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Captopril

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Name

Captopril

EINECS 263-607-1
CAS No. 62571-86-2 Density 1.272 g/cm3
PSA 96.41000 LogP 0.56580
Solubility soluble in water Melting Point 104-108 °C(lit.)
Formula C9H15NO3S Boiling Point 427 °C at 760 mmHg
Molecular Weight 217.289 Flash Point 212.1 °C
Transport Information N/A Appearance white crystalline powder
Safety 36/37-37/39-26-36-22 Risk Codes 43-63-36/37/38-40
Molecular Structure Molecular Structure of 62571-86-2 (Captopril) Hazard Symbols HarmfulXn, IrritantXi
Synonyms

acepress;Captopril;dilabar;lopril;acediur;sa333;cesplon;acepril;aceplus;capoten;

Article Data 33

Captopril Synthetic route

147-85-3

L-proline

62571-86-2

captopril

613256-52-3

β-hydroxy-α-methyl-N-acryloyl-(S)-proline

62571-86-2

captopril

Conditions
ConditionsYield
Stage #1: β-hydroxy-α-methyl-N-acryloyl-(S)-proline With thionyl chloride In tetrahydrofuran at 20℃; for 5h;
Stage #2: With ammonium sulfide In tetrahydrofuran at 0 - 20℃; for 3.5h;
87%
114857-98-6

(S)-1-((S)-3-tert-Butylsulfanyl-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid tert-butyl ester

62571-86-2

captopril

Conditions
ConditionsYield
With mercury(II) diacetate; trifluoroacetic acid Yield given;

N-(6-Methyl-pyridin-2-yl)-3-propionylamino-benzamide; compound with (S)-1-((S)-3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid

A

62571-86-2

captopril

B

87055-70-7

N-(6-Methyl-pyridin-2-yl)-3-propionylamino-benzamide

Conditions
ConditionsYield
In chloroform-d1 at 25℃; Equilibrium constant;

N-(6-Methyl-pyridin-2-yl)-3-((S)-2-phenyl-butyrylamino)-benzamide; compound with (S)-1-((S)-3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid

A

62571-86-2

captopril

B

143956-57-4

N-(6-Methyl-pyridin-2-yl)-3-((S)-2-phenyl-butyrylamino)-benzamide

Conditions
ConditionsYield
In chloroform-d1 at 25℃; Equilibrium constant;

N-(6-Methyl-pyridin-2-yl)-3-((R)-2-phenyl-butyrylamino)-benzamide; compound with (S)-1-((S)-3-mercapto-2-methyl-propionyl)-pyrrolidine-2-carboxylic acid

A

62571-86-2

captopril

B

143956-58-5

N-(6-Methyl-pyridin-2-yl)-3-((R)-2-phenyl-butyrylamino)-benzamide

Conditions
ConditionsYield
In chloroform-d1 at 25℃; Equilibrium constant;

(S)-1-[(S)-3-chloro-2-methylpropanoyl]pyrrolidine-2-carboxylic acid

62571-86-2

captopril

Conditions
ConditionsYield
With ammonium sulfide In methanol for 24h; Heating;1.86 g
With sodium hydrogen sulfide In water; toluene at 125℃; under 10343.2 Torr; for 0.5h; Temperature; Time; Inert atmosphere; Flow reactor;
80629-35-2

1-(3-bromo-2S-methylpropionyl)-pyrrolidine-2S-carboxylic acid

62571-86-2

captopril

Conditions
ConditionsYield
With ammonium sulfide In methanol for 24h; Heating;1.95 g
17912-60-6

H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2

64806-05-9

Captopril disulfide

A

50-56-6

oxytocin

B

62571-86-2

captopril

Conditions
ConditionsYield
In water at 25℃; for 5h; Equilibrium constant; pH 7.0;
17912-60-6

H-Cys-Tyr-Ile-Gln-Asn-Cys-Pro-Leu-Gly-NH2

64806-05-9

Captopril disulfide

A

62571-86-2

captopril

B

C52H81N13O15S3

C

C52H81N13O15S3

Conditions
ConditionsYield
In water at 25℃; for 5h; Rate constant; Equilibrium constant; pH 7.0;

Captopril 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.

Captopril Standards and Recommendations

%

Captopril Specification

Captopril, with the CAS NO. 62571-86-2, is 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 is white crystalline powder. It has also been investigated for use in the treatment of cancer.

Physical properties about Captopril are: (1)ACD/LogP: 0.185; (2)ACD/LogD (pH 5.5): -1.64; (3)ACD/LogD (pH 7.4): -3.25; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.552; (12)Molar Refractivity: 54.488 cm3; (13)Molar Volume: 170.339 cm3; (14)Polarizability: 21.601 10-24cm3; (15)Surface Tension: 55.7949981689453 dyne/cm; (16)Density: 1.276 g/cm3; (17)Flash Point: 222.132 °C; (18)Enthalpy of Vaporization: 76.89 kJ/mol; (19)Boiling Point: 443.684 °C at 760 mmHg

When you are using Captopril, please be cautious about it as the following:
1. Wear suitable protective clothing and gloves;
2. Wear suitable gloves and eye/face protection;
3. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
4. Wear suitable protective clothing;
5. Do not breathe dust;

You can still convert the following datas into molecular structure:
(1)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;
(2)InChIKey=FAKRSMQSSFJEIM-RQJHMYQMSA-N;
(3)SmilesN1([C@@H](CCC1)C(O)=O)C([C@@H](CS)C)=O

The toxicity data is as follows:

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: OTHER CHANGES 

KIDNEY, URETER, AND BLADDER: URINE VOLUME DECREASED
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: HEMATURIA

KIDNEY, URETER, AND BLADDER: PROTEINURIS

KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI
Annals of Internal Medicine. Vol. 112, Pg. 550, 1990.
man TDLo oral 239mg/kg/6W-I (239mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

SENSE ORGANS AND SPECIAL SENSES: CHANGE IN FUNCTION: TASTE

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) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Annals of Internal Medicine. Vol. 94, Pg. 58, 1981.
women TDLo oral 10mg/kg (10mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
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)   Annals of Internal Medicine. Vol. 104, Pg. 126, 1986.
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.

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