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Quinapril hydrochloride(CAS No. 82586-55-8)

Quinapril hydrochloride C25H31ClN2O5 (cas 82586-55-8) Molecular Structure

82586-55-8 Structure

Identification and Related Records

【Name】
Quinapril hydrochloride
【Iupac 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
【CAS Registry number】
82586-55-8
【Synonyms】
3-Isoquinolinecarboxylicacid,2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-,monohydrochloride, (3S)- (9CI)
Accupril
Accuprin
Accupro
Accupro20
Accupron
Acequide
Acequin
Acuitel
Acuprel
Acupril
Asig
CI 906
Korec
Korectic
PD 109452-2
3-Isoquinolinecarboxylicacid,2-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-,hydrochloride (1:1), (3S)-
Quinazil
Quinopril
【Molecular Formula】
C25H31ClN2O5 (Products with the same molecular formula)
【Molecular Weight】
474.98
【Inchi】
InChI=1/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
【Canonical SMILES】
CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3=CC=CC=C3CC2C(=O)O.Cl
【Isomers smiles】
CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3=CC=CC=C3C[C@H]2C(=O)O.
Cl
【MOL File】
82586-55-8.mol

Chemical and Physical Properties

【Appearance】
white crystalline solid
【Melting Point】
120-130 °C
【Boiling Point】
662 °C at 760 mmHg
【Flash Point】
354.1 °C
【Storage temp】
2-8°C
【Computed Properties】
Molecular Weight:474.97704 [g/mol]
Molecular Formula:C25H31ClN2O5
H-Bond Donor:3
H-Bond Acceptor:6
Rotatable Bond Count:10
Exact Mass:474.19215
MonoIsotopic Mass:474.19215
Topological Polar Surface Area:95.9
Heavy Atom Count:33
Formal Charge:0
Complexity:648
Isotope Atom Count:0
Defined Atom Stereocenter Count:3
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:2

Safety and Handling

【Safety Statements 】
22-24/25
【Safety】

Safety Statements: 22-24/25?
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.
RTECS; NW7176000

【Formulations/Preparations】
CI-906; PD-109452-2; Accupril; Accuprin; Accupro; Acequin; Acuitel; Korec; Quinazil
Quinaprilat /Diacid of Quinapril/
Acequide; Koretic /Mixture with Hydrochlorothiazide/
The main ingredient in the drug Accupril ... (tablets)
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl quinapril hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

?Quinapril hydrochloride (CAS NO.82586-55-8) is also named as (S)-2-((S)-N-((S)-1-Carboxy-3-phenylpropyl)alanyl)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid, 1-ethyl ester, monohydrochloride ; 3-Isoquinolinecarboxylic acid, 2-(2-((1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)-1,2,3,4-tetrahydro-, monohydrochloride, (3S-(2(R*(R*)),3R*)) ; Accupril ; Accuprin ; Accupron ; Acequin ; Acuitel ; Acuprel ; Asig ; CI906 ; Conan ; Continucor ; Ectren ; HSDB 7046 ; Hemokvin ; Korec ; Koretic ; Lidaltrin ; PD 109452-2 ; Quinapril ; Quinapril HCl ; Quinazil ; UNII-33067B3N2M?.?Quinapril hydrochloride (CAS NO.82586-55-8) is?white crystalline solid.

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Preparation: M.L. Hoefle, S. Klutchko, EP 49605; eidem, US 4344949 (both 1982 to Warner-Lambert)...Synthesis of novel crystalline and purified form: O.P. Goel, U. Krolls, US 4761479 (1988 to Warner-Lambert)
【Usage】
An angiotensin converting enzyme (ACE) inhibitor. Antihypertensive

Biomedical Effects and Toxicity

【Pharmacological Action】
- A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility.
- Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
【Therapeutic Uses】
... /Quinapril/ has proven to be very useful for the treatment of hypertension ... . /Salt not specified/
The angiotensin converting enzyme (ACE) inhibitors appear to confer a special advantage in the treatment of patients with diabetes, slowing the development of diabetic glomerulopathy. They also have been shown to be effective in slowing the progression of other forms of chronic renal disease, such as glomerulosclerosis, & many of these patients also have hypertension. An ACE inhibitor is probably the preferred initial agent in the treatment of hypertensive patients with left ventricular hypertrophy. Patients with hypertension & ischemic heart disease are candidates for treatment with ACE inhibitors; this includes treatment in the immediate post-myocardial infarction period which has been shown to lead to improved ventricular function & reduced morbidity & mortality. /ACE inhibitors/ /Salt not specified/
The combination of ... quinapril and hydrochlorothiazide is indicated in the treatment of hypertension. Fixed-dosage combinations generally are not recommended for initial therapy, but are utilized in maintenance therapy after the required dose is established in order to increase convenience, economy, and patient compliance. /Included in US product labeling/ /Salt not specified/
Angiotensin converting enzyme (ACE) inhibitor /Salt not specified/
Angiotensin II & nitric oxide (NO) may play a role in hypertensive cardiovascular remodeling ...The effects of long-term treatment with quinapril ... on expression of endothelial NO synthase (eNOS), ACE, & angiotensin II type 1 (AT1) receptor in the left ventricle /were evaluated/... These relations to myocardial remodeling in deoxycorticosterone acetate (DOCA)-salt hypertensive rats /were also evaluated/. Deoxycorticosterone acetate-salt rats were induced with weekly injections of DOCA (30 mg/kg) & 1% saline in drinking water after right nephrectomy. Quinapril (DOCA-QUI, 10 mg/kg/day, subdepressor dose) ... or vehicle (DOCA-V) were given after induction of DOCA-salt hypertension for 5 wks, & age-matched sham-operated rats (ShC) served as a control group. The eNOS expression in the left ventricle were significantly decreased in DOCA-V compared with ShC, & were significantly increased in DOCA-QUI ... compared with ShC & DOCA-V. The gene expression of ACE, AT1 receptor, & type I collagen mRNA were significantly increased in DOCA-V compared with ShC, & significantly suppressed in DOCA-QUI compared with DOCA-V. The DOCA-V rats demonstrated a significant incr of the wall-to-lumen ratio, perivascular fibrosis, & myocardial fibrosis, with all these parameters being significantly improved by quinapril. Myocardial remodeling in DOCA-salt hypertensive rats was significantly ameliorated by a subdepressor dose of quinapril, which may be due to an incr in eNOS mRNA & protein expression & a decr in ACE & AT1 receptor mRNA expression in the left ventricle. /Cmpd identity not verifiable/ /Salt not specified/ [Hara K, et al; Am J Hypertens 14(4 Pt 1): 321-330 (2001)]
【Biomedical Effects and Toxicity】
Absorption (bioavailability) of quinapril is 60%; time to peak serum concn is 2 hr; half-life (elimination) is 2 hr; protein binding is 97%; metabolism is in the liver. /from table/ /Salt not specified/
Quinapril is rapidly absorbed (peak concns are achieved in 1 hr, but the peak may be delayed after food), & its rate but not extent of oral absorption (60%) may be reduced by food. Quinapril is metabolized to quinaprilat & to other minor metabolites, & quinaprilat is excreted in the urine (61%) & the feces (37%). Peak concns of quinaprilat in plasma are achieved in about 2 hr. Conversion of quinapril to quinaprilat is reduced in patients with diminished liver function. The initial half-life of quinaprilat is about 2 hr; a prolonged terminal half-life of about 25 hr may be due to high-affinity binding of the drug to tissue ACE. /Salt not specified/

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