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

• ChemBase ID: 103979
• Molecular Formular: C10H14N2O4
• Molecular Mass: 226.22916
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid; (2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
• IUPAC Traditional name: @carbidopa; carbidopa; (2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
• Synonyms: (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

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.5892224
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -1.3181038
• LogD (pH = 7.4): -2.5354536
• Log P: -1.1881938
• Molar Refractivity: 68.7683 cm^3
• Polarizability: 22.328514 Å^3
• Polar Surface Area: 115.81 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Brown Solid; powder; white solid
• Melting Point: 175-178°C (dec.); 208°C
• Optical Rotation: [α]26/D -13.82°, c = 0.3 in methanol(lit.)
• Absorption Wavelength: εmax/282.5 nm, methanol 2950

Safety Information

• Storage Condition: -20°C, Protect from light; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: MW5298000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... DDC(1644)
• Mechanism of Action: Dopa-decarboxylase inhibitor

Product Information

• Purity: ≥98% (TLC)
• Application(s): Antiparkinsonian agent; Used in treatment of parkinsonism

DETAILS

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.

REFERENCES

• Sletzinger, M., et al.: J. Med. Chem., 6, 101 (1963)
• Karady, S. et al., J.O.C., 1971, 36, 1949, (synth)
• Lotti, V., Adv. Neurol., 1973, 2, 91, (rev, pharmacol)
• Rao, S.K. et al., Adv. Neurol., 1973, 3, 73, (rev, metab, pharmacol)
• Falck, R.L., Drug Intell. Clin. Pharm., 1976, 10, 84, (rev)
• 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