Quinapril-d5 | CAS#1279029-79-6 | Quinapril quantification internal standard

MedKoo Cat#: 463961 | Name: Quinapril-d5

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Description:

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

Quinapril-d5 is intended for use as an internal standard for the quantification of quinapril by GC- or LC-MS. Quinapril is a prodrug form of the angiotensin converting enzyme (ACE) inhibitor quinaprilat. In vivo, quinapril reduces mean arterial pressure in renal hypertensive and spontaneously hypertensive rats. It inhibits angiotensin I-induced pressor responses in normotensive rats and dogs. Quinapril prevents left ventricular heart failure in CHF 14.6 cardiomyopathic hamsters. Formulations containing quinapril have been used in the treatment of hypertension, heart failure, and diabetic nephropathy.

Chemical Structure

Quinapril-d5

CAS#1279029-79-6

Theoretical Analysis

MedKoo Cat#: 463961

Name: Quinapril-d5

CAS#: 1279029-79-6

Chemical Formula: C25H25D5N2O5

Exact Mass: 443.2469

Molecular Weight: 443.55

Elemental Analysis: C, 67.70; H, 7.95; N, 6.32; O, 18.03

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 400.00	2 Weeks
5mg	USD 1,000.00	2 Weeks

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Synonym

Quinapril-d5; Quinapril d5; CI-906-d5; CI906-d5; CI 906-d5; CI 906 d5; CI906 d5; CI-906 d5;

IUPAC/Chemical Name

(S)-2-(((S)-1-ethoxy-1-oxo-4-(phenyl-d5)butan-2-yl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

InChi Key

JSDRRTOADPPCHY-BNPIMZLHSA-N

InChi Code

InChI=1S/C25H30N2O5/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30)/t17-,21-,22-/m0/s1/i4D,5D,6D,9D,10D

SMILES Code

O=C([C@H]1N(CC2=C(C1)C=CC=C2)C([C@@H](N[C@H](C(OCC)=O)CCC3=C(C([2H])=C(C([2H])=C3[2H])[2H])[2H])C)=O)O

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 methanol

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

View handling instruction

Biological target:

Quinapril has a role as an EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor, a prodrug and an antihypertensive agent. It is a member of isoquinolines, a dicarboxylic acid monoester, an ethyl ester and a tertiary carboxamide.

In vitro activity:

Ureteropelvic junction obstruction (UPJO) is a common renal obstructive disorder, but its pathogenic mechanisms remain largely unclear. The expressions of angiotensin-converting enzyme (ACE) and aminopeptidase N (AP-N) in HK2 cells were inhibited by quinapril and siRNA, respectively. Suppression of ACE and AP-N expression mediates congenital UPJO pathogenesis by repressing renal tubular epithelial proliferation, promoting ROS production, and enhancing inflammatory factor expression. Reference: Exp Cell Res. 2020 Aug 1;393(1):112086. https://pubmed.ncbi.nlm.nih.gov/32416091/

In vivo activity:

Hyperglycemia is associated with a higher cardiovascular risk, as evidenced by increased carotid-intima media thickness (CIMT) in youth with diabetes. Three randomized controlled trials evaluated the effects of metformin, quinapril, and atorvastatin. The difference in CIMT was -0.01 mm for quinapril compared to placebo. Some pharmacological interventions may decrease CIMT in children with type 1 diabetes. However, there is great uncertainty with respect to their effects and no strong conclusions can be drawn. Further evidence is required. Reference: Front Clin Diabetes Healthc. 2022 Jul 4;3:882504. https://pubmed.ncbi.nlm.nih.gov/36992735/

	Solvent	mg/mL	mM
Solubility
	Methanol	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 443.55 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. Liu R, Zhang W, Luo M, Qin X, Yang F, Wei Q. iTRAQ-based proteomics and in vitro experiments reveals essential roles of ACE and AP-N in the renin-angiotensin system-mediated congenital ureteropelvic junction obstruction. Exp Cell Res. 2020 Aug 1;393(1):112086. doi: 10.1016/j.yexcr.2020.112086. Epub 2020 May 13. PMID: 32416091. 2. Müns G, Vishwanatha JK, Rubinstein I. Regulation of angiotensin I-converting enzyme in cultured bovine bronchial epithelial cells. J Cell Biochem. 1993 Dec;53(4):352-9. doi: 10.1002/jcb.240530413. PMID: 8300752. 3. Epure AM, Anker D, Di Bernardo S, da Costa BR, Sekarski N, Chiolero A. Interventions to Decrease Carotid-Intima Media Thickness in Children and Adolescents With Type 1 Diabetes: A Systematic Review and Meta-Analysis. Front Clin Diabetes Healthc. 2022 Jul 4;3:882504. doi: 10.3389/fcdhc.2022.882504. PMID: 36992735; PMCID: PMC10012108. 4. Crilly S, Parry-Jones A, Wang X, Selley JN, Cook J, Tapia VS, Anderson CS, Allan SM, Kasher PR. Zebrafish drug screening identifies candidate therapies for neuroprotection after spontaneous intracerebral haemorrhage. Dis Model Mech. 2022 Mar 1;15(3):dmm049227. doi: 10.1242/dmm.049227. Epub 2022 Mar 29. PMID: 35098999; PMCID: PMC8990924.

In vitro protocol:

In vivo protocol:

1. Epure AM, Anker D, Di Bernardo S, da Costa BR, Sekarski N, Chiolero A. Interventions to Decrease Carotid-Intima Media Thickness in Children and Adolescents With Type 1 Diabetes: A Systematic Review and Meta-Analysis. Front Clin Diabetes Healthc. 2022 Jul 4;3:882504. doi: 10.3389/fcdhc.2022.882504. PMID: 36992735; PMCID: PMC10012108. 2. Crilly S, Parry-Jones A, Wang X, Selley JN, Cook J, Tapia VS, Anderson CS, Allan SM, Kasher PR. Zebrafish drug screening identifies candidate therapies for neuroprotection after spontaneous intracerebral haemorrhage. Dis Model Mech. 2022 Mar 1;15(3):dmm049227. doi: 10.1242/dmm.049227. Epub 2022 Mar 29. PMID: 35098999; PMCID: PMC8990924.

1: Alessi K, Parmar M. Fosinopril. 2020 Dec 2. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 32119367. 2: Tandan N, Cassagnol M. Quinapril. 2020 Nov 4. In: StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing; 2020 Jan–. PMID: 32491330. 3: Fischer NM, Nieuwenhuis TO, Singh B, Yenokyan G, Segars JH. Angiotensin- Converting Enzyme Inhibitors Reduce Uterine Fibroid Incidence in Hypertensive Women. J Clin Endocrinol Metab. 2021 Jan 23;106(2):e650-e659. doi: 10.1210/clinem/dgaa718. PMID: 33035320; PMCID: PMC7823233. 4: Drugs for hypertension. Med Lett Drugs Ther. 2020 May 18;62(1598):73-80. PMID: 32555118. 5: Liu R, Zhang W, Luo M, Qin X, Yang F, Wei Q. iTRAQ-based proteomics and in vitro experiments reveals essential roles of ACE and AP-N in the renin- angiotensin system-mediated congenital ureteropelvic junction obstruction. Exp Cell Res. 2020 Aug 1;393(1):112086. doi: 10.1016/j.yexcr.2020.112086. Epub 2020 May 13. PMID: 32416091. 6: Dorosch T, Ganzer CA, Lin M, Seifan A. Efficacy of Angiotensin-Converting Enzyme Inhibitors and Angiotensin Receptor Blockers in the Preventative Treatment of Episodic Migraine in Adults. Curr Pain Headache Rep. 2019 Sep 12;23(11):85. doi: 10.1007/s11916-019-0823-8. PMID: 31515634. 7: Expanded table: Some drugs for HFrEF. Med Lett Drugs Ther. 2019 Apr 8;61(1569):e57-e62. PMID: 31169798. 8: Drugs for chronic heart failure. Med Lett Drugs Ther. 2019 Apr 8;61(1569):49-54. PMID: 31169796. 9: Ikemura N, Yamaori S, Kobayashi C, Kamijo S, Murayama N, Yamazaki H, Ohmori S. Inhibitory effects of antihypertensive drugs on human cytochrome P450 2J2 activity: Potent inhibition by azelnidipine and manidipine. Chem Biol Interact. 2019 Jun 1;306:1-9. doi: 10.1016/j.cbi.2019.04.005. Epub 2019 Apr 6. PMID: 30965050. 10: Stasiak A, Gola J, Kraszewska K, Mussur M, Kobos J, Mazurek U, Stark H, Fogel WA. Experimental autoimmune myocarditis in rats and therapeutic histamine H1 - H4 receptor inhibition. J Physiol Pharmacol. 2018 Dec;69(6). doi: 10.26402/jpp.2018.6.13. Epub 2019 Mar 18. PMID: 30898985. 11: Desai RJ, Sarpatwari A, Dejene S, Khan NF, Lii J, Rogers JR, Dutcher SK, Raofi S, Bohn J, Connolly JG, Fischer MA, Kesselheim AS, Gagne JJ. Comparative effectiveness of generic and brand-name medication use: A database study of US health insurance claims. PLoS Med. 2019 Mar 13;16(3):e1002763. doi: 10.1371/journal.pmed.1002763. PMID: 30865626; PMCID: PMC6415809. 12: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Quinapril. 2019 Feb 28. PMID: 30000147. 13: Pang XF, Liu RM, Xia YF. Effects of inhibitors of the renin-angiotensin system on reducing blood pressure and expression of inflammatory factors in CHD patients: A network meta-analysis. J Cell Physiol. 2019 May;234(5):5988-5997. doi: 10.1002/jcp.27147. Epub 2018 Dec 7. PMID: 30537058. 14: Hubers SA, Kohm K, Wei S, Yu C, Nian H, Grabert R, Sexton DJ, Brown NJ. Endogenous bradykinin and B1-B5 during angiotensin-converting enzyme inhibitor- associated angioedema. J Allergy Clin Immunol. 2018 Nov;142(5):1636-1639.e5. doi: 10.1016/j.jaci.2018.06.037. Epub 2018 Jul 21. PMID: 30036596; PMCID: PMC6226317. 15: Gromotowicz-Poplawska A, Stankiewicz A, Mikita J, Aleksiejczuk M, Marcinczyk N, Szemraj J, Chabielska E. Beneficial effect of combined spironolactone and quinapril treatment on thrombosis and hemostasis in 2K1C hypertensive rats. J Physiol Pharmacol. 2018 Apr;69(2). doi: 10.26402/jpp.2018.2.10. Epub 2018 Jul 4. PMID: 29980144. 16: Desai RJ, Sarpatwari A, Dejene S, Khan NF, Lii J, Rogers JR, Dutcher SK, Raofi S, Bohn J, Connolly J, Fischer MA, Kesselheim AS, Gagne JJ. Differences in rates of switchbacks after switching from branded to authorized generic and branded to generic drug products: cohort study. BMJ. 2018 Apr 3;361:k1180. doi: 10.1136/bmj.k1180. PMID: 29615391; PMCID: PMC5881140. 17: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Angiotensin-Converting Enzyme Inhibitors. 2018 Feb 11. PMID: 31644219. 18: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Quinapril. 2018 Feb 11. PMID: 31643770. 19: Sun S, Wei Y, Wang H, Cao Y, Deng B. A novel electrochemiluminescence sensor coupled with capillary electrophoresis for simultaneous determination of quinapril hydrochloride and its metabolite quinaprilat hydrochloride in human plasma. Talanta. 2018 Mar 1;179:213-220. doi: 10.1016/j.talanta.2017.10.050. Epub 2017 Nov 4. PMID: 29310224. 20: Rajzer M, Wojciechowska W, Kameczura T, Olszanecka A, Fedak D, Terlecki M, Kawecka-Jaszcz K, Czarnecka D. The effect of antihypertensive treatment on arterial stiffness and serum concentration of selected matrix metalloproteinases. Arch Med Sci. 2017 Jun;13(4):760-770. doi: 10.5114/aoms.2016.58825. Epub 2016 Mar 23. PMID: 28721143; PMCID: PMC5510502.