Related Searches: Captopril

Captopril(CAS No. 62571-86-2)

Captopril C9H15NO3S (cas 62571-86-2) Molecular Structure

62571-86-2 Structure

Identification and Related Records

【Name】
Captopril
【Iupac name】
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
【CAS Registry number】
62571-86-2
【Synonyms】
Acepril
D-3-Mercapto-2-methylpropanoyl-L-proline
Garranil
Acepress
(2R)-1-[(2S)-2-methyl-3-sulfanyl-propanoyl]pyrrolidine-2-carboxylate
SQ 14225
(2S)-1-[(2S)-2-methyl-3-sulfanyl-propanoyl]pyrrolidine-2-carboxylic acid
Captopril [USAN:BAN:INN:JAN]
1-Pyrrolidinecarboxylic acid, 1-(D-3-mercapto-2-methyl-1-propionyl)-, L-(S,S)-
1-[(2S)-2-methyl-3-sulfanylpropanoyl]-L-proline
Cesplon
(2S)-1-(3-Mercapto-2-methylpropionyl)-L-proline
SQ 14,225
Lopril
Tensiomin
Aceplus
L-Proline, 1-(3-mercapto-2-methyl-1-oxopropyl)-, (S)-
Captopryl
1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline
Prestwick_103
Tensoprel
L-Proline, 1-((2S)-3-mercapto-2-methyl-1-oxopropyl)-
Capoten
1-(D-3-Mercapto-2-methyl-1-oxopropyl)-L-proline (S,S)
Tenosbon
Capoten (TN)
Apopril (TN)
D-2-Methyl-3-mercaptopropanoyl-L-proline
【EINECS(EC#)】
263-607-1
【Molecular Formula】
C9H15NO3S (Products with the same molecular formula)
【Molecular Weight】
217.28
【Inchi】
InChI=1/C9H15NO3S/c1-6(5-14)8(11)10-4-2-3-7(10)9(12)13/h6-7,14H,2-5H2,1H3,(H,12,13)/t6-,7+/m1/s1
【Canonical SMILES】
CC(CS)C(=O)N1CCCC1C(=O)O
【Isomers smiles】
C[C@H](CS)C(=O)N1CCC[C@H]1C(=O)O
【MOL File】
62571-86-2.mol

Chemical and Physical Properties

【Appearance】
White to off-white crystalline power
【Density】
1.272 g/cm3
【Melting Point】
103-108℃
【Boiling Point】
427 °C at 760 mmHg
【Refractive Index】
-127.5 ° (C=1.7, EtOH)
【Flash Point】
212.1 °C
【Alpha】
-129.5 o (C=1, ETOH)
【Water】
soluble
【Solubilities】
soluble in water
【Color/Form】
White to off-white, crystalline powder
Crystals from ethyl acetate/hexane
【Stability】
Stable. Incompatible with strong oxidizing agents.
【Storage temp】
Store in a cool, dry place. Store in a tightly closed container.
【Spectral properties】
Specific optical rotation -131.0 deg @ 22 deg C/D (approx 1.7% in ethanol)
【Computed Properties】
Molecular Weight:217.2853 [g/mol]
Molecular Formula:C9H15NO3S
XLogP3:0.3
H-Bond Donor:2
H-Bond Acceptor:4
Rotatable Bond Count:3
Exact Mass:217.077264
MonoIsotopic Mass:217.077264
Topological Polar Surface Area:58.6
Heavy Atom Count:14
Formal Charge:0
Complexity:244
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:3
Feature 3D Anion Count:1
Feature 3D Hydrophobe Count:1
Feature 3D Ring Count:1
Effective Rotor Count:5
Conformer Sampling RMSD:0.6
CID Conformer Count:33

Safety and Handling

【Hazard Codes】
Xi:Irritant
【Risk Statements】
R36/37/38
【Safety Statements 】
S26;S37/39
【Safety】

Hazard Codes:?HarmfulXn,IrritantXi
Risk Statements: 43-63-36/37/38-40
R43:May cause sensitization by skin contact.?
R63:Possible risk of harm to the unborn child.?
R36/37/38:Irritating to eyes, respiratory system and skin.?
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 36/37-37/39-26-36-22
S36/37:Wear suitable protective clothing and gloves.?
S37/39:Wear suitable gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S22:Do not breathe dust.
WGK Germany: 2
RTECS: UY0550000
Moderately toxic by intravenous route. Mildly toxic by ingestion. Human systemic effects: blood pressure lowering, changes in kidney function, decreased urine volume or anuria, dermatitis, dyspnea, hemolysis with or without anemia, metabolic changes, somnolence, ureter or bladder tubules failure. An experimental teratogen. Experimental reproductive effects. Used to treat refractory systemic hypertension and as an experimental drug in heart failure. When heated to decomposition it emits very toxic fumes of NOx and SOx. See also MERCAPTANS.

【Formulations/Preparations】
Oral tablets: 25, 50, and 100 mg Capoten (scored).
Oral tablets 25 mg with Hydrochlorothiazide 15 mg, Capozide 25/15 (scored), Squibb; 25 mg with hydrochlorothiazide 25 mg, Capozide 25/25 (scored), Squibb; 50 mg with Hydrochlorothiazide 15 mg, Capozide 50/15 (scored), Squibb; 50 mg with Hydroxhlorothiazide 25 mg, Capozide 50/25 (scored), Squibb. /Captopril combinations/
Oral tablets 12.5 mg, 25 mg, 50 mg, 100 mg Capoten (scored), Squibb.
Each tablet for oral administration contains 12.5 mg, 25 mg, 50 mg or 100 mg of Captopril and the following inactive ingredients: anhydrous lactose, colloidal silicon dioxide, crospovidone, microcrystalline cellulose and stearic acid.
12.5-150 mg/d
【Exposure Standards and Regulations】
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
【Specification】

? Captopril ,?its cas register number is 62571-86-2. It also can be called?(2S)-1-(3-Mercapto-2-methylpropionyl)-L-proline ;
?(S)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline ; 1-((2S)-3-Mercapto-2-methylpropionyl)-L-proline?; 1-(D-3-Mercapto-2-methyl-1-oxopropyl)-L-proline (S,S) ; 3-Mercapto-2-methylpropionyl-proline ; Alopresin ; Asisten ;?Captoprilum ; Cesplon ; D-3-Mercapto-2-methylpropanoyl-L-proline ; D-3-Mercapto-2-methylpropionylproline ; Garranil ;?Lopirin ; Tensoprel ; UNII-9G64RSX1XD . Captopril (CAS NO.62571-86-2) is?white crystalline powder.

【Octanol/Water Partition Coefficient】
log Kow= 0.34 [Ranadive SA et al; Pharm Res 9: 1480-6 (1992)] PubMed Abstract
【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

Prepn: M.A. Ondetti, D.W. Cushman, Ger. pat. 2,703,828; eidem, US pats. 4,046,889 and 4,105,776 (1977, 1977, 1978 all to Squibb).
【Usage】

Orally active angiotensin-converting enzyme (ACE) inhibitor

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】
Angiotensin-Converting Enzyme Inhibitors; Antihypertensive Agents
Captopril is used in the management of mild to severe hypertension. The drug has been used as monotherapy or in combination with other classes of antihypertensive agents.
Captopril is used in conjunction with cardiac glycosides and diuretics in the management of congestive heart failure resistant to or inadequately controlled by cardiac glycosides and diuretics.
A simplified protocol for administration of captopril as a test for renovascular hypertension is described and the specificity, sensitivity, and predictive value of each criterion of the test are reported in 100 hypertensive patients who were given a single 50 mg dose of captopril. Twenty-nine patients had renovascular hypertension; the remainder were diagnosed as having essential hypertension. In this patient population, a post captopril plasma renin activity of 5.7 ng angiotensin/ml/hr or greater had a 100% sensitivity and an 80% specificity for renovascular hypertension. An absolute increase in plasma renin activity with captopril of 4.7 ng angiotensin/ml/hr or greater had a lower sensitivity of 90% and a specificity of 87%, whereas a fractional increase in plasma renin activity after captopril of 150% or higher had the lowest sensitivity of 69% and a specificity of 86%. A subgroup analysis of 38 patients who were receiving diuretic therapy demonstrated that the test sensitivity was unchanged but the specificity was reduced. It was concluded that a single post captopril plasma renin activity value of 5.7 ng angiotensin/ml/hr or greater is a simplified screening test for renovascular hypertension, with excellent sensitivity and acceptable specificity, and that this test is well tolerated, inexpensive and easy to perform. [Frederickson ED et al; Arch Intern Med 150 (Mar): 569-72 (1990)]
【Biomedical Effects and Toxicity】
Approximately 60-75% of an oral dose of captopril is rapidly absorbed from the GI tract in fasting healthy individuals or hypertensive patients. Food may decrease absorption of captopril by up to 25-40%, although there is some evidence that this effect is not clinically important. Following oral administration of a single 100-mg dose of captopril in fasting healthy individuals in one study, average peak blood drug concentrations of 800 ng/mL were attained in 1 hour.
Animal studies indicate that captopril is rapidly distributed into most body tissues, except the CNS. Captopril crosses the placenta in humans and is distributed into milk in concentrations about 1% of maternal blood concentrations. Captopril is approximately 25-30% bound to plasma proteins, mainly albumin.
Captopril and its metabolites are excreted in urine. Renal excretion of unchanged captopril occurs principally via tubular secretion. In patients with normal renal function, more than 95% of an absorbed dose is excreted in urine in 24 hours; about 40-50% of the drug excreted in urine is unchanged captopril and the remainder is mainly the disulfide dimer of captopril and captoprilcysteine disulfide. In one study in healthy individuals, about 20% of a single dose of captopril was recovered in feces in 5 days, apparently representing unabsorbed drug. Captopril is removed by hemodialysis.
The elimination half-life of unchanged captopril appears to be less than 2 hours in patients with normal renal function. The elimination half-life of captopril and its metabolites is correlated with creatinine clearance and increases to about 20-40 hours in patients with creatinine clearances less than 20 ml/minute and as long as 6.5 days in anuric patients.
Captopril has rapid onset with relatively short duration of action, whereas enalapril and lisinopril have slower onset and relatively long duration of action. ... Captopril and its disulfide metabolites are primarily excreted in the urine with minor elimination in the feces. In those patients with severe congestive heart failure the angiotensin converting enzyme inhibitors produce a reduction in systemic vascular resistance, blood pressure, pulmonary capillary wedge pressure, and pulmonary artery pressure. These drugs may produce improvement in cardiac output and stroke volume and, with chronic administration, may promote regression of left ventricular hypertrophy. The antihypertensive effects of the angiotensin converting enzyme inhibitors are enhanced when these agents are combined with a diuretic. Captopril and enalapril have been shown to be of particular benefits as adjunctive therapy in patients with congestive heart failure, both in terms of subjective improvement of patient symptoms, and in improving overall hemodynamic status. [Raia JJ Jr et al; DICP 24 (5): 506-25 (1990)] PubMed Abstract
Most of the drug is eliminated in urine, 40% to 50% as captopril and the rest as captopril disulfide dimers and captopril-cysteine disulfide.

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