Metaproterenol Hemisulfate | CAS#5874-97-5 | CAS#586-06-1 | Asthmatic

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

MedKoo CAT#: 525613

CAS#: 5874-97-5 (sulfate)

Description: Metaproterenol, also known as Th-152 and Orciprenaline, is used for asthmatic children with therapeutic serum theophylline concentrations. In the recommended doses, metaproterenol can improve pulmonary function in asthmatic children who have abnormal pulmonary function while being maintained on theophylline.

Chemical Structure

Metaproterenol Hemisulfate

CAS# 5874-97-5 (sulfate)

Instruction

Theoretical Analysis

MedKoo Cat#: 525613
Name: Metaproterenol Hemisulfate
CAS#: 5874-97-5 (sulfate)
Chemical Formula: C22H36N2O10S
Exact Mass: 0.00
Molecular Weight: 520.590
Elemental Analysis: C, 50.76; H, 6.97; N, 5.38; O, 30.73; S, 6.16

Price and Availability

Size	Price	Availability	Quantity
1g	USD 350	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.

Related CAS #: 5874-97-5 (sulfate) 586-06-1 (free)

Synonym: Th-152; Th 152; Th152; Metaprel; Metaproterenol; Metaproterenol Polistirex; Alotec; Alupent; Astmopent; Orciprenaline; Orciprenaline Sulfate; Metaproterenol Hemisulfate

IUPAC/Chemical Name: 5-(1-hydroxy-2-(isopropylamino)ethyl)benzene-1,3-diol hemisulfate

InChi Key: MKFFGUZYVNDHIH-UHFFFAOYSA-N

InChi Code: InChI=1S/2C11H17NO3.H2O4S/c2*1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8;1-5(2,3)4/h2*3-5,7,11-15H,6H2,1-2H3;(H2,1,2,3,4)

SMILES Code: OS(O)(=O)=O.CC(NCC(C1=CC(O)=CC(O)=C1)O)C.CC(NCC(C2=CC(O)=CC(O)=C2)O)C

Appearance: White to off-white crystalline 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# 586-06-1 (Orciprenaline)

Instruction:

View handling instruction

Biological target:	Metaproterenol hemisulfate (Orciprenaline hemisulfate) is a β2-adrenergic receptor (β2AR) agonist with an IC50 of 68 nM.
In vitro activity:	In-vitro, β-adrenergic agonists (epinephrine or metaproterenol) and prostaglandin-E2 markedly increased MDA-MB-231HM secretion of the pro-metastatic factors IL-6, IL-8, and VEGF, whereas cortisol reduced their secretion, effects that were maintained even 12 h after the washout of these agonists. Reference: Brain Behav Immun. 2023 Jan 13;109:175-187. https://pubmed.ncbi.nlm.nih.gov/36646396/
In vivo activity:	The aim of this study was to determine the α1-adrenoceptor antagonist activity of terbutaline and its structurally close resorcinol, orciprenaline, in rat isolated small mesenteric arteries set up for myography. Concentration-response curves to methoxamine were competitively antagonised by terbutaline (30-300 μM) or orciprenaline (30-300 μM) with a pKB of 4.70 ± 0.09 or 4.79 ± 0.17, respectively. Reference: Eur J Pharmacol. 2020 Sep 5;882:173304. https://pubmed.ncbi.nlm.nih.gov/32592771/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	62.5	214.54

Preparing Stock Solutions

The following data is based on the product molecular weight 520.59 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. Haldar R, Berger LS, Rossenne E, Radin A, Eckerling A, Sandbank E, Sloan EK, Cole SW, Ben-Eliyahu S. Perioperative escape from dormancy of spontaneous micro-metastases: A role for malignant secretion of IL-6, IL-8, and VEGF, through adrenergic and prostaglandin signaling. Brain Behav Immun. 2023 Jan 13;109:175-187. doi: 10.1016/j.bbi.2023.01.005. Epub ahead of print. PMID: 36646396. 2. Moteki H, Kimura M, Ogihara M. Activation of extracellular-signal regulated kinase by epidermal growth factor is potentiated by cAMP-elevating agents in primary cultures of adult rat hepatocytes. Biol Pharm Bull. 2011;34(10):1542-52. doi: 10.1248/bpb.34.1542. PMID: 21963493. 3. Khammy MM, Truong CKH, Wright CE, Angus JA. The β2-adrenoceptor agonist bronchodilators terbutaline and orciprenaline are also weak α1-adrenoceptor antagonists. Eur J Pharmacol. 2020 Sep 5;882:173304. doi: 10.1016/j.ejphar.2020.173304. Epub 2020 Jun 24. PMID: 32592771.
In vitro protocol:	1. Haldar R, Berger LS, Rossenne E, Radin A, Eckerling A, Sandbank E, Sloan EK, Cole SW, Ben-Eliyahu S. Perioperative escape from dormancy of spontaneous micro-metastases: A role for malignant secretion of IL-6, IL-8, and VEGF, through adrenergic and prostaglandin signaling. Brain Behav Immun. 2023 Jan 13;109:175-187. doi: 10.1016/j.bbi.2023.01.005. Epub ahead of print. PMID: 36646396. 2. Moteki H, Kimura M, Ogihara M. Activation of extracellular-signal regulated kinase by epidermal growth factor is potentiated by cAMP-elevating agents in primary cultures of adult rat hepatocytes. Biol Pharm Bull. 2011;34(10):1542-52. doi: 10.1248/bpb.34.1542. PMID: 21963493.
In vivo protocol:	1. Khammy MM, Truong CKH, Wright CE, Angus JA. The β2-adrenoceptor agonist bronchodilators terbutaline and orciprenaline are also weak α1-adrenoceptor antagonists. Eur J Pharmacol. 2020 Sep 5;882:173304. doi: 10.1016/j.ejphar.2020.173304. Epub 2020 Jun 24. PMID: 32592771.

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1: Schilero GJ, Grimm D, Spungen AM, Lenner R, Lesser M. Bronchodilator responses to metaproterenol sulfate among subjects with spinal cord injury. J Rehabil Res Dev. 2004 Jan-Feb;41(1):59-64. PubMed PMID: 15273898.

2: Elyan BM, Sidhom MB, Plakogiannis FM. Evaluation of the effect of different fatty acids on the percutaneous absorption of metaproterenol sulfate. J Pharm Sci. 1996 Jan;85(1):101-5. PubMed PMID: 8926573.

3: Karpel JP, Pesin J, Greenberg D, Gentry E. A comparison of the effects of ipratropium bromide and metaproterenol sulfate in acute exacerbations of COPD. Chest. 1990 Oct;98(4):835-9. PubMed PMID: 2145136.

4: Nussbaum E, Eyzaguirre M, Galant SP. Dose-response relationship of inhaled metaproterenol sulfate in preschool children with mild asthma. Pediatrics. 1990 Jun;85(6):1072-5. PubMed PMID: 2187175.

5: McCalden TA, Porter J, Kamarei A. Aerosol delivery of liposome metaproterenol sulfate. Proc West Pharmacol Soc. 1990;33:171-3. PubMed PMID: 2274531.

6: Appel D, Karpel JP, Sherman M. Epinephrine improves expiratory flow rates in patients with asthma who do not respond to inhaled metaproterenol sulfate. J Allergy Clin Immunol. 1989 Jul;84(1):90-8. PubMed PMID: 2754149.

7: Linn WS, Avol EL, Shamoo DA, Peng RC, Spier CE, Smith MN, Hackney JD. Effect of metaproterenol sulfate on mild asthmatics' response to sulfur dioxide exposure and exercise. Arch Environ Health. 1988 Nov-Dec;43(6):399-406. PubMed PMID: 3196076.

8: Menon P, Hilman BC, Menon V, Bairnsfather L. Assessment of response to oral metaproterenol sulfate by forced oscillation in young children. Ann Allergy. 1988 Jun;60(6):547-51. PubMed PMID: 3382060.

9: Rogers JC. Combined inhalation of cromolyn sodium and metaproterenol sulfate in life-threatening asthma. J Fam Pract. 1988 Feb;26(2):193-5. PubMed PMID: 3123591.

10: McCalden TA, Abra RA, Mihalko PJ. Bronchodilator effects of some liposome formulations of metaproterenol sulfate in guinea pigs. Proc West Pharmacol Soc. 1988;31:129-32. PubMed PMID: 3211892.

11: Nussbaum E, Galant SP. Bronchodilator effects of oral metaproterenol sulfate in preschool children with asthma. J Pediatr. 1987 Jan;110(1):148-51. PubMed PMID: 3794877.

12: Karpel JP, Appel D, Breidbart D, Fusco MJ. A comparison of atropine sulfate and metaproterenol sulfate in the emergency treatment of asthma. Am Rev Respir Dis. 1986 May;133(5):727-9. PubMed PMID: 3706879.

13: Berkowitz R, Schwartz E, Bukstein D, Grunstein M, Chai H. Albuterol protects against exercise-induced asthma longer than metaproterenol sulfate. Pediatrics. 1986 Feb;77(2):173-8. PubMed PMID: 3945530.

14: Salzman GA, Pyszczynski DR. A comparison of two delivery methods for aerosolized metaproterenol sulfate. J Asthma. 1986;23(6):297-301. PubMed PMID: 3818510.

15: Appel DW. Effect of aminophylline when added to metaproterenol sulfate and beclomethasone dipropionate aerosol. J Allergy Clin Immunol. 1984 Feb;73(2):291-7. PubMed PMID: 6699312.

16: Berquist WE, Rachelefsky GS, Rowshan N, Siegel S, Katz R, Welch M. Quantitative gastroesophageal reflux and pulmonary function in asthmatic children and normal adults receiving placebo, theophylline, and metaproterenol sulfate therapy. J Allergy Clin Immunol. 1984 Feb;73(2):253-8. PubMed PMID: 6699308.

17: Sane RT, Sawant SV, Doshi VJ, Mhalas JG, Paarikh AK, Gijare AS, Deshpande DS. Simple colorimetric method for determination of metaproterenol sulfate in pharmaceuticals. J Assoc Off Anal Chem. 1984 Jan-Feb;67(1):137-8. PubMed PMID: 6698920.

18: Peerless AG, Rachelefsky GS, Mickey MR, Katz RM, Siegel SC. Bronchodilator characteristics of nebulized metaproterenol sulfate, isoetharine, and atropine in chronic asthma. J Allergy Clin Immunol. 1983 Dec;72(6):702-8. PubMed PMID: 6358329.

19: Kelly HW, Menendez R, Murphy S, Tuttle W. Metaproterenol sulfate for asthmatic children with therapeutic serum theophylline concentrations. Clin Pharm. 1982 Jan-Feb;1(1):49-54. PubMed PMID: 6764162.

20: Geumei AM, Miller WF, Miller J, Gast LR. Bronchodilator effect of a new oral beta adrenoreceptor stimulant, Th1165a. A comparison with metaproterenol sulfate. Chest. 1976 Oct;70(4):460-5. PubMed PMID: 789024.

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