Product Name

Droxidopa

CAS Number

23651-95-8

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Product Name:
Droxidopa
CAS Number:
23651-95-8
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.
Mode of Action:

Droxidopa crosses the blood-brain barrier where it is converted to norepinephrine via decarboxylation by L-aromatic-amino-acid decarboxylase. Increased levels of norepinephrine in the central nervous system (CNS) may be beneficial to patients in a wide range of indications. 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.

IUPAC:
(2R, 3S)-2-amino-3-(3, 4-dihydroxyphenyl)-3-hydroxypropanoic acid
PubChem:
3171
DrugBank:
DB06262
Formula:
C18H24O3
Molecular Mass:
213.1873
Synonyms:
Droxydopa L-dihydroxyphenylserine L-DOPS L-threo-3,4-dihydroxyphenylserine
SMILES:
N[C@H]([C@@H](O)C1=CC(O)=C(O)C=C1)C(O)=O
InChi:
QXWYKJLNLSIPIN-SFYZADRCSA-N
General Reference:
General Reference:

  1. Kaufmann H: L-dihydroxyphenylserine (Droxidopa): a new therapy for neurogenic orthostatic hypotension: the US experience. Clin Auton Res. 2008 Mar;18 Suppl 1:19-24. Epub 2008 Mar 27. Pubmed
  2. Balk SH, Yoshioka H, Yukawa H, Harayama S: Synthesis of L-threo-3, 4-dihydroxyphenylserine (L-threo-DOPS) with thermostabilized low-specific L-threonine aldolase from Streptomyces coelicolor A3. J Microbiol Biotechnol. 2007 May;17(5):721-7. Pubmed
  3. Mathias CJ: L-dihydroxyphenylserine (Droxidopa) in the treatment of orthostatic hypotension: the European experience. Clin Auton Res. 2008 Mar;18 Suppl 1:25-9. Epub 2008 Mar 27. Pubmed
  4. Goldstein DS: L-Dihydroxyphenylserine (L-DOPS): a norepinephrine prodrug. Cardiovasc Drug Rev. 2006 Fall-Winter;24(3-4):189-203. Pubmed
  5. Goldstein DS, Holmes C, Kaufmann H, Freeman R: Clinical pharmacokinetics of the norepinephrine precursor L-threo-DOPS in primary chronic autonomic failure. Clin Auton Res. 2004 Dec;14(6):363-8. Pubmed
  6. Goldstein DS: L-Dihydroxyphenylserine (L-DOPS): a norepinephrine prodrug. Cardiovasc Drug Rev. 2006 Fall-Winter;24(3-4):189-203. Pubmed

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