Droxidopa

HCID 92974CAS 23651-95-8

基本情報

標準SMILES: N[C@H](C(=O)O)[C@H](O)c1ccc(O)c(O)c1
InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N
分子式: C9H11NO5
平均分子量: 213.19 g/mol
単同位体質量: 213.06372245

概要

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.

名称と識別子

優先名称: Droxidopa
IUPAC: (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

名称と別名

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

名称をさらに表示

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

データベース識別子

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

物性

構造計算による物性

XLogP: -3.2
極性表面積: 124 Å²
水素結合供与体数: 5
水素結合受容体数: 6
回転可能結合数: 3
重原子数: 15
形式電荷: 0
複雑度: 235

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 2 件

FDA approved drugs -> Active ingredient

安全と法規制

GHS分類

GHS Classification · 6 件

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]

危険有害性情報

Hazard Classes and Categories · 2 件

Skin Irrit. 2 (100%)

毒性情報

Hepatotoxicity · 1 件

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 件

Drug Induced Liver Injury Rank (DILIrank 2.0)

Droxidopa

vNo-DILI-concern

No match

DOI:10.1016/j.drudis.2016.02.015

化学と産業

薬理情報

ATC Code · 2 件

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 件

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 件

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 件

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