Banner
targets (1)
for drugs
Identification
Name Carbidopa
Accession Number DB00190 (APRD00160)
Type small molecule
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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Alpha-Methyldopahydrazine
  • C-DOPA
  • Carbidopa Anhydrous
  • Carbidopa Monohydrate
  • Carbidopum [INN-Latin]
  • MK-486
  • N-Aminomethyldopa
Brand names
  • Atamet
  • HMD
  • Lodosin
  • Lodosyn
Brand name mixtures
  • Apo-Levocarb (carbidopa + levodopa)
  • Apo-Levocarb CR Controlled-Release Tablets (carbidopa + levodopa)
  • Atamet (carbidopa + levodopa)
  • Dom-Levo-Carbidopa (carbidopa + levodopa)
  • Novo-Levocarbidopa (carbidopa + levodopa)
  • Nu-Levocarb (carbidopa + levodopa)
  • Sinemet (carbidopa + levodopa)
  • Sinemet CR (carbidopa + levodopa)
Categories
  • Dopamine Agents
  • Antiparkinson Agents
  • Antidyskinetics
  • Enzyme Inhibitors
CAS number 28860-95-9
Weight Average: 226.2292
Monoisotopic: 226.095356946
Chemical Formula C10H14N2O4
InChI Key InChIKey=TZFNLOMSOLWIDK-JTQLQIEISA-N
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
Plain Text
IUPAC Name
(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
SMILES
C[C@@](CC1=CC(O)=C(O)C=C1)(NN)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Amino Acids
  • Amphetamines
  • Catecholamines and Derivatives
Substructures
  • Hydroxy Compounds
  • Phenols and Derivatives
  • Acetates
  • Benzene and Derivatives
  • Carboxylic Acids and Derivatives
  • Catechols
  • Phenethylamines
  • Aromatic compounds
  • Hydrazine Derivatives
  • Amino Acids
  • Phenyl Esters
  • Amphetamines
  • Catecholamines and Derivatives
Pharmacology
Indication For treatment of the symptoms of idiopathic Parkinson's disease (paralysis agitans), post-encephalitic parkinsonism
Pharmacodynamics Carbidopa, a noncompetitive decarboxylase inhibitor, is used in combination with levodopa for the treatment of Parkinson's disease.
Mechanism of action When mixed with levodopa, carbidopa inhibits the peripheral conversion of levodopa to dopamine and the decarboxylation of oxitriptan to serotonin by aromatic L-amino acid decarboxylase. This results in increased amount of levodopa and oxitriptan available for transport to the CNS. Carbidopa also inhibits the metabolism of levodopa in the GI tract, thus, increasing the bioavailability of levodopa.
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.
Volume of distribution Not Available
Protein binding 76%
Metabolism

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]
Route of 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.
Half life 1-2 hours
Clearance Not Available
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
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Aton pharma inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Prices
Unit description Cost Unit
Carbidopa powder 27.54 USD g
Lodosyn 25 mg tablet 2.53 USD tablet
Patents Not Available
Properties
State solid
Melting point 203-205oC
Experimental Properties
Property Value Source
water solubility 3.8 mg/L PhysProp
logP -1.9 PhysProp
Predicted Properties
Property Value Source
water solubility 3.73e+00 g/l ALOGPS
logP -0.16 ALOGPS
logP -1.22 ChemAxon Molconvert
logS -1.78 ALOGPS
pKa 9.29 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 5 ChemAxon Molconvert
polar surface area 115.81 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 68.77 ChemAxon Molconvert
polarizability 21.90 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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
  2. 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
Resource Link
KEGG Drug D00558 Link_out
PubChem Compound 34359 Link_out
PubChem Substance 46508775 Link_out
ChemSpider 31640 Link_out
ChEBI 3395 Link_out
ChEMBL 3395 Link_out
Therapeutic Targets Database DAP000592 Link_out
PharmGKB PA448794 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic/sinemet.htm Link_out
Drugs.com http://www.drugs.com/cdi/carbidopa.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Carbidopa Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (73.4 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Aromatic-L-amino-acid decarboxylase

Pharmacological action: yes
Actions: inhibitor

Catalyzes the decarboxylation of L-3,4- dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine

Organism class: human
UniProt ID: P20711 Link_out
Gene: DDC Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Durso R, Evans JE, Josephs E, Szabo G, Evans B, Fernandez HH, Browne TR: Variable absorption of carbidopa affects both peripheral and central levodopa metabolism. J Clin Pharmacol. 2000 Aug;40(8):854-60. Pubmed
  3. Yee RE, Cheng DW, Huang SC, Namavari M, Satyamurthy N, Barrio JR: Blood-brain barrier and neuronal membrane transport of 6-[18F]fluoro-L-DOPA. Biochem Pharmacol. 2001 Nov 15;62(10):1409-15. Pubmed
  4. Kaufmann H, Saadia D, Voustianiouk A, Goldstein DS, Holmes C, Yahr MD, Nardin R, Freeman R: Norepinephrine precursor therapy in neurogenic orthostatic hypotension. Circulation. 2003 Aug 12;108(6):724-8. Epub 2003 Jul 28. Pubmed
  5. Orlefors H, Sundin A, Lu L, Oberg K, Langstrom B, Eriksson B, Bergstrom M: Carbidopa pretreatment improves image interpretation and visualisation of carcinoid tumours with 11C-5-hydroxytryptophan positron emission tomography. Eur J Nucl Med Mol Imaging. 2006 Jan;33(1):60-5. Epub 2005 Sep 24. Pubmed
  6. Calabrese V, Mancuso C, Ravagna A, Perluigi M, Cini C, De Marco C, Butterfield DA, Stella AM: In vivo induction of heat shock proteins in the substantia nigra following L-DOPA administration is associated with increased activity of mitochondrial complex I and nitrosative stress in rats: regulation by glutathione redox state. J Neurochem. 2007 May;101(3):709-17. Epub 2007 Jan 4. Pubmed
  7. Gilbert JA, Frederick LM, Ames MM: The aromatic-L-amino acid decarboxylase inhibitor carbidopa is selectively cytotoxic to human pulmonary carcinoid and small cell lung carcinoma cells. Clin Cancer Res. 2000 Nov;6(11):4365-72. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:01

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.