345,461,1995
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