MedKoo Biosciences

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

MedKoo CAT#: 318387

CAS#: 73590-58-6 (free form)

Description: Omeprazole 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. Omeprazole is a proton pump inhibitor and as such blocks the release of stomach acid.

Chemical Structure

Omeprazole

CAS# 73590-58-6 (free form)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318387
Name: Omeprazole
CAS#: 73590-58-6 (free form)
Chemical Formula: C17H19N3O3S
Exact Mass: 345.11
Molecular Weight: 345.416
Elemental Analysis: C, 59.11; H, 5.54; N, 12.17; O, 13.90; S, 9.28

Price and Availability

Size	Price	Availability	Quantity
50g	USD 350
100g	USD 550
500g	USD 950
1kg	USD 1650
5kg	USD 6950
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 95510-70-6 (sodium) 73590-58-6 (free form) 119141-88-7 (S-isomer) 95510-71-7 (potassium)

Synonym: Omeprazole, H 168-68, Losec, Prilosec, Zegerid, H 16868, H 168 68

IUPAC/Chemical Name: 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole

InChi Key: SUBDBMMJDZJVOS-UHFFFAOYSA-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)

SMILES Code: O=S(C1=NC2=CC=C(OC)C=C2N1)CC3=NC=C(C)C(OC)=C3C

Appearance: White to off-white 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, not in water

Shelf Life: >2 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:

Product Data:

Product Data

Instruction:

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Biological target:	Omeprazole (H 16868) is a proton pump inhibitor (PPI).
In vitro activity:	The antibacterial effects of omeprazole (100, 200 and 300 mg/L) were assessed using bacterial growth curves. A dose-related permanent inhibition was seen with actively growing Gram-positive cocci. A reduced and only temporary effect was observed with Gram-negative bacilli. After 1 day the bacterial count of Helicobacter pylori in the presence of omeprazole 200 mg/L was reduced from 10(4) cfu/mL for the control to zero. Reference: J Antimicrob Chemother. 1996 Jan;37(1):145-50. https://pubmed.ncbi.nlm.nih.gov/8647756/
In vivo activity:	This study revisited the effect of omeprazole treatment on the degree of anxiety-like behaviours in a cysteamine hydrochloride (HCl) induced mouse model of GI disorder using open field test (OFT), light-dark box (LDB) test and elevated plus maze (EPM). Results revealed that omeprazole treatment mitigates anxiety-related behaviours in the cysteamine HCl induced animal model of GI disorder. Thus, this study assuredly supports and validates the anxiolytic properties of omeprazole. Reference: Heliyon. 2022 Jun 24;8(6):e09787. https://pubmed.ncbi.nlm.nih.gov/35800723/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	86.85
	DMSO	66.3	192.04
	DMSO:PBS (pH 7.2) (1:1)	0.5	1.45
	Ethanol	9.0	26.06
	Water	0.7	1.94

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.

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

Formulation protocol:	1. Scaringi L, Cornacchione P, Fettucciari K, Rosati E, Rossi R, Marconi P, Capodicasa E. Activity inhibition of cytolytic lymphocytes by omeprazole. Scand J Immunol. 1996 Sep;44(3):204-14. doi: 10.1046/j.1365-3083.1996.d01-300.x. PMID: 8795713. 2. Jonkers D, Stobberingh E, Stockbrügger R. Omeprazole inhibits growth of gram-positive and gram-negative bacteria including Helicobacter pylori in vitro. J Antimicrob Chemother. 1996 Jan;37(1):145-50. doi: 10.1093/jac/37.1.145. PMID: 8647756. 3. Sri Rethinavel H, Selvaraj DB, Balakrishnan SJ, Vergil Andrews JF, Joseph JHM, Kandasamy M. Omeprazole treatment manifests anxiolytic effects in a cysteamine hydrochloride induced mouse model of gastrointestinal disorder. Heliyon. 2022 Jun 24;8(6):e09787. doi: 10.1016/j.heliyon.2022.e09787. PMID: 35800723; PMCID: PMC9253648. 4. Rudra DS, Pal U, Chowdhury N, Maiti NC, Bagchi A, Swarnakar S. Omeprazole prevents stress induced gastric ulcer by direct inhibition of MMP-2/TIMP-3 interactions. Free Radic Biol Med. 2022 Mar;181:221-234. doi: 10.1016/j.freeradbiomed.2022.02.007. Epub 2022 Feb 10. PMID: 35150824.
In vitro protocol:	1. Scaringi L, Cornacchione P, Fettucciari K, Rosati E, Rossi R, Marconi P, Capodicasa E. Activity inhibition of cytolytic lymphocytes by omeprazole. Scand J Immunol. 1996 Sep;44(3):204-14. doi: 10.1046/j.1365-3083.1996.d01-300.x. PMID: 8795713. 2. Jonkers D, Stobberingh E, Stockbrügger R. Omeprazole inhibits growth of gram-positive and gram-negative bacteria including Helicobacter pylori in vitro. J Antimicrob Chemother. 1996 Jan;37(1):145-50. doi: 10.1093/jac/37.1.145. PMID: 8647756.
In vivo protocol:	1. Sri Rethinavel H, Selvaraj DB, Balakrishnan SJ, Vergil Andrews JF, Joseph JHM, Kandasamy M. Omeprazole treatment manifests anxiolytic effects in a cysteamine hydrochloride induced mouse model of gastrointestinal disorder. Heliyon. 2022 Jun 24;8(6):e09787. doi: 10.1016/j.heliyon.2022.e09787. PMID: 35800723; PMCID: PMC9253648. 2. Rudra DS, Pal U, Chowdhury N, Maiti NC, Bagchi A, Swarnakar S. Omeprazole prevents stress induced gastric ulcer by direct inhibition of MMP-2/TIMP-3 interactions. Free Radic Biol Med. 2022 Mar;181:221-234. doi: 10.1016/j.freeradbiomed.2022.02.007. Epub 2022 Feb 10. PMID: 35150824.

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1: Banihani SA. Omeprazole and Semen Quality. Basic Clin Pharmacol Toxicol. 2016 Mar;118(3):181-3. doi: 10.1111/bcpt.12529. Epub 2015 Dec 28. Review. PubMed PMID: 26572503.

2: Qi Q, Wang R, Liu L, Zhao F, Wang S. Comparative effectiveness and tolerability of esomeprazole and omeprazole in gastro-esophageal reflux disease: A systematic review and meta-analysis. Int J Clin Pharmacol Ther. 2015 Oct;53(10):803-10. doi: 10.5414/CP202396. Review. PubMed PMID: 26329348.

3: Akinseye OA, Alfishawy M, Radparvar F, Bakshi S. Trazodone and omeprazole interaction causing frequent second-degree Mobitz type 1 atrioventricular (AV) block (Wenckebach phenomenon) and syncope: a case report and literature review. Am J Case Rep. 2015 May 27;16:319-21. doi: 10.12659/AJCR.893427. Review. PubMed PMID: 26017199; PubMed Central PMCID: PMC4456984.

4: Bliden KP, Brener M, Gesheff MG, Franzese CJ, Tabrizchi A, Tantry U, Gurbel PA. PA tablets: investigational compounds combining aspirin and omeprazole for cardioprotection. Future Cardiol. 2013 Nov;9(6):785-97. doi: 10.2217/fca.13.67. Review. PubMed PMID: 24180537.

5: Gandi P, Vasireddi SR, Gurram SR, Darasani K. Evaluation of the Antibacterial efficacy of Omeprazole with Sodium Hypochlorite as an Endodontic Irrigating Solution- An Invivo Study. J Int Oral Health. 2013 Apr;5(2):14-20. Review. PubMed PMID: 24155586; PubMed Central PMCID: PMC3768071.

6: Xia XM, Wang H. Gastroesophageal Reflux Disease Relief in Patients Treated with Rabeprazole 20 mg versus Omeprazole 20 mg: A Meta-Analysis. Gastroenterol Res Pract. 2013;2013:327571. doi: 10.1155/2013/327571. Epub 2013 Sep 9. Review. PubMed PMID: 24106498; PubMed Central PMCID: PMC3782839.

7: Gigante A, Tagarro I. Non-steroidal anti-inflammatory drugs and gastroprotection with proton pump inhibitors: a focus on ketoprofen/omeprazole. Clin Drug Investig. 2012 Apr 1;32(4):221-33. doi: 10.2165/11596670-000000000-00000. Review. PubMed PMID: 22350497.

8: Solana MJ, López-Herce J. Pharmacokinetics of intravenous omeprazole in critically ill paediatric patients. Eur J Clin Pharmacol. 2010 Apr;66(4):323-30. doi: 10.1007/s00228-009-0774-9. Epub 2009 Dec 30. Review. PubMed PMID: 20041322.

9: Thakor AS, Burke A, Handfield-Jones S, Sinha A, Palmer M, Burns A. Toxic epidermal necrolysis and neutropaenia: complications of omeprazole. Australas J Dermatol. 2009 Aug;50(3):207-10. doi: 10.1111/j.1440-0960.2009.00540.x. Review. PubMed PMID: 19659985.

10: Van Der Straeten F, Al-Afandi A, De Paepe K, Bovy J, Plaizier-Vercammen J. [Pharmacy compounding of an omeprazole suspension]. J Pharm Belg. 2009 Jun;(2):54-63. Review. French. PubMed PMID: 19739529.

11: Castell D. Review of immediate-release omeprazole for the treatment of gastric acid-related disorders. Expert Opin Pharmacother. 2005 Nov;6(14):2501-10. Review. PubMed PMID: 16259581.

12: Omeprazole/Antacid-powder suspension-Santarus: omeprazole/sodium bicarbonate powder-Santarus, SAN 05. Drugs R D. 2004;5(6):349-50. Review. PubMed PMID: 15563239.

13: Omeprazole/antacid-powder suspension--Santarus: Acitrel, Rapinex Powder for oral suspension, SAN 05. Drugs R D. 2004;5(4):234-5. Review. PubMed PMID: 15230632.

14: Torregrosa E, Rovira RE, Calvo C, Hernández-Jaras J, Maduell F, García H. [Acute interstitial nephritis associated with omeprazole therapy]. Nefrologia. 2004;24 Suppl 3:61-3. Review. Spanish. PubMed PMID: 15219071.

15: Yamamoto T, Matsumoto J, Kosaihira T, Nomoto M, Kitajima S, Arima T. [A case of gastric fundic polyps during long-term treatment of reflux esophagitis with omeprazole]. Nihon Shokakibyo Gakkai Zasshi. 2003 Apr;100(4):421-5. Review. Japanese. PubMed PMID: 12722347.

16: Zimmermann AE, Walters JK, Katona BG, Souney PE, Levine D. A review of omeprazole use in the treatment of acid-related disorders in children. Clin Ther. 2001 May;23(5):660-79; discussion 645. Review. PubMed PMID: 11394727.

17: Thomson AB. Are the orally administered proton pump inhibitors equivalent? A comparison of lansoprazole, omeprazole, pantoprazole, and rabeprazole. Curr Gastroenterol Rep. 2000 Dec;2(6):482-93. Review. PubMed PMID: 11079051.

18: Furuta T, Takashima M, Shirai N, Xiao F, Hanai H, Ohashi K, Ishizaki T. Cure of refractory duodenal ulcer and infection caused by Helicobacter pylori by high doses of omeprazole and amoxicillin in a homozygous CYP2C19 extensive metabolizer patient. Clin Pharmacol Ther. 2000 Jun;67(6):684-9. Review. PubMed PMID: 10872651.

19: Welage LS, Berardi RR. Evaluation of omeprazole, lansoprazole, pantoprazole, and rabeprazole in the treatment of acid-related diseases. J Am Pharm Assoc (Wash). 2000 Jan-Feb;40(1):52-62; quiz 121-3. Review. PubMed PMID: 10665250.

20: Bradford GS, Taylor CT. Omeprazole and vitamin B12 deficiency. Ann Pharmacother. 1999 May;33(5):641-3. Review. PubMed PMID: 10369631.

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