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Substance Name: Omeprazole [USAN:USP:INN:BAN:JAN]
RN: 73590-58-6
UNII: KG60484QX9
InChIKey: SUBDBMMJDZJVOS-UHFFFAOYSA-N

Note

  • A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.

Molecular Formula

  • C17-H19-N3-O3-S

Molecular Weight

  • 345.4211
 

Classification Codes

  • Anti-Ulcer Agents
  • Depressant (Gastric Acid Secretory)
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Gastrointestinal Agents
  • Human Data
  • Mutation Data
  • Proton Pump Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Omeprazole
  • Omeprazole [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Omeprazole

Synonyms

  • (+-)-Omeprazole
  • 1H-Benzimidazole, 5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulfinyl)-
  • 2-(((3,5-Dimethyl-4-methoxy-2-pyridyl)methyl)sulfinyl)-5-methoxy-1H-benzimidazole
  • 5-Methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl)benzimidazole
  • Antra
  • Antra MUPS
  • Audazol
  • Aulcer
  • Belmazol
  • CCRIS 7099
  • Ceprandal
  • Danlox
  • Demeprazol
  • Desec
  • Dizprazol
  • Dudencer
  • Elgam
  • Emeproton
  • Epirazole
  • Erbolin
  • Exter
  • Gasec
  • Gastrimut
  • Gastrogard
  • Gastroloc
  • Gibancer
  • H 168/68
  • HSDB 3575
  • Indurgan
  • Inhibitron
  • Inhipump
  • Lensor
  • Logastric
  • Lomac
  • Losec
  • Mepral
  • Miol
  • Miracid
  • Mopral
  • Morecon
  • Nilsec
  • Nopramin
  • Ocid
  • Olexin
  • Omapren
  • Omebeta 20
  • Omed
  • Omegast
  • OMEP
  • Omepral
  • Omeprazol
  • Omeprazol [INN-Spanish]
  • Omeprazole
  • Omeprazole delayed-release
  • Omeprazolum
  • Omeprazolum [INN-Latin]
  • Omeprazon
  • Omeprol
  • Omesek
  • Omez
  • Omezol
  • Omezolan
  • Omid
  • Omisec
  • Omizac
  • OMP
  • Ompanyt
  • OMZ
  • 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
  • UNII-KG60484QX9
  • Victrix
  • Zefxon
  • Zegerid
  • Zepral
  • Zimor
  • Zoltum

Systematic Names

  • 1H-Benzimidazole, 5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulfinyl)-
  • Omeprazole

Registry Numbers

CAS Registry Number

  • 73590-58-6

FDA UNII

  • KG60484QX9

Other Registry Numbers

  • 131959-78-9
  • 172964-80-6

System Generated Number

  • 0073590586

Structure Descriptors

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

Smiles

Cc1cnc(c(c1OC)C)CS(=O)c2[nH]c3ccc(cc3n2)OC

Toxicity

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 (0.8mg/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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 156 deg C   EXP
log P (octanol-water) 2.23 (none)   EXP
Water Solubility 82.3 mg/L 25 EST
Vapor Pressure 9.16E-13 mm Hg 25 EST
Henry's Law Constant 3.04E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.56E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.