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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
- All
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- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
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
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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/s1InChIKey
WTDRDQBEARUVNC-LURJTMIESA-NSmiles
N[C@@H](Cc1ccc(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.