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C4042

Sigma-Aldrich

Captopril

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

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C9H15NO3S
CAS Number:
62571-86-2
Molecular Weight:
217.29
Beilstein:
477887
EC Number:
263-607-1
MDL number:
MFCD00168073
UNSPSC Code:
12352200
PubChem Substance ID:
57654003
NACRES:
NA.77

product name

Captopril, ≥98% (HPLC), powder

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

SMILES string

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

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

InChI key

FAKRSMQSSFJEIM-RQJHMYQMSA-N

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

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.
Angiotensin converting enzyme inhibitor. Inhibits the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density.

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

Signal Word

Danger

Hazard Statements

H341,H360F

Hazard Classifications

Muta. 2 - Repr. 1B

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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)
Identification of antihypertensive peptides derived from low molecular weight casein hydrolysates generated during fermentation by Bifidobacterium longum KACC 91563
Ha GE, et al.
Korean journal for food science of animal resources, 35(6), 738-738 (2015)
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)
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
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