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62571-86-2 分子结构
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(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid

ChemBase编号:1067
分子式:C9H15NO3S
平均质量:217.2853
单一同位素质量:217.07726435
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
IUPAC传统名
captopril
(2S)-1-[(2S)-2-methyl-3-sulfanylpropanoyl]pyrrolidine-2-carboxylic acid
商标名
Acepress
Acepril
Alopresin
Apopril
Capoten
Captolane
Captoril
Cesplon
Dilabar
Garranil (discontinued)
Hipertil
Hypertil
Lopirin
Lopril
Tenosbon
Tensoprel
别名
N-[(S)-3-巯基-2-甲基丙酰基]-L-脯氨酸
卡托普利
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
CAS号
62571-86-2
EC号
263-607-1
MDL号
MFCD00168073
Beilstein号
477887
PubChem SID
46506879
160964530
24278149
24893111
PubChem CID
44093
CHEBI ID
3380
ATC码
C09AA01
CHEMBL
1560
Chemspider ID
40130
DrugBank ID
DB01197
KEGG ID
D00251
美国药典/FDA物质标识码
9G64RSX1XD
维基百科标题
Captopril
Medline Plus
a682823

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 4.018635  质子受体
质子供体 LogD (pH = 5.5) -0.7646909 
LogD (pH = 7.4) -2.422175  Log P 0.72692126 
摩尔折射率 54.6349 cm3 极化性 21.422962 Å3
极化表面积 57.61 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.02  LOG S -1.68 
溶解度 4.52e+00 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Chloroform expand 查看数据来源
Dichloromethane expand 查看数据来源
Ethanol expand 查看数据来源
Freely soluble expand 查看数据来源
H2O: soluble0.1 g/mL, very slightly hazy, colorless expand 查看数据来源
Methanol expand 查看数据来源
外观
White Solid expand 查看数据来源
white to off-white powder expand 查看数据来源
熔点
103-104°C expand 查看数据来源
104-108 °C(lit.) expand 查看数据来源
比旋光度
[α]20/D -129°, c = 1.7 in ethanol expand 查看数据来源
疏水性(logP)
0.6 expand 查看数据来源
0.89 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
RTECS编号
UY0550000 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
63-43 expand 查看数据来源
安全公开号
36/37 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS08 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H317-H361 expand 查看数据来源
GHS警示性声明
P280 expand 查看数据来源
个人保护装置
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 查看数据来源
作用靶点
Hormone expand 查看数据来源
给药途径
oral expand 查看数据来源
生物利用度
70–75% expand 查看数据来源
排泄
renal expand 查看数据来源
半衰期
1.9 hours expand 查看数据来源
代谢
hepatic expand 查看数据来源
法定药品分级
Rx-only expand 查看数据来源
妊娠期药物分类
D (Australia) expand 查看数据来源
相关基因信息
human ... ACE(1636) expand 查看数据来源
human ... ACE(1636), AGTR1(185), AGTR2(186), ECE1(1889)rat ... Ace(24310) expand 查看数据来源
human ... ACE(1636), ECE1(1889)rat ... Ace(24310) expand 查看数据来源
生物活性机理
ACE inhibitor expand 查看数据来源
angiotensin-antagonist expand 查看数据来源
apparent primary action involves suppression of the renin-angiotensin-aldosterone-system expand 查看数据来源
decrease in plasma-volume expand 查看数据来源
decreases plasma-angiotensin-2 concentration expand 查看数据来源
increased plasma-renin causes decrease in aldosterone-secretion resulting in: small increases in serum-potassium expand 查看数据来源
increased sodium-excretion expand 查看数据来源
increases plasma levels of PGE2 and PGE2-alpha metabolites. expand 查看数据来源
increases plasma-renin activity resulting from loss of negative feedback on renin release due to reduced angiotensin-2 concentration expand 查看数据来源
Increases urinary excretion of PGE2 expand 查看数据来源
May increase prostaglandin synthesis expand 查看数据来源
May inhibit local angiotensin 2 at vascular and renal sites so attenuating catecholamine release expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
≥99.0% (HPLC) expand 查看数据来源
95% expand 查看数据来源
97% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
适用性
meets USP testing specifications expand 查看数据来源
简要说明
Diastereomers expand 查看数据来源
应用领域
Antihypertensive agent expand 查看数据来源
Drug used for diagnosis and treatment of renin-dependent hypertension expand 查看数据来源
Exp. drug for treatment of myocardial infarction expand 查看数据来源
Smooth muscle relaxant expand 查看数据来源
Empirical Formula (Hill Notation)
C9H15NO3S expand 查看数据来源

详细说明

详细说明

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:
InterBioScreen -  BB_NC-2104 external link
Diastereomers
Sigma Aldrich -  C4042 external link
Biochem/physiol Actions
血管紧张素转换酶抑制剂。抑制血管紧张素 II 的形成,血管紧张素 II 是生物活性多肽,可促进血管生成并增加微血管密度。
包装
5, 25 g in glass bottle
Sigma Aldrich -  441600 external link
Biochem/physiol Actions
血管紧张素转换酶抑制剂。抑制血管紧张素 II 的形成,血管紧张素 II 是生物活性多肽,可促进血管生成并增加微血管密度。
Sigma Aldrich -  21751 external link
Biochem/physiol Actions
血管紧张素转换酶抑制剂。抑制血管紧张素 II 的形成,血管紧张素 II 是生物活性多肽,可促进血管生成并增加微血管密度。
Sigma Aldrich -  C8856 external link
Biochem/physiol Actions
血管紧张素转换酶抑制剂。抑制血管紧张素 II 的形成,血管紧张素 II 是生物活性多肽,可促进血管生成并增加微血管密度。
Toronto Research Chemicals -  C175750 external link
Orally active angiotensin-converting enzyme (ACE) inhibitor.

参考文献

参考文献

供应商提供 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)
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  • Migdalof, B.H. et al., Drug Metab. Rev., 1984, 15, 841, (rev)
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  • 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
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  • 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
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专利

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