WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H584458
CAS#: 88824-78-6 (HCl)
Description: Cilazapril, also known as Ro 31 2848, is a potent ACE inhibitor used for hypertension. Cilazapril is a prodrug that is hydrolyzed after absorption to its main metabolite cilazaprilat. Cilazapril is a monoethyl ester, which acts as an angiotensin-converting enzyme (ACE) inhibitor. The inhibitor functions by inhibiting the ability of ACE to cleave bonds of angiotensin I and Hip-His-Leu. It is known that the diacid form of Cilazapril is more potent that enalapril at inhibiting ACE.
Hodoodo Cat#: H584458
Name: Cilazapril HCl
CAS#: 88824-78-6 (HCl)
Chemical Formula: C22H32ClN3O5
Exact Mass: 417.23
Molecular Weight: 453.964
Elemental Analysis: C, 58.21; H, 7.11; Cl, 7.81; N, 9.26; O, 17.62
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Related CAS #: 88768-40-5 (anhydrous) 92077-78-6 (hydrate) 88824-78-6 (HCl) 116299-83-3 (HBr),
Synonym: Cilazapril; Ro 34-2848; Ro-34-2848; Ro34-2848
IUPAC/Chemical Name: 6H-Pyridazino(1,2-a)(1,2)diazepine-1-carboxylic acid, 9-(((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)octahydro-10-oxo-, (1S,9S)-, hydrochloride
InChi Key: QCYBBLWVNJYHEC-YOTVLOEGSA-N
InChi Code: InChI=1S/C22H31N3O5.ClH/c1-2-30-22(29)18(13-12-16-8-4-3-5-9-16)23-17-10-6-14-24-15-7-11-19(21(27)28)25(24)20(17)26;/h3-5,8-9,17-19,23H,2,6-7,10-15H2,1H3,(H,27,28);1H/t17-,18-,19-;/m0./s1
SMILES Code: O=C([C@@H]1CCCN2N1C([C@@H](N[C@H](C(OCC)=O)CCC3=CC=CC=C3)CCC2)=O)O.[H]Cl
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: >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:
| Biological target: | |
| In vitro activity: | |
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The following data is based on the product molecular weight 453.96 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: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Khalil A, Kashif M. Development of UV-visible spectrophotometric methods for the quantitative and in silico studies for cilazapril optimized by response surface methodology. Drug Dev Ind Pharm. 2021 Jul;47(7):1100-1111. doi: 10.1080/03639045.2021.1957918. Epub 2021 Aug 6. PMID: 34286656.
2: Stanisz M, Klapiszewski Ł, Mlynarczyk DT, Stanisz BJ, Jesionowski T. Lignin- Based Spherical Structures and Their Use for Improvement of Cilazapril Stability in Solid State. Molecules. 2020 Jul 9;25(14):3150. doi: 10.3390/molecules25143150. PMID: 32660132; PMCID: PMC7397289.
3: Regulska K, Regulski M, Wzgarda A, Kotowska A, Ignasiak A, Ćwiertnia B, Stanisz B. Does Polyvinylpyrrolidone Improve the Chemical Stability of Cilazapril in Solid State? Iran J Pharm Res. 2019 Spring;18(2):579-595. doi: 10.22037/ijpr.2019.1100640. PMID: 31531043; PMCID: PMC6706751.
4: Šljivic J, Protic A, Otaševic B, Golubovic J, Zecevic M, Krmar J. Multicriteria Optimization Methodology in Stability-Indicating Method Development of Cilazapril and Hydrochlorothiazide. J Chromatogr Sci. 2017 Jul 1;55(6):625-637. doi: 10.1093/chromsci/bmx018. PMID: 28334985.
5: Narayanam M, Sahu A, Singh S. Use of LC-MS/TOF, LC-MS(n), NMR and LC-NMR in characterization of stress degradation products: Application to cilazapril. J Pharm Biomed Anal. 2015;111:190-203. doi: 10.1016/j.jpba.2015.03.038. Epub 2015 Apr 3. PMID: 25890215.
6: Stanisz BJ, Paszun SK, Zalewska A. Stability of cilazapril in pediatric oral suspensions prepared from commercially available tablet dosage forms. Acta Pol Pharm. 2014 Jul-Aug;71(4):661-6. PMID: 25272892.
7: Saber RA, Attia AK, Salem WM. Thermal analysis study of antihypertensive drugs telmisartan and cilazapril. Adv Pharm Bull. 2014;4(3):283-7. doi: 10.5681/apb.2014.041. Epub 2014 Feb 7. PMID: 24754013; PMCID: PMC3992965.
8: Paszun SK, Stanisz BJ, Gradowska A. Cilazapril stability in the presence of hydrochlorothiazide in model mixtures and fixed dose combination. Acta Pol Pharm. 2013 Nov-Dec;70(6):1079-85. PMID: 24383331.
9: Paszun SK, Stanisz B, Pawłowski W. Rapid and simple stability indicating HPLC method for the determination of cilazapril in pure substance and pharmaceutical formulation in comparison with classic and derivative spectrophotometric methods. Acta Pol Pharm. 2012 Mar-Apr;69(2):193-201. PMID: 22568033.
10: Kolocouri F, Dotsikas Y, Apostolou C, Kousoulos C, Soumelas GS, Loukas YL. Advantages of automation in plasma sample preparation prior to HPLC/MS/MS quantification: application to the determination of cilazapril and cilazaprilat in a bioequivalence study. J AOAC Int. 2011 May-Jun;94(3):758-64. PMID: 21797003.
11: Zaki SA, Nilofer AR. Cilazapril-induced pleural effusion: A case report and review of the literature. Ann Thorac Med. 2011 Jul;6(3):157-8. doi: 10.4103/1817-1737.82459. PMID: 21760854; PMCID: PMC3131765.
12: Madej A, Gierek-Ciaciura S, Haberka M, Lekston-Madej J, Basiak M, Domańska O, Okopień B. Effects of bisoprolol and cilazapril on the central retinal artery blood flow in patients with essential hypertension--preliminary results. Ups J Med Sci. 2010 Nov;115(4):249-52. doi: 10.3109/03009734.2010.487951. Epub 2010 Sep 22. PMID: 20858158; PMCID: PMC2971482.
13: Kupeli E, Ulubay G, Ulasli SS, Kilic D. Cilazapril-induced pleural effusion: A case report and review of the literature. Ann Thorac Med. 2010 Jul;5(3):171-3. doi: 10.4103/1817-1737.65043. PMID: 20835313; PMCID: PMC2930657.
14: Skoczylas A, Adamczak M, Chudek J, Wiecek A. Cilazapril increases plasma ghrelin concentration in obese patients with arterial hypertension. Endokrynol Pol. 2010 Jan-Feb;61(1):21-7. PMID: 20205100.
15: Radovanović MR, Miletić GM, Radovanović MS. [Successful treatment of polymedicamentous poisoning with metoprolol, diltiazem and cilazapril]. Vojnosanit Pregl. 2009 Nov;66(11):904-8. Serbian. doi: 10.2298/vsp0911904r. PMID: 20017422.
16: Sung SH, Wu TC, Lin SJ, Chen JW. Efficacy of a very-low-dose combination of perindopril and indapamide--preterax compared with cilazapril monotherapy in patients with inadequate blood pressure control--a randomized, double-blind, add-on study. J Chin Med Assoc. 2008 May;71(5):247-53. doi: 10.1016/S1726-4901(08)70115-1. PMID: 18490229.
17: Zhang SS, Sun GY, Liu ZY. [The study of the effect of Cilazapril and valsartan on angiotensin 1 and angiotensin 2 receptors mRNA expression and myocardial interstitial collagen metabolism after myocardial infarction in rats]. Zhongguo Wei Zhong Bing Ji Jiu Yi Xue. 2008 Apr;20(4):240-1. Chinese. PMID: 18419964.
18: Tuncer M, Gunes Y, Guntekin U, Gumrukcuoglu HA, Eryonucu B. Short-term effects of cilazapril and atenolol on P-wave dispersion in patients with hypertension. Adv Ther. 2008 Feb;25(2):99-105. doi: 10.1007/s12325-008-0012-3. PMID: 18297254.
19: Hosgor I, Ahmad S. Impact of cilazapril on fibrinolytic system in hypertensive patients. Blood Coagul Fibrinolysis. 2008 Jan;19(1):101-5. doi: 10.1097/MBC.0b013e3282f21fc9. PMID: 18180626.
20: Sonmez A, Yilmaz MI, Korkmaz A, Topal T, Caglar K, Kaya A, Eyileten T, Yenicesu M, Oguz Y, Basal S, Ipcioglu OM, Vural A. Hyperbaric oxygen treatment augments the efficacy of cilazapril and simvastatin regimens in an experimental nephrotic syndrome model. Clin Exp Nephrol. 2008 Apr;12(2):110-118. doi: 10.1007/s10157-007-0017-2. Epub 2008 Jan 5. PMID: 18175058.
