Compound: levodopa
SMILES: O=C(O)[C@@H](N)Cc1cc(O)c(O)cc1
InChIKey: WTDRDQBEARUVNC-LURJTMIESA-N
Synonyms: levodopa, L-dopa, 59-92-7, 3,4-dihydroxy-L-phenylalanine, Dopar, 3-Hydroxy-L-tyrosine, Larodopa, Bendopa, 3-(3,4-Dihydroxyphenyl)-L-alanine, Levopa, Brocadopa, Dopaidan, Dopalina, Dopasol, Eldopal, Insulamina, Pardopa, Cidandopa, Dopaflex, Maipedopa, Deadopa, Eldopar, Prodopa, Syndopa, Veldopa, Helfo-Dopa, (-)-Dopa, Doparkine, Dopastral, Dopaston, Doparl, Doprin, (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid, Dihydroxy-L-phenylalanine, Eldopatec, Eurodopa, L-3,4-Dihydroxyphenylalanine, Ledopa, L-o-Hydroxytyrosine, L-Tyrosine, 3-hydroxy-, Biodopa, Levodopum, (-)-3-(3,4-Dihydroxyphenyl)-L-alanine, Dopaston SE, 3,4-Dihydroxyphenyl-L-alanine, Helfo DOPA, Laradopa, Sobiodopa, Cerepap, Parda, beta-(3,4-Dihydroxyphenyl)-L-alanine, L-(-)-Dopa, L-Dihydroxyphenylalanine, L-beta-(3,4-Dihydroxyphenyl)alanine, Inbrija, Ro 4-6316, L Dopa, L-O-Dihydroxyphenylalanine, CVT-301, beta-(3,4-Dihydroxyphenyl)alanine, alanine, 3-(3,4-dihydroxyphenyl)-, L-, L(-)-Dopa, beta-(3,4-Dihydroxyphenyl)-alpha-L-alanine, L-beta-(3,4-Dihydroxyphenyl)-alpha-alanine, Alanine, 3-(3,4-dihydroxyphenyl)-, (-)-, NSC-118381, DTXSID9023209, CHEBI:15765, beta-(3,4-Dihydroxyphenyl)-alpha-alanine, NSC118381, DHIVY COMPONENT LEVODOPA, DTXCID303209, DUOPA COMPONENT LEVODOPA, RYTARY COMPONENT LEVODOPA, 46627O600J, CREXONT COMPONENT LEVODOPA, STALEVO COMPONENT LEVODOPA, CORBILTA COMPONENT LEVODOPA, V-1512, (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoate, LEVODOPA/CARBIDOPA/ENTACAPONE ORION COMPONENT LEVODOPA, 3 Hydroxy L tyrosine, L 3,4 Dihydroxyphenylalanine, L-Dopa Phenolic, RefChem:6454, L DOPA 4X, L-Dopa 1514, N04BA01, (--)-3-(3,4-Dihydroxyphenyl)-L-alanine, (--)-2Amino-3-(3,4-dihydroxyphenyl)propanoic Acid, 200-445-2, (2S)-2-azaniumyl-3-(3,4-dihydroxyphenyl)propanoate, Dopa, 3,4-Dihydroxyphenylalanine, Dopal-fher, Levedopa, Sinemet, L-(o-Dihydroxyphenyl)alanine, Parcopa, Weldopa, L-3-(3,4-Dihydroxyphenyl)alanine, MFCD00002598, (S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid, L-3-Hydroxytyrosine, component of Sinemet, Dopar (TN), (-)-(3,4-Dihydroxyphenyl)alanine, L-.beta.-(3,4-Dihydroxyphenyl)alanine, CHEMBL1009, .beta.-(3,4-Dihydroxyphenyl)-L-alanine, L-(3,4-Dihydroxyphenyl)alanine, .beta.-(3,4-Dihydroxyphenyl)alanine, CAS-59-92-7, NCGC00016270-04, L-(3,4-Dihydroxyphenyl)-.alpha.-alanine, Phenylalanine, 3,4-dihydroxy-, Atamet, Levodopum [INN-Latin], BDBM50130192, 65170-01-6, L-3, CCRIS 3766, HSDB 3348, WLN: QVYZ1R CQ DQ, 3,4-Dihydroxyphenylalanine (VAN), SR-01000075384, EINECS 200-445-2, NSC 118381, L-3,4-Dihydrophenylalanine, Dopastone, Dopicar, Prolopa, Brocadopa;, Larodopa;, Bendopa;, Levodopa RS, Levopa;, Levodopa CRS, Dopar;, UNII-46627O600J, Prestwick_185, Levodopa (Sinemet), L-DOPA; Levodopa, Madopa (Salt/Mix), Levodopa [USAN:USP:INN:BAN:JAN], L-DOPA (Standard), Spectrum_000454, 4-dihydroxyphenylalanine, LEVODOPA [HSDB], LEVODOPA [USAN], LEVODOPA [INN], LEVODOPA [JAN], LEVODOPA [MI], LEVODOPA [VANDF], Prestwick0_000017, Prestwick1_000017, Prestwick2_000017, Prestwick3_000017, Spectrum2_000496, Spectrum4_000539, Spectrum5_001899, Lopac-D-9628, Levodopa (JP15/USP), LEVODOPA [MART.], bmse000322, Epitope ID:150927, LEVODOPA [USP-RS], LEVODOPA [WHO-DD], LEVODOPA [WHO-IP], DOPA, L-, 3, 4-Dihydroxyphenylalanine, Alanine,4-dihydroxyphenyl)-, LEVODOPA [EMA EPAR], Lopac0_000454, SCHEMBL22655, BSPBio_000053, BSPBio_002354, KBioGR_001177, KBioSS_000934, L-4-5-Dihydroxyphenylalanine, MLS000028514, BIDD:GT0158, DivK1c_000452, SPECTRUM2300205, Levodopa (JP18/USP/INN), SPBio_000391, SPBio_001974, LEVODOPA [EP IMPURITY], LEVODOPA [ORANGE BOOK], BPBio1_000059, GTPL3639, orb1310238, orb3141124, SCHEMBL3857245, LEVODOPA [EP MONOGRAPH], b-(3,4-Dihydroxyphenyl)alanine, LEVODOPA [USP MONOGRAPH], SCHEMBL29373537, WLN: QVYZ1R CQ DQ -L, 3, 4-Dihydroxy-L-phenylalanine, BDBM60928, HMS501G14, HY-N0304R, KBio1_000452, KBio2_000934, KBio2_003502, KBio2_006070, PARCOPA COMPONENT LEVODOPA, LEVODOPUM [WHO-IP LATIN], MSK1487, Alanine,4-dihydroxyphenyl)-, L-, CARBILEV COMPONENT LEVODOPA, CHEBI:233994, DOPASNAP COMPONENT LEVODOPA, IPX203 COMPONENT LEVODOPA, L-(3, 4-Dihydroxyphenyl)alanine, NINDS_000452, GLXC-07334, HMS1568C15, HMS1922J14, HMS2090O08, HMS2093N04, HMS2095C15, HMS2230B04, HMS3261K10, HMS3712C15, Pharmakon1600-02300205, HY-N0304, IPX-203 COMPONENT LEVODOPA, Levodopa;3,4-Dihydroxyphenylalanine, b-(3,4-Dihydroxyphenyl)-L-alanine, Inbrija (levodopa inhalation powder), LEVODOPA COMPONENT OF PARCOPA, LEVODOPA COMPONENT OF SINEMET, Tox21_110338, Tox21_500454, CCG-39571, EBC-12565, HB1925, L-3-(3,4-dihydroxy-phenyl)alanine, L-3-(3,4-dihydroxyphenyl)-Alanine, NSC759573, PDSP1_001541, PDSP2_001525, s1726, SBB017533, Alanine, 3-(3,4-dihydroxyphenyl)-, Alanine,4-dihydroxyphenyl)-, (-)-, LEVODOPA COMPONENT OF CARBILEV, AKOS010396267, b-(3,4-Dihydroxyphenyl)-a-L-alanine, L-b-(3,4-Dihydroxyphenyl)-a-alanine, L-DOPA (3,4-Dihydroxyphenylalanine), .beta.-(3, 4-Dihydroxyphenyl)alanine, AC-8432, CS-1945, DB01235, FD15635, LP00454, NSC-759573, SDCCGMLS-0066924.P001, SDCCGSBI-0050439.P004, IDI1_000452, NCGC00015384-01, NCGC00016270-01, NCGC00016270-06, NCGC00016270-07, NCGC00016270-09, NCGC00016270-10, NCGC00016270-22, NCGC00093869-04, NCGC00261139-01, AS-13287, BP-12850, SMR000058312, ST086623, SY010977, SBI-0050439.P003, L-(3, 4-Dihydroxyphenyl)-.alpha.-alanine, D0600, D9628, EU-0100454, NS00068395, 2-Amino-3-(3,4-dihydroxyphenyl)propanoicacid, EN300-52637, Alanine, 3-(3, 4-dihydroxyphenyl)-, (-)-, C00355, D 9628, D00059, D70595, 3,4-Dihydroxy-L-phenylalanine, >=98% (TLC), AB00052418-06, AB00052418-07, AB00052418_08, AB00052418_09, F358380, Q300989, (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoicacid, SR-01000075384-1, SR-01000075384-4, SR-01000075384-6, SR-01000075384-7, (S)-2-Amino-3-(3,4-dihydroxyphenyl) propanoic acid, BRD-K34730807-001-15-0, BRD-K34730807-001-16-8, BRD-K34730807-001-17-6, (S)-2-Amino-3-(3,4-dihydroxy-phenyl)-propionic acid, F0347-4695, Levodopa Working Standard (Secondary Reference Standard), Levodopa, British Pharmacopoeia (BP) Reference Standard, Levodopa, European Pharmacopoeia (EP) Reference Standard, Z756440064, (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acidL-dopa, 1E83F927-C221-46AA-B90A-81B33C5F3868, 3,4-Dihydroxy-L-phenylalanine, Vetec(TM) reagent grade, 98%, Levodopa, United States Pharmacopeia (USP) Reference Standard, 3,4-Dihydroxy-L-phenylalanine, certified reference material, TraceCERT(R), Levodopa, Pharmaceutical Secondary Standard; Certified Reference Material, 122769-74-8
Theoretical properties:
molecular_formula: C9H11NO4
molecular_weight: 197.19 g/mol
exact_mass: 197.06880783 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 3
heavy_atom_count: 14
topological_polar_surface_area: 104 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless to white crystals or crystalline powder; needles from water
color: Colorless to white crystals or crystalline powder; needles from water
odor: Odorless
solubility: 5mM
Descriptions:
{"pubchem": "Levodopa can cause developmental toxicity according to state or federal government labeling requirements.", "chebi": "An optically active form of dopa having <small>L</small>-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease", "chembl": "LEVODOPA is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Levodopa, also known as L-DOPA, is a dopaminergic medication which is used in the treatment of Parkinson's disease (PD) 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).\n\nSide 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 major reason for enhanced risks for levodopa induced dyskinesia (LID) and OFF phases during late PD is the progressive dying of nigrostriatal dopaminergic neurons. This results in the conversion of levodopa into dopamine in serotonergic neurons (which cannot re-uptake dopamine and have no proper regulatory capacity for dopamine synthesis) becoming the major dopamine source in the dorsal striatum, leading to the striatal dopamine concentration following the pulsatile oral administration of levodopa with large fluctuations (see the schematic graph figure). On the other hand, in a disease like Segawa syndrome, in which dopamine synthesis is low but without progressive degeneration of dopaminergic neurons,  lifelong administration of low doses of levodopa is believed to be without serious side effects. \nLevodopa was first synthesized and isolated in the early 1910s. The antiparkinsonian effects of levodopa were discovered in the 1950s and 1960s. Following this, it was introduced for the treatment of Parkinson's disease in 1970."}