Home > Compound List > Compound details
62571-86-2 molecular structure
click picture or here to close

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

ChemBase ID: 1067
Molecular Formular: C9H15NO3S
Molecular Mass: 217.2853
Monoisotopic Mass: 217.07726435
SMILES and InChIs

SMILES:
SC[C@H](C(=O)N1[C@@H](CCC1)C(=O)O)C
Canonical SMILES:
SC[C@H](C(=O)N1CCC[C@H]1C(=O)O)C
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

Cite this record

CBID:1067 http://www.chembase.cn/molecule-1067.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
IUPAC Traditional name
captopril
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
Brand Name
Acepress
Acepril
Alopresin
Apopril
Capoten
Captolane
Captoril
Cesplon
Dilabar
Garranil (discontinued)
Hipertil
Hypertil
Lopirin
Lopril
Tenosbon
Tensoprel
Synonyms
Captoprilum [INN-Latin]
Captopryl
L-Captopril
Captopril
Capoten
(S)-1-((S)-3-mercapto-2-methylpropanoyl)pyrrolidine-2-carboxylic acid
([2S]-N-[3-Mercapto-2-methylpropionyl]-L-proline
SQ-14225
N-[(S)-3-Mercapto-2-methylpropionyl]-L-proline
Captopril
Acenorm
Acepril
Capace
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
N-[(S)-3-巯基-2-甲基丙酰基]-L-脯氨酸
卡托普利
CAS Number
62571-86-2
EC Number
263-607-1
MDL Number
MFCD00168073
Beilstein Number
477887
PubChem SID
24893111
160964530
24278149
46506879
PubChem CID
44093
CHEBI ID
3380
ATC CODE
C09AA01
CHEMBL
1560
Chemspider ID
40130
DrugBank ID
DB01197
KEGG ID
D00251
Unique Ingredient Identifier
9G64RSX1XD
Wikipedia Title
Captopril
Medline Plus
a682823

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.018635  H Acceptors
H Donor LogD (pH = 5.5) -0.7646909 
LogD (pH = 7.4) -2.422175  Log P 0.72692126 
Molar Refractivity 54.6349 cm3 Polarizability 21.422962 Å3
Polar Surface Area 57.61 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.02  LOG S -1.68 
Solubility (Water) 4.52e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Ethanol expand Show data source
Freely soluble expand Show data source
H2O: soluble0.1 g/mL, very slightly hazy, colorless expand Show data source
Methanol expand Show data source
Apperance
White Solid expand Show data source
white to off-white powder expand Show data source
Melting Point
103-104°C expand Show data source
104-108 °C(lit.) expand Show data source
Optical Rotation
[α]20/D -129°, c = 1.7 in ethanol expand Show data source
Hydrophobicity(logP)
0.6 expand Show data source
0.89 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
RTECS
UY0550000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63-43 expand Show data source
Safety Statements
36/37 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H317-H361 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Target
Hormone expand Show data source
Admin Routes
oral expand Show data source
Bioavailability
70–75% expand Show data source
Excretion
renal expand Show data source
Half Life
1.9 hours expand Show data source
Metabolism
hepatic expand Show data source
Legal Status
Rx-only expand Show data source
Pregnancy Category
D (Australia) expand Show data source
Gene Information
human ... ACE(1636) expand Show data source
human ... ACE(1636), AGTR1(185), AGTR2(186), ECE1(1889)rat ... Ace(24310) expand Show data source
human ... ACE(1636), ECE1(1889)rat ... Ace(24310) expand Show data source
Mechanism of Action
ACE inhibitor expand Show data source
angiotensin-antagonist expand Show data source
apparent primary action involves suppression of the renin-angiotensin-aldosterone-system expand Show data source
decrease in plasma-volume expand Show data source
decreases plasma-angiotensin-2 concentration expand Show data source
increased plasma-renin causes decrease in aldosterone-secretion resulting in: small increases in serum-potassium expand Show data source
increased sodium-excretion expand Show data source
increases plasma levels of PGE2 and PGE2-alpha metabolites. expand Show data source
increases plasma-renin activity resulting from loss of negative feedback on renin release due to reduced angiotensin-2 concentration expand Show data source
Increases urinary excretion of PGE2 expand Show data source
May increase prostaglandin synthesis expand Show data source
May inhibit local angiotensin 2 at vascular and renal sites so attenuating catecholamine release expand Show data source
Purity
≥98% (HPLC) expand Show data source
≥99.0% (HPLC) expand Show data source
95% expand Show data source
97% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
Description
Diastereomers expand Show data source
Application(s)
Antihypertensive agent expand Show data source
Drug used for diagnosis and treatment of renin-dependent hypertension expand Show data source
Exp. drug for treatment of myocardial infarction expand Show data source
Smooth muscle relaxant expand Show data source
Empirical Formula (Hill Notation)
C9H15NO3S expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals InterBioScreen InterBioScreen Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB01197 external link
Item Information
Drug Groups approved
Description Captopril is a potent, competitive inhibitor of angiotensin-converting enzyme (ACE), the enzyme responsible for the conversion of angiotensin I (ATI) to angiotensin II (ATII). ATII regulates blood pressure and is a key component of the renin-angiotensin-aldosterone system (RAAS). Captopril may be used in the treatment of hypertension.
Indication For the treatment of essential or renovascular hypertension (usually administered with other drugs, particularly thiazide diuretics). May be used to treat congestive heart failure in combination with other drugs (e.g. cardiac glycosides, diuretics, β-adrenergic blockers). May improve survival in patients with left ventricular dysfunction following myocardial infarction. May be used to treat nephropathy, including diabetic nephropathy.
Pharmacology Captopril, an ACE inhibitor, antagonizes the effect of the RAAS. The RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from the granular cells of the juxtaglomerular apparatus in the kidneys. In the blood stream, renin cleaves circulating angiotensinogen to ATI, which is subsequently cleaved to ATII by ACE. ATII increases blood pressure using a number of mechanisms. First, it stimulates the secretion of aldosterone from the adrenal cortex. Aldosterone travels to the distal convoluted tubule (DCT) and collecting tubule of nephrons where it increases sodium and water reabsorption by increasing the number of sodium channels and sodium-potassium ATPases on cell membranes. Second, ATII stimulates the secretion of vasopressin (also known as antidiuretic hormone or ADH) from the posterior pituitary gland. ADH stimulates further water reabsorption from the kidneys via insertion of aquaporin-2 channels on the apical surface of cells of the DCT and collecting tubules. Third, ATII increases blood pressure through direct arterial vasoconstriction. Stimulation of the Type 1 ATII receptor on vascular smooth muscle cells leads to a cascade of events resulting in myocyte contraction and vasoconstriction. In addition to these major effects, ATII induces the thirst response via stimulation of hypothalamic neurons. ACE inhibitors inhibit the rapid conversion of ATI to ATII and antagonize RAAS-induced increases in blood pressure. ACE (also known as kininase II) is also involved in the enzymatic deactivation of bradykinin, a vasodilator. Inhibiting the deactivation of bradykinin increases bradykinin levels and may sustain its effects by causing increased vasodilation and decreased blood pressure.
Toxicity Symptoms of overdose include emesis and decreased blood pressure. Side effects include dose-dependent rash (usually maculopapular), taste alterations, hypotension, gastric irritation, cough, and angioedema.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Major metabolites are captopril-cysteine disulfide and the disulfide dimer of captopril. Metabolites may undergo reversible interconversion.
Absorption 60-75% in fasting individuals; food decreases absorption by 25-40% (some evidence indicates that this is not clinically significant)
Half Life 2 hours
Protein Binding 25-30% bound to plasma proteins, primarily albumin
References
Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9. [Pubmed]
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. [Pubmed]
Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S2051 external link
Research Area: Cancer
Biological Activity:
Sigma Aldrich - C4042 external link
Biochem/physiol Actions
Angiotensin converting enzyme inhibitor. Inhibits the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density.
Packaging
5, 25 g in glass bottle
Sigma Aldrich - 441600 external link
Biochem/physiol Actions
Angiotensin converting enzyme inhibitor. Inhibits the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density.
Sigma Aldrich - 21751 external link
Biochem/physiol Actions
Angiotensin converting enzyme inhibitor. Inhibits the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density.
Sigma Aldrich - C8856 external link
Biochem/physiol Actions
Angiotensin converting enzyme inhibitor. Inhibits the formation of angiotensin II, a bioactive peptide that stimulates angiogenesis and increases microvessel density.
Toronto Research Chemicals - C175750 external link
Orally active angiotensin-converting enzyme (ACE) inhibitor.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Atkinson AB, Robertson JI: Captopril in the treatment of clinical hypertension and cardiac failure. Lancet. 1979 Oct 20;2(8147):836-9. Pubmed
  • • Smith CG, Vane JR: The discovery of captopril. FASEB J. 2003 May;17(8):788-9. Pubmed
  • • 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. Pubmed
  • • Rubin, B., et al.: Eur. J Pharmacol., 51, 377 (1978)
  • • Ger. Pat., 1977, Squibb, 2 703 828; CA, 88, 7376c, (synth)
  • • Ondetti, M.A. et al., Science (Washington, D.C.), 1977, 196, 441, (use)
  • • Cardoni, A.A. et al., Drug Intell. Clin. Pharm., 1981, 15, 932, (pharmacol, rev)
  • • Horovitz, Z.P. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 148, (pharmacol)
  • • Kadin, H., Anal. Profiles Drug Subst., 1982, 11, 79, (synth, prop, detn, pharmacol, rev)
  • • Shimazaki, M. et al., Chem. Pharm. Bull., 1982, 30, 3139, (synth)
  • • Condon, M.E. et al., J. Med. Chem., 1982, 25, 250, (synth)
  • • Migdalof, B.H. et al., Drug Metab. Rev., 1984, 15, 841, (rev)
  • • Aboul-Enein, H.Y. et al., Spectrosc. Lett., 1985, 18, 419, (pmr, conformn)
  • • Drummer, O.H. et al., Med. Res. Rev., 1986, 6, 75, (rev, metab)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1331
  • • Bashiardes, C. et al., Tet. Lett., 1987, 28, 5563, (synth)
  • • ACE Inhibitors: Current Use and Future Prospects, (ed. Schachter, M.), Martin Dunitz, London, 1995, (book)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 836
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCO750
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle