General
Preferred name
orciprenaline
Synonyms
METAPROTERENOL ()
Alupent Obstetric ()
Orciprenaline Sulfate ()
TH-152 ()
Metaproterenol hemisulfate ()
Metaproterenol Sulfate ()
Orciprenaline sulfate ()
Metaproterenol sulfate, orciprenaline sulfate ()
Metaproterenol (hemisulfate) ()
Metaproterenol hemisulfate salt ()
Prometa ()
Orciprenaline sulphate ()
Alupent ()
Metaproterenol sulphate ()
P&D ID
PD001867
CAS
586-06-1
5874-97-5
Tags
natural product
drug
available
Approved by
FDA
First approval
1973
Drug Status
approved
withdrawn
Drug indication
Bronchodilator
Asthma
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS Orciprenaline (also known as metaproterenol), a synthetic amine, is structurally and pharmacologically similar to isoproterenol. Orciprenaline is used exclusively as a bronchodilator. The pharmacological effects of beta adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (ATP) to cyclic- 3',5'- adenosine monophosphate (c-AMP). Increased cAMP levels lead to relaxation of bronchial smooth muscles and inhibition of the release of inalammatory mediators from mast cells that are involved in promoting immediate hypersensitivity .
MOA Orciprenaline stimulates the β2-adrenergic receptor expressed in the lungs, uterus, and vasculature supplying skeletal muscles by acting as a moderately selective agonist. It exerts minimal or no effect on alpha-adrenergic receptors. Intracellularly, the actions of orciprenaline are mediated by cAMP, the production of which is augmented by beta stimulation. The drug is believed to work by activating adenylate cyclase, the enzyme responsible for producing the cellular mediator cAMP.
DESCRIPTION Orciprenaline is a β-adrenoceptor agonist. (GtoPdb)
DESCRIPTION beta2-Adrenoceptor agonist (LOPAC library)
DESCRIPTION Orciprenaline is a moderately selective beta-adrenergic agonist used in the treatment of asthma and bronchospasms. It stimulates receptors of the smooth muscle in the lungs, uterus, and vasculature supplying skeletal muscle, with minimal or no effect on alpha-adrenergic receptors. It is believed to work by activating adenylate cyclase, the enzyme responsible for producing the cellular mediator cAMP. It was developed by Boehringer-Ingelheim and has been withdraw from the market. (BOC Sciences Bioactive Compounds)
DESCRIPTION Metaproterenol hemisulfate salt is the hemisulfate salt form of Metaproterenol, which is a moderately selective beta-adrenergic agonist. It is used in the treatment of asthma and bronchospasms. It was developed by Boehringer-Ingelheim and has been withdraw from the market. (BOC Sciences Bioactive Compounds)
Compound Sets
30
BOC Sciences Bioactive Compounds
orciprenaline-cas-586-06-1-item-72315
metaproterenol-hemisulfate-salt-cas-5874-97-5-375669
Cayman Chemical Bioactives
23611
ChEMBL Approved Drugs
CHEMBL776
CHEMBL1568057
ChEMBL Drugs
CHEMBL776
CHEMBL1568057
Concise Guide to Pharmacology 2017/18
7250
Concise Guide to Pharmacology 2019/20
7250
Concise Guide to Pharmacology 2021/22
7250
Concise Guide to Pharmacology 2023/24
7250
DrugBank
DB00816
DrugBank Approved Drugs
DB00816
DrugCentral
1720
DrugCentral Approved Drugs
1720
DrugMAP
DMTQS9A
DrugMAP Approved Drugs
DMTQS9A
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
7250
LOPAC library
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL776
MedChem Express Bioactive Compound Library
HY-B1276
NCATS Inxight Approved Drugs
53QOG569E0
NIH Clinical Collections (NCC)
NPC Screening Collection
Other bioactive compounds
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
metaproterenol-sulfate
TargetMol Bioactive Compound Library
T0277
The Spectrum Collection
Withdrawn 2.0
w242
External IDs
62
Properties
(calculated by RDKit )
Molecular Weight
211.12
Hydrogen Bond Acceptors
4
Hydrogen Bond Donors
4
Rotatable Bonds
4
Ring Count
1
Aromatic Ring Count
1
cLogP
1.13
TPSA
72.72
Fraction CSP3
0.45
Chiral centers
1.0
Largest ring
6.0
QED
0.6
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Selectivity
beta2
Pathway
GPCR/G protein
Neuronal Signaling
Target
??-adrenergic receptor
Adrenergic Receptor
ATC
R03AB03
R03CB03
R03CB53
Toxicity type
cardiovascular
Solubility
Soluble in DMSO, not in water
DMSO (Sparingly), Methanol (Sparingly)
Source data