WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 330196
CAS#: 81938-43-4 (calcium)
Description: Zofenopril, also known as SQ 26991, is a ACE inhibitor that protects the heart and helps reduce high blood pressure. Zofenopril appeared significantly more effective in reducing hypertension than two older antihypertensive drugs, atenolol and enalapril, and was associated with fewer adverse effects. Zofenopril is a prodrug with zofenoprilat as the active metabolite.
MedKoo Cat#: 330196
Name: Zofenopril calcium
CAS#: 81938-43-4 (calcium)
Chemical Formula: C44H44CaN2O8S4
Exact Mass:
Molecular Weight: 897.16
Elemental Analysis: C, 58.91; H, 4.94; Ca, 4.47; N, 3.12; O, 14.27; S, 14.29
Related CAS #: 81938-43-4 (calcium) 81872-10-8 (free form)
Synonym: Zofenopril calcium; SQ-26991; SQ26991; SQ 26991; Zoprace;
IUPAC/Chemical Name: calcium (2S,4S)-1-((S)-3-(benzoylthio)-2-methylpropanoyl)-4-(phenylthio)pyrrolidine-2-carboxylate
InChi Key: NSYUKKYYVFVMST-LETVYOFWSA-L
InChi Code: InChI=1S/2C22H23NO4S2.Ca/c2*1-15(14-28-22(27)16-8-4-2-5-9-16)20(24)23-13-18(12-19(23)21(25)26)29-17-10-6-3-7-11-17;/h2*2-11,15,18-19H,12-14H2,1H3,(H,25,26);/q;;+2/p-2/t2*15-,18+,19+;/m11./s1
SMILES Code: O=C([C@H]1N(C([C@H](C)CSC(C2=CC=CC=C2)=O)=O)C[C@@H](SC3=CC=CC=C3)C1)[O-].O=C([C@H]4N(C([C@H](C)CSC(C5=CC=CC=C5)=O)=O)C[C@@H](SC6=CC=CC=C6)C4)[O-].[Ca+2]
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
The following data is based on the product molecular weight 897.16 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 |
1: Omboni S, Borghi C. Efficacy of Zofenopril Alone or in Combination with Hydrochlorothiazide in Patients with Kidney Dysfunction. Curr Clin Pharmacol. 2019;14(1):5-15. doi: 10.2174/1574884713666181025145404. PubMed PMID: 30360726.
2: Borghi C, Omboni S, Reggiardo G, Bacchelli S, Esposti DD, Ambrosioni E. Efficacy of zofenopril in combination with thiazide diuretics in patients with acute myocardial infarction: a pooled individual data analysis of four randomized, double-blind, controlled, prospective studies. Ther Clin Risk Manag. 2018 Jul 9;14:1185-1190. doi: 10.2147/TCRM.S165629. eCollection 2018. PubMed PMID: 30022831; PubMed Central PMCID: PMC6042489.
3: Borghi C, Omboni S, Reggiardo G, Bacchelli S, Degli Esposti D, Ambrosioni E; SMILE (Survival of Myocardial Infarction Long-Term Evaluation) Working Project. Efficacy of zofenopril in combination with amlodipine in patients with acute myocardial infarction: a pooled individual patient data analysis of four randomized, double-blind, controlled, prospective studies. Curr Med Res Opin. 2018 Oct;34(10):1869-1874. doi: 10.1080/03007995.2018.1496076. Epub 2018 Jul 31. PubMed PMID: 29972310.
4: Borghi C, Omboni S, Reggiardo G, Bacchelli S, Esposti DD, Ambrosioni E; SMILE Working Project. Effects of the concomitant administration of xanthine oxidase inhibitors with zofenopril or other ACE-inhibitors in post-myocardial infarction patients: a meta-analysis of individual data of four randomized, double-blind, prospective studies. BMC Cardiovasc Disord. 2018 Jun 5;18(1):112. doi: 10.1186/s12872-018-0800-x. PubMed PMID: 29866077; PubMed Central PMCID: PMC5987407.
5: Borghi C, Omboni S, Novo S, Vinereanu D, Ambrosio G, Ambrosioni E. Efficacy and Safety of Zofenopril Versus Ramipril in the Treatment of Myocardial Infarction and Heart Failure: A Review of the Published and Unpublished Data of the Randomized Double-Blind SMILE-4 Study. Adv Ther. 2018 May;35(5):604-618. doi: 10.1007/s12325-018-0697-x. Epub 2018 Apr 17. Review. PubMed PMID: 29667144; PubMed Central PMCID: PMC5960496.
6: Fayed AS, Rezk MR, Marzouk HM, Abbas SS. A Capillary Zone Electrophoresis Method with Multiresponse Chemometric Optimization for the Simultaneous Determination of Zofenopril Calcium and Hydrochlorothiazide in Presence of Hydrochlorothiazide Major Impurities. J Chromatogr Sci. 2018 Mar 15. doi: 10.1093/chromsci/bmy014. [Epub ahead of print] PubMed PMID: 29554245.
7: Rezk MR, Fayed AS, Marzouk HM, Abbas SS. A Validated High-Performance Thin-Layer Chromatographic Method for the Simultaneous Determination of Zofenopril Calcium and Hydrochlorothiazide in the Presence of the Hydrochlorothiazide Impurities: Chlorothiazide and Salamide. J AOAC Int. 2018 Jul 1;101(4):1031-1041. doi: 10.5740/jaoacint.17-0095. Epub 2017 Sep 11. PubMed PMID: 28893345.
8: Omboni S, Malacco E, Napoli C, Modesti PA, Manolis A, Parati G, Agabiti-Rosei E, Borghi C. Erratum to: Efficacy of Zofenopril vs. Irbesartan in Combination with a Thiazide Diuretic in Hypertensive Patients with Multiple Risk Factors not Controlled by a Previous Monotherapy: A Review of the Double-Blind, Randomized "Z" Studies. Adv Ther. 2017 Jun;34(6):1498-1499. doi: 10.1007/s12325-017-0537-4. PubMed PMID: 28452039; PubMed Central PMCID: PMC5487858.
9: Omboni S, Malacco E, Napoli C, Modesti PA, Manolis A, Parati G, Agabiti-Rosei E, Borghi C. Efficacy of Zofenopril vs. Irbesartan in Combination with a Thiazide Diuretic in Hypertensive Patients with Multiple Risk Factors not Controlled by a Previous Monotherapy: A Review of the Double-Blind, Randomized "Z" Studies. Adv Ther. 2017 Apr;34(4):784-798. doi: 10.1007/s12325-017-0497-8. Epub 2017 Mar 4. Review. Erratum in: Adv Ther. 2017 Jun;34(6):1498-1499. PubMed PMID: 28260186; PubMed Central PMCID: PMC5406448.
10: Borghi C, Omboni S, Novo S, Vinereanu D, Ambrosio G, Ambrosioni E. Early Treatment With Zofenopril and Ramipril in Combination With Acetyl Salicylic Acid in Patients With Left Ventricular Systolic Dysfunction After Acute Myocardial Infarction: Results of a 5-Year Follow-up of Patients of the SMILE-4 Study. J Cardiovasc Pharmacol. 2017 May;69(5):298-304. doi: 10.1097/FJC.0000000000000473. PubMed PMID: 28195948; PubMed Central PMCID: PMC5426698.
11: Borghi C, Omboni S, Reggiardo G, Bacchelli S, Degli Esposti D, Ambrosioni E; : on behalf of the SMILE (Survival of Myocardial Infarction Long-term Evaluation) Working Project. Cardioprotective role of zofenopril in hypertensive patients with acute myocardial infarction: a pooled individual data analysis of the SMILE studies. Blood Press. 2017 Aug;26(4):211-219. doi: 10.1080/08037051.2017.1281712. Epub 2017 Feb 3. PubMed PMID: 28155333.
12: Ristic P, Srejovic I, Nikolic T, Stojic I, Ristic D, Zivkovic V, Jakovljevic VL. The effects of zofenopril on cardiac function and pro-oxidative parameters in the streptozotocin-induced diabetic rat heart. Mol Cell Biochem. 2017 Feb;426(1-2):183-193. doi: 10.1007/s11010-016-2890-z. Epub 2016 Nov 24. PubMed PMID: 27882442.
13: Borghi C, Omboni S, Reggiardo G, Bacchelli S, Degli Esposti D, Ambrosioni E. Efficacy of Zofenopril Compared With Placebo and Other Angiotensin-converting Enzyme Inhibitors in Patients With Acute Myocardial Infarction and Previous Cardiovascular Risk Factors: A Pooled Individual Data Analysis of 4 Randomized, Double-blind, Controlled, Prospective Studies. J Cardiovasc Pharmacol. 2017 Jan;69(1):48-54. doi: 10.1097/FJC.0000000000000440. PubMed PMID: 27798417; PubMed Central PMCID: PMC5207231.
14: Gómez-Roso M, Montero MJ, Carrón R, Sevilla MA. Zofenopril exerts a cardiovascular protective effect on rats infused with angiotensin II beyond angiotensin-converting enzyme inhibition. J Pharm Pharmacol. 2016 Nov;68(11):1422-1429. doi: 10.1111/jphp.12641. Epub 2016 Sep 27. PubMed PMID: 27670145.
15: Borghi C, Omboni S, Novo S, Vinereanu D, Ambrosio G, Ambrosioni E; SMILE-4 Working Party. Zofenopril and ramipril in patients with left ventricular systolic dysfunction after acute myocardial infarction: A propensity analysis of the Survival of Myocardial Infarction Long-term Evaluation (SMILE) 4 study. J Renin Angiotensin Aldosterone Syst. 2016 Oct 5;17(4). pii: 1470320316656480. Print 2016 Oct. PubMed PMID: 27708111; PubMed Central PMCID: PMC5843868.
16: Napoli C, Omboni S, Borghi C; ZAMES (Zofenopril in Advanced MEtabolic Syndrome) Study Group. Fixed-dose combination of zofenopril plus hydrochlorothiazide vs. irbesartan plus hydrochlorothiazide in hypertensive patients with established metabolic syndrome uncontrolled by previous monotherapy. The ZAMES study (Zofenopril in Advanced MEtabolic Syndrome). J Hypertens. 2016 Nov;34(11):2287-97. doi: 10.1097/HJH.0000000000001079. PubMed PMID: 27653164.
17: Donnarumma E, Ali MJ, Rushing AM, Scarborough AL, Bradley JM, Organ CL, Islam KN, Polhemus DJ, Evangelista S, Cirino G, Jenkins JS, Patel RA, Lefer DJ, Goodchild TT. Zofenopril Protects Against Myocardial Ischemia-Reperfusion Injury by Increasing Nitric Oxide and Hydrogen Sulfide Bioavailability. J Am Heart Assoc. 2016 Jul 5;5(7). pii: e003531. doi: 10.1161/JAHA.116.003531. PubMed PMID: 27381758; PubMed Central PMCID: PMC5015391.
18: Borghi C, Omboni S, Novo S, Vinereanu D, Ambrosio G, Ambrosioni E; SMILE-4 Working Party. Zofenopril and Ramipril in Combination with Acetyl Salicylic Acid in Postmyocardial Infarction Patients with Left Ventricular Systolic Dysfunction: A Retrospective Analysis of the SMILE-4 Randomized, Double-Blind Study in Diabetic Patients. Cardiovasc Ther. 2016 Apr;34(2):76-84. doi: 10.1111/1755-5922.12175. PubMed PMID: 26789425.
19: Modesti PA, Omboni S, Taddei S, Ghione S, Portaluppi F, Pozzilli P, Volpe M, Arca M, Calabrò P, Fulgheri PL, Bucci M, Berra S, Villani GQ, Vladoianu M, Popescu E, Velican VG, Pirvu O. Zofenopril or irbesartan plus hydrochlorothiazide in elderly patients with isolated systolic hypertension untreated or uncontrolled by previous treatment: a double-blind, randomized study. J Hypertens. 2016 Mar;34(3):576-87; discussion 587. doi: 10.1097/HJH.0000000000000805. PubMed PMID: 26703917.
20: Borghi C, Omboni S, Reggiardo G, Bacchelli S, Degli Esposti D, Ambrosioni E. Cardioprotective role of zofenopril in patients with acute myocardial infarction: a pooled individual data analysis of four randomised, double-blind, controlled, prospective studies. Open Heart. 2015 Sep 8;2(1):e000220. doi: 10.1136/openhrt-2014-000220. eCollection 2015. PubMed PMID: 26380097; PubMed Central PMCID: PMC4567784.
