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MedKoo Cat#: 525613 | Name: Metaproterenol Hemisulfate
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Description:

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

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)

Theoretical Analysis

MedKoo Cat#: 525613

Name: Metaproterenol Hemisulfate

CAS#: 5874-97-5 (sulfate)

Chemical Formula: C22H36N2O10S

Exact Mass: 0.0000

Molecular Weight: 520.59

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 350.00 2 Weeks
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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)
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/
Solvent mg/mL mM comments
Solubility
DMSO 62.5 214.54
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

Recalculate based on batch purity %
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.
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.