Basic information
- Name:
Captopril
- CAS No.:
62571-86-2
- Molecular Structure:
- Formula:
- C9H15NO3S
- 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;
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Chemistry
IUPAC Name: (2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
Empirical Formula: C9H15NO3S
Molecular Weight: 217.2853g/mol
EINECS: 263-607-1
Structure of Captopril (CAS NO.62571-86-2):
Index of Refraction: 1.55
Molar Refractivity: 54.44 cm3
Molar Volume: 170.7 cm3
Polarizability: 21.58×10-24cm3
Surface Tension: 54.3 dyne/cm
Density: 1.272 g/cm3
Flash Point: 212.1 °C
Enthalpy of Vaporization: 74.79 kJ/mol
Melting Point: 104-108 °C(lit.)
Boiling Point: 427 °C at 760 mmHg
Vapour Pressure: 1.73E-08 mmHg at 25°C
Solubility: H2O: 0.1 g/mL, very slightly hazy, colorless
Stability: Stable. Incompatible with strong oxidizing agents.
Product Categories: Active Pharmaceutical Ingredients;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API's;Angiotensin
Canonical SMILES: CC(CS)C(=O)N1CCCC1C(=O)O
Isomeric SMILES: C[C@H](CS)C(=O)N1CCC[C@H]1C(=O)O
InChI: InChI=1S/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
InChIKey: FAKRSMQSSFJEIM-RQJHMYQMSA-N
History
Captopril was developed in 1975 by three researchers at the U.S. drug company Squibb (now Bristol-Myers Squibb): Miguel Ondetti, Bernard Rubin and David Cushman. Squibb filed for U.S. patent protection on the drug in February 1976 and U.S. Patent 4,046,889 was granted in September 1977. Captopril gained FDA approval on April 6, 1981. The drug went generic in the U.S. in February 1996 as a result of the end of market exclusivity for Bristol-Myers Squibb.
Uses
Captopril 's main uses are based on its vasodilatation and inhibition of some renal function activities.Additionally, it has shown mood-elevating properties in some patients. It has also been investigated for use in the treatment of cancer.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| dog | LD | oral | > 600mg/kg (600mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980Vol. -, Pg. 137, 1980. |
| man | LDLo | oral | 2500ug/kg/3D- (2.5mg/kg) | KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Postgraduate Medical Journal. Vol. 60, Pg. 561, 1984. |
| man | LDLo | oral | 2680ug/kg/5D- (2.68mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Southern Medical Journal. Vol. 86, Pg. 1269, 1993. |
| man | LDLo | oral | 16mg/kg (16mg/kg) | Journal of Toxicology, Clinical Toxicology. Vol. 28, Pg. 379, 1990. | |
| man | TDLo | oral | 2679ug/kg/5D- (2.679mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Israel Journal of Medical Sciences. Vol. 21, Pg. 892, 1985. |
| man | TDLo | oral | 4mg/kg/8D-I (4mg/kg) | BEHAVIORAL: TOXIC PSYCHOSIS | American Journal of Psychiatry. Vol. 142, Pg. 270, 1985. |
| man | TDLo | oral | 7143ug/kg/2D- (7.143mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | British Medical Journal. Vol. 294, Pg. 91, 1987. |
| man | TDLo | oral | 12500ug/kg/25 (12.5mg/kg) | BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA | Canadian Medical Association Journal. Vol. 129, Pg. 525, 1983. |
| man | TDLo | oral | 87mg/kg/18W-I (87mg/kg) | KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI KIDNEY, URETER, AND BLADDER: PROTEINURIS KIDNEY, URETER, AND BLADDER: HEMATURIA | Annals of Internal Medicine. Vol. 112, Pg. 550, 1990. |
| man | TDLo | oral | 239mg/kg/6W-I (239mg/kg) | SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" BLOOD: NORMOCYTIC ANEMIA | American Journal of Medicine. Vol. 71, Pg. 493, 1981. |
| monkey | LD | oral | > 1500mg/kg (1500mg/kg) | GASTROINTESTINAL: NAUSEA OR VOMITING | "Captopril and Hypertension, Collection of Papers presented at a Symposium, Princeton, N.J., 1979?," Case, David B., et al. eds., New York, Plenum Publishing, 1980Vol. -, Pg. 137, 1980. |
| mouse | LD50 | intravenous | 663mg/kg (663mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 297, 1983. | |
| mouse | LD50 | oral | 2500mg/kg (2500mg/kg) | Pharmaceutical Chemistry Journal Vol. 22, Pg. 212, 1988. | |
| mouse | LD50 | subcutaneous | > 2400mg/kg (2400mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 24, Pg. 2439, 1982. | |
| rat | LD50 | intravenous | 554mg/kg (554mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 297, 1983. | |
| rat | LD50 | oral | 4245mg/kg (4245mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 14, Pg. 297, 1983. | |
| rat | LD50 | subcutaneous | > 600mg/kg (600mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 24, Pg. 2439, 1982. | |
| women | LDLo | oral | 1500ug/kg/7W (1.5mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Annals of Internal Medicine. Vol. 94, Pg. 58, 1981. |
| women | TDLo | oral | 10mg/kg (10mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION | Annals of Emergency Medicine. Vol. 20, Pg. 1125, 1991. |
| women | TDLo | oral | 10mg/kg/10D-I (10mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | British Medical Journal. Vol. 294, Pg. 91, 1987. |
| women | TDLo | oral | 14mg/kg/2W-I (14mg/kg) | KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" | Annals of Internal Medicine. Vol. 104, Pg. 126, 1986. |
Safety Profile
Hazard Codes: 
Xn,
Xi
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.
Standards and Recommendations
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.
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