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Identification
Name Orciprenaline
Accession Number DB00816 (APRD00210)
Type small molecule
Groups approved
Description

A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Metaproterenol
  • Metaproterenol Sulfate
  • Orciprenalina [INN-Spanish]
  • Orciprenaline Sulfate
  • Orciprenalinum [INN-Latin]
Brand names
  • Alotec
  • Alupent
  • Metaprel
  • Metaproterenol Polistirex
  • Novasmasol
  • Prometa
Brand name mixtures Not Available
Categories
  • Sympathomimetics
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
  • Tocolytic Agents
CAS number 586-06-1
Weight Average: 211.2576
Monoisotopic: 211.120843415
Chemical Formula C11H17NO3
InChI Key InChIKey=LMOINURANNBYCM-UHFFFAOYSA-N
InChI
InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3
Plain Text
IUPAC Name
5-{1-hydroxy-2-[(propan-2-yl)amino]ethyl}benzene-1,3-diol
SMILES
CC(C)NCC(O)C1=CC(O)=CC(O)=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Benzyl Alcohols and Derivatives
  • Phenols and Derivatives
  • Phenethylamines
  • Resorcinols
Substructures
  • Hydroxy Compounds
  • Benzyl Alcohols and Derivatives
  • Aliphatic and Aryl Amines
  • Phenols and Derivatives
  • Benzene and Derivatives
  • Amino Alcohols
  • Phenethylamines
  • Aromatic compounds
  • Alcohols and Polyols
  • Phenyl Esters
  • Resorcinols
Pharmacology
Indication For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.
Pharmacodynamics Orciprenaline (also known as metaproterenol), a synthetic amine, is structurally and pharmacologically similar to isoproterenol. Orciprenaline is used exclusively as a bronchodilator. The pharmacologic 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 c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.
Mechanism of action Orciprenaline 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. 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.
Absorption 3% (oral bioavailability of 40%)
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Hepatic and gastric. The major metabolite, orciprenaline-3-0-sulfate, is produced in the gastrointestinal tract. Orciprenaline is not metabolized by catechol-0-methyltransferase nor have glucuronide conjugates been isolated to date.
Route of elimination Not Available
Half life 6 hours
Clearance Not Available
Toxicity Symptoms of overdose include angina, hypertension or hypotension, arrhythmias, nervousness, headache, tremor, dry mouth, palpitation, nausea, dizziness, fatigue, malaise and insomnia. LD50=42 mg/kg (orally in rat).
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Boehringer ingelheim pharmaceuticals inc
  • Astrazeneca lp
  • Dey lp
  • Nephron pharmaceuticals corp
  • Novex pharma
  • Wockhardt eu operations (swiss) ag
  • Muro pharmaceutical inc
  • Boehringer ingelheim
  • Morton grove pharmaceuticals inc
  • Silarx pharmaceuticals inc
  • Teva pharmaceuticals usa inc
  • Teva pharmaceuticals usa
  • American therapeutics inc
  • Par pharmaceutical inc
  • Usl pharma inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Syrup Oral
Prices
Unit description Cost Unit
Metaproterenol sulfate powder 6.14 USD g
Metaproterenol 10 mg tablet 1.0 USD tablet
Metaproterenol 20 mg tablet 0.22 USD tablet
Apo-Orciprenaline 2 mg/ml Syrup 0.06 USD ml
Patents Not Available
Properties
State solid
Melting point 100 oC
Experimental Properties
Property Value Source
water solubility 9.7mg/L PhysProp
logP 1 PhysProp
Predicted Properties
Property Value Source
water solubility 6.92e+00 g/l ALOGPS
logP -0.32 ALOGPS
logP 0.13 ChemAxon Molconvert
logS -1.48 ALOGPS
pKa 10.63 ChemAxon Molconvert
hydrogen acceptor count 4 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 72.72 ChemAxon Molconvert
rotatable bond count 4 ChemAxon Molconvert
refractivity 58.40 ChemAxon Molconvert
polarizability 23.09 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00685 Link_out
KEGG Compound C07144 Link_out
PubChem Compound 4086 Link_out
PubChem Substance 46504464 Link_out
ChemSpider 3944 Link_out
Therapeutic Targets Database DNC000927 Link_out
PharmGKB PA450390 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic2/metaproterenol.htm Link_out
Wikipedia http://en.wikipedia.org/wiki/Orciprenaline Link_out
ATC Codes
  • R03CB03
  • R03AB03
AHFS Codes
  • 12:12.08.12
PDB Entries Not Available
FDA label Not Available
MSDS show (54.2 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals.
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Kimura M, Ogihara M: Stimulation by transforming growth factor-alpha of DNA synthesis and proliferation of adult rat hepatocytes in primary cultures: modulation by alpha- and beta-adrenoceptor agonists. J Pharmacol Exp Ther. 1999 Oct;291(1):171-80. Pubmed
  2. Gelmont DM, Balmes JR, Yee A: Hypokalemia induced by inhaled bronchodilators. Chest. 1988 Oct;94(4):763-6. Pubmed
  3. Fitch KD: The use of anti-asthmatic drugs. Do they affect sports performance? Sports Med. 1986 Mar-Apr;3(2):136-50. Pubmed
  4. Singh H, Linas S: Beta 2-adrenergic function in cultured rat proximal tubule epithelial cells. Am J Physiol. 1996 Jul;271(1 Pt 2):F71-7. Pubmed
  5. Hu DN, Woodward DF, McCormick SA: Influence of autonomic neurotransmitters on human uveal melanocytes in vitro. Exp Eye Res. 2000 Sep;71(3):217-24. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:43

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.