Droxidopa

HCID 92974

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Basic information

CAS: 23651-95-8
Standard SMILES: N[C@H](C(=O)O)[C@H](O)c1ccc(O)c(O)c1
InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N
Molecular formula: C9H11NO5
Average molar mass: 213.19 g/mol
Monoisotopic mass: 213.06372245

Overview

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.

Names & identifiers

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

Names & synonyms

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

Show more names

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

Database identifiers

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

Properties

Computed structural propertiesFilling in

XLogP: -3.2
Topological polar surface area: 124 Å²
Hydrogen bond donors: 5
Hydrogen bond acceptors: 6
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 235

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Human Drugs · 2 items

FDA approved drugs -> Active ingredient

Safety & regulation

GHS classification

GHS Classification · 6 items

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]

Hazard information

Hazard Classes and Categories · 2 items

Skin Irrit. 2 (100%)

Toxicology

Hepatotoxicity · 1 item

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 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Droxidopa

vNo-DILI-concern

No match

DOI:10.1016/j.drudis.2016.02.015

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system

QC - Cardiovascular system

Pharmacodynamics · 1 item

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 item

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 items

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