62571-86-2 Captopril AKSci J10167
 
 
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  J10167    AKSci Reference Standard
Captopril
, 99%
 
(2S)-1-(3-Mercapto-2-methylpropionyl)-L-proline
N-[(S)-3-Mercapto-2-methylpropionyl]-L-proline
(S)-(-)-1-(3-Mercapto-2-methyl-1-oxopropyl)-L-proline
more..




IDENTITY
CAS Number:62571-86-2
MDL Number:MFCD00168073
MF:C9H15NO3S
MW:217.29
EINECS:263-607-1
BRN:477887
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:99%
Physical Form (at 20°C):Solid
Melting Point:103-110°C
Optical Rotation:-125° to -134° (c=1, EtOH)
Long-Term Storage:Store long-term in a cool, dry place
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:Soluble in water or ethanol
Application(s):Angiotensin-converting enzyme (ACE) inhibitor

REVIEW

 There are two isoforms of ACE: the somatic isoform, which exists as a glycoprotein comprised of a single polypeptide chain of 1277; and the testicular isoform, which has a lower molecular mass and is thought to play a role in sperm maturation and binding of sperm to the oviduct epithelium. Somatic ACE has two functionally active domains, N and C, which arise from tandem gene duplication. Although the two domains have high sequence similarity, they play distinct physiological roles. The C-domain is predominantly involved in blood pressure regulation while the N-domain plays a role in hematopoietic stem cell differentiation and proliferation. ACE inhibitors bind to and inhibit the activity of both domains, but have much greater affinity for and inhibitory activity against the C-domain. Captopril, one of the few ACE inhibitors that is not a prodrug, competes with ATI for binding to ACE and inhibits and enzymatic proteolysis of ATI to ATII. Decreasing ATII levels in the body decreases blood pressure by inhibiting the pressor effects of ATII as described in the Pharmacology section above. Captopril also causes an increase in plasma renin activity likely due to a loss of feedback inhibition mediated by ATII on the release of renin and/or stimulation of reflex mechanisms via baroreceptors. Captopril's affinity for ACE is approximately 30,000 times greater than that of ATI.

REFERENCES
[1]Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9.
[2] Patchett AA, Harris E, Tristram EW, Wyvratt MJ, Wu MT, Taub D, Peterson ER, Ikeler TJ, ten Broeke J, Payne LG, Ondeyka DL, Thorsett ED, Greenlee WJ, Lohr NS, Hoffsommer RD, Joshua H, Ruyle WV, Rothrock JW, Aster SD, Maycock AL, Robinson FM, Hirschmann R, Sweet CS, Ulm EH, Gross DM, Vassil TC, Stone CA: A new class of angiotensin-converting enzyme inhibitors. Nature. 1980 Nov 20;288(5788):280-3.
[3] Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Danger

Hazard Statements
H341; H360

Precautionary Statements
P201; P202; P261; P272; P280; P302+P352; P308+P313; P321; P333+P313; P363; P405; P501


Current as of June 22, 2024

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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CATEGORIES

 APIs and Bioactives > ACE Inhibitors


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