Etamicastat HCl

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

MedKoo CAT#: 319707

CAS#: 677773-32-9 (HCl)

Description: Etamicastat, also known as BIA 5-453, is a potent, reversible, peripherally selective dopamine β-hydroxylase inhibitor (DBH inhibitor). Chronic dopamine ß-hydroxylase inhibition with etamicastat effectively decreases blood pressure, although does not prevent the development of hypertension in the spontaneously hypertensive rat.

Chemical Structure

Etamicastat HCl

CAS# 677773-32-9 (HCl)

Instruction

Theoretical Analysis

MedKoo Cat#: 319707
Name: Etamicastat HCl
CAS#: 677773-32-9 (HCl)
Chemical Formula: C14H16ClF2N3OS
Exact Mass: 0.00
Molecular Weight: 347.809
Elemental Analysis: C, 48.35; H, 4.64; Cl, 10.19; F, 10.92; N, 12.08; O, 4.60; S, 9.22

Price and Availability

Size	Price	Availability	Quantity
1g	USD -1
2g	USD -1
5g	USD -1
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.

Related CAS #: 677773-32-9 (HCl) 760173-05-5 (free base)

Synonym: BIA 5-453; BIA5-453; BIA-5-453; Etamicastat

IUPAC/Chemical Name: (R)-5-(2-aminoethyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydro-2H-imidazole-2-thione hydrochloride

InChi Key: CKRDOSZCFINPAD-RFVHGSKJSA-N

InChi Code: InChI=1S/C14H15F2N3OS.ClH/c15-9-3-8-4-11(7-20-13(8)12(16)5-9)19-10(1-2-17)6-18-14(19)21;/h3,5-6,11H,1-2,4,7,17H2,(H,18,21);1H/t11-;/m1./s1

SMILES Code: FC1=CC(F)=C(OC[C@H](N2C(CCN)=CNC2=S)C3)C3=C1.[H]Cl

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, not in water

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: Related CAS# 760173-05-5(Etamicastat free base) 677773-32-9(Etamicastat HCl )

Instruction:

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Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 347.81 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:
In vitro protocol:
In vivo protocol:

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1: Igreja B, Wright LC, Soares-da-Silva P. Sustained high blood pressure reduction with etamicastat, a peripheral selective dopamine β-hydroxylase inhibitor. J Am Soc Hypertens. 2015 Dec 19. pii: S1933-1711(15)00838-4. doi: 10.1016/j.jash.2015.12.011. [Epub ahead of print] PubMed PMID: 26803288.

2: Loureiro AI, Bonifácio MJ, Fernandes-Lopes C, Pires N, Igreja B, Wright LC, Soares-da-Silva P. Role of P-glycoprotein and permeability upon the brain distribution and pharmacodynamics of etamicastat: a comparison with nepicastat. Xenobiotica. 2015;45(9):828-39. doi: 10.3109/00498254.2015.1018985. Epub 2015 Jun 10. PubMed PMID: 25915108.

3: Loureiro AI, Soares-da-Silva P. Distribution and pharmacokinetics of etamicastat and its N-acetylated metabolite (BIA 5-961) in dog and monkey. Xenobiotica. 2015;45(10):903-11. doi: 10.3109/00498254.2015.1024780. Epub 2015 Apr 14. PubMed PMID: 25869244.

4: Pires NM, Igreja B, Moura E, Wright LC, Serrão MP, Soares-da-Silva P. Blood pressure decrease in spontaneously hypertensive rats folowing renal denervation or dopamine β-hydroxylase inhibition with etamicastat. Hypertens Res. 2015 Sep;38(9):605-12. doi: 10.1038/hr.2015.50. Epub 2015 Apr 9. PubMed PMID: 25854989.

5: Bonifácio MJ, Sousa F, Neves M, Palma N, Igreja B, Pires NM, Wright LC, Soares-da-Silva P. Characterization of the interaction of the novel antihypertensive etamicastat with human dopamine-β-hydroxylase: comparison with nepicastat. Eur J Pharmacol. 2015 Mar 15;751:50-8. doi: 10.1016/j.ejphar.2015.01.034. Epub 2015 Jan 29. PubMed PMID: 25641750.

6: Pires NM, Loureiro AI, Igreja B, Lacroix P, Soares-da-Silva P. Cardiovascular safety pharmacology profile of etamicastat, a novel peripheral selective dopamine-β-hydroxylase inhibitor. Eur J Pharmacol. 2015 Mar 5;750:98-107. doi: 10.1016/j.ejphar.2015.01.035. Epub 2015 Jan 30. PubMed PMID: 25641747.

7: Igreja B, Pires NM, Bonifácio MJ, Loureiro AI, Fernandes-Lopes C, Wright LC, Soares-da-Silva P. Blood pressure-decreasing effect of etamicastat alone and in combination with antihypertensive drugs in the spontaneously hypertensive rat. Hypertens Res. 2015 Jan;38(1):30-8. doi: 10.1038/hr.2014.143. Epub 2014 Oct 9. PubMed PMID: 25298210.

8: Loureiro AI, Bonifácio MJ, Fernandes-Lopes C, Igreja B, Wright LC, Soares-da-Silva P. Etamicastat, a new dopamine-ß-hydroxylase inhibitor, pharmacodynamics and metabolism in rat. Eur J Pharmacol. 2014 Oct 5;740:285-94. doi: 10.1016/j.ejphar.2014.07.027. Epub 2014 Jul 21. PubMed PMID: 25058908.

9: Almeida L, Nunes T, Costa R, Rocha JF, Vaz-da-Silva M, Soares-da-Silva P. Etamicastat, a novel dopamine β-hydroxylase inhibitor: tolerability, pharmacokinetics, and pharmacodynamics in patients with hypertension. Clin Ther. 2013 Dec;35(12):1983-96. doi: 10.1016/j.clinthera.2013.10.012. Epub 2013 Dec 2. PubMed PMID: 24296323.

10: Loureiro AI, Rocha JF, Fernandes-Lopes C, Nunes T, Wright LC, Almeida L, Soares-da-Silva P. Human disposition, metabolism and excretion of etamicastat, a reversible, peripherally selective dopamine β-hydroxylase inhibitor. Br J Clin Pharmacol. 2014 Jun;77(6):1017-26. doi: 10.1111/bcp.12274. PubMed PMID: 24168152; PubMed Central PMCID: PMC4093927.

11: Loureiro AI, Fernandes-Lopes C, Bonifácio MJ, Wright LC, Soares-da-Silva P. N-acetylation of etamicastat, a reversible dopamine-β-hydroxylase inhibitor. Drug Metab Dispos. 2013 Dec;41(12):2081-6. doi: 10.1124/dmd.113.053736. Epub 2013 Sep 6. PubMed PMID: 24013186.

12: Nunes T, Rocha JF, Vaz-da-Silva M, Falcão A, Almeida L, Soares-da-Silva P. Pharmacokinetics and tolerability of etamicastat following single and repeated administration in elderly versus young healthy male subjects: an open-label, single-center, parallel-group study. Clin Ther. 2011 Jun;33(6):776-91. doi: 10.1016/j.clinthera.2011.05.048. PubMed PMID: 21704242.

13: Vaz-da-Silva M, Nunes T, Rocha JF, Falcão A, Almeida L, Soares-da-Silva P. Effect of food on the pharmacokinetic profile of etamicastat (BIA 5-453). Drugs R D. 2011;11(2):127-36. doi: 10.2165/11587080-000000000-00000. PubMed PMID: 21548660; PubMed Central PMCID: PMC3585837.

14: Rocha JF, Vaz-Da-Silva M, Nunes T, Igreja B, Loureiro AI, Bonifácio MJ, Wright LC, Falcão A, Almeida L, Soares-Da-Silva P. Single-dose tolerability, pharmacokinetics, and pharmacodynamics of etamicastat (BIA 5-453), a new dopamine β-hydroxylase inhibitor, in healthy subjects. J Clin Pharmacol. 2012 Feb;52(2):156-70. doi: 10.1177/0091270010390805. PubMed PMID: 21343348.

15: Nunes T, Rocha JF, Vaz-da-Silva M, Igreja B, Wright LC, Falcão A, Almeida L, Soares-da-Silva P. Safety, tolerability, and pharmacokinetics of etamicastat, a novel dopamine-β-hydroxylase inhibitor, in a rising multiple-dose study in young healthy subjects. Drugs R D. 2010;10(4):225-42. doi: 10.2165/11586310-000000000-00000. PubMed PMID: 21171669; PubMed Central PMCID: PMC3585840.

16: Beliaev A, Learmonth DA, Soares-da-Silva P. Synthesis and biological evaluation of novel, peripherally selective chromanyl imidazolethione-based inhibitors of dopamine beta-hydroxylase. J Med Chem. 2006 Feb 9;49(3):1191-7. PubMed PMID: 16451083.

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