Droxidopa

• CAT Number: A000347
• CAS Number: 23651-95-8
• Molecular Formula: C9H11NO5
• Molecular Weight: 213.19
• Purity: ≥95%
• Synonyms: 23651-95-8; L-DOPS; Northera; (2S,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid; Threo-Dopaserine
• Target: Neuronal Signaling
• Storage: <label class=
• InChI: 1S/C9H11NO5/c10-7(9(14)15)8(13)4-1-2-5(11)6(12)3-4/h1-3,7-8,11-13H,10H2,(H,14,15)/t7-,8+/m0/s1
• InChIKey: QXWYKJLNLSIPIN-JGVFFNPUSA-N
• SMILES: C1=CC(=C(C=C1C(C(C(=O)O)N)O)O)O

Droxidopa is a synthetic amino acid precursor which acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline) and it is used to increase the concentrations of these neurotransmitters in the body and brain. Unlike norepinephrine and epinephrine themselves, droxidopa is capable of crossing the protective blood–brain barrier (BBB). It is metabolized by aromatic L-amino acid decarboxylase (AAAD), also known as DOPA decarboxylase (DDC). Droxidopa works by increasing the levels of norepinephrine and epinephrine in the peripheral nervous system (PNS), which induces tachycardia or increased heart rate and hypertension or increased blood pressure, thus enabling the body to maintain blood flow upon and while standing. (Source: http://en.wikipedia.org/wiki/Droxidopa).

Reference

1: White WB, Hewitt LA, Mehdirad AA. Impact of the Norepinephrine Prodrug
Droxidopa on the QTc Interval in Healthy Individuals. Clin Pharmacol Drug Dev.
2017 Oct 11. doi: 10.1002/cpdd.393. [Epub ahead of print] PubMed PMID: 29024579.

2: Patrick K, Martin T. Effectiveness of droxidopa compared to midodrine in
standing blood pressure and orthostatic tolerance in adults with neurogenic
orthostatic hypotension: a systematic review protocol. JBI Database System Rev
Implement Rep. 2017 Sep;15(9):2287-2294. doi: 10.11124/JBISRIR-2016-003306.
PubMed PMID: 28902695.

3: Gupta F, Karabin B, Mehdirad A. Erratum to: Titrating droxidopa to maximize
symptomatic benefit in a patient with Parkinson disease and neurogenic
orthostatic hypotension. Clin Auton Res. 2017 Sep 9. doi:
10.1007/s10286-017-0458-y. [Epub ahead of print] PubMed PMID: 28889359.

4: Sun G, Zhou Z, Luo Z, Wang H, Chen L, Xu Y, Li S, Jian W, Zeng J, Hu B, Han X,
Lin Y, Wang Z. Highly Enantioselective Synthesis of syn-β-Hydroxy α-Dibenzylamino
Esters via DKR Asymmetric Transfer Hydrogenation and Gram-Scale Preparation of
Droxidopa. Org Lett. 2017 Aug 18;19(16):4339-4342. doi:
10.1021/acs.orglett.7b01982. Epub 2017 Aug 3. PubMed PMID: 28770608.

5: Gupta F, Karabin B, Mehdirad A. Titrating droxidopa to maximize symptomatic
benefit in a patient with Parkinson disease and neurogenic orthostatic
hypotension. Clin Auton Res. 2017 Jul;27(Suppl 1):15-16. doi:
10.1007/s10286-017-0430-x. Epub 2017 Jul 11. Erratum in: Clin Auton Res. 2017 Sep
9;:. PubMed PMID: 28699047; PubMed Central PMCID: PMC5550519.

6: Vernino S, Claassen D. Polypharmacy: droxidopa to treat neurogenic orthostatic
hypotension in a patient with Parkinson disease and type 2 diabetes mellitus.
Clin Auton Res. 2017 Jul;27(Suppl 1):33-34. doi: 10.1007/s10286-017-0435-5. Epub
2017 Jul 3. PubMed PMID: 28674868; PubMed Central PMCID: PMC5524866.

7: Kremens D, Lew M, Claassen D, Goodman BP. Adding droxidopa to fludrocortisone
or midodrine in a patient with neurogenic orthostatic hypotension and Parkinson
disease. Clin Auton Res. 2017 Jul;27(Suppl 1):29-31. doi:
10.1007/s10286-017-0434-6. Epub 2017 Jul 3. PubMed PMID: 28674867; PubMed Central
PMCID: PMC5524861.

8: Guan YQ, Gao M, Deng X, Lv H, Zhang X. Rhodium-catalyzed asymmetric
hydrogenation of tetrasubstituted β-acetoxy-α-enamido esters and efficient
synthesis of droxidopa. Chem Commun (Camb). 2017 Jul 18;53(58):8136-8139. doi:
10.1039/c7cc03902f. PubMed PMID: 28653712.

9: Mehdirad A, Karabin B, Gupta F. Managing neurogenic orthostatic hypotension
with droxidopa in a patient with Parkinson disease, atrial fibrillation, and
hypertension. Clin Auton Res. 2017 Jul;27(Suppl 1):25-27. doi:
10.1007/s10286-017-0433-7. Epub 2017 Jun 20. PubMed PMID: 28634637; PubMed
Central PMCID: PMC5524863.

10: Claassen D, Lew M. Initiating droxidopa for neurogenic orthostatic
hypotension in a patient with Parkinson disease. Clin Auton Res. 2017
Jul;27(Suppl 1):13-14. doi: 10.1007/s10286-017-0429-3. Epub 2017 Jun 19. PubMed
PMID: 28631224; PubMed Central PMCID: PMC5524864.