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(2S)-1-[(2S)-2-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid dihydrate

ChemBase编号:73253
分子式:C18H28N2O7
平均质量:384.42412
单一同位素质量:384.18965125
SMILES和InChIs

SMILES:
c1cccc(c1)CC[C@@H](C(=O)O)N[C@H](C(=O)N1[C@@H](CCC1)C(=O)O)C.O.O
Canonical SMILES:
OC(=O)[C@@H](N[C@H](C(=O)N1CCC[C@H]1C(=O)O)C)CCc1ccccc1.O.O
InChI:
InChI=1S/C18H24N2O5.2H2O/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13;;/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25);2*1H2/t12-,14-,15-;;/m0../s1
InChIKey:
MZYVOFLIPYDBGD-MLZQUWKJSA-N

引用这个纪录

CBID:73253 http://www.chembase.cn/molecule-73253.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-{[(1S)-1-carboxy-3-phenylpropyl]amino}propanoyl]pyrrolidine-2-carboxylic acid dihydrate
IUPAC传统名
enalaprilat dihydrate
别名
Enalaprilat dihydrate
(2S)-1-[(2S)-2-[[(1S)-1-Carboxy-3-phenyl-propyl]amino]propanoyl]pyrrolidine-2-carboxylic acid
Vasotec
Enalaprilat dihydrate
CAS号
84680-54-6
S1657
EC号
278-459-3
MDL号
MFCD00941393
PubChem SID
162038173
PubChem CID
6917719

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
PubChem 6917719 external link

理论计算性质

理论计算性质

JChem
质子供体 LogD (pH = 5.5) -2.2588751 
LogD (pH = 7.4) -4.0126777  Log P -1.0502586 
摩尔折射率 90.0569 cm3 极化性 35.51059 Å3
极化表面积 106.94 Å2 可自由旋转的化学键
里宾斯基五规则 true  Acid pKa 3.132935 
质子受体

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
DMSO: soluble64 mg/mL expand 查看数据来源
H2O: soluble14 mg/mL at 60 °C (warming for 5 minutes) expand 查看数据来源
保存条件
-20°C expand 查看数据来源
RTECS编号
TW3590600 expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
保存温度
room temp expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
成盐信息
dihydrate expand 查看数据来源
Empirical Formula (Hill Notation)
C18H24N2O5 ·2H2O expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals -  S1657 external link
Research Area
Description Cardiovascular Disease
Biological Activity
Description Enalaprilat is an angiotensin-converting enzyme (ACE) inhibitor with IC50 of 1.94 nM.
Targets ACE
IC50 1.94 nM [1]
In Vitro Enalaprilat has high affinity for human endothelial ACE with IC50 of 1.94 nM in vitro binding assay by displacing a saturating concentration of [125I]351A, a radiolabeled lisinopril analogue from ACE binding sites, and shows bradykinin/angiotensin I selectivity ratio of 1.00 calculated from double displacement experiments. [1] Enalaprilat has the strong inhibitory effect on Aβ42-to-Aβ40-converting activity found in the N-domain of ACE, exhibiting a 10-fold lower IC50 (0.003~0.01 μM) than captopril (0.03~0.1 μM). [2] Enalaprilat (100 nM) blocks protein kinase C epsilon by directly activating bradykinin B1 receptor at the canonical Zn2+ binding site, leading to prolonged nitric oxide (NO) production in cytokine-treated human lung microvascular endothelial cells. [3] Enalaprilat attenuates the IGF-I induced neonatal rat cardiac fibroblast growth (30% reduction) in a concentration-dependent fashion, with IC50 of 90 mM. [4]
In Vivo Enalaprilat has unfavourable ionisation characteristics to allow sufficient potency for oral administration, thus Enalaprilat is only suitable for intravenous administration, which is overcome by the esterification with ethanol to produce Enalapril. Administration of Enalaprilat induces a significant reduction of MAP at 70 minutes compared with the placebo group during haemorrhagic shock in rats, and results in a 50% reduction of CO, a general tendency of EB extravasation which is significant in the kidney and lungs, and a significant increase in ileal EB extravasation (53%). [5] Enalaprilat has no effect in nonhypertrophied hearts, but significantly attenuates the greater increase in left ventricular end-diastolic pressure in hypertrophied hearts compared with no drug (65±7 versus 50±5 mm Hg, p<0.01).>[6]
Clinical Trials Phase III has been completed in the extension study of comparing the long-term safety of Valsartan versus Enalapril, and the effectiveness of the combination of Valsartan and Enalapril versus Enalapril alone in children with hypertension.
Features Enalaprilat is the first dicarboxylate-containing ACE inhibitor developed partly to overcome limitations of captopril.
Protocol
Kinase Assay [1]
Single displacement binding assay The binding assay is based on the competitive displacement of [125I]351A by Enalaprilat performed on whole endothelial cells. Subconfluent HUVECs in 6-well plates are rinsed with 2 mL binding buffer (140 mM NaCl, 2.7 mM KCl, 1.8 mM CaCl2, 1.03 mM MgCl2, 0.42 mM NaH2PO4, 10 mM HEPES, 2 mM sodium pyruvate and 5 mM glucose, pH 7.4), and the culture medium is replaced with 2.5 mL fresh binding buffer containing 5% fetal bovine serum (FBS). The Enalaprilat (2.5-12.5 μL, 0.1-50 nM) or equivalent volumes of diluent are added to the binding buffer. A saturating amount of [125I]351A (10 μL, typically 106 cpm) is then added to each sample and the plates are incubated at 37 °C for 2 hours in a thermostatic bath. The cells are then rinsed twice with 1.5 mL binding buffer. Finally, the cells are extracted with 0.5 mL NaOH 1 N, incubated for 5 minutes, and the radioactivity is counted with a gamma counter. The ratio of specific [125I]351A bound to total bound activity (B/B0) is calculated, and the inhibitory potency of Enalaprilat expressed as the concentration of ACE inhibitors able to displace 50% of the bound radioligand, i.e. the IC50.
Cell Assay [4]
Cell Lines Rat cardiac fibroblasts cell lines
Concentrations Dissolved in DMSO, final concentrations 1 nM - 10 μM
Incubation Time 24 hours
Methods After 24 hours incubation in serum-free medium (DMEM), cells are stimulated with IGF-I (1-100 nM) and coincubated with Enalaprilat (1 nM-10 μM) for 24 hours. Cellular proliferation is assessed by 5-bromo-2'-deoxyuridine (BrdU) incorporation during the last 4 hours of the 24 hours incubation period using a colorimetric immunoassay. The extinctions are measured at 450 nm in an ELISA plate reader. All values consist of an n=9.
Animal Study [5]
Animal Models Male Sprague–Dawley rats
Formulation Dissolved in a vehicle solution (1 mg in 950 μL of phosphate buffered saline and 50 μL 1M Na2CO3).
Doses 1 mg/kg
Administration I.V. bolus
References
[1] Ceconi C, et al. Eur J Pharmacol, 2007, 577(1-3), 1-6.
[2] Zou K, et al. J Biol Chem, 2009, 284(46), 31914-31920.
[3] Stanisavljevic S, et al. J Pharmacol Exp Ther, 2006, 316(3), 1153-1158.
[4] van Eickels M, et al. Br J Pharmacol, 2000, 131(8), 1592-1596.
[5] Schumacher J, et al. Br J Anaesth, 2006, 96(4), 437-443.
[6] Eberli FR, et al. Circ Res, 1992, 70(5), 931-943.
Sigma Aldrich -  E9658 external link
Biochem/physiol Actions
Enalaprilat is an inhibitor of angiotensin converting enzyme (ACE), antihypertensive, and a Bradykinin B1 receptor activator. Enalaprilat has nM potency versus ACE and also activates B1 receptors to release NO.

专利

专利

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