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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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1977))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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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
ChEMBL Ligand CHEMBL1201236
DrugBank Ligand DB00190
DrugCentral Ligand 496
GtoPdb PubChem SID 178101851
PubChem CID 34359
RCSB PDB Ligand 142
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Wikipedia Carbidopa

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(S)-(-)-Carbidopa (links to external site)
Cat. No. 0455