3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid

• ChemBase编号: 103979
• 分子式: C10H14N2O4
• 平均质量: 226.22916
• 单一同位素质量: 226.09535694
• SMILES: CC(Cc1cc(O)c(O)cc1)(NN)C(=O)O
• Canonical SMILES: NNC(C(=O)O)(Cc1ccc(c(c1)O)O)C
• InChI: InChI=1S/C10H14N2O4/c1-10(12-11,9(15)16)5-6-2-3-7(13)8(14)4-6/h2-4,12-14H,5,11H2,1H3,(H,15,16)
• InChIKey: TZFNLOMSOLWIDK-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid; (2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
• IUPAC传统名: @carbidopa; carbidopa; (2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
• 别名: (S)-3-(3,4-Dihydroxyphenyl)-2-hydrazino-2-methylpropanoic acid; S-(-)-α-Hydrazino-3,4-dihydroxy-2-methylbenzenepropanoic acid; S-(-)-Carbidopa; α-Hydrazino-3,4-dihydroxy-α-methyl-benzenepropanoic Acid; DL-α-Hydrazino-3,4-dihydroxy-α-methylhydrocinnamic Acid; α-Hydrazino-α-methyldopa; dl-MK 485; NSC 92521; D,L-Carbidopa; S(-)-α-Hydrazino-3,4-dihydroxy-α-methylbenzenepropanoic acid; S(-)-CARBIDOPA; (S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid; Lodosyn; Lodysin; Menesit; Neo-Dopaston; Carbidopa

登记号

• CAS号: 302-53-4; 28860-95-9
• EC号: 249-271-9
• MDL号: MFCD00069231
• PubChem SID: 162091364; 24277889; 24892402
• PubChem CID: 2563

理论计算性质

• Acid pKa: 3.5892224
• 质子受体: 6
• 质子供体: 5
• LogD (pH = 5.5): -1.3181038
• LogD (pH = 7.4): -2.5354536
• Log P: -1.1881938
• 摩尔折射率: 68.7683 cm^3
• 极化性: 22.328514 Å^3
• 极化表面积: 115.81 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Water
• 外观: Brown Solid; powder; white solid
• 熔点: 175-178°C (dec.); 208°C
• 比旋光度: [α]26/D -13.82°, c = 0.3 in methanol(lit.)
• 紫外吸收波长: εmax/282.5 nm, methanol 2950

安全信息

• 保存条件: -20°C, Protect from light; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS编号: MW5298000
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: -20°C

药理学性质

• 相关基因信息: human ... DDC(1644)
• 生物活性机理: Dopa-decarboxylase inhibitor

产品相关信息

• 纯度: ≥98% (TLC)
• 应用领域: Antiparkinsonian agent; Used in treatment of parkinsonism

详细说明

MP Biomedicals - 02153757

Used as a Parkinson's Disease therapeutic in combination with L-DOPA.

Sigma Aldrich - C1335

Biochem/physiol Actions
Peripheral inhibitor of L-aromatic amino acid decarboxylase. When co-administered with L-DOPA, it prevents extra-CNS conversion to dopamine, thereby increasing CNS concentrations of effective compounds. Selectively cytotoxic to human pulmonary carcinoid and small cell lung carcinoma cells by increasing H2O2 in these cell lines, which are sensitive to reactive oxygen species.1

Sigma Aldrich - C126

Caution
Light sensitive
Biochem/physiol Actions
Peripheral inhibitor of L-aromatic amino acid decarboxylase. When co-administered with L-DOPA, it prevents extra-CNS conversion to dopamine, thereby increasing CNS concentrations of effective compounds. Selectively cytotoxic to human pulmonary carcinoid and small cell lung carcinoma cells by increasing H2O2 in these cell lines, which are sensitive to reactive oxygen species.1

Toronto Research Chemicals - C175915

An inhibitor of aromatic amino acid decarboxylase.

参考文献

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• Pinder, R.M. et al., Drugs, 1976, 11, 329, (rev)
• Lotti, V.J. et al., Clin. Ther., 1977, 1, 66, (Sinemet)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 840
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CBQ500