Captopril supplier | CasNO.62571-86-2

Name
Captopril
EINECS 263-607-1
CAS No. 62571-86-2
Article Data33
CAS DataBase
Density 1.272 g/cm³
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
Appearance white crystalline powder
Safety 36/37-37/39-26-36-22
Risk Codes 43-63-36/37/38-40
Molecular Structure
Hazard Symbols Xn, Xi
Synonyms acepress;Captopril;dilabar;lopril;acediur;sa333;cesplon;acepril;aceplus;capoten;
PSA 96.41000
LogP 0.56580

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

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

: 62571-86-2
captopril

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

...Expand

: 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

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

...Expand

: 34223-44-4
Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2

: 64806-05-9
Captopril disulfide

A: 113-79-1, 5591-81-1, 66513-06-2, 66513-07-3, 76023-59-1, 89576-32-9
Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2

B: 62571-86-2
captopril

Conditions

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

...Expand

: 34223-44-4
Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2

: 64806-05-9
Captopril disulfide

A: 62571-86-2
captopril

B: C55H80N16O15S3

C: C55H80N16O15S3

Conditions

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

...Expand

: C52H81N13O15S3

: C52H81N13O15S3

A: 50-56-6
oxytocin

B: 62571-86-2
captopril

Conditions

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

...Expand

: C55H80N16O15S3

: C55H80N16O15S3

A: 113-79-1, 5591-81-1, 66513-06-2, 66513-07-3, 76023-59-1, 89576-32-9
Cys-Tyr-Phe-Gln-Asn-Cys-Pro-Arg-Gly-NH2

B: 62571-86-2
captopril

Conditions

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

...Expand

: 97716-22-8
(2S,2'S)-1-<3-(Acetylthio)-2-methylpropionyl>prolin-methylester

: 62571-86-2
captopril

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 5h; Hydrolysis;

: 122130-63-6
S-Nitrosocaptopril

: 62571-86-2
captopril

Conditions

Conditions	Yield
With ethylenediaminetetraacetic acid; sodium hydrogensulfite In phosphate buffer at 25℃; pH=7.4; Kinetics; Substitution;

: 60460-30-2
dehydrochlorinationby-product-N-acryloylproline

: 62571-86-2
captopril

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 47 percent / H2O; tetrahydrofuran / 48 h / 20 °C / ultrasound 2.1: 70 percent / H2 / 5 percent Pd/C / ethyl acetate / 4 h / 20 °C / 760 Torr 3.1: SOCl2 / tetrahydrofuran / 5 h / 20 °C 3.2: 87 percent / aq. NH4SH / tetrahydrofuran / 3.5 h / 0 - 20 °C View Scheme

: 147-85-3
L-proline

3-CH3O-phenyl halide: 3-CH3O-phenyl halide

: 62571-86-2
captopril

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 70 percent / aq. KOH / acetone / 3 h / 20 °C 2.1: 47 percent / H2O; tetrahydrofuran / 48 h / 20 °C / ultrasound 3.1: 70 percent / H2 / 5 percent Pd/C / ethyl acetate / 4 h / 20 °C / 760 Torr 4.1: SOCl2 / tetrahydrofuran / 5 h / 20 °C 4.2: 87 percent / aq. NH4SH / tetrahydrofuran / 3.5 h / 0 - 20 °C View Scheme

: 613256-50-1
β-hydroxy-α-methylene-N-acryloyl-(S)-proline

: 62571-86-2
captopril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 70 percent / H2 / 5 percent Pd/C / ethyl acetate / 4 h / 20 °C / 760 Torr 2.1: SOCl2 / tetrahydrofuran / 5 h / 20 °C 2.2: 87 percent / aq. NH4SH / tetrahydrofuran / 3.5 h / 0 - 20 °C View Scheme

: 2812-46-6
proline tert-butyl ester

: 62571-86-2
captopril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: trifluoroacetic acid, mercuric acetate View Scheme

: sodium ureido dithiocarbonate

: 7664-93-9
sulfuric acid

: 80629-35-2
1-(3-bromo-2S-methylpropionyl)-pyrrolidine-2S-carboxylic acid

: 7440-66-6
zinc

: 62571-86-2
captopril

Conditions

Conditions	Yield
With hydrogenchloride; sodium bicarbonate In hexane; ethyl acetate

...Expand

: S-allylthio-captopril

: 70-18-8
GLUTATHIONE

A: 870-23-5
prop-2-ene-1-thiol

B: 27025-41-8
Oxidized glutathione

C: 78636-30-3
S-glutathionylthio-captopril

D: 62571-86-2
captopril

E: Allylglutathione sulphide

Conditions

Conditions	Yield
at 20℃; for 20h; pH=6.5; aq. phosphate buffer;

...Expand

: S-allylthio-captopril

: 70-18-8
GLUTATHIONE

A: 870-23-5
prop-2-ene-1-thiol

B: 78636-30-3
S-glutathionylthio-captopril

C: 62571-86-2
captopril

D: Allylglutathione sulphide

Conditions

Conditions	Yield
at 20℃; for 3h; pH=6.5; aq. phosphate buffer;

...Expand

: S-allylthio-captopril

: 70-18-8
GLUTATHIONE

A: 62571-86-2
captopril

B: Allylglutathione sulphide

Conditions

Conditions	Yield
at 20℃; for 0.3h; pH=6.5; aq. phosphate buffer;

...Expand

: 64838-55-7
(2S)-1-[(2S)-3-acetylthio-2-methylpropanoyl]pyrrolidine-2-carboxylic acid

: 62571-86-2
captopril

Conditions

Conditions	Yield
With ammonia

: 147-85-3
L-proline

: 62571-86-2
captopril

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide 2: ammonia View Scheme

: 64806-05-9
Captopril disulfide

: 62571-86-2
captopril

Conditions

Conditions	Yield
With palladium on activated charcoal; hydrogen; zinc In dichloromethane; water at 80℃; under 4500.45 Torr; Acidic conditions;

: (S)-3-mercapto-2-methyl propionyl chloride

: 147-85-3
L-proline

: 62571-86-2
captopril

Conditions

Conditions	Yield
With sodium hydroxide at 0 - 20℃; for 3h; pH=7 - 9;
With sodium hydroxide at 0 - 20℃; for 3h; pH=7 - 9;
With sodium hydroxide at 0 - 20℃; for 3h; pH=7 - 9;

: 2-acetyl-1-((trifluoromethyl)thio)-1,2-dihydro-3H-1λ3-benzo[d][1,2]iodazol-3-one

: 62571-86-2
captopril

: ((S)-2-methyl-3-((trifluoromethyl)disulfanyl)propanoyl)-L-proline

Conditions

Conditions	Yield
at 20℃; for 0.5h; Inert atmosphere;	99%

: C21H28N7O6PolS3

: 62571-86-2
captopril

: 1354829-75-6
C21H34N4O5S3

Conditions

Conditions	Yield
In water; N,N-dimethyl-formamide for 0.5h;	96%

: 1-(hexadecynyl)-1,2-benziodoxol-3(1H)-one

: 62571-86-2
captopril

: (S)-1-((S)-3-(hexadec-1-yn-1-ylthio)-2-methylpropanoyl)pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Stage #1: captopril With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In tetrahydrofuran; water Stage #2: 1-(hexadecynyl)-1,2-benziodoxol-3(1H)-one In tetrahydrofuran; water at 23℃; for 0.0833333h;	94%

: 312929-01-4
3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one

: 62571-86-2
captopril

: 1327278-84-1
1-{(S)-3-[(2-oxo-2H-chromene-3-carbonyl)thio]-2-methylpropanoyl}pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 25℃; for 1h;	92%

: 62571-86-2
captopril

: zinc(II) oxide

: Zn(2+)*C9H13NO3S(2-) = [Zn(C9H13NO3S)]

Conditions

Conditions	Yield
In methanol at 20℃;	91.4%

: 62571-86-2
captopril

: ((R)-2-methylpropanoyl-3-d)-L-proline

Conditions

Conditions	Yield
With di-tert-butyl peroxide; water-d2; ethydiphenylphosphine oxide In dichloromethane at 20℃; for 10h; Solvent; Irradiation; Green chemistry;	91%

: 62571-86-2
captopril

: 7646-85-7
zinc(II) chloride

: Zn(2+)*C9H13NO3S(2-) = [Zn(C9H13NO3S)]

Conditions

Conditions	Yield
With sodium hydroxide In water	90.3%

: 1286276-26-3
7-methoxy-3-(1H-benzotriazol-1-ylcarbonyl)-2H-chromene-2-one

: 62571-86-2
captopril

: 1327278-90-9
1-{(S)-3-[(7-methoxy-2-oxo-2H-chromene-3-carbonyl)thio]-2-methylpropanoyl}pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 25℃; for 1h;	90%

: 1286276-78-5
3-(1H-benzotriazol-1-ylcarbonyl)-7-(diethylamino)-2H-chromen-2-one

: 62571-86-2
captopril

: 1327278-88-5
1-((S)-3-{[7-(diethylamino)-2-oxo-2H-chromene-3-carbonyl]thio}-2-methylpropanoyl)pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In water; acetonitrile at 25℃; for 1h;	90%

: 62571-86-2
captopril

: 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one

: 1443746-71-1
(S)-1-((S)-2-methyl-3-(((triisopropylsilyl)ethynyl)thio)propanoyl)pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
Stage #1: captopril With N,N,N',N'-tetramethylguanidine In tetrahydrofuran; water at 20℃; for 0.0833333h; Stage #2: 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one In tetrahydrofuran; water at 20℃; for 0.0833333h; chemoselective reaction;	90%

: aquocobalamin chloride

: 62571-86-2
captopril

: CapSCbl

Conditions

Conditions	Yield
In water Kinetics; soln. captopril in water (pH adjusted to 4.3) was added dropwise to soln. HOCbl*HCl in water (pH adjusted to 6.6), final react. mixt. pH 4.2, 3 h at 0°C in the dark; soln. was poured into chilled acetone (-20°C), ppt. was filtered,washed with chilled acetone (-20°C), Et2O (-20°C) and dri ed in vacuo (50°C, 5E-2 mbar) overnight;	88%

: 76-83-5
trityl chloride

: 62571-86-2
captopril

: (2-methyl-3-(tritylthio)propanoyl)proline

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 12h; Inert atmosphere;	86%
In N,N-dimethyl-formamide at 20℃; for 5h;

: 62571-86-2
captopril

: 158440-71-2
[14C]-Irofulven

: C24H31NO5S

Conditions

Conditions	Yield
With sulfuric acid In acetone at 20℃; for 12h; Condensation;	84%

: 62571-86-2
captopril

: 23500-15-4
1-(1-oxo-2-methylpropyl)-L-proline

Conditions

Conditions	Yield
With triethyl borane; tributylphosphine; triethyl phosphite In acetonitrile for 36h; Irradiation;	83%

: 67-56-1
methanol

: 62571-86-2
captopril

: methyl 1-(3-mercapto-2-methylpropanoyl)pyrrolidine-2-carboxylate

Conditions

Conditions	Yield
With thionyl chloride at 0 - 60℃;	82%
With thionyl chloride at 0 - 60℃; for 7h;	50%

: 31643-49-9
4-Nitrophthalonitrile

: 62571-86-2
captopril

: 1446888-23-8
4-captopril phthalonitrile

Conditions

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 20℃; for 48h; Inert atmosphere;	76.3%

: dimethyl-4-nitrophenylsulfonium trifluoromethanesulfonate

: 62571-86-2
captopril

: ((S)-2-methyl-3-((4-nitrophenyl)thio)propanoyl)-L-proline

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 3h; Inert atmosphere; Schlenk technique;	75%

: 62571-86-2
captopril

: 75-03-6
ethyl iodide

: ethyl 1-(3-(ethylthio)-2-methylpropanoyl)pyrrolidine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: captopril With potassium carbonate In acetone at 20℃; for 1h; Stage #2: ethyl iodide In acetone at 50℃; for 24h;	72%

: (S)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)-2-propylpentanamide

: 62571-86-2
captopril

: ((S)-2-methyl-3-(((2-propylpentanoyl)phenylalanyl)thio)propanoyl)proline

Conditions

Conditions	Yield
Stage #1: (S)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-1-oxo-3-phenylpropan-2-yl)-2-propylpentanamide; captopril In methanol; water at 20℃; for 0.0833333h; Stage #2: With potassium hydrogencarbonate In methanol; water	71%

: 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-propylpentan-1-one

: 62571-86-2
captopril

: ((S)-2-methyl-3-((2-propylpentanoyl)thio)propanoyl)proline

Conditions

Conditions	Yield
Stage #1: 1-(1H-benzo[d][1,2,3]triazol-1-yl)-2-propylpentan-1-one; captopril In methanol; water at 20℃; for 0.0833333h; Stage #2: With potassium hydrogencarbonate In methanol; water	70%

: 7-(2-(3,3-dimethyl-1λ3-benzo[d][1,2]iodaoxol-1(3H)-yl)-1,1,2,2-tetrafluoroethoxy)-4-methyl-2H-chromen-2-one

: 62571-86-2
captopril

: C21H21F4NO6S

Conditions

Conditions	Yield
In dichloromethane at -78℃; for 1h;	68%

: (S)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-methyl-1-oxobutan-2-yl)-2-propylpentanamide

: 62571-86-2
captopril

: ((S)-2-methyl-3-(((2-propylpentanoyl)valyl)thio)propanoyl)proline

Conditions

Conditions	Yield
Stage #1: (S)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)-3-methyl-1-oxobutan-2-yl)-2-propylpentanamide; captopril In methanol; water at 20℃; for 0.0833333h; Stage #2: With potassium hydrogencarbonate In methanol; water	68%

: 98-88-4
benzoyl chloride

: 62571-86-2
captopril

: S-benzoylcaptopril

Conditions

Conditions	Yield
With sodium hydroxide In water; toluene at 5 - 20℃; for 1h;	65%

: 62571-86-2
captopril

: 151013-83-1
hexachloro[60]fullerene

C105H71N5O15S5: C105H71N5O15S5

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In toluene for 0.0833333h;	63%

: 62571-86-2
captopril

: ((S)-3-(((4-methoxyphenyl)ethynyl)thio)-2-methylpropanoyl)-L-proline

Conditions

Conditions	Yield
With pyridine; (1,2-dimethoxyethane)dichloronickel(II); (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile In N,N-dimethyl-formamide; acetonitrile at 20℃; for 0.5h; Inert atmosphere; Sealed tube; Irradiation;	61%

: 62571-86-2
captopril

: 75-36-5
acetyl chloride

: 64838-55-7
(2S)-1-[(2S)-3-acetylthio-2-methylpropanoyl]pyrrolidine-2-carboxylic acid

Conditions

Conditions	Yield
With triethylamine In dichloromethane at -5 - 20℃; for 4.5h; pH=8 - 9;	59.8%
With triethylamine In dichloromethane at -5 - 20℃; for 4.5h; pH=8-9;	503.9 mg
for 0.0833333h;

: 10196-18-6
zinc(II) nitrate

: 62571-86-2
captopril

: Zn(2+)*C9H13NO3S(2-) = [Zn(C9H13NO3S)]

Conditions

Conditions	Yield
With NH3 In water (inert atmosphere); pH 8.5, stirring 1 h; concn. (vac.), cooling to 4°C for 1 d, filtration, washing (H2O),drying (vac.); elem. anal.;	51%

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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