loading...| Preferred Name |
L DOPA |
|
| Synonyms |
Eldopal (-)-3-(3, 4-dihydroxyphenyl)-L-alanine Insulamina Dopal Syndopa Deadopa Doparkine Dopaston Veldopa Pardopa Eldopar Weldopa Dopasol Levedopa Dopaidan Dopastral Laradopa beta-(3, 4-dihydroxyphenyl)alanine (2S)-2-amino-3-(3, 4-dihydroxyphenyl)propanoic acid Eurodopa Brocadopa Bendopa Prodopa beta-(3, 4-dihydroxyphenyl)-L-alanine Dopaflex Helfo-Dopa Larodopa 3, 4-DIHYDROXYPHENYLALANINE L-beta-(3, 4-Dihydroxyphenyl)alanine Dopalina Maipedopa 3, 4-dihydroxyphenylalanine DOPA Doparl Dopal-Fher Parda Doprin 3, 4-Dihydroxy-L-phenylalanine Levopa Cidandopa Eldopatec Ledopa L-Dihydroxyphenylalanine (-)-dopa Dopar 3,4-DIHYDROXYPHENYLALANINE beta-(3,4-dihydroxyphenyl)alanine levodopum L-beta-(3,4-Dihydroxyphenyl)alanine beta-(3,4-dihydroxyphenyl)-L-alanine Dihydroxy-L-phenylalanine 3-Hydroxy-L-tyrosine 3,4-Dihydroxy-L-phenylalanine (-)-3-(3,4-dihydroxyphenyl)-L-alanine levodopa L-dopa L-Dopa L-DOPA (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid |
|
| Definitions |
An amino acid precursor of dopamine with antiparkinsonian properties. L-DOPA is a prodrug that is converted to dopamine by DOPA decarboxylase and can cross the blood-brain barrier. When in the brain, L-DOPA is decarboxylated to dopamine and stimulates the dopaminergic receptors. (Adapted from NCI Thesaurus) Levodopa is 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. (PubChem) Pharmacology: Levodopa (L-dopa) is used to replace dopamine lost in Parkinson's disease because dopamine itself cannot cross the blood-brain barrier where its precursor can. However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as carbidopa, without which 90% is metabolised in the gut wall, and with a COMT inhibitor if possible; this prevents about a 5% loss. The form given therapeutically is therefore a prodrug which avoids decarboxylation in the stomach and periphery, can cross the blood-brain barrier, and once in the brain is converted to the neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase. Mechanism of action: Striatal dopamine levels in symptomatic Parkinson's disease are decreased by 60 to 80%, striatal dopaminergic neurotransmission may be enhanced by exogenous supplementation of dopamine through administration of dopamine's precursor, levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier and is decarboxylated to dopamine. This newly formed dopamine then is available to stimulate dopaminergic receptors, thus compensating for the depleted supply of endogenous dopamine. Drug type: Approved. Small Molecule. Drug category: Antidyskinetics. Antiparkinson Agents. Dopamine Agents An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease |
|
| ID |
http://purl.obolibrary.org/obo/CHEBI_15765 |
|
| alternative label |
(-)-dopa Dopar 3,4-DIHYDROXYPHENYLALANINE beta-(3,4-dihydroxyphenyl)alanine levodopum L-beta-(3,4-Dihydroxyphenyl)alanine beta-(3,4-dihydroxyphenyl)-L-alanine Dihydroxy-L-phenylalanine 3-Hydroxy-L-tyrosine 3,4-Dihydroxy-L-phenylalanine (-)-3-(3,4-dihydroxyphenyl)-L-alanine levodopa L-dopa L-Dopa L-DOPA (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid |
|
| charge |
0 |
|
| createdDate |
August 21, 2009 |
|
| database_cross_reference |
PMID:23389938 Reaxys:2215169 HMDB:HMDB0000181 Wikipedia:L-DOPA Beilstein:6060047 PDBeChem:DAH_LFOH PMID:23196068 PMID:23127496 COMe:MOL000169 Beilstein:2215169 CAS:59-92-7 KEGG:C00355 PMID:23389842 Wikipedia:Levodopa KEGG:D00059 KNApSAcK:C00001357 PMID:23390548 PMID:23206800 DrugBank:DB01235 PMID:23211937 LINCS:LSM-5481 Gmelin:365846 PMID:18690870 PMID:22491024 MetaCyc:L-DIHYDROXY-PHENYLALANINE PMID:22592937 PMID:23038403 Drug_Central:1567 PMID:23357114 PMID:8301021 PMID:29438107 |
|
| definition |
An amino acid precursor of dopamine with antiparkinsonian properties. L-DOPA is a prodrug that is converted to dopamine by DOPA decarboxylase and can cross the blood-brain barrier. When in the brain, L-DOPA is decarboxylated to dopamine and stimulates the dopaminergic receptors. (Adapted from NCI Thesaurus) Levodopa is 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. (PubChem) Pharmacology: Levodopa (L-dopa) is used to replace dopamine lost in Parkinson's disease because dopamine itself cannot cross the blood-brain barrier where its precursor can. However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as carbidopa, without which 90% is metabolised in the gut wall, and with a COMT inhibitor if possible; this prevents about a 5% loss. The form given therapeutically is therefore a prodrug which avoids decarboxylation in the stomach and periphery, can cross the blood-brain barrier, and once in the brain is converted to the neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase. Mechanism of action: Striatal dopamine levels in symptomatic Parkinson's disease are decreased by 60 to 80%, striatal dopaminergic neurotransmission may be enhanced by exogenous supplementation of dopamine through administration of dopamine's precursor, levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier and is decarboxylated to dopamine. This newly formed dopamine then is available to stimulate dopaminergic receptors, thus compensating for the depleted supply of endogenous dopamine. Drug type: Approved. Small Molecule. Drug category: Antidyskinetics. Antiparkinson Agents. Dopamine Agents An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease |
|
| formula |
C9H11NO4 |
|
| has characteristic |
http://purl.obolibrary.org/obo/CHEBI_76924 http://purl.obolibrary.org/obo/CHEBI_48560 http://purl.obolibrary.org/obo/CHEBI_59174 http://purl.obolibrary.org/obo/CHEBI_50910 http://purl.obolibrary.org/obo/CHEBI_75771 http://purl.obolibrary.org/obo/CHEBI_62215 http://purl.obolibrary.org/obo/CHEBI_35219 |
|
| has exact synonym |
L-dopa L-Dopa L-DOPA (2S)-2-amino-3-(3,4-dihydroxyphenyl)propanoic acid |
|
| has role |
http://purl.obolibrary.org/obo/CHEBI_76924 http://purl.obolibrary.org/obo/CHEBI_48560 http://purl.obolibrary.org/obo/CHEBI_59174 http://purl.obolibrary.org/obo/CHEBI_50910 http://purl.obolibrary.org/obo/CHEBI_75771 http://purl.obolibrary.org/obo/CHEBI_62215 http://purl.obolibrary.org/obo/CHEBI_35219 |
|
| has_alternative_id |
CHEBI:49933 CHEBI:11693 CHEBI:41871 CHEBI:1377 CHEBI:19825 CHEBI:13098 CHEBI:75987 |
|
| has_obo_namespace |
chebi_ontology |
|
| has_related_synonym |
(-)-dopa Dopar 3,4-DIHYDROXYPHENYLALANINE beta-(3,4-dihydroxyphenyl)alanine levodopum L-beta-(3,4-Dihydroxyphenyl)alanine beta-(3,4-dihydroxyphenyl)-L-alanine Dihydroxy-L-phenylalanine 3-Hydroxy-L-tyrosine 3,4-Dihydroxy-L-phenylalanine (-)-3-(3,4-dihydroxyphenyl)-L-alanine levodopa |
|
| id |
CHEBI:15765 |
|
| in_subset | ||
| 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 |
|
| is conjugate acid of | ||
| is enantiomer of | ||
| is tautomer of | ||
| label |
L-dopa L DOPA |
|
| mass |
197.18798 |
|
| monoisotopicmass |
197.06881 |
|
| notation |
CHEBI:15765 |
|
| note |
An amino acid precursor of dopamine with antiparkinsonian properties. L-DOPA is a prodrug that is converted to dopamine by DOPA decarboxylase and can cross the blood-brain barrier. When in the brain, L-DOPA is decarboxylated to dopamine and stimulates the dopaminergic receptors. (Adapted from NCI Thesaurus) Levodopa is 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. (PubChem) Pharmacology: Levodopa (L-dopa) is used to replace dopamine lost in Parkinson's disease because dopamine itself cannot cross the blood-brain barrier where its precursor can. However, L-DOPA is converted to dopamine in the periphery as well as in the CNS, so it is administered with a peripheral DDC (dopamine decarboxylase) inhibitor such as carbidopa, without which 90% is metabolised in the gut wall, and with a COMT inhibitor if possible; this prevents about a 5% loss. The form given therapeutically is therefore a prodrug which avoids decarboxylation in the stomach and periphery, can cross the blood-brain barrier, and once in the brain is converted to the neurotransmitter dopamine by the enzyme aromatic-L-amino-acid decarboxylase. Mechanism of action: Striatal dopamine levels in symptomatic Parkinson's disease are decreased by 60 to 80%, striatal dopaminergic neurotransmission may be enhanced by exogenous supplementation of dopamine through administration of dopamine's precursor, levodopa. A small percentage of each levodopa dose crosses the blood-brain barrier and is decarboxylated to dopamine. This newly formed dopamine then is available to stimulate dopaminergic receptors, thus compensating for the depleted supply of endogenous dopamine. Drug type: Approved. Small Molecule. Drug category: Antidyskinetics. Antiparkinson Agents. Dopamine Agents An optically active form of dopa having L-configuration. Used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease |
|
| preferred label |
L DOPA |
|
| prefLabel |
L DOPA |
|
| smiles |
N[C@@H](Cc1ccc(O)c(O)c1)C(O)=O |
|
| synonym |
Eldopal (-)-3-(3, 4-dihydroxyphenyl)-L-alanine Insulamina Dopal Syndopa Deadopa Doparkine Dopaston Veldopa Pardopa Eldopar Weldopa Dopasol Levedopa Dopaidan Dopastral Laradopa beta-(3, 4-dihydroxyphenyl)alanine (2S)-2-amino-3-(3, 4-dihydroxyphenyl)propanoic acid Eurodopa Brocadopa Bendopa Prodopa beta-(3, 4-dihydroxyphenyl)-L-alanine Dopaflex Helfo-Dopa Larodopa 3, 4-DIHYDROXYPHENYLALANINE L-beta-(3, 4-Dihydroxyphenyl)alanine Dopalina Maipedopa 3, 4-dihydroxyphenylalanine DOPA Doparl Dopal-Fher Parda Doprin 3, 4-Dihydroxy-L-phenylalanine Levopa Cidandopa Eldopatec Ledopa L-Dihydroxyphenylalanine |
|
| subClassOf |
http://purl.obolibrary.org/obo/CHEBI_49168 |