Compound: droxidopa
SMILES: O=C(O)[C@@H](N)[C@H](O)c1cc(O)c(O)cc1
InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N
Synonyms: droxidopa, 23651-95-8, L-DOPS, DOPS, (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid, Northera, threo-Dopaserine, L-threo-DOPS, L-Threodops, L-dihydroxyphenylserine, droxidopum, SM 5688, L-threo-dihydroxyphenylserine, L-Tyrosine, beta,3-dihydroxy-, threo-, DTXSID6046422, CHEBI:31524, J7A92W69L7, threo DOPS, threo-DOPS, (-)-(2S,3R)-2-AMINO-3-(3,4-DIHYDROXYPHENYL)-3-HYDROXYPROPANOIC ACID, 3,4 threo DOPS, 3,4-threo-DOPS, 3,4 Dihydroxyphenylserine, erythro 3,4 Dihydroxyphenylserine, DL threo 3,4 Dihydroxyphenylserine, RefChem:56670, C01CA27, DTXCID801475428, 688-528-3, DL-threo-Droxidopa, 3916-18-5, DL-threo-3,4-Dihydroxyphenylserine, DL-threo-DOPS, DL-threo-Dihydroxyphenylserine, Threo-dihydroxyphenylserine, L-threo-Droxidopa, (betaR)-beta,3-dihydroxy-L-tyrosine, Droxidopa (L-DOPS), L-Tyrosine, beta,3-dihydroxy-, (betaR)-, L-threo 3,4-Dihydroxyphenylserine, Serine, 3-(3,4-dihydroxyphenyl)-, DL-threo-, 24A0V01WKS, 1260173-94-1, L-threo-3,4-dihydroxyphenylserine, Droxydopa, Norethra, Droxidopa [Latin], threo-beta,3-Dihydroxy-DL-tyrosine, EINECS 223-480-5, beta,3-Dihydroxy-DL-tyrosine threo-, 3,4-Dihydroxyphenylserine, L-DOPS;DOPS;SM5688, BRN 2852792, UNII-24A0V01WKS, DL-threo-3-(3,4-Dihydroxyphenyl)serine, Droxidopa (L-DOPS,SM-5688), Droxidopa [USAN:INN:JAN], UNII-J7A92W69L7, Northera (TN), L-threo DOPS, Droxidopa (Standard), Dops (TN), L-threo-3-(3,4-Dihydroxyphenyl)serine, DL-Tyrosine, beta,3-dihydroxy-, threo-, DROXIDOPA [INN], DROXIDOPA [JAN], DROXIDOPA [MI], threo-2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropionic acid, DROXIDOPA [USAN], DL-Tyrosine, .beta.,3-dihydroxy-, threo-, DROXIDOPA [VANDF], DROXIDOPA [MART.], DROXIDOPA [WHO-DD], L-threo-(3,4-dihydroxyphenyl)serine hydrochloride, 1-14-00-00685 (Beilstein Handbook Reference), SCHEMBL134299, GTPL7391, orb1305333, Droxidopa (JP18/USAN/INN), DROXIDOPA [ORANGE BOOK], CHEMBL2103827, SCHEMBL29388035, (2RS,3RS)-2-Amino-3-(3,4-dihydroxy-phenyl)-3-hydroxy-propionic acid;DL-DOPS;DL-Droxidopa, DTXSID201017236, (2S,3R)-2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropionic Acid, BDBM50103611, EBC-26216, HY-13458R, MFCD00799030, s3041, L-DOPS, >=98% (HPLC), (-)-(2S,3R)-2-Amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propionic acid, (2S,3R)-3,4-dihydroxy-phenylserine, AKOS015889899, CCG-222060, DB06262, FT28252, SM-5688, NCGC00344531-04, AS-61328, DA-52703, DA-75128, HY-13458, L-Tyrosine, |A,3-dihydroxy-, (|AR)-, H-DL--(3,4-Dihydroxyphenyl)-DL-Ser-OH, D4235, L-Tyrosine, beta,3-dihydroxy-, (beta-R)-, NS00045584, THREO-3,4-DIHYDROXYPHENYLSERINE, L-, 3,4-DIHYDROXYPHENYLSERINE-THREO, DL-, DL-threo- beta -(3,4-Dihydroxyphenyl)serine, (-)-threo-3-(3,4-Dihydroxyphenyl)-L-serine, D01277, D90266, SBI-0654105.0001, Serine, 3-(3,4-dihydroxyphenyl)-, L-threo-, AB01566868_01, EN300-9430063, F787591, Q907853, SR-01000883755, SR-01000883755-1, BRD-K20372197-001-02-3, BRD-K20372197-001-03-1, L-TYROSINE, .BETA.,3-DIHYDROXY-, (.BETA.R)-, D-TYROSINE, .BETA.,3-DIHYDROXY-, (.BETA.S)-REL-, 23651-95-8,1260173-94-1(HCl), (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxy-propanoic acid, (-)-(2S,3R)-2-amino-3-hydroxy-3-(3,4-dihydroxyphenyl)propanoic acid
Theoretical properties:
molecular_formula: C9H11NO5
molecular_weight: 213.19 g/mol
exact_mass: 213.06372245 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 3
heavy_atom_count: 15
topological_polar_surface_area: 124 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Droxidopa is a serine derivative that is L-serine substituted at the beta-position by a 3,4-dihydroxyphenyl group. A prodrug for noradrenalone, it is used for treatment of neurogenic orthostatic hypotension. It has a role as an antihypertensive agent, a prodrug and a vasoconstrictor agent. It is a L-tyrosine derivative and a member of catechols.
chebi: A serine derivative that is <small>L</small>-serine substituted at the β-position by a 3,4-dihydroxyphenyl group. A prodrug for noradrenalone, it is used for treatment of neurogenic orthostatic hypotension
chembl: DROXIDOPA is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Droxidopa, also known as L-threo-dihydroxyphenylserine (L-DOPS) and sold under the brand names Northera and Dops among others, is sympathomimetic medication which is used in the treatment of hypotension (low blood pressure) and for other indications. It is taken by mouth.
Side effects of droxidopa include headache, dizziness, nausea, and hypertension, among others. Droxidopa is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitter norepinephrine (noradrenaline). Hence, it acts as a non-selective agonist of the α- and β-adrenergic receptors. Unlike norepinephrine, but similarly to levodopa (L-DOPA), droxidopa is capable of crossing the protective blood–brain barrier (BBB).
Droxidopa was first described by 1971. It was approved for use in Japan in 1989 and was introduced in the United States in 2014.