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

• ChemBase ID: 75
• Molecular Formular: C10H14N2O4
• Molecular Mass: 226.22916
• Monoisotopic Mass: 226.09535694
• SMILES: OC(=O)[C@@](NN)(Cc1cc(O)c(O)cc1)C
• Canonical SMILES: NN[C@](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)/t10-/m0/s1
• InChIKey: TZFNLOMSOLWIDK-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
• IUPAC Traditional name: carbidopa
• Brand Name: Atamet; HMD; Lodosin; Lodosyn
• Synonyms: Lodosyn; Alpha-Methyldopahydrazine; Carbidopa Anhydrous; Carbidopa Monohydrate; Carbidopum [INN-Latin]; N-Aminomethyldopa; C-DOPA; MK-486; Carbidopa

Database IDs

• CAS Number: 28860-95-9
• PubChem SID: 160963538
• PubChem CID: 34359

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: -0.16
• LOG S: -1.78
• Solubility (Water): 3.73e+00 g/l

PROPERTIES

Physical Property

• Solubility: 3.8 mg/L
• Hydrophobicity(logP): -1.9

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00190

• Drug Groups: approved
• Description: An inhibitor of DOPA decarboxylase, preventing conversion of levodopa to dopamine. It is used in parkinson disease to reduce peripheral adverse effects of levodopa. It has no antiparkinson actions by itself. [PubChem]
• Indication: For treatment of the symptoms of idiopathic Parkinson's disease (paralysis agitans), post-encephalitic parkinsonism
• Pharmacology: Carbidopa, a noncompetitive decarboxylase inhibitor, is used in combination with levodopa for the treatment of Parkinson's disease.
• Toxicity: Symptoms of a carbidopa toxicity include muscle spasms or weakness, spasms of the eyelid, nausea, vomiting, diarrhea, an irregular heartbeat, confusion, agitation, hallucinations, and unconsciousness.
• Affected Organisms: Humans and other mammals
• Biotransformation: The loss of the hydrazine functional group (probably as molecular nitrogen) represents the major metabolic pathway for carbidopa. There are several metabolites of carbidopa metabolism including 3-(3,4-dihydroxyphenyl)-2-methylpropionic acid, 3-(4-hydroxy-3-methoxyphenyl)-2-methylpropionic acid, 3-(3-hydroxyphenyl)-2-methylpropionic acid, 3-(4-hydroxy-3-methoxyphenyl)-2-methyllactic acid, 3-(3-hydroxyphenyl)-2-methyllactic acid, and 3,4-dihydroxyphenylacetone (1,2). [PMID: 4150141]
• Absorption: Rapidly decarboxylated to dopamine in extracerebral tissues so that only a small portion of a given dose is transported unchanged to the central nervous system.
• Half Life: 1-2 hours
• Protein Binding: 76%
• Elimination: In clinical pharmacologic studies, simultaneous administration of separate tablets of carbidopa and levodopa produced greater urinary excretion of levodopa in proportion to the excretion of dopamine when compared to the two drugs administered at separate times.
• References: Vickers S, Stuart EK, Bianchine JR, Hucker HB, Jaffe ME, Rhodes RE, Vandenheuvel WJ: Metabolism of carbidopa (1-(-)-alpha-hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamic acid monohydrate), an aromatic amino acid decarboxylase inhibitor, in the rat, rhesus monkey, and man. Drug Metab Dispos. 1974 Jan-Feb;2(1):9-22. [Pubmed] ; Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1891

Research Area: Neurological Disease
Biological Activity:
Carbidopa is an aromatic-L-amino-acid decarboxylase inhibitor with an IC50 of 29 ± 2 μM. [1] It increases the plasma half-life of levodopa from 50 minutes to 1½ hours. CarbiDOPA cannot cross the blood brain barrier, so it inhibits only peripheral DDC. It thus prevents the conversion of L-DOPA to dopamine peripherally. This reduces the side effects caused by dopamine on the periphery,besides, it increases the concentration of L-DOPA and dopamine in the brain. [2]

REFERENCES

• Vickers S, Stuart EK, Bianchine JR, Hucker HB, Jaffe ME, Rhodes RE, Vandenheuvel WJ: Metabolism of carbidopa (1-(-)-alpha-hydrazino-3,4-dihydroxy-alpha-methylhydrocinnamic acid monohydrate), an aromatic amino acid decarboxylase inhibitor, in the rat, rhesus monkey, and man. Drug Metab Dispos. 1974 Jan-Feb;2(1):9-22. Pubmed
• Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. Pubmed
• http://en.wikipedia.org/wiki/Carbidopa