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Substance Name: Levodopa [USAN:USP:INN:BAN:JAN]
RN: 59-92-7
UNII: 46627O600J
InChIKey: WTDRDQBEARUVNC-LURJTMIESA-N

Note

  • The naturally occurring form of DIHYDROXYPHENYLALANINE and the immediate precursor of DOPAMINE. Unlike dopamine itself, it can be taken orally and crosses the blood-brain barrier. It is rapidly taken up by dopaminergic neurons and converted to DOPAMINE. It is used for the treatment of PARKINSONIAN DISORDERS and is usually given with agents that inhibit its conversion to dopamine outside of the central nervous system.

Molecular Formula

  • C9-H11-N-O4

Molecular Weight

  • 197.189
 

Classification Codes

  • Anti-Dyskinesia Agents
  • Antiparkinson Agents
  • Antiparkinsonian
  • Central Nervous System Agents
  • Dopamine Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Mutation Data
  • Neurotransmitter Agents
  • Reproductive Effect
  • Tumor Data

Names and Synonyms

Name of Substance

  • Levodopa
  • Levodopa [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Levodopa

Synonyms

  • (-)-3-(3,4-Dihydroxyphenyl)-L-alanine
  • (-)-Dopa
  • 2-Amino-3-(3,4-dihydroxyphenyl)propanoic acid
  • 3,4-Dihydroxy-L-phenylalanine
  • 3,4-Dihydroxyphenyl-L-alanine
  • 3,4-Dihydroxyphenylalanine (VAN)
  • 3-Hydroxy-L-tyrosine
  • Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-
  • Alanine, 3-(3,4-dihydroxyphenyl)-, L-
  • Bendopa
  • beta-(3,4-Dihydroxyphenyl)-alpha-alanine
  • beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine
  • beta-(3,4-Dihydroxyphenyl)-L-alanine
  • Biodopa
  • Brocadopa
  • CCRIS 3766
  • Cerepap
  • Cerepar
  • Cidandopa
  • CVT-301
  • DA
  • Deadopa
  • Dihydroxy-L-phenylalanine
  • DOPA
  • Dopaflex
  • Dopaidan
  • Dopal
  • Dopal-fher
  • Dopalina
  • Dopar
  • Doparkine
  • Doparl
  • Dopasol
  • Dopaston
  • Dopaston SE
  • Dopastral
  • Doprin
  • EINECS 200-445-2
  • Eldopal
  • Eldopar
  • Eldopatec
  • Eurodopa
  • Helfo DOPA
  • Helfo-dopa
  • HSDB 3348
  • Inbrija
  • Insulamina
  • L-(-)-Dopa
  • L-(o-Dihydroxyphenyl)alanine
  • L-3-(3,4-Dihydroxyphenyl)alanine
  • L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine
  • L-beta-(3,4-Dihydroxyphenyl)alanine
  • L-DOPA
  • L-O-Dihydroxyphenylalanine
  • L-o-Hydroxytyrosine
  • L-Tyrosine, 3-hydroxy-
  • Larodopa
  • Levodopa
  • Levodopum
  • Levodopum [INN-Latin]
  • Levopa
  • Maipedopa
  • NSC 118381
  • Pardopa
  • Prodopa
  • Ro 4-6316
  • Sobiodopa
  • Syndopa
  • UNII-46627O600J
  • Veldopa

Systematic Names

  • Alanine, 3-(3,4-dihydroxyphenyl)-, L-
  • L-DOPA
  • L-Tyrosine, 3-hydroxy-
  • Levodopa

Superlist Name

  • Levodopa

Mixture Names

  • Madopa
  • Sinemet

Registry Numbers

CAS Registry Number

  • 59-92-7

FDA UNII

  • 46627O600J

Other Registry Numbers

  • 23734-74-9
  • 25525-15-9
  • 34241-25-3
  • 72572-99-7
  • 72573-00-3
  • 88250-23-1
  • 90638-38-3

System Generated Number

  • 0000059927

Structure Descriptors

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

InChIKey

WTDRDQBEARUVNC-LURJTMIESA-N

Smiles

N[C@@H](Cc1ccc(O)c(O)c1)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 100mg/kg (100mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
human TDLo oral 13gm/kg/1Y (13000mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)		 Journal of Neurology, Neurosurgery and Psychiatry. Vol. 34, Pg. 668, 1971.
human TDLo oral 156gm/kg/10Y (156000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"		 Journal of Neurology, Neurosurgery and Psychiatry. Vol. 34, Pg. 502, 1971.
mouse LD50 intraperitoneal 588mg/kg (588mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE		 Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974.
mouse LD50 intravenous 450mg/kg (450mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974.
mouse LD50 oral 2363mg/kg (2363mg/kg) BEHAVIORAL: EXCITEMENT Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974.
mouse LD50 subcutaneous 4449mg/kg (4449mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

PERIPHERAL NERVE AND SENSATION: LOCAL ANESTHETIC		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 3, Pg. 186, 1972.
mouse LDLo unreported 3500mg/kg (3500mg/kg) AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 153, Pg. 161, 1930.
rabbit LD50 oral 609mg/kg (609mg/kg)   Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974.
rat LD50 intraperitoneal 624mg/kg (624mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: EXCITEMENT

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE		 Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974.
rat LD50 intravenous > 100mg/kg (100mg/kg)   Drugs in Japan Vol. 6, Pg. 905, 1982.
rat LD50 oral 1780mg/kg (1780mg/kg) BEHAVIORAL: AGGRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: EXCITEMENT		 Toxicology and Applied Pharmacology. Vol. 28, Pg. 1, 1974.
rat LD50 subcutaneous 2gm/kg (2000mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 3, Pg. 186, 1972.
women TDLo oral 320mg/kg/4D-I (320mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

GASTROINTESTINAL: NAUSEA OR VOMITING		 American Heart Journal. Vol. 110, Pg. 488, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 285 dec deg C   EXP
pKa Dissociation Constant 2.32 (none) 25 EXP
log P (octanol-water) -2.39E+00 (none)   EXP
Water Solubility 5000 mg/L 20 EXP
Vapor Pressure 1.24E-10 mm Hg 25 EST
Henry's Law Constant 1.30E-18 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.66E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.