Synonym
Quinapril Hydrochloride; Accupril; Accuprin; Acequin; Korec;Accupril; CI 906; CI-906; PD 109452-2; PD-109,452-2; quinapril; quinapril hydrochloride;
IUPAC/Chemical Name
(3S)-2-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,4-dihydro-1H-isoquinoline-3-carboxylic acid;hydrochloride
InChi Key
IBBLRJGOOANPTQ-JKVLGAQCSA-N
InChi Code
InChI=1S/C25H30N2O5.ClH/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);1H/t17-,21-,22-;/m0./s1
SMILES Code
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3=CC=CC=C3CC2C(=O)O.Cl
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
Biological target:
Quinapril’s target catalyses the formation of angiotensin II from its precursor, angiotensin I. Angiotensin II is a potent vasoconstrictor and thus preventing its formation causes vasodilation and an increased capillary blood volume.
In vitro activity:
To determine the transport mechanisms of quinapril and cephalexin in Caco-2 cell monolayers, a cell culture model of the human small intestinal epithelium was utilized. This study found that transport of quinapril in the Caco-2 cells is through a combination of the carrier-mediated proton gradient-dependent peptide transporter and passive diffusion.
Reference: Pharm Res. 1995 Aug;12(8):1120-5. https://pubmed.ncbi.nlm.nih.gov/7494822/
In vivo activity:
Women on an angiotensin-converting enzyme inhibitor (ACEi) experienced a 31.8% reduced odds of developing clinically recognized leiomyoma compared to nonusers (one being quinapril (odds ratio 0.62; 95% CI, 0.41-0.92) demonstrated a significant association with reduced leiomyoma incidence. ACEi use was associated with a reduced odds of developing clinically recognized leiomyoma in adult hypertensive women.
Reference: J Clin Endocrinol Metab. 2021 Jan 23;106(2):e650-e659. https://pubmed.ncbi.nlm.nih.gov/33035320/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
210.54 |
| Water |
50.0 |
105.27 |
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
474.98
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. Nagornaya AA, Magomedov S, Gorchakova NA, Belenichev IF, Ghekman IS, Kuzub TA. [Influence of quinaprin in combination with angioline on the connective tissue components in the rats serum with experimental hypertension]. Lik Sprava. 2015 Jul-Sep;(5-6):116-20. Ukrainian. PMID: 27089728.
2. Hu M, Zheng L, Chen J, Liu L, Zhu Y, Dantzig AH, Stratford RE Jr. Mechanisms of transport of quinapril in Caco-2 cell monolayers: comparison with cephalexin. Pharm Res. 1995 Aug;12(8):1120-5. doi: 10.1023/a:1016247523311. PMID: 7494822.
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. Fujita T, Ishihara K, Yasuda S, Nakamura T, Maeda M, Kobayashi M, Sahashi K, Ikeda Y, Kumagai Y, Majima M. In vivo kinetics of indoxyl sulfate in humans and its renal interaction with angiotensin-converting enzyme inhibitor quinapril in rats. J Pharmacol Exp Ther. 2012 Jun;341(3):626-33. doi: 10.1124/jpet.111.187732. Epub 2012 Mar 2. PMID: 22389425.
In vitro protocol:
1. Nagornaya AA, Magomedov S, Gorchakova NA, Belenichev IF, Ghekman IS, Kuzub TA. [Influence of quinaprin in combination with angioline on the connective tissue components in the rats serum with experimental hypertension]. Lik Sprava. 2015 Jul-Sep;(5-6):116-20. Ukrainian. PMID: 27089728.
2. Hu M, Zheng L, Chen J, Liu L, Zhu Y, Dantzig AH, Stratford RE Jr. Mechanisms of transport of quinapril in Caco-2 cell monolayers: comparison with cephalexin. Pharm Res. 1995 Aug;12(8):1120-5. doi: 10.1023/a:1016247523311. PMID: 7494822.
In vivo protocol:
1. 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.
2. Fujita T, Ishihara K, Yasuda S, Nakamura T, Maeda M, Kobayashi M, Sahashi K, Ikeda Y, Kumagai Y, Majima M. In vivo kinetics of indoxyl sulfate in humans and its renal interaction with angiotensin-converting enzyme inhibitor quinapril in rats. J Pharmacol Exp Ther. 2012 Jun;341(3):626-33. doi: 10.1124/jpet.111.187732. Epub 2012 Mar 2. PMID: 22389425.
1: Stolarczyk M, Maślanka A, Apola A, Krzek J. Determination of losartan
potassium, quinapril hydrochloride and hydrochlorothiazide in pharmaceutical
preparations using derivative spectrophotometry and chromatographic-densitometric
method. Acta Pol Pharm. 2013 Nov-Dec;70(6):967-76. PubMed PMID: 24383320.
2: Hailu SA, Bogner RH. Complex effects of drug/silicate ratio, solid-state
equivalent pH, and moisture on chemical stability of amorphous quinapril
hydrochloride coground with silicates. J Pharm Sci. 2011 Apr;100(4):1503-15. doi:
10.1002/jps.22387. Epub 2010 Nov 24. PubMed PMID: 24081473.
3: Hailu SA, Bogner RH. Solid-state surface acidity and pH-stability profiles of
amorphous quinapril hydrochloride and silicate formulations. J Pharm Sci. 2010
Jun;99(6):2786-99. doi: 10.1002/jps.22051. PubMed PMID: 20091829.
4: Stanisz B, Paszun S, Strzyzycka N, Ptaszyński E. Influence of humidity and
hydroxypropyl cellulose, hydroxypropylmethyl cellulose, glyceryl behenate or
magnesium stearate on the degradation kinetics of quinapril hydrochloride in
solid phase. Acta Pol Pharm. 2010 Jan-Feb;67(1):99-102. PubMed PMID: 20210086.
5: Hailu SA, Bogner RH. Effect of the pH grade of silicates on chemical stability
of coground amorphous quinapril hydrochloride and its stabilization using
pH-modifiers. J Pharm Sci. 2009 Sep;98(9):3358-72. doi: 10.1002/jps.21767. PubMed
PMID: 19363809.
6: Stanisz B. Kinetics of degradation of quinapril hydrochloride in tablets.
Pharmazie. 2003 Apr;58(4):249-51. PubMed PMID: 12749406.
7: Guo Y, Byrn SR, Zografi G. Physical characteristics and chemical degradation
of amorphous quinapril hydrochloride. J Pharm Sci. 2000 Jan;89(1):128-43. PubMed
PMID: 10664545.
8: Owada A, Nonoguchi H, Terada Y, Marumo F, Tomita K. Effects of quinapril
hydrochloride in patients with essential hypertension and impaired renal
function. Clin Exp Hypertens. 1997 May;19(4):495-502. PubMed PMID: 9140710.
9: Miller MA, Texter M, Gmerek A, Robbins J, Shurzinske L, Canter D. Quinapril
hydrochloride effects on renal function in patients with renal dysfunction and
hypertension: a drug-withdrawal study. Cardiovasc Drugs Ther. 1994
Apr;8(2):271-5. PubMed PMID: 7918140.
10: Hausin RJ, Codding PW. Molecular and crystal structures of MDL27,467A
hydrochloride and quinapril hydrochloride, two ester derivatives of potent
angiotensin converting enzyme inhibitors. J Med Chem. 1991 Feb;34(2):511-7.
PubMed PMID: 1995872.
11: Rojanasthien N, Nasangiam N, Kumsorn B, Roongapinun S, Jengjareon A.
Pharmacokinetics and bioequivalence study of the two 20-mg quinapril
hydrochloride tablet formulations in healthy Thai male volunteers. J Med Assoc
Thai. 2008 May;91(5):739-46. PubMed PMID: 18672641.
12: Bhavar GB, Chatpalliwar VA, Patil DD, Surana SJ. Validated HPTLC Method for
Simultaneous Determination of Quinapril Hydrochloride and Hydrochlorothiazide in
a Tablet Dosage Form. Indian J Pharm Sci. 2008 Jul-Aug;70(4):529-31. doi:
10.4103/0250-474X.44612. PubMed PMID: 20046789; PubMed Central PMCID: PMC2792558.
13: Stanisz B. The influence of pharmaceutical excipients on quinapril
hydrochloride stability. Acta Pol Pharm. 2005 May-Jun;62(3):189-93. PubMed PMID:
16193811.
14: Stanisz B. The stability of quinapril hydrochloride--a mixture of amorphous
and crystalline forms (QHCl-AC)--in solid phase. Acta Pol Pharm. 2003
Nov-Dec;60(6):443-9. PubMed PMID: 15080591.
15: Guo Y, Byrn SR, Zografi G. Effects of lyophilization on the physical
characteristics and chemical stability of amorphous quinapril hydrochloride.
Pharm Res. 2000 Aug;17(8):930-5. PubMed PMID: 11028937.
16: McGuire EJ, Anderson JA, Gough AW, Herman JR, Pegg DG, Theiss JC, de la
Iglesia FA. Preclinical toxicology studies with the angiotensin-converting enzyme
inhibitor quinapril hydrochloride (Accupril). J Toxicol Sci. 1996
Nov;21(4):207-14. Review. PubMed PMID: 8959644.
