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AB141333

Captopril, ACE inhibitor

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(1 Publication)

MW 217.29 Da, Purity >98%. Potent ACE inhibitor (IC50 = 21 nM). Reversible and competitive leukotriene A4 hydrolase inhibitor (Ki = 6 μM, leukotriene B4 formation). Vasodilatory and antihypertensive effects in vivo. Orally active.

View Alternative Names

ACE 1, ACE T, ACE-related carboxypeptidase, ACE2_HUMAN, ACEH, ACE_HUMAN, Angiotensin I Converting Enzyme (peptidyl dipeptidase A) 2, Angiotensin I converting enzyme, Angiotensin I converting enzyme 1, Angiotensin I converting enzyme 2, Angiotensin I converting enzyme peptidyl dipeptidase A 1, Angiotensin converting enzyme 2, Angiotensin converting enzyme like protein, Angiotensin converting enzyme somatic isoform, Angiotensin converting enzyme testis specific isoform, Angiotensin forming enzyme precursor, Angiotensin-converting enzyme, Angiotensin-converting enzyme homolog, Angiotensinogenase, Angiotensinogenase precursor, CD 143, CD143 antigen, Carboxycathepsin, Coagulation factor II, Cyclooxygenase, Cyclooxygenase 2b, Cyclooxygenase 3, included, Cyclooxygenase-1, Cyclooxygenase-2, DCP 1, DKFZP434A014, Dipeptidyl carboxypeptidase 1, Dipeptidyl carboxypeptidase I, EC 1.14.99.1, EC 3.4.17, FLJ10761, FLJ17564, Factor II, GRIPGHS, Glucocorticoid-regulated inflammatory Prostaglandin G/H synthase, Glucocorticoid-regulated inflammatory cyclooxygenase, HNFJ2, Kininase II, LKHA4_HUMAN, LTA-4 hydrolase, LTA4, LTA4H, Leukotriene A(4) hydrolase, Leukotriene A-4 hydrolase, MGC26566, MVCD3, Macrophage activation-associated marker protein P71/73, OTTHUMP00000022963, OTTHUMP00000033524, PCOX1, PES-2, PGG/HS, PGH synthase 1, PGH synthase 2, PGH1_HUMAN, PGH2_HUMAN, PGHS-1, PGHS-2, PHS 1, PHS 2, PHS II, PT, PTGHS, PTGS1, PTGS2, Partial COX1 proteins, included, Peptidase P, Peptidyl dipeptidase A, Prepro coagulation factor II, Processed angiotensin-converting enzyme 2, Prostaglandin G/H synthase, Prostaglandin G/H synthase 1, Prostaglandin G/H synthase 2, Prostaglandin G/H synthase 2 precursor, Prostaglandin G/H synthase and cyclooxygenase, Prostaglandin H2 synthase 1, Prostaglandin H2 synthase 2, Prostaglandin-endoperoxide synthase 1, Prostaglandin-endoperoxide synthase 1 (prostaglandin G/H synthase and cyclooxygenase), Prostaglandin-endoperoxide synthase 2, Prothrombin, REN, RENI_HUMAN, RPRGL2, Ren1, Renin, Renin precursor renal, Serine protease, THPH1, THRB_HUMAN, TIS10, TIS10 protein, Testicular ECA, Thrombin heavy chain, angiotensin I converting enzyme peptidyl-dipeptidase A 1 transcript, angiotensin-forming enzyme, coagulation factor II (thrombin), fj02a10, hCox 2, metalloprotease MPROT 15, prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase), prothrombin B-chain, ptgs2a, soluble form, unp1239, wu:fj02a10

1 Images
Chemical Structure - Captopril, ACE inhibitor (AB141333)
  • Chemical Structure

Lab

Chemical Structure - Captopril, ACE inhibitor (AB141333)

2D chemical structure image of ab141333, Captopril, ACE inhibitor

Key facts

CAS number

62571-86-2

Purity

>98%

Form

Solid

form

Molecular weight

217.29 Da

Molecular formula

C<sub>9</sub>H<sub>1</sub><sub>5</sub>NO<sub>3</sub>S

PubChem

44093

Nature

Synthetic

Solubility

Soluble in water to 100 mM

Soluble in DMSO to 100 mM

Soluble in ethanol to 100 mM

Biochemical name

Captopril

Biological description

Potent ACE inhibitor (IC50 = 21 nM). Reversible and competitive leukotriene A4 hydrolase inhibitor (Ki = 6 μM, leukotriene B4 formation). Vasodilatory and antihypertensive effects in vivo. Orally active.

Canonical smiles

CC(CS)C(=O)N1CCCC1C(=O)O

Isomeric smiles

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

InChi

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

IUPAC Name

(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid

Product details

In aqueous solution, this product undergoes a free radical dimerisation to form captopril disulfide. This dimerisation is oxygen-facilitated and has been found to be pH dependent and catalysed by metal ions. To delay oxidation use a lower pH (maximum stability at pH <4), incorporate a chelating agent or antioxidant, degas solutions, minimise headspace or increase product concentration.

Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
+4°C
Appropriate long-term storage conditions
+4°C
Storage information
The product can be stored for up to 12 months

Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

COX2 or Cyclooxygenase 2 along with its counterpart COX1 (Cyclooxygenase 1) are enzymes that catalyze the conversion of arachidonic acid to prostaglandins which play roles in inflammation and pain signaling. COX2 is often inducible and expressed in response to inflammatory stimuli while COX1 is constitutively expressed in most tissues providing protective gastric lining and renal function. Cyclooxygenase enzymes belong to the family of heme-containing proteins and have a mass of approximately 72 kDa. The Angiotensin Converting Enzyme 1 (ACE1) and ACE2 are proteases involved in regulating blood pressure by cleaving angiotensin peptides. ACE2 also has a critical role in viral entry by serving as a receptor for some coronaviruses. Renin a component of the renin-angiotensin system initiates a cascade by hydrolyzing angiotensinogen to angiotensin I. Leukotriene A4 hydrolase (LTA4H) is an enzyme that converts leukotriene A4 (LTA4) to leukotriene B4 a potent chemoattractant involved in immune responses.
Biological function summary

These proteins participate in distinct but sometimes overlapping processes critical to maintaining homeostasis. Cyclooxygenase enzymes especially COX2 are often involved in inflammatory pathways and are often overexpressed in response to cytokines and growth factors. ACE1 and ACE2 balance blood pressure and fluid-electrolyte balance with ACE inhibitors like captopril reducing blood pressure by blocking the conversion of angiotensin I to angiotensin II. The renin-angiotensin system of which these proteins are part governs a complex network influencing cardiovascular and renal function. LTA4H plays its role in the inflammatory response generating leukotriene B4 which acts as a powerful leukocyte activator.

Pathways

COX2 COX1 and LTA4H are vital players in the arachidonic acid metabolic pathway influencing inflammation through various eicosanoids. COX enzymes relate to prostaglandin synthesis facilitating pain and fever responses. In contrast ACE1 and renin often linked to the ACE inhibitors' action—like that of captopril—function within the renin-angiotensin-aldosterone system (RAAS) managing blood pressure regulation. These pathways exemplify how hormonal signaling cascades integrate to affect physiological states like hypertension and inflammation.

COX2 is well-known for its association with inflammatory diseases such as arthritis and certain cancers where its overexpression promotes chronic inflammation and tumorigenesis. ACE1 is significantly implicated in cardiovascular diseases including hypertension and heart failure with ACE inhibitors like captopril playing an essential role in treatment strategies. ACE2 relevant due to its receptor function for some coronaviruses including SARS-CoV-2 highlights its role in viral entry and related respiratory diseases. LTA4H by producing leukotriene B4 can contribute to conditions like asthma linking to airway inflammation and immune cell activation.

Product protocols

Publications (1)

Recent publications for all applications. Explore the full list and refine your search

Therapeutic advances in urology 12:1756287220927994 PubMed35173811

2020

The effects of docetaxel and/or captopril in expression of TGF-β1, MMP-1, CTGF, and PAI-1 as markers of anterior urethral stricture in an animal model.

Applications

Unspecified application

Species

Unspecified reactive species

Wikan Kurniawan,Marsetyawan Heparis Nur Ekandaru Soesatyo,Teguh Aryandono
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