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carbidopa   Click here for help

GtoPdb Ligand ID: 5159

Synonyms: Duodopa® | Lodosyn® | MK 486 [4]
Approved drug PDB Ligand
carbidopa is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: Carbidopa was originally approved by the FDA in combination with levodopa in 1975. It is an inhibitor of L-Aromatic amino-acid decarboxylase (a.k.a. L-Dopa decarboxylase) [1,4] that decreases the peripheral decarboxylation of levodopa to dopamine. The competitive or noncompetitive nature of carbidopa's interaction with L-Dopa decarboxylase is complex. Two published papers that discuss the kinetics of the inhibitor/enzyme interaction are [4] and [1], and from analysis of these it would appear that due to the slow dissociation of carbidopa from L-Dopa decarboxylase, once the enzyme/inhibitor complex has formed substrate is unable to displace the inhibitor. Carbidopa is described as a competitive inhibitor in these articles [2-3].
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 5
Rotatable bonds 4
Topological polar surface area 115.81
Molecular weight 226.1
XLogP 0.02
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES NNC(C(=O)O)(Cc1ccc(c(c1)O)O)C
Isomeric 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
InChI Key TZFNLOMSOLWIDK-JTQLQIEISA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. US FDA (1977)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(2S)-3-(3,4-dihydroxyphenyl)-2-hydrazinyl-2-methylpropanoic acid
International Nonproprietary Names Click here for help
INN number INN
3258 carbidopa
Synonyms Click here for help
Duodopa® | Lodosyn® | MK 486 [4]
Database Links Click here for help
CAS Registry No. 28860-95-9
ChEBI CHEBI:39585
ChEMBL Ligand CHEMBL1201236
DrugBank Ligand DB00190
DrugCentral Ligand 496
GtoPdb PubChem SID 178101851
PubChem CID 34359
RCSB PDB Ligand 142
Search Google for chemical match using the InChIKey TZFNLOMSOLWIDK-JTQLQIEISA-N
Search Google for chemicals with the same backbone TZFNLOMSOLWIDK
Search PubMed clinical trials carbidopa
Search PubMed titles carbidopa
Search PubMed titles/abstracts carbidopa
UniChem Compound Search for chemical match using the InChIKey TZFNLOMSOLWIDK-JTQLQIEISA-N
UniChem Connectivity Search for chemical match using the InChIKey TZFNLOMSOLWIDK-JTQLQIEISA-N
Wikipedia Carbidopa

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MedChemExpress
Carbidopa (links to external site)
Cat. No. HY-B0311
(Same CID)