Droxidopa

HCID 92974CAS 23651-95-8

기본 정보

표준 SMILES: N[C@H](C(=O)O)[C@H](O)c1ccc(O)c(O)c1
InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N
분자식: C9H11NO5
평균 분자량: 213.19 g/mol
단동위원소 질량: 213.06372245

개요

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.

이름 및 식별자

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

이름 및 동의어

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

이름 더 보기

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

데이터베이스 식별자

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

물성

구조 계산 물성

XLogP: -3.2
극성 표면적: 124 Å²
수소 결합 공여자 수: 5
수소 결합 수용자 수: 6
회전 가능 결합 수: 3
무거운 원자 수: 15
형식 전하: 0
복잡도: 235

실험 및 물리화학적 성질

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 2건

FDA approved drugs -> Active ingredient

안전 및 규제

GHS 분류

GHS Classification · 6건

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]

유해성 정보

Hazard Classes and Categories · 2건

Skin Irrit. 2 (100%)

독성 정보

Hepatotoxicity · 1건

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 · 6건

Drug Induced Liver Injury Rank (DILIrank 2.0)

Droxidopa

vNo-DILI-concern

No match

DOI:10.1016/j.drudis.2016.02.015

화학 및 산업

약리 정보

ATC Code · 2건

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1건

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 · 1건

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 · 6건

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