Home
    Disclaimer
    Droxidopa molecular structure

    Droxidopa Stats & Data

    L-threo-3,4-dihydroxyphenylserine
    NPS DataHub
    MW213.19
    FormulaC9H11NO5
    CAS23651-95-8
    IUPAC(2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
    SMILESO=C([O-])C(N)C(O)c1ccc(O)c(O)c1.[H+]
    InChIKeyQXWYKJLNLSIPIN-JGVFFNPUSA-N
    Chemical Class Opioid
    Psychoactive Class Depressant

    Pharmacology

    DrugBank
    Half-life 2-3 hours. State Solid Absorption Oral bioavailability is 90%.

    Description

    Droxidopa is a precursor of noradrenaline that is used in the treatment of Parkinsonism. It is approved for use in Japan and is currently in trials in the U.S. The racaemic form (dl-threo-3,4-dihydroxyphenylserine) has also been used, and has been investigated in the treatment of orthostatic hypotension. There is a deficit of noradrenaline as well as of dopamine in Parkinson's disease and it has been proposed that this underlies the sudden transient freezing seen usually in advanced disease. Though L-DOPS has been used in Japan and Southeast Asia already for some time, it is also currently in clinical trials at the phase III point in the United States (U.S.), Canada, Australia, and throughout Europe. Provided L-DOPS successfully completes clinical trials, it could be approved for the treatment of neurogenic orthostatic hypotension (NOH) as early as 2011. Additionally, phase II clinical trials for intradialytic hypotension are also underway. Chelsea Therapeutics obtained orphan drug status (ODS) for L-DOPS in the U.S. for NOH, and that of which associated with Parkinson's disease , pure autonomic failure, and multiple system atrophy, and is the pharmaceutical company developing it in that country.

    Mechanism of Action

    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.

    Pharmacodynamics

    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.

    Metabolism

    Droxidopa is metabolized by aromatic L-amino acid decarboxylase.

    Toxicity

    Droxidopa has minimal toxic effects and an acute, oral LD50 of more than 5 g/kg in mice, rats, dogs, and monkeys. Side effects occur in in 0.78% of patients and include nausea, headache, increased blood pressure, hallucination, and anorexia.

    Indication

    For treatment of neurogenic orthostatic hypotension (NOH) associated with various disorders including Multiple System Atrophy, Familial Amyloid Polyneuropathy, hemodialysis induced hypotension and Parkinson's Disease. Also investigated for use/treatment in neurologic disorders, nephropathy, blood (blood forming organ disorders, unspecified), and dizzy/fainting spells.

    Elimination

    Droxidopa is mainly excreted in the urine, with the main metabolite being 3-O-methyldihydroxyphenylserine.

    Effect Profile

    Curated
    Opioid 5.1

    Strong euphoria with moderate itching/nausea, mild sedation

    Euphoria / Warmth×3
    9
    Analgesia×2
    0
    Sedation / Relaxation×1
    5
    Itching / Nausea×1
    6

    Tolerance & Pharmacokinetics

    drugs.wiki

    Tolerance Decay

    Full tolerance 1d Half tolerance 21d Baseline ~35d
    ← Back to Droxidopa