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Substance Name: Captopril [USAN:USP:INN:BAN:JAN]
RN: 62571-86-2
UNII: 9G64RSX1XD
InChIKey: FAKRSMQSSFJEIM-RQJHMYQMSA-N

Note

  • A potent and specific inhibitor of PEPTIDYL-DIPEPTIDASE A. It blocks the conversion of ANGIOTENSIN I to ANGIOTENSIN II, a vasoconstrictor and important regulator of arterial blood pressure. Captopril acts to suppress the RENIN-ANGIOTENSIN SYSTEM and inhibits pressure responses to exogenous angiotensin.

Molecular Formula

  • C9-H15-N-O3-S

Molecular Weight

  • 217.2875
 

Classification Codes

  • Angiotensin-Converting Enzyme Inhibitors
  • Antihypertensive
  • Antihypertensive Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Enzyme Inhibitor (Angiotensin-Converting)
  • Enzyme Inhibitors
  • Human Data
  • Protease Inhibitors
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Captopril
  • Captopril [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Captopril

Synonyms

  • (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-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline
  • 1-(D-3-Mercapto-2-methyl-1-oxopropyl)-L-proline (S,S)
  • 3-Mercapto-2-methylpropionyl-proline
  • Acediur
  • Aceplus
  • Acepress
  • Acepril
  • Alopresin
  • Asisten
  • Capoten
  • Captolane
  • Captopril
  • Captoprilum
  • Captoprilum [INN-Latin]
  • Captopryl
  • Captoril
  • Cesplon
  • D-2-Methyl-3-mercaptopropanoyl-L-proline
  • D-3-Mercapto-2-methylpropanoyl-L-proline
  • D-3-Mercapto-2-methylpropionylproline
  • Dilabar
  • EINECS 263-607-1
  • Farcopril
  • Garranil
  • HSDB 6527
  • Hypertil
  • Hypopress
  • Isopresol
  • L-Captopril
  • Lopirin
  • Lopirin [Switzerland]
  • Lopril
  • Novocaptopril
  • SA 333
  • SQ 14,225
  • SQ 14225
  • Tenosbon
  • Tensoprel
  • UNII-9G64RSX1XD
  • Zapto

Systematic Names

  • 1-Pyrrolidinecarboxylic acid, 1-(D-3-mercapto-2-methyl-1-propionyl)-, L-(S,S)-
  • Captopril
  • L-Proline, 1-((2S)-3-mercapto-2-methyl-1-oxopropyl)-
  • L-Proline, 1-(3-mercapto-2-methyl-1-oxopropyl)-, (S)-

Mixture Name

  • Capozide

Registry Numbers

CAS Registry Number

  • 62571-86-2

FDA UNII

  • 9G64RSX1XD

Other Registry Numbers

  • 138452-88-7
  • 225661-74-5
  • 70903-77-4

System Generated Number

  • 0062571862

Structure Descriptors

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

Smiles

N1([C@@H](CCC1)C(O)=O)C([C@@H](CS)C)=O

Toxicity

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)   Southern Medical Journal. Vol. 86, Pg. 1269, 1993.
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: PROTEINURIS

KIDNEY, URETER, AND BLADDER: CHANGES PRIMARILY IN GLOMERULI

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) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)		 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.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 106 deg C   EXP
log P (octanol-water) 0.34 (none)   EXP
Water Solubility 1.82E+04 mg/L 25 EST
Vapor Pressure 3.64E-06 mm Hg 25 EST
Henry's Law Constant 3.89E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.83E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.