REPROTEROL

Details

Stereochemistry	RACEMIC
Molecular Formula	C18H23N5O5
Molecular Weight	389.4057
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=C(N(CCCNCC(O)C3=CC(O)=CC(O)=C3)C=N2)C(=O)N(C)C1=O

InChI

InChIKey=WVLAAKXASPCBGT-UHFFFAOYSA-N

InChI=1S/C18H23N5O5/c1-21-16-15(17(27)22(2)18(21)28)23(10-20-16)5-3-4-19-9-14(26)11-6-12(24)8-13(25)7-11/h6-8,10,14,19,24-26H,3-5,9H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C18H23N5O5
Molecular Weight	389.4057
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22198635 | https://www.ncbi.nlm.nih.gov/pubmed/18677973 | https://www.ncbi.nlm.nih.gov/pubmed/10364735

Reproterol is a short-acting β2 adrenoreceptor agonist used in the treatment of asthma. Reproterol increases the generation of cAMP in isolated peripheral blood monocytes in vitro more effectively than does orciprenaline. In the presence of the highly potent but nonselective ß-antagonist, propranolol, the cAMP-generating action of reproterol was inhibited only partially. Reproterol has gained wide use when it was licensed as a fixed combination therapy with cromoglycate. Until today, the bronchodilator effects of reproterol and the bronchoprotective and anti-inflammatory actions of cromoglycate combined in one inhaler remain the successful fixed combination of a disease-modifying and symptomatic drug for the treatment of asthma.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-2 adrenergic receptor 203 Target ID: CHEMBL210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10364735\|https://www.ncbi.nlm.nih.gov/pubmed/15219266\|https://www.ncbi.nlm.nih.gov/pubmed/4074604	Agonist 2678
Phosphodiesterase, mouse 2 Target ID: Phosphodiesterase, mouse Sources: https://www.ncbi.nlm.nih.gov/pubmed/15219266	Inhibitor 8297		52.0 µM [IC50]

PubMed

Title	Date	PubMed
Screening of beta-2 agonists and confirmation of fenoterol, orciprenaline, reproterol and terbutaline with gas chromatography-mass spectrometry as tetrahydroisoquinoline derivatives.	2001 Feb 10	11232861
[Exercise-induced asthma. The spray belongs in the "athletic shoe"].	2001 Jul 19	11499151
Conductimetric determination of reproterol HCl and pipazethate HCl and salbutamol sulphate in their pharmaceutical formulations.	2001 Oct	11489383
[With the correct training conditions and appropriate prophylaxis. To make asthma patients fit for sports].	2003 Apr 10	15104273
Inhibition by reproterol of cAMP PDE in intact mastocytoma P-815 cells.	2004	15219266
Different mechanisms of action of beta2-adrenergic receptor agonists: a comparison of reproterol, fenoterol and salbutamol on monocyte cyclic-AMP and leukotriene B4 production in vitro.	2004 Jul 30	15337638
Effect of reproterol either alone or combined with disodium cromoglycate on airway responsiveness to methacholine.	2005	15939309
Mononuclear cell membranes: stabilization by reproterol and cromoglycate, destabilization by fenoterol and salbutamol.	2006	16572921
Prevention of exercise-induced asthma by a fixed combination of disodium cromoglycate plus reproterol compared with montelukast in young patients.	2008	18677973
Multiresidue analysis of beta-agonists in bovine and porcine urine, feed and hair using liquid chromatography electrospray ionisation tandem mass spectrometry.	2008 May	18180910
Exercise-induced asthma: critical analysis of the protective role of montelukast.	2009 Oct 22	21437147
Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories.	2010 Apr	20155493

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:48:38 UTC 2023` Edited by `admin` on `Fri Dec 15 18:48:38 UTC 2023`
Record UNII	11941YC6RN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

REPROTEROL

Official Name

English

1H-PURINE-2,6-DIONE, 7-(3-((2-(3,5-DIHYDROXYPHENYL)-2-HYDROXYETHYL)AMINO)PROPYL)-3,7-DIHYDRO-1,3-DIMETHYL-

Systematic Name

English

reproterol [INN]

Common Name

English

Reproterol [WHO-DD]

Common Name

English

D-1959

Code

English

REPROTEROL [MI]

Common Name

English

7-(3-((.BETA.,3,5-TRIHYDROXYPHENETHYL)AMINO)PROPYL)THEOPHYLLINE

Systematic Name

English

Classification Tree Code System Code

WHO-ATC

R03CC14