Levodopa

Levodopa
Skeletal formula of levodopa
Ball-and-stick model of the zwitterionic form of levodopa found in the crystal structure[1]
Clinical data
Pronunciation/ˌɛlˈdpə/, /ˌlɛvˈdpə/
Trade namesLarodopa, Dopar, Inbrija, others
Other namesL-DOPA
AHFS/Drugs.comProfessional Drug Facts
MedlinePlusa619018
License data
Pregnancy
category
Routes of
administration
By mouth, inhalation, enteral (tube), subcutaneous (as foslevodopa)
Drug classDopamine precursor; Dopamine receptor agonist
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only (some forms are OTC)
  • EU: Rx-only
Pharmacokinetic data
Bioavailability30%
MetabolismAromatic-l-amino-acid decarboxylase
MetabolitesDopamine
Elimination half-life0.75–1.5 hours
ExcretionRenal 70–80%
Identifiers
  • (S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.000.405 Edit this at Wikidata
Chemical and physical data
FormulaC9H11NO4
Molar mass197.190 g·mol−1
3D model (JSmol)
  • O=C(O)[C@@H](N)Cc1cc(O)c(O)cc1
  • InChI=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 checkY
  • Key:WTDRDQBEARUVNC-LURJTMIESA-N checkY
  (verify)

Levodopa, also known as L-DOPA and sold under many brand names, is a dopaminergic medication which is used in the treatment of Parkinson's disease and certain other conditions like dopamine-responsive dystonia and restless legs syndrome.[3] The drug is usually used and formulated in combination with a peripherally selective aromatic L-amino acid decarboxylase (AAAD) inhibitor like carbidopa or benserazide.[3] Levodopa is taken by mouth, by inhalation, through an intestinal tube, or by administration into fat (as foslevodopa).[3]

Side effects of levodopa include nausea, the wearing-off phenomenon, dopamine dysregulation syndrome, and levodopa-induced dyskinesia, among others.[3] The drug is a centrally permeable monoamine precursor and prodrug of dopamine and hence acts as a dopamine receptor agonist.[3] Chemically, levodopa is an amino acid, a phenethylamine, and a catecholamine.[3]

Levodopa was first synthesized and isolated in the early 1910s.[3] The antiparkinsonian effects of levodopa were discovered in the 1950s and 1960s.[3] Following this, it was introduced for the treatment of Parkinson's disease in 1970.[3]

  1. ^ Howard ST, Hursthouse MB, Lehmann CW, Poyner EA (1995). "Experimental and theoretical determination of electronic properties in Ldopa". Acta Crystallogr. B. 51 (3): 328–337. Bibcode:1995AcCrB..51..328H. doi:10.1107/S0108768194011407. S2CID 96802274.
  2. ^ a b "Levodopa Use During Pregnancy". Drugs.com. 12 July 2019. Retrieved 27 September 2020.
  3. ^ a b c d e f g h i Whitfield AC, Moore BT, Daniels RN (December 2014). "Classics in chemical neuroscience: levodopa". ACS Chem Neurosci. 5 (12): 1192–1197. doi:10.1021/cn5001759. PMID 25270271.

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