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Merck

C4042

Captopril

≥98% (HPLC), powder, angiotensin converting enzyme inhibitor

Sinónimos:

N-[(S)-3-Mercapto-2-methylpropionyl]-L-proline

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Fórmula empírica (notación de Hill):
C9H15NO3S
Número CAS:
62571-86-2
Peso molecular:
217.29
NACRES:
NA.77
PubChem Substance ID:
57654003
UNSPSC Code:
12352200
EC Number:
263-607-1
MDL number:
MFCD00168073
Beilstein/REAXYS Number:
477887
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

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Nombre del producto

Captopril, ≥98% (HPLC), powder

InChI key

FAKRSMQSSFJEIM-RQJHMYQMSA-N

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

SMILES string

C[C@H](CS)C(=O)N1CCC[C@H]1C(O)=O

biological source

synthetic

assay

≥98% (HPLC)

form

powder

color

white to off-white

mp

104-108 °C (lit.)

solubility

water: 100 mg/mL, clear to very slightly hazy, colorless to faintly yellow

originator

Bristol-Myers Squibb

storage temp.

room temp

Quality Level

100

Gene Information

human ... ACE(1636), AGTR1(185), AGTR2(186), ECE1(1889)
rat ... Ace(24310)

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Application

Captopril has been used:
  • to examine the influence of timing of captopril treatment on efficacy in transverse aortic constriction (TAC) mice
  • as an angiotensin-converting enzyme inhibitor and orally administered to unrestrained Wistar Kyoto rats in an approach to study its effects of angiogenesis inhibition and interdependency with other drugs
  • used as a positive control in spectrophotometric assay to study the angiotensin-converting enzyme inhibitory activity

Biochem/physiol Actions

Angiotensin converting enzyme inhibitor. Inhibits the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density.
Captopril is known to decrease the cardiovascular complications arising due to myocardial infarction. It is an effective drug in treating diabetic nephropathy and renal disease. Captopril acts by reducing cardiac related inflammation, fibrosis and calcification.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Neuropeptidases page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bristol-Myers Squibb. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Muta. 2 - Repr. 1B

Clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
WXBF2208V
BCCG9863
BCCJ2935
BCCF8602
BCCC6129

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Henryk Zieliński et al.
Foods (Basel, Switzerland), 9(7) (2020-07-03)
The angiotensin converting enzyme (ACE) inhibitory activity and phenolics profile of fermented flours and of baked and digested buckwheat biscuits was studied. The fermentation of buckwheat flour by select lactic acid bacteria (LAB) caused a decrease in ACE inhibitory activity
Captopril prevents experimental autoimmune myocarditis
Godsel LM, et al.
Journal of Immunology, 171(1), 346-352 (2003)
Tami A Martino et al.
Journal of the American College of Cardiology, 57(20), 2020-2028 (2011-05-14)
Our objective was to test the hypothesis that there is a significant diurnal variation for the therapeutic benefit of angiotensin-converting enzyme (ACE) inhibitors on pressure-overload cardiovascular hypertrophy. Physiological and molecular processes exhibit diurnal rhythms that may affect efficacy of disease
Valsartan, captopril, or both in myocardial infarction complicated by heart failure, left ventricular dysfunction, or both
Pfeffer MA, et al.
The New England Journal of Medicine, 349(20), 1893-1906 (2003)
The primary benefits of angiotensin-converting enzyme inhibition on cardiac remodeling occur during sleep time in murine pressure overload hypertrophy
Martino TA, et al.
Journal of the American College of Cardiology, 57(20), 2020-2028 (2011)
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