Droxidopa

HCID 92974CAS 23651-95-8

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Grundinformationen

Standard-SMILES: N[C@H](C(=O)O)[C@H](O)c1ccc(O)c(O)c1
InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N
Summenformel: C9H11NO5
Durchschnittliche Molmasse: 213,19 g/mol
Monoisotopische Masse: 213,06372245

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: Droxidopa
IUPAC: (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Namen und Synonyme

droxidopa23651-95-8L-DOPSDOPS(2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acidNortherathreo-DopaserineL-threo-DOPSL-ThreodopsL-dihydroxyphenylserinedroxidopumSM 5688

Weitere Namen anzeigen

L-threo-dihydroxyphenylserineL-Tyrosine, beta,3-dihydroxy-, threo-CHEBI:31524J7A92W69L7DTXSID6046422threo DOPSthreo-DOPS(-)-(2S,3R)-2-AMINO-3-(3,4-DIHYDROXYPHENYL)-3-HYDROXYPROPANOIC ACID

Datenbank-Bezeichner

CAS: 23651-95-8、3916-18-5
PubChem CID: 92974
DTXSID: DTXSID201017236
ChEMBL: CHEMBL2103827
ChEBI: CHEBI:31524
UNII: 24A0V01WKS、J7A92W69L7
EC Number: 223-480-5、688-528-3
Nikkaji: J22.085J

Eigenschaften

Berechnete Struktureigenschaften

XLogP: -3,2
Polarare Oberfläche (TPSA): 124 Å²
H-Brücken-Donoren: 5
H-Brücken-Akzeptoren: 6
Frei drehbare Bindungen: 3
Schwere Atome: 15
Formalladung: 0
Komplexität: 235

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

Gefahrenhinweise

Hazard Classes and Categories · 2 Einträge

Skin Irrit. 2 (100%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Liver test abnormalities have not been reported in patients taking droxidopa, but the agent has had limited clinical use. There were no episodes of clinically apparent liver injury reported in the preregistration trials of droxidopa, and since its approval there have been no published reports of droxidopa hepatotoxicity. Thus, liver injury from droxidopa is likely to be rare, if it occurs at all.

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Droxidopa

vNo-DILI-concern

No match

DOI:10.1016/j.drudis.2016.02.015

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 Eintrag

Droxidopa is an orally active synthetic precursor of norepinephrine that increases the deficient supply of norepinephrine in patients with NOH, thereby improving orthostatic blood pressure and alleviating associated symptoms of lightheadedness, dizziness, blurred vision, and syncope through the induction of tachycardia (increased heart rate) and hypertension.

Mechanism of Action · 1 Eintrag

Droxidopa crosses the blood-brain barrier where it is converted to norepinephrine via decarboxylation by L-aromatic-amino-acid decarboxylase. Norephinephrine acts at alpha-adrenergic receptors as a vasoconstrictor and at beta-adrenergic receptors as a heart stimulator and artery dilator.

Biological Half-Life2-3 hours.

Metabolism/MetabolitesDroxidopa is metabolized by aromatic L-amino acid decarboxylase.

FDA Pharmacological Classification · 6 Einträge

J7A92W69L7

DROXIDOPA

Chemical Structure [CS] - Catecholamines

Physiologic Effects [PE] - Increased Blood Pressure

The physiologic effect of droxidopa is by means of Increased Blood Pressure.

DROXIDOPA