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55-40-3 分子结构
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(2S)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid

ChemBase编号:843
分子式:C10H13NO4
平均质量:211.21452
单一同位素质量:211.0844579
SMILES和InChIs

SMILES:
OC(=O)C(N)(Cc1cc(O)c(O)cc1)C
Canonical SMILES:
OC(=O)C(Cc1ccc(c(c1)O)O)(N)C
InChI:
InChI=1S/C10H13NO4/c1-10(11,9(14)15)5-6-2-3-7(12)8(13)4-6/h2-4,12-13H,5,11H2,1H3,(H,14,15)/t10-/m0/s1
InChIKey:
CJCSPKMFHVPWAR-JTQLQIEISA-N

引用这个纪录

CBID:843 http://www.chembase.cn/molecule-843.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)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid
IUPAC传统名
methyldopa
α methyldopa
商标名
Aldoclor-150
Aldoclor-250
Aldomet
Aldometil
Aldomin
Aldoril 15
Aldoril 25
Aldoril D30
Aldoril D50
Apo-Methyldopa
Bayer 1440 L
Baypresol
Becanta
Dopamet
Dopamethyperpax
Dopatec
Dopegyt
Grospisk
Hyperpax
Hypolag
Medomet
Medopa
Medopal
Medopren
Methoplain
Novomedopa
Nu-Medopa
Presinol
Presolisin
Sedometil
Sembrina
别名
3-(3,4-二羟基苯基)-2-甲基-L-丙氨酸
L-甲基多巴
甲基多巴 倍半水合物
Alphamethyldopa
Alpha medopa
AMD
L-Methyl Dopa
Methyldopa anhydrous
Methyldopate
Methyldopate HCL
Mk. b51
Methyldopa
Aldoril
Dopamet
Dopegyt
MK-351
3-(3,4-Dihydroxyphenyl)-2-methyl-L-alanine
Methyl-L-DOPA
Methyl-DOPA sesquihydrate
L-α-Methyl-DOPA
α-METHYL-L-β-3,4-DIHYDROXYPHENYLALANINE
3-Hydroxy-α-methyltyrosine
3-(3,4-Dihydroxyphenyl)-2-methylalanine
DL-α-Methyl DOPA
Metholes
Mulfasin
rac α-Methyl DOPA
CAS号
55-40-3
41372-08-1
555-30-6
EC号
209-089-2
MDL号
MFCD00004186
Beilstein号
2417244
PubChem SID
46508535
160964306
24863565
PubChem CID
38853

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 1.7286927  质子受体
质子供体 LogD (pH = 5.5) -1.3594157 
LogD (pH = 7.4) -1.3670306  Log P -1.3594803 
摩尔折射率 53.7914 cm3 极化性 20.989363 Å3
极化表面积 103.78 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P -2.02  LOG S -1.97 
溶解度 2.26e+00 g/l 

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
1000 mg/L expand 查看数据来源
熔点
≥300 °C expand 查看数据来源
比旋光度
[α]20/D -13.0±1°, c = 1% in H2O expand 查看数据来源
疏水性(logP)
-1.7 expand 查看数据来源
保存条件
0°C expand 查看数据来源
-20°C expand 查看数据来源
RTECS编号
AY5950000 expand 查看数据来源
YP2860000 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
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
纯度
≥99.0% (sum of enantiomers, TLC) 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
下载链接 expand 查看数据来源
杂质
~12% water expand 查看数据来源
≤0.5% alanine expand 查看数据来源
Empirical Formula (Hill Notation)
C10H13NO4 · 1.5H2O expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02155519 external link
(L-α-Methyl-DOPA) Crystalline
DrugBank -  DB00968 external link
Item Information
Drug Groups approved
Description An alpha-2 adrenergic agonist that has both central and peripheral nervous system effects. Its primary clinical use is as an antihypertensive agent. [PubChem]
Indication For use in the treatment of hypertension.
Pharmacology Methyldopa is an aromatic-amino-acid decarboxylase inhibitor in animals and in man. Only methyldopa, the L-isomer of alpha-methyldopa, has the ability to inhibit dopa decarboxylase and to deplete animal tissues of norepinephrine. In man the antihypertensive activity appears to be due solely to the L-isomer. About twice the dose of the racemate (DL-alpha-methyldopa) is required for equal antihypertensive effect. Methyldopa has no direct effect on cardiac function and usually does not reduce glomerular filtration rate, renal blood flow, or filtration fraction. Cardiac output usually is maintained without cardiac acceleration. In some patients the heart rate is slowed. Normal or elevated plasma renin activity may decrease in the course of methyldopa therapy. Methyldopa reduces both supine and standing blood pressure. Methyldopa usually produces highly effective lowering of the supine pressure with infrequent symptomatic postural hypotension. Exercise hypotension and diurnal blood pressure variations rarely occur.
Toxicity The oral LD50 of methyldopa is greater than 1.5 g/kg in both the mouse and the rat. Symptoms of overdose include bloating, constipation, diarrhea, dizziness, extreme drowsiness, gas, light-headedness, nausea, severely low blood pressure, slow heartbeat, vomiting, and weakness.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic, extensively metabolized. The known urinary metabolites are: a-methyldopa mono-0-sulfate; 3-0-methyl-a-methyldopa; 3,4-dihydroxyphenylacetone; a-methyldopamine; 3-0-methyl-a-methyldopamine and their conjugates.
Absorption Absorption from the gastrointestinal tract is variable but averages approximately 50%.
Half Life The plasma half-life of methyldopa is 105 minutes.
Protein Binding Low (less than 20%).
Elimination Methyldopa is extensively metabolized. The known urinary metabolites are: α-methyldopa mono-O-sulfate; 3-0-methyl-α-methyldopa; 3,4-dihydroxyphenylacetone; α-methyldopamine; 3-0-methyl-α-methyldopamine and their conjugates. Approximately 70 percent of the drug which is absorbed is excreted in the urine as methyldopa and its mono-O-sulfate conjugate. Methyldopa crosses the placental barrier, appears in cord blood, and appears in breast milk.
Clearance * Renal cl=130 mL/min [healthy]
References
Mah GT, Tejani AM, Musini VM: Methyldopa for primary hypertension. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD003893. [Pubmed]
McCoy S, Baldwin K: Pharmacotherapeutic options for the treatment of preeclampsia. Am J Health Syst Pharm. 2009 Feb 15;66(4):337-44. [Pubmed]
Sica DA: Centrally acting antihypertensive agents: an update. J Clin Hypertens (Greenwich). 2007 May;9(5):399-405. [Pubmed]
van Zwieten PA: Development and trends in the drug treatment of essential hypertension. J Hypertens Suppl. 1992 Dec;10(7):S1-12. [Pubmed]
Rosenthal T, Oparil S: The effect of antihypertensive drugs on the fetus. J Hum Hypertens. 2002 May;16(5):293-8. [Pubmed]
van Zwieten PA, Timmermans PB: Pharmacology and characterization of central alpha-adrenoceptors involved in the effect of centrally acting antihypertensive drugs. Chest. 1983 Feb;83(2 Suppl):340-3. [Pubmed]
van Zwieten PA: Pharmacology of centrally acting hypotensive drugs. Br J Clin Pharmacol. 1980;10 Suppl 1:13S-20S. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals -  S1642 external link
Research Area: Neurological Disease
Biological Activity:
Methyldopa (Aldomet) is a DOPA decarboxylase competitive inhibitor with an ED50 of 21.8 mg/kg. It is also known as aromatic L-amino acid decarboxylase, which converts L-DOPA into dopamine. Dopamine is a precursor for norepinephrine (noradrenaline) and subsequently epinephrine (adrenaline). This inhibition results in reduced dopaminergic and adrenergic neurotransmission in the peripheral nervous system. [1] The antihypertensive agents lofexidine (ED50, 0.03 mg/kg), guanabenz (ED50, 0.019 mg/kg), p-aminoclonidine (ED50, 0.23 mg/kg), methyldopa (ED50, 21.8 mg/kg), hydralazine (ED50, 0.98 mg/kg), prazosin (ED50, 0.72 mg/kg), minoxidil (ED50, 12.4 mg/kg) and pergolide (ED50, 0.021 mg/kg) were generalized to clonidine in a dose-dependent manner. [2] Methyldopa (Aldomet) is a psychoactive molecule used as a sympatholytic or antihypertensive.o
Sigma Aldrich -  37862 external link
Other Notes
抗菌性1
Toronto Research Chemicals -  M303800 external link
Antihypertensive agent.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Mah GT, Tejani AM, Musini VM: Methyldopa for primary hypertension. Cochrane Database Syst Rev. 2009 Oct 7;(4):CD003893. Pubmed
  • McCoy S, Baldwin K: Pharmacotherapeutic options for the treatment of preeclampsia. Am J Health Syst Pharm. 2009 Feb 15;66(4):337-44. Pubmed
  • Sica DA: Centrally acting antihypertensive agents: an update. J Clin Hypertens (Greenwich). 2007 May;9(5):399-405. Pubmed
  • van Zwieten PA: Development and trends in the drug treatment of essential hypertension. J Hypertens Suppl. 1992 Dec;10(7):S1-12. Pubmed
  • Rosenthal T, Oparil S: The effect of antihypertensive drugs on the fetus. J Hum Hypertens. 2002 May;16(5):293-8. Pubmed
  • van Zwieten PA, Timmermans PB: Pharmacology and characterization of central alpha-adrenoceptors involved in the effect of centrally acting antihypertensive drugs. Chest. 1983 Feb;83(2 Suppl):340-3. Pubmed
  • van Zwieten PA: Pharmacology of centrally acting hypotensive drugs. Br J Clin Pharmacol. 1980;10 Suppl 1:13S-20S. Pubmed
  • http://en.wikipedia.org/wiki/Methyldopa
  • Beckett, et al.: J. Pharm. Pharmacol., 7, 433 (1955)
  • Sletzinger, et al.: J. Med. Chem., 6, 101 (1955)
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专利

专利

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