Chemical Component Summary

Name3,4-DIHYDROXYPHENYLALANINE
SynonymsL-DOPA
Identifiers(2S)-2-azanyl-3-[3,4-bis(oxidanyl)phenyl]propanoic acid
FormulaC9 H11 N O4
Molecular Weight197.188
TypeL-PEPTIDE LINKING
Isomeric SMILESc1cc(c(cc1C[C@@H](C(=O)O)N)O)O
InChIInChI=1S/C9H11NO4/c10-6(9(13)14)3-5-1-2-7(11)8(12)4-5/h1-2,4,6,11-12H,3,10H2,(H,13,14)/t6-/m0/s1
InChIKeyWTDRDQBEARUVNC-LURJTMIESA-N

Chemical Details

Formal Charge0
Atom Count25
Chiral Atom Count1
Bond Count25
Aromatic Bond Count6

Drug Info: DrugBank

DrugBank IDDB01235 
NameLevodopa
Groups approved
DescriptionLevodopa is a prodrug of dopamine that is administered to patients with Parkinson's due to its ability to cross the blood-brain barrier[Label]. Levodopa can be metabolised to dopamine on either side of the blood-brain barrier and so it is generally administered with a dopa decarboxylase inhibitor like carbidopa to prevent metabolism until after it has crossed the blood-brain barrier[Label,A177781]. Once past the blood-brain barrier, levodopa is metabolized to dopamine and supplements the low endogenous levels of dopamine to treat symptoms of Parkinson's[Label]. The first developed drug product that was approved by the FDA was a levodopa and carbidopa combined product called Sinemet that was approved on May 2, 1975[A177781,L6133].
Synonyms
  • β-(3,4-dihydroxyphenyl)alanine
  • L-beta-(3,4-Dihydroxyphenyl)alanine
  • Levodopa
  • L-3,4-dihydroxyphenylalanine
  • β-(3,4-dihydroxyphenyl)-L-alanine
Brand Names
  • Stalevo
  • Nu-levocarb - Tablets 25 Mg/250 mg
  • Apo-levocarb - Tab 10mg/100mg
  • Carbidopa, Levodopa and Entacapone
  • Ratio-levodopa/carbidopa
IndicationLevodopa on its own is formulated as an oral inhalation powder indicated for intermittent treatment of off episodes in Parkinson's patients who are already being treated with carbidopa and levodopa[FDA Label]. Levodopa is most commonly formulated as an oral tablet with a peripheral dopa decarboxylase inhibitor indicated for treatment of Parkinson's disease, post-encephalitic parkinsonism, and symptomatic parkinsonism following carbon monoxide intoxication or manganese intoxication[F4579].
Categories
  • Amines
  • Amino Acids
  • Amino Acids, Aromatic
  • Amino Acids, Cyclic
  • Amino Acids, Peptides, and Proteins
ATC-Code
  • N04BA03
  • N04BA01
  • N04BA02
CAS number59-92-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Dopamine D1 receptorMRTLNTSAMDGTGLVVERDFSVRILTACFLSLLILSTLLGNTLVCAAVIR...unknownagonist
Dopamine D5 receptorMLPPGSNGTAYPGQFALYQQLAQGNAVGGSAGAPPLGPSQVVTACLLTLL...unknownagonist
Dopamine D2 receptorMDPLNLSWYDDDLERQNWSRPFNGSDGKADRPHYNYYATLLTLLIAVIVF...unknownagonist
Dopamine D3 receptorMASLSQLSSHLNYTCGAENSTGASQARPHAYYALSYCALILAIVFGNGLV...unknownagonist
Dopamine D4 receptorMGNRSTADADGLLAGRGPAAGASAGASAGLAGQGAAALVGGVLLIGAVLA...unknownagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL1009
PubChem 6047, 6971033
ChEMBL CHEMBL1009
ChEBI CHEBI:57504, CHEBI:15765
CCDC/CSD LDOPAC01, AYICOC