Fenoterol hydrobromide | β2-AR agonist | CAS#1944-12-3

MedKoo Cat#: 562631 | Name: Fenoterol hydrobromide

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Description:

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

Fenoterol is β2-Adrenergic receptor (β2-AR) agonist. Fenoterol is chemically closely related to metaproterenol (orciprenaline). It has a higher bronchodilating potency than metaproterenol, albuterol (salbutamol in Europe) or terbutaline. The beta 2 selectivity of fenoterol at normal oral and inhaled doses is the same as for albuterol and terbutaline. Its pharmacodynamic effects are similar to those of other selective beta 2-adrenoceptor agonists.

Chemical Structure

Fenoterol hydrobromide

CAS#1944-12-3 (HBr)

Theoretical Analysis

MedKoo Cat#: 562631

Name: Fenoterol hydrobromide

CAS#: 1944-12-3 (HBr)

Chemical Formula: C17H22BrNO4

Exact Mass: 0.0000

Molecular Weight: 384.27

Elemental Analysis: C, 53.14; H, 5.77; Br, 20.79; N, 3.65; O, 16.65

Price and Availability

Size	Price	Availability	Quantity
1g	USD 550.00	2 Weeks

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Related CAS #

1944-10-1 (HCl) 1944-12-3 (HBr) 13392-18-2 (free base) 130156-24-0 (RS isomer) 36369-23-0 (RS isomer HBr)

Synonym

Fenoterol hydrobromide; Fenoterol HBr; Phenoterol hydrobromide; TH 1165A; TH-1165A; TH1165A; Berotec; hydroxyphenylorciprenaline;

IUPAC/Chemical Name

5-[1-Hydroxy-2-[1-(4-hydroxyphenyl)propan-2-ylamino]ethyl]benzene-1,3-diol hydrobromide

InChi Key

SGZRQMALQBXAIQ-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H21NO4.BrH/c1-11(6-12-2-4-14(19)5-3-12)18-10-17(22)13-7-15(20)9-16(21)8-13;/h2-5,7-9,11,17-22H,6,10H2,1H3;1H

SMILES Code

OC1=CC(C(O)CNC(C)CC2=CC=C(O)C=C2)=CC(O)=C1.[H]Br

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

Certificate of Analysis

View CoA: current batch, Lot#T20R05C26

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 384.27 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

1: Hudalla H, Bruckner T, Pöschl J, Strowitzki T, Kuon RJ. Antenatal exposure to fenoterol is not associated with the development of retinopathy of prematurity in infants born before 32 weeks of gestation. Arch Gynecol Obstet. 2020 Mar;301(3):687-692. doi: 10.1007/s00404-020-05463-z. Epub 2020 Feb 28. PMID: 32112180. 2: Pozzoli C, Bertini S, Poli E, Placenza G, Menozzi A. Relaxing effects of clenbuterol, ritodrine, salbutamol and fenoterol on the contractions of horse isolated bronchi induced by different stimuli. Res Vet Sci. 2020 Feb;128:43-48. doi: 10.1016/j.rvsc.2019.10.022. Epub 2019 Oct 31. PMID: 31710963. 3: Wongwaree S, Daengsuwan T. Comparison efficacy of randomized nebulized magnesium sulfate and ipratropium bromide/fenoterol in children with moderate to severe asthma exacerbation. Asian Pac J Allergy Immunol. 2019 Aug 18. doi: 10.12932/AP-190717-0118. Epub ahead of print. PMID: 31421659. 4: Omar MA, Hammad MA, Awad M. Utility of Europium ion characteristic peak for quantitation of Fenoterol hydrobromide and Salmeterol xinafoate in different matrices; application to stability studies. Spectrochim Acta A Mol Biomol Spectrosc. 2019 Jun 15;217:182-189. doi: 10.1016/j.saa.2019.03.072. Epub 2019 Mar 25. PMID: 30933783. 5: Stoiber B, Haslinger C, Schäffer MK, Zimmermann R, Schäffer L. Effect of dual tocolysis with fenoterol and atosiban in human myometrium. J Perinat Med. 2019 Feb 25;47(2):190-194. doi: 10.1515/jpm-2018-0010. PMID: 30218606. 6: Schulz D, Schlieckau F, Fill Malfertheiner S, Reuschel E, Seelbach-Göbel B, Ernst W. Effect of betamethasone, indomethacin and fenoterol on neonatal and maternal mononuclear cells stimulated with Escherichia coli. Cytokine. 2019 Apr;116:97-105. doi: 10.1016/j.cyto.2018.12.017. Epub 2019 Jan 28. PMID: 30703694. 7: Omar MA, Hammad MA, Awad M. New enhanced spectrofluorimetric approach for picogram detection of Fenoterol hydrobromide through Von Pechman synthesis of coumarins. Spectrochim Acta A Mol Biomol Spectrosc. 2018 Nov 5;204:702-707. doi: 10.1016/j.saa.2018.06.108. Epub 2018 Jul 2. PMID: 29982162. 8: Hudalla H, Karmen C, Bruckner T, Wallwiener S, Fluhr H, Michael Z, Freis A, Maul H, Strowitzki T, Pöschl J, Kuon RJ. Tocolysis with the β2-sympathomimetic fenoterol does not increase the occurrence of infantile hemangioma in preterm and term infants. Arch Gynecol Obstet. 2018 Sep;298(3):521-527. doi: 10.1007/s00404-018-4830-5. Epub 2018 Jun 25. PMID: 29938346. 9: Tzvetkov MV, Matthaei J, Pojar S, Faltraco F, Vogler S, Prukop T, Seitz T, Brockmöller J. Increased Systemic Exposure and Stronger Cardiovascular and Metabolic Adverse Reactions to Fenoterol in Individuals with Heritable OCT1 Deficiency. Clin Pharmacol Ther. 2018 May;103(5):868-878. doi: 10.1002/cpt.812. Epub 2017 Dec 8. PMID: 28791698. 10: Velzel J, Vlemmix F, Opmeer BC, Molkenboer JF, Verhoeven CJ, van Pampus MG, Papatsonis DN, Bais JM, Vollebregt KC, van der Esch L, Van der Post JA, Mol BW, Kok M. Atosiban versus fenoterol as a uterine relaxant for external cephalic version: randomised controlled trial. BMJ. 2017 Jan 26;356:i6773. doi: 10.1136/bmj.i6773. PMID: 28126898; PMCID: PMC5421458. 11: Śliwiński L, Cegieła U, Pytlik M, Folwarczna J, Janas A, Zbrojkiewicz M. Effects of fenoterol on the skeletal system depend on the androgen level. Pharmacol Rep. 2017 Apr;69(2):260-267. doi: 10.1016/j.pharep.2016.09.023. Epub 2016 Sep 29. PMID: 28126642. 12: Wang W, Chen J, Li XG, Xu J. Anti-inflammatory activities of fenoterol through β-arrestin-2 and inhibition of AMPK and NF-κB activation in AICAR- induced THP-1 cells. Biomed Pharmacother. 2016 Dec;84:185-190. doi: 10.1016/j.biopha.2016.09.044. Epub 2016 Sep 19. PMID: 27657826. 13: Fuchs T, Pomorski M, Grobelak K, Zimmer M. The T/QRS ratio values in pregnancies complicated by threatened preterm labour treated with intravenous infusions of fenoterol. J Perinat Med. 2015 Jul;43(4):467-72. doi: 10.1515/jpm-2014-0042. PMID: 25153544. 14: Wang W, Zhang Y, Xu M, Zhang YY, He B. Fenoterol inhibits LPS-induced AMPK activation and inflammatory cytokine production through β-arrestin-2 in THP-1 cell line. Biochem Biophys Res Commun. 2015 Jun 26;462(2):119-23. doi: 10.1016/j.bbrc.2015.04.097. Epub 2015 Apr 28. PMID: 25930996. 15: Reinartz MT, Kälble S, Wainer IW, Seifert R. Interaction of fenoterol stereoisomers with β2-adrenoceptor-G sα fusion proteins: antagonist and agonist competition binding. Naunyn Schmiedebergs Arch Pharmacol. 2015 May;388(5):517-24. doi: 10.1007/s00210-015-1086-5. Epub 2015 Jan 31. PMID: 25637582. 16: Reinartz MT, Kälble S, Littmann T, Ozawa T, Dove S, Kaever V, Wainer IW, Seifert R. Structure-bias relationships for fenoterol stereoisomers in six molecular and cellular assays at the β2-adrenoceptor. Naunyn Schmiedebergs Arch Pharmacol. 2015 Jan;388(1):51-65. doi: 10.1007/s00210-014-1054-5. Epub 2014 Oct 24. PMID: 25342094. 17: Tedesco D, Zanasi R, Wainer IW, Bertucci C. Stereochemical and conformational study on fenoterol by ECD spectroscopy and TD-DFT calculations. J Pharm Biomed Anal. 2014 Mar;91:92-6. doi: 10.1016/j.jpba.2013.12.018. Epub 2013 Dec 30. PMID: 24441217. 18: Plazinska A, Pajak K, Rutkowska E, Jimenez L, Kozocas J, Koolpe G, Tanga M, Toll L, Wainer IW, Jozwiak K. Comparative molecular field analysis of fenoterol derivatives interacting with an agonist-stabilized form of the β₂-adrenergic receptor. Bioorg Med Chem. 2014 Jan 1;22(1):234-46. doi: 10.1016/j.bmc.2013.11.030. Epub 2013 Nov 23. PMID: 24326276; PMCID: PMC3908673. 19: Orlovius AK, Guddat S, Gütschow M, Thevis M, Schänzer W. In vitro synthesis and characterisation of three fenoterol sulfoconjugates detected in fenoterol post-administration urine samples. Anal Bioanal Chem. 2013 Nov;405(29):9477-87. doi: 10.1007/s00216-013-7383-2. PMID: 24121469. 20: Plazinska A, Kolinski M, Wainer IW, Jozwiak K. Molecular interactions between fenoterol stereoisomers and derivatives and the β₂-adrenergic receptor binding site studied by docking and molecular dynamics simulations. J Mol Model. 2013 Nov;19(11):4919-30. doi: 10.1007/s00894-013-1981-y. Epub 2013 Sep 17. PMID: 24043542; PMCID: PMC3825559.