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MedKoo Cat#: 574831 | Name: (R)-Omeprazole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

(R)-Omeprazole is the R-enantiomer of Omeprazole -- a molecule which binds covalently to the proton pump and inhibits gastric secretion. It may be used as an anti-ulcerative.

Chemical Structure

(R)-Omeprazole
(R)-Omeprazole
CAS#119141-89-8

Theoretical Analysis

MedKoo Cat#: 574831

Name: (R)-Omeprazole

CAS#: 119141-89-8

Chemical Formula: C17H19N3O3S

Exact Mass: 345.1147

Molecular Weight: 345.42

Elemental Analysis: C, 59.11; H, 5.54; N, 12.17; O, 13.90; S, 9.28

Price and Availability

Size Price Availability Quantity
1mg USD 500.00 2 Weeks
10mg USD 1,600.00 2 Weeks
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Related CAS #
No Data
Synonym
(+)-Omeprazole; (R)-Omeprazole
IUPAC/Chemical Name
5-Methoxy-2-[(R)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
InChi Key
SUBDBMMJDZJVOS-XMMPIXPASA-N
InChi Code
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)/t24-/m1/s1
SMILES Code
O=[S@@](C1=NC2=CC(OC)=CC=C2N1)CC3=NC=C(C)C(OC)=C3C
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 345.42 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Association with polymorphic marmoset cytochrome P450 2C19 of in vivo hepatic clearances of chirally separated R-omeprazole and S-warfarin using individual marmoset physiologically based pharmacokinetic models. Xenobiotica. 2018 Oct;48(10):1072-1077. doi: 10.1080/00498254.2017.1393121. Epub 2017 Nov 10. PMID: 29034770. 8: Xu Y, Hong T, Chen X, Ji Y. Affinity capillary electrophoresis and fluorescence spectroscopy for studying enantioselective interactions between omeprazole enantiomer and human serum albumin. Electrophoresis. 2017 May;38(9-10):1366-1373. doi: 10.1002/elps.201600375. Epub 2017 Mar 16. PMID: 28229517. 9: Jana K, Bandyopadhyay T, Ganguly B. Revealing the Mechanistic Pathway of Acid Activation of Proton Pump Inhibitors To Inhibit the Gastric Proton Pump: A DFT Study. J Phys Chem B. 2016 Dec 29;120(51):13031-13038. doi: 10.1021/acs.jpcb.6b09334. Epub 2016 Dec 19. PMID: 27992223. 10: Uehara S, Kawano M, Murayama N, Uno Y, Utoh M, Inoue T, Sasaki E, Yamazaki H. Oxidation of R- and S-omeprazole stereoselectively mediated by liver microsomal cytochrome P450 2C19 enzymes from cynomolgus monkeys and common marmosets. Biochem Pharmacol. 2016 Nov 15;120:56-62. doi: 10.1016/j.bcp.2016.09.010. Epub 2016 Sep 21. PMID: 27641812. 11: Sørensen AM, Hansen CH, Bonomo S, Olsen L, Jørgensen FS, Weisser JJ, Kretschmann AC, Styrishave B. Enantioselective endocrine disrupting effects of omeprazole studied in the H295R cell assay and by molecular modeling. Toxicol In Vitro. 2016 Aug;34:71-80. doi: 10.1016/j.tiv.2016.03.007. Epub 2016 Mar 19. PMID: 27002602. 12: Novotna A, Dvorak Z. Omeprazole and lansoprazole enantiomers induce CYP3A4 in human hepatocytes and cell lines via glucocorticoid receptor and pregnane X receptor axis. PLoS One. 2014 Aug 20;9(8):e105580. doi: 10.1371/journal.pone.0105580. PMID: 25141173; PMCID: PMC4139355. 13: Wu F, Gaohua L, Zhao P, Jamei M, Huang SM, Bashaw ED, Lee SC. Predicting nonlinear pharmacokinetics of omeprazole enantiomers and racemic drug using physiologically based pharmacokinetic modeling and simulation: application to predict drug/genetic interactions. Pharm Res. 2014 Aug;31(8):1919-29. doi: 10.1007/s11095-013-1293-z. Epub 2014 Mar 4. PMID: 24590877. 14: Yamada S, Shiohira H, Yasui-Furukori N, Tateishi T, Akamine Y, Uno T. The (R)-omeprazole hydroxylation index reflects CYP2C19 activity in healthy Japanese volunteers. Eur J Clin Pharmacol. 2013 Jul;69(7):1423-8. doi: 10.1007/s00228-013-1480-1. Epub 2013 Feb 24. PMID: 23435615. 15: Shiohira H, Yasui-Furukori N, Yamada S, Tateishi T, Akamine Y, Uno T. Hydroxylation of R(+)- and S(-)-omeprazole after racemic dosing are different among the CYP2C19 genotypes. Pharm Res. 2012 Aug;29(8):2310-6. doi: 10.1007/s11095-012-0757-x. Epub 2012 May 2. PMID: 22549736. 16: Ogilvie BW, Yerino P, Kazmi F, Buckley DB, Rostami-Hodjegan A, Paris BL, Toren P, Parkinson A. The proton pump inhibitor, omeprazole, but not lansoprazole or pantoprazole, is a metabolism-dependent inhibitor of CYP2C19: implications for coadministration with clopidogrel. Drug Metab Dispos. 2011 Nov;39(11):2020-33. doi: 10.1124/dmd.111.041293. Epub 2011 Jul 27. PMID: 21795468. 17: Vyas S, Patel A, Ladva KD, Joshi HS, Bapodra AH. Development and validation of a stability indicating method for the enantioselective estimation of omeprazole enantiomers in the enteric-coated formulations by high-performance liquid chromatography. J Pharm Bioallied Sci. 2011 Apr;3(2):310-4. doi: 10.4103/0975-7406.80766. PMID: 21687365; PMCID: PMC3103931. 18: Agatonovic-Kustrin S, Markovic N, Ginic-Markovic M, Mangan M, Glass BD. Compatibility studies between mannitol and omeprazole sodium isomers. J Pharm Biomed Anal. 2008 Sep 29;48(2):356-60. doi: 10.1016/j.jpba.2008.02.009. Epub 2008 Feb 17. PMID: 18374534. 19: Löfgren S, Baldwin RM, Hiratsuka M, Lindqvist A, Carlberg A, Sim SC, Schülke M, Snait M, Edenro A, Fransson-Steen R, Terelius Y, Ingelman-Sundberg M. Generation of mice transgenic for human CYP2C18 and CYP2C19: characterization of the sexually dimorphic gene and enzyme expression. Drug Metab Dispos. 2008 May;36(5):955-62. doi: 10.1124/dmd.107.019349. Epub 2008 Feb 14. PMID: 18276835. 20: Foti RS, Wahlstrom JL. CYP2C19 inhibition: the impact of substrate probe selection on in vitro inhibition profiles. Drug Metab Dispos. 2008 Mar;36(3):523-8. doi: 10.1124/dmd.107.019265. Epub 2007 Nov 29. PMID: 18048485.

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