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28860-95-9 molecular structure
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(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 and InChIs

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

Cite this record

CBID:75 http://www.chembase.cn/molecule-75.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
IUPAC Traditional name
carbidopa
Brand Name
Atamet
HMD
Lodosin
Lodosyn
Synonyms
Alpha-Methyldopahydrazine
Carbidopa Anhydrous
Carbidopa Monohydrate
Carbidopum [INN-Latin]
N-Aminomethyldopa
C-DOPA
MK-486
Carbidopa
Lodosyn
CAS Number
28860-95-9
PubChem SID
160963538
PubChem CID
34359

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
Selleck Chemicals
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CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.5892224  H Acceptors
H Donor LogD (pH = 5.5) -1.3181038 
LogD (pH = 7.4) -2.5354536  Log P -1.1881938 
Molar Refractivity 68.7683 cm3 Polarizability 22.328514 Å3
Polar Surface Area 115.81 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.16  LOG S -1.78 
Solubility (Water) 3.73e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
3.8 mg/L expand Show data source
Hydrophobicity(logP)
-1.9 expand Show data source
Storage Condition
-20°C expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank - DB00190 external link
Item Information
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 external link
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

REFERENCES

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  • • 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
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PATENTS

PATENTS

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