METAPROTERENOL SULFATE

First approved in 1973

Details

Stereochemistry	RACEMIC
Molecular Formula	2C11H17NO3.H2O4S
Molecular Weight	520.594
Optical Activity	( + / - )
Defined Stereocenters	0 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CC(C)NCC(O)C1=CC(O)=CC(O)=C1.CC(C)NCC(O)C2=CC(O)=CC(O)=C2

InChI

InChIKey=MKFFGUZYVNDHIH-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C11H17NO3
Molecular Weight	211.2576
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.drugs.com/pro/metaproterenol-tablets.html | https://www.drugbank.ca/drugs/DB00816

Metaproterenol, also known as Orciprenaline, is a brochodilator that is FDA approved for the treatment of bronchial asthma and for reversible bronchospasm which may occur in association with bronchitis and emphysema. Metaproterenol Sulfate is a potent beta-adrenergic stimulator with a rapid onset of action. It is postulated that beta-adrenergic stimulants produce many of their pharmacological effects by activation of adenyl cyclase, the enzyme which catalyzes the conversion of adrenosine triphosphate to cyclic adenosine monosphosphate. Metaproterenol is a moderately selective beta(2)-adrenergic agonist that stimulates receptors of the smooth muscle in the lungs, uterus, and vasculature supplying skeletal muscle, with minimal or no effect on alpha-adrenergic receptors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=170791 \| https://www.drugbank.ca/drugs/DB00816	Agonist 2678		4.81 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bronchial asthma 50 Sources: https://www.drugs.com/pro/metaproterenol.html https://www.dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=170791	Primary		Approved 8429	Metaproterenol Approved Use Metaproterenol Sulfate Inhalation Solution is indicated as a bronchodilator for bronchial asthma and for reversible bronchospasm which may occur in association with bronchitis and emphysema. Launch Date 1.12924803E11

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.1 h REVIEW https://pubmed.ncbi.nlm.nih.gov/1969785/	single, oral		METAPROTERENOL plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 mL 3 times / day multiple, oral Dose: 10 mL, 3 times / day Route: oral Route: multiple Dose: 10 mL, 3 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display	unhealthy, adults n = 1120 Health Status: unhealthy Condition: bronchial asthma Age Group: adults Population Size: 1120 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display	Other AEs: Tachycardia, Headache... Other AEs: Tachycardia (6.1%) Headache (1.1%) Nervousness (4.8%) Nausea (1.3%) Tremor (1.6%) Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display

AEs

AE	Significance	Dose	Population
Headache	1.1%	10 mL 3 times / day multiple, oral Dose: 10 mL, 3 times / day Route: oral Route: multiple Dose: 10 mL, 3 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display	unhealthy, adults n = 1120 Health Status: unhealthy Condition: bronchial asthma Age Group: adults Population Size: 1120 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display
Nausea	1.3%	10 mL 3 times / day multiple, oral Dose: 10 mL, 3 times / day Route: oral Route: multiple Dose: 10 mL, 3 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display	unhealthy, adults n = 1120 Health Status: unhealthy Condition: bronchial asthma Age Group: adults Population Size: 1120 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display
Tremor	1.6%	10 mL 3 times / day multiple, oral Dose: 10 mL, 3 times / day Route: oral Route: multiple Dose: 10 mL, 3 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display	unhealthy, adults n = 1120 Health Status: unhealthy Condition: bronchial asthma Age Group: adults Population Size: 1120 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display
Nervousness	4.8%	10 mL 3 times / day multiple, oral Dose: 10 mL, 3 times / day Route: oral Route: multiple Dose: 10 mL, 3 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display	unhealthy, adults n = 1120 Health Status: unhealthy Condition: bronchial asthma Age Group: adults Population Size: 1120 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display
Tachycardia	6.1%	10 mL 3 times / day multiple, oral Dose: 10 mL, 3 times / day Route: oral Route: multiple Dose: 10 mL, 3 times / day Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display	unhealthy, adults n = 1120 Health Status: unhealthy Condition: bronchial asthma Age Group: adults Population Size: 1120 Sources: https://dailymed.nlm.nih.gov/dailymed/fda/fdaDrugXsl.cfm?setid=43ff5156-e08b-4dc4-93a6-8c727676daa1&type=display

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 512	OCT1 327

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 543	inhibitor 3277 Sources: https://pubs.acs.org/doi/abs/10.1021/jm8003152	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
OCT1 327	substrate 3367 Sources: https://www.sciencedirect.com/science/article/pii/S0006295219304307	yes [Km 780.5 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY561898	https://www.001chemical.com/chem/586-06-1
3B Scientific (Wuhan) Corp	3B2-1654	http://www.3bsc.com/index/pro_info.php?id=55373
AHH Chemical co.,ltd	MR-1011805	http://www.ahhchemical.com/product/MR-1011805.html
AK Scientific, Inc. (AKSCI)	V0056	http://www.aksci.com/item_detail.php?cat=V0056
Achemica	ACMC-20m2sn	http://www.achemica.com/prodinfo/?id=185227
Aurora Fine Chemicals LLC	A06.997.184	http://online.aurorafinechemicals.com/info?ID=A06.997.184
BioSynth	M-3070	http://www.biosynth.com/index.asp?topic_id=97&g=19&m=249&feld=katno&wert=M-3070
Chem Scene	CS-0013668	http://www.chemscene.com/586-06-1.html
ChemMol	49427934	http://www.chemmol.com/chemmol/49427934.html
Clearsynth	CS-O-30706	https://www.clearsynth.com/en/CSO30706.html
Hairui	HR131174	http://www.hairuichem.com/en/product/586-06-1.html
MedChem Express	HY-B1276A	https://www.medchemexpress.com/metaproterenol.html
Molcore	MC561898	https://www.molcore.com/product/586-06-1
MuseChem	I008480	https://www.musechem.com/product/I008480.html
OChem	12582	http://www.ocheminc.com/index.php?act=psearch&pid=586O061
Smolecule	S538196	http://www.smolecule.com/products/s538196
THE BioTek	bt-277610	https://www.thebiotek.com/product/inhibitors/bt-277610
iChemical	EBD47055	http://www.ichemical.com/chemicals/cas-586-06-1
mcule	MCULE-8722254342	https://mcule.com/MCULE-8722254342/

PubMed

Title	Date	PubMed
Intravenous isoprenaline and orciprenaline as a guide to the drug treatment of Stokes-Adams attacks.	1968 Feb 17	5639626
Myocardial necrosis in the rat: a comparison between isoprenaline, orciprenaline, salbutamol and terbutaline.	1973	4773536
Comparison of fenoterol and orciprenaline with regard to broncho-dilating action and beta 2-selectivity.	1980	6248395
Objective and subjective tremor responses to oral beta 2 agents on first exposure. A comparison of metaproterenol and terbutaline.	1982 Oct	6751176
Combination low-dose metaproterenol-theophylline therapy in asthma.	1983	6343341
Bronchodilator and side effects of different modes of administration of metaproterenol: inhaled, oral, and in combination.	1986 Mar	3513564
Bronchodilator effects of oral metaproterenol sulfate in preschool children with asthma.	1987 Jan	3794877
Hypokalemia induced by inhaled bronchodilators.	1988 Oct	3168573
Bradycardia due to biperiden.	1989 Jan	2710809
Case of psychosis due to prednisone-clarithromycin interaction.	1998 Sep	9788033
Chronic beta-adrenoreceptor stimulation in vivo decreased Bcl-2 and increased Bax expression but did not activate apoptotic pathways in mouse heart.	2004 Mar	15052282
Pleiotropic beta-agonist-promoted receptor conformations and signals independent of intrinsic activity.	2007 Feb	16980553
Synthesis, pharmacological and in silico evaluation of 1-(4-di-hydroxy-3,5-dioxa-4-borabicyclo[4.4.0]deca-7,9,11-trien-9-yl)-2-(tert-butylamino)ethanol, a compound designed to act as a beta2 adrenoceptor agonist.	2009 Jul	19168263
Biomarker panel of cardiac and skeletal muscle troponins, fatty acid binding protein 3 and myosin light chain 3 for the accurate diagnosis of cardiotoxicity and musculoskeletal toxicity in rats.	2012 Dec 16	22878004
Genomic biomarkers for cardiotoxicity in rats as a sensitive tool in preclinical studies.	2013 Oct	23558518

Patents

Sample Use Guides

In Vivo Use Guide

Metaproterenol Sulfate Inhalation Solution is for administration with the aid of an intermittent positive pressure breathing apparatus (IPPB) or air driven nebulizer. The usual adult dose is one vial per nebulization treatment. Each vial of 0.4% is equivalent to 0.2 mL Metaproterenol Sulfate Inhalation Solution 5% diluted 2.5 mL with Normal Saline. Each vial of 0.6% is equivalent to 0.3 mL Metaproterenol Sulfate Inhalation Solution 5% diluted to 2.5 mL with Normal Saline. Usually, treatment need not be repeated more often than every four hours to relieve acute attacks of bronchospasm. As part of a total treatment program in chronic bronchospastic pulmonary diseases, Metaproterenol Sulfate Inhalation Solution may be administered three or four times a day.

Route of Administration: Respiratory

In Vitro Use Guide

Metaproterenol (10(-4), 10(-5) and 10(-6)M) significantly inhibited the in vitro development of memory CTL activity of young mice.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:01:09 UTC 2023` Edited by `admin` on `Fri Dec 15 15:01:09 UTC 2023`
Record UNII	GJ20H50YF0
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

METAPROTERENOL SULFATE

Official Name

English

METAPROTERENOL SULFATE [USP MONOGRAPH]

Common Name

English

ORCIPRENALINE SULFATE [MART.]

Common Name

English

TH-152

Code

English

(±)-3,5-DIHYDROXY-.ALPHA.-((ISOPROPYLAMINO)METHYL)BENZYL ALCOHOL SULPHATE (2:1)

Systematic Name

English

METAPROTERENOL SULFATE [ORANGE BOOK]

Common Name

English

ORCIPRENALINE SULFATE [EP MONOGRAPH]

Common Name

English

1,3-BENZENEDIOL, 5-(1-HYDROXY-2-(1-METHYLETHYL)AMINO)ETHYL-, (±)-, SULPHATE (2:1) (SALT)

Common Name

English

(±)-3,5-DIHYDROXY-.ALPHA.-((ISOPROPYLAMINO)METHYL)BENZYL ALCOHOL SULFATE (2:1)

Systematic Name

English

ORCIPRENALINE SULFATE

Common Name

English

METAPROTERENOL SULFATE [USP-RS]

Common Name

English

Orciprenaline sulfate [WHO-DD]

Common Name

English

ORCIPRENALINE SULPHATE

Common Name

English

1,3-BENZENEDIOL, 5-(1-HYDROXY-2-(1-METHYLETHYL)AMINO)ETHYL-, (±)-, SULFATE (2:1) (SALT)

Common Name

English

ALUPENT

Brand Name

English

METAPROTERENOL SULFATE [VANDF]

Common Name

English

METAPROTERENOL SULPHATE

Common Name

English

METAPROTERENOL SULFATE [USAN]

Common Name

English

PROMETA

Brand Name

English

ORCIPRENALINE SULFATE [JAN]

Common Name

English

METAPROTERENOL SULFATE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C319