Levodopa

Levodopa
	Skeletal formula of levodopa
	Ball-and-stick model of the zwitterionic form of levodopa found in the crystal structure
Clinical data
Pronunciation	/ˌɛlˈdoʊpə/, /ˌlɛvoʊˈdoʊpə/
Trade names	Larodopa, Dopar, Inbrija, others
Other names	L-DOPA
AHFS/Drugs.com	Professional Drug Facts
MedlinePlus	a619018
License data	EU EMA: by INN; US DailyMed: Levodopa;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth, inhalation, enteral (tube), subcutaneous (as foslevodopa)
Drug class	Dopamine precursor; Dopamine receptor agonist
ATC code	N04BA01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only); US: ℞-only (some forms are OTC); EU: Rx-only;
Pharmacokinetic data
Bioavailability	30%
Metabolism	Aromatic-l-amino-acid decarboxylase
Metabolites	• Dopamine
Elimination half-life	0.75–1.5 hours
Excretion	Renal 70–80%
Identifiers
	IUPAC name (S)-2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid;
CAS Number	59-92-7 ;
PubChem CID	6047;
IUPHAR/BPS	3639;
DrugBank	DB01235 ;
ChemSpider	5824 ;
UNII	46627O600J;
KEGG	D00059 ;
ChEBI	CHEBI:15765 ;
ChEMBL	ChEMBL1009 ;
Chemical and physical data
Formula	C9H11NO4
Molar mass	197.190 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H](N)Cc1cc(O)c(O)cc1;
	InChI 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 ; Key:WTDRDQBEARUVNC-LURJTMIESA-N ;
	(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. The drug is usually used and formulated in combination with a peripherally selective aromatic L-amino acid decarboxylase (AAAD) inhibitor like carbidopa or benserazide. Levodopa is taken by mouth, by inhalation, through an intestinal tube, or by administration into fat (as foslevodopa).

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

The antiparkinsonian effects of levodopa were discovered in the 1950s and 1960s. Following this, it was introduced for the treatment of Parkinson's disease.

^ 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.
^ ^a ^b "Levodopa Use During Pregnancy". Drugs.com. 12 July 2019. Retrieved 27 September 2020.

[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.

[Drugs.com_pregnancy-2] "Levodopa Use During Pregnancy". Drugs.com. 12 July 2019. Retrieved 27 September 2020.

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