Droxidopa | SM-5688 | Northera | CAS#23651-95-8

Droxidopa
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 314206

CAS#: 23651-95-8

Description: 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 bloodÂ–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).

Chemical Structure

Droxidopa

CAS# 23651-95-8

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 314206
Name: Droxidopa
CAS#: 23651-95-8
Chemical Formula: C9H11NO5
Exact Mass: 213.06
Molecular Weight: 213.190
Elemental Analysis: C, 50.70; H, 5.20; N, 6.57; O, 37.52

Price and Availability

Size	Price	Availability
25mg	USD 250	2 weeks
50mg	USD 450	2 weeks
100mg	USD 650	2 weeks
200mg	USD 950	2 weeks
500mg	USD 1750	2 weeks
1g	USD 2650	2 weeks
2g	USD 4950	2 weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: SM5688; SM 5688; SM-5688; Droxidopa; trade name: Northera; LDOPS; L-threodihydroxyphenylserine

IUPAC/Chemical Name: (2R,3S)-2-Amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

InChi Key: QXWYKJLNLSIPIN-SFYZADRCSA-N

InChi Code: 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+/m1/s1

SMILES Code: O=C(O)[C@H](N)[C@H](C1=CC=C(O)C(O)=C1)O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO.

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Droxidopa (L-DOPS) is a psychoactive drug and acts as a prodrug to the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline).
In vitro activity:	TBD
In vivo activity:	This study aimed to evaluate the effects of droxidopa (an oral synthetic precursor of norepinephrine) on the hemodynamic and renal alterations of portal hypertensive rats. The acute administration of droxidopa in PVL and BDL rats caused a significant and maintained increase in arterial pressure and mesenteric arterial resistance, with a significant decrease of mesenteric arterial and portal blood flow, without changing portal pressure and renal blood flow. Chronic droxidopa therapy in BDL rats produced the same beneficial hemodynamic effects observed in the acute study, did not alter liver function parameters, and caused a 50% increase in 24hour diuresis volume (7.4 ± 0.9 mL/100g in BDL vehicle versus 11.8 ± 2.5 mL/100g in BDL droxidopa; P = 0.01). Droxidopa-treated rats also showed a decreased ratio of p-eNOS/eNOS and p-AKT/AKT and increased activity of RhoK in SMA. The same chronic treatment in CCl(4) rats caused similar hemodynamic effects and produced significant increases in diuresis volume and 24-hour natriuresis (0.08 ± 0.02 mmol/100g in CCl(4) vehicle versus 0.23 ± 0.03 mmol/100g in CCl(4) droxidopa; P = 0.014). Reference: Hepatology. 2012 Nov;56(5):1849-60. https://pubmed.ncbi.nlm.nih.gov/22610782/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	1.8	8.44

Preparing Stock Solutions

The following data is based on the product molecular weight 213.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. Dela Peña I, Shen G, Shi WX. Droxidopa alters dopamine neuron and prefrontal cortex activity and improves attentiondeficit/hyperactivity disorder-like behaviors in rats. Eur J Pharmacol. 2021 Feb 5;892:173826. doi: 10.1016/j.ejphar.2020.173826. Epub 2020 Dec 19. PMID: 33347825. 2. Coll M, Rodriguez S, Raurell I, Ezkurdia N, Brull A, Augustin S, Guardia J, Esteban R, Martell M, Genescà J. Droxidopa, an oral norepinephrine precursor, improves hemodynamic and renal alterations of portal hypertensive rats. Hepatology. 2012 Nov;56(5):184960. doi: 10.1002/hep.25845. Epub 2012 Oct 14. PMID: 22610782.
In vitro protocol:	TBD
In vivo protocol:	1. Dela Peña I, Shen G, Shi WX. Droxidopa alters dopamine neuron and prefrontal cortex activity and improves attentiondeficit/hyperactivity disorder-like behaviors in rats. Eur J Pharmacol. 2021 Feb 5;892:173826. doi: 10.1016/j.ejphar.2020.173826. Epub 2020 Dec 19. PMID: 33347825. 2. Coll M, Rodriguez S, Raurell I, Ezkurdia N, Brull A, Augustin S, Guardia J, Esteban R, Martell M, Genescà J. Droxidopa, an oral norepinephrine precursor, improves hemodynamic and renal alterations of portal hypertensive rats. Hepatology. 2012 Nov;56(5):184960. doi: 10.1002/hep.25845. Epub 2012 Oct 14. PMID: 22610782.

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1: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Droxidopa. 2017 Apr 17. PMID: 31643765.

2: Strassheim V, Newton JL, Tan MP, Frith J. Droxidopa for orthostatic hypotension: a systematic review and meta-analysis. J Hypertens. 2016 Oct;34(10):1933-41. doi: 10.1097/HJH.0000000000001043. PMID: 27442791.

3: Hoxhaj P, Shah S, Muyolema Arce VE, Khan W, Sadeghzadegan A, Singh S, Collado GF, Goyal A, Khawaja I, Botlaguduru D, Razzaq W, Abdin ZU, Gupta I. Ampreloxetine Versus Droxidopa in Neurogenic Orthostatic Hypotension: A Comparative Review. Cureus. 2023 May 11;15(5):e38907. doi: 10.7759/cureus.38907. PMID: 37303338; PMCID: PMC10257554.

4: Keating GM. Droxidopa: a review of its use in symptomatic neurogenic orthostatic hypotension. Drugs. 2015 Feb;75(2):197-206. doi: 10.1007/s40265-014-0342-1. PMID: 25559422.

5: Livezey SN, Shah NB, DeClercq J, Keefe J, Choi L, Shibao C, Zuckerman AD. Droxidopa management by an integrated health-system specialty pharmacy team. J Am Pharm Assoc (2003). 2022 Nov-Dec;62(6):1904-1911. doi: 10.1016/j.japh.2022.06.002. Epub 2022 Jun 13. PMID: 35787811.

6: Pérez-Lloret S, Quarracino C, Otero-Losada M, Rascol O. Droxidopa for the treatment of neurogenic orthostatic hypotension in neurodegenerative diseases. Expert Opin Pharmacother. 2019 Apr;20(6):635-645. doi: 10.1080/14656566.2019.1574746. Epub 2019 Feb 7. PMID: 30730771.

7: Elgebaly A, Abdelazeim B, Mattar O, Gadelkarim M, Salah R, Negida A. Meta- analysis of the safety and efficacy of droxidopa for neurogenic orthostatic hypotension. Clin Auton Res. 2016 Jun;26(3):171-80. doi: 10.1007/s10286-016-0349-7. Epub 2016 Mar 7. PMID: 26951135.

8: Palma JA, Kaufmann H. Management of Orthostatic Hypotension. Continuum (Minneap Minn). 2020 Feb;26(1):154-177. doi: 10.1212/CON.0000000000000816. PMID: 31996627; PMCID: PMC7339914.

9: White WB, Hauser RA, Rowse GJ, Ziemann A, Hewitt LA. Cardiovascular Safety of Droxidopa in Patients With Symptomatic Neurogenic Orthostatic Hypotension. Am J Cardiol. 2017 Apr 1;119(7):1111-1115. doi: 10.1016/j.amjcard.2016.11.066. Epub 2017 Jan 6. PMID: 28159196.

10: Palma JA, Kaufmann H. Orthostatic Hypotension in Parkinson Disease. Clin Geriatr Med. 2020 Feb;36(1):53-67. doi: 10.1016/j.cger.2019.09.002. Epub 2019 Sep 6. PMID: 31733702; PMCID: PMC7029426.

11: Buoli M, Serati M, Cahn W. Alternative pharmacological strategies for adult ADHD treatment: a systematic review. Expert Rev Neurother. 2016;16(2):131-44. doi: 10.1586/14737175.2016.1135735. Epub 2016 Jan 14. PMID: 26693882.

12: Park JW, Okamoto LE, Shibao CA, Biaggioni I. Pharmacologic treatment of orthostatic hypotension. Auton Neurosci. 2020 Dec;229:102721. doi: 10.1016/j.autneu.2020.102721. Epub 2020 Aug 28. PMID: 32979782; PMCID: PMC7704612.

13: Bejjani A, Zhang Y, Behrens A, Murray B, Shah N. Droxidopa in the Management of Hepatorenal Syndrome. J Pharm Pract. 2023 Aug;36(4):1030-1034. doi: 10.1177/08971900221087974. Epub 2022 Apr 15. PMID: 35426352.

14: Ricci F, De Caterina R, Fedorowski A. Orthostatic Hypotension: Epidemiology, Prognosis, and Treatment. J Am Coll Cardiol. 2015 Aug 18;66(7):848-860. doi: 10.1016/j.jacc.2015.06.1084. PMID: 26271068.

15: Kaufmann H. Droxidopa for symptomatic neurogenic orthostatic hypotension: what can we learn? Clin Auton Res. 2017 Jul;27(Suppl 1):1-3. doi: 10.1007/s10286-017-0426-6. Epub 2017 Jun 16. PMID: 28623419.

16: Ferguson-Myrthil N. Droxidopa for Symptomatic Neurogenic Hypotension. Cardiol Rev. 2017 Sep/Oct;25(5):241-246. doi: 10.1097/CRD.0000000000000151. PMID: 28604565.

17: Stewart JM, Boris JR, Chelimsky G, Fischer PR, Fortunato JE, Grubb BP, Heyer GL, Jarjour IT, Medow MS, Numan MT, Pianosi PT, Singer W, Tarbell S, Chelimsky TC; Pediatric Writing Group of the American Autonomic Society. Pediatric Disorders of Orthostatic Intolerance. Pediatrics. 2018 Jan;141(1):e20171673. doi: 10.1542/peds.2017-1673. Epub 2017 Dec 8. PMID: 29222399; PMCID: PMC5744271.

18: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Parkinson Disease Agents. 2021 Oct 25. PMID: 31644162.

19: Marsili L, Duque KR, Sturchio A, Sobrero G, Premoli I, Dwivedi AK, Espay AJ, Merola A. Droxidopa reduces postural sway in Parkinson disease patients with orthostatic hypotension. Parkinsonism Relat Disord. 2022 Jun;99:62-64. doi: 10.1016/j.parkreldis.2022.05.002. Epub 2022 May 13. PMID: 35605513.

20: Amjad F, Polenchar B, Favit A. Droxidopa Persistence in Neurogenic Orthostatic Hypotension May Be Affected by Titration Approach. Int J Gen Med. 2021 Aug 13;14:4485-4490. doi: 10.2147/IJGM.S304012. PMID: 34421309; PMCID: PMC8371398.

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