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Showing drug card for Orciprenaline (DB00816)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:12
Primary Accession Number DB00816
Secondary Accession Number
  • APRD00210
Name Orciprenaline
Drug Type
  • Approved
  • Small Molecule
Description A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem]
Synonyms
  1. Metaproterenol
  2. Metaproterenol Sulfate
  3. Orciprenalina [INN-Spanish]
  4. Orciprenaline Sulfate
  5. Orciprenalinum [INN-Latin]
Brand Names
  1. Alotec
  2. Alupent
  3. Metaprel
  4. Metaproterenol Polistirex
  5. Novasmasol
  6. Prometa
Brand Mixtures Not Available
Chemical IUPAC Name 5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,3-diol
Chemical Formula C11H17NO3
Chemical Structure Structure
CAS Registry Number 586-06-1
InChI Identifier InChI=1/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
InChI Key LMOINURANNBYCM-UHFFFAOYAL
KEGG Drug D00685 Link Image
KEGG Compound C07144 Link Image
PubChem Compound 4086 Link Image
PubChem Substance 9353 Link Image
ChEBI ID Not Available
PharmGKB ID PA450390 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic2/metaproterenol.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Orciprenaline Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference O. Thoma, K. Zeile, U.S. Pat. 3,341,594 (1967)
Average Molecular Weight 211.2576
Monoisotopic Molecular Weight 211.1208
State Solid
Melting Point 100 oC
Experimental Water Solubility 9.7mg/L Source: PhysProp
Predicted Water Solubility 6.92e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1 Source: PhysProp
Predicted LogP -0.31 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -1.48 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC(C)NC[C@H](O)C1=CC(O)=CC(O)=C1
Canonical SMILES CC(C)NCC(O)C1=CC(O)=CC(O)=C1
Drug Category
  • Adrenergic beta-Agonists
  • Bronchodilator Agents
  • Sympathomimetics
  • Tocolytic Agents
ATC Codes
AHFS Codes
  • 12:12.08.12
Indication For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.
Pharmacology 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%)
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).
Protein Binding Not Available
Biotransformation 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.
Half Life 6 hours
Dosage Forms
Form Route
Syrup Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acebutolol Antagonism
Alseroxylon Increased arterial pressure
Amitriptyline The tricyclic increases the sympathomimetic effect
Amoxapine The tricyclic increases the sympathomimetic effect
Atenolol Antagonism
Betaxolol Antagonism
Bevantolol Antagonism
Bisoprolol Antagonism
Carteolol Antagonism
Carvedilol Antagonism
Clomipramine The tricyclic increases the sympathomimetic effect
Deserpidine Increased arterial pressure
Desipramine The tricyclic increases the sympathomimetic effect
Doxepin The tricyclic increases the sympathomimetic effect
Esmolol Antagonism
Imipramine The tricyclic increases the sympathomimetic effect
Isocarboxazid Increased arterial pressure
Labetalol Antagonism
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Metoprolol Antagonism
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect
Nadolol Antagonism
Nortriptyline The tricyclic increases the sympathomimetic effect
Oxprenolol Antagonism
Pargyline Increased arterial pressure
Penbutolol Antagonism
Phenelzine Increased arterial pressure
Pindolol Antagonism
Practolol Antagonism
Propranolol Antagonism
Protriptyline The tricyclic increases the sympathomimetic effect
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Sotalol Antagonism
Timolol Antagonism
Tranylcypromine Increased arterial pressure
Trimipramine The tricyclic increases the sympathomimetic effect
Food Interactions
  • Avoid high doses of caffeine.
  • Take without regard to meals.
Pathways Not Available
General References
  1. Drugs.com Link Image
  2. Wikipedia Link Image
  3. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Beta-2 adrenergic receptor
Drug Target 1 [top]
Target 1 ID 766
Target 1 Name Beta-2 adrenergic receptor
Target 1 Synonyms
  1. Beta-2 adrenoceptor
  2. Beta-2 adrenoreceptor
Target 1 Gene Name ADRB2
Target 1 Protein Sequence >Beta-2 adrenergic receptor 
MGQPGNGSAFLLAPNRSHAPDHDVTQQRDEVWVVGMGIVMSLIVLAIVFGNVLVITAIAK
FERLQTVTNYFITSLACADLVMGLAVVPFGAAHILMKMWTFGNFWCEFWTSIDVLCVTAS
IETLCVIAVDRYFAITSPFKYQSLLTKNKARVIILMVWIVSGLTSFLPIQMHWYRATHQE
AINCYANETCCDFFTNQAYAIASSIVSFYVPLVIMVFVYSRVFQEAKRQLQKIDKSEGRF
HVQNLSQVEQDGRTGHGLRRSSKFCLKEHKALKTLGIIMGTFTLCWLPFFIVNIVHVIQD
NLIRKEVYILLNWIGYVNSGFNPLIYCRSPDFRIAFQELLCLRRSSLKAYGNGYSSNGNT
GEQSGYHVEQEKENKLLCEDLPGTEDFVGHQGTVPSDNIDSQGRNCSTNDSLL
Target 1 Number of Residues 419
Target 1 Molecular Weight 46557
Target 1 Theoretical pI 7.44
Target 1 GO Classification
Function
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
amine receptor activity
adrenoceptor activity
beta-adrenergic receptor activity
beta2-adrenergic receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in beta2-adrenergic receptor activity
Target 1 Specific Function 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
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 35-58
  • 72-95
  • 107-129
  • 151-174
  • 197-220
  • 275-298
  • 306-329
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 29371 Link Image
Target 1 UniProtKB/Swiss-Prot ID P07550 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ADRB2_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1242 bp 
ATGGGGCAACCCGGGAACGGCAGCGCCTTCTTGCTGGCACCCAATAGAAGCCATGCGCCG
GACCACGACGTCACGCAGCAAAGGGACGAGGTGTGGGTGGTGGGCATGGGCATCGTCATG
TCTCTCATCGTCCTGGCCATCGTGTTTGGCAATGTGCTGGTCATCACAGCCATTGCCAAG
TTCGAGCGTCTGCAGACGGTCACCAACTACTTCATCACTTCACTGGCCTGTGCTGATCTG
GTCATGGGCCTGGCAGTGGTGCCCTTTGGGGCCGCCCATATTCTTATGAAAATGTGGACT
TTTGGCAACTTCTGGTGCGAGTTTTGGACTTCCATTGATGTGCTGTGCGTCACGGCCAGC
ATTGAGACCCTGTGCGTGATCGCAGTGGATCGCTACTTTGCCATTACTTCACCTTTCAAG
TACCAGAGCCTGCTGACCAAGAATAAGGCCCGGGTGATCATTCTGATGGTGTGGATTGTG
TCAGGCCTTACCTCCTTCTTGCCCATTCAGATGCACTGGTACCGGGCCACCCACCAGGAA
GCCATCAACTGCTATGCCAATGAGACCTGCTGTGACTTCTTCACGAACCAAGCCTATGCC
ATTGCCTCTTCCATCGTGTCCTTCTACGTTCCCCTGGTGATCATGGTCTTCGTCTACTCC
AGGGTCTTTCAGGAGGCCAAAAGGCAGCTCCAGAAGATTGACAAATCTGAGGGCCGCTTC
CATGTCCAGAACCTTAGCCAGGTGGAGCAGGATGGGCGGACGGGGCATGGACTCCGCAGA
TCTTCCAAGTTCTGCTTGAAGGAGCACAAAGCCCTCAAGACGTTAGGCATCATCATGGGC
ACTTTCACCCTCTGCTGGCTGCCCTTCTTCATCGTTAACATTGTGCATGTGATCCAGGAT
AACCTCATCCGTAAGGAAGTTTACATCCTCCTAAATTGGATAGGCTATGTCAATTCTGGT
TTCAATCCCCTTATCTACTGCCGGAGCCCAGATTTCAGGATTGCCTTCCAGGAGCTTCTG
TGCCTGCGCAGGTCTTCTTTGAAGGCCTATGGGAATGGCTACTCCAGCAACGGCAACACA
GGGGAGCAGAGTGGATATCACGTGGAACAGGAGAAAGAAAATAAACTGCTGTGTGAAGAC
CTCCCAGGCACGGAAGACTTTGTGGGCCATCAAGGTACTGTGCCTAGCGATAACATTGAT
TCACAAGGGAGGAATTGTAGTACAAATGACTCACTGCTGTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID ADRB2 Link Image
Target 1 GenAtlas ID ADRB2 Link Image
Target 1 HGNC ID HGNC:286 Link Image
Target 1 Chromosome Location 5
Target 1 Locus 5q31-q32
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Cao TT, Deacon HW, Reczek D, Bretscher A, von Zastrow M: A kinase-regulated PDZ-domain interaction controls endocytic sorting of the beta2-adrenergic receptor. Nature. 1999 Sep 16;401(6750):286-90. [PubMed Link Image]
  2. Moffett S, Rousseau G, Lagace M, Bouvier M: The palmitoylation state of the beta(2)-adrenergic receptor regulates the synergistic action of cyclic AMP-dependent protein kinase and beta-adrenergic receptor kinase involved in its phosphorylation and desensitization. J Neurochem. 2001 Jan;76(1):269-79. [PubMed Link Image]
  3. O'Dowd BF, Hnatowich M, Caron MG, Lefkowitz RJ, Bouvier M: Palmitoylation of the human beta 2-adrenergic receptor. Mutation of Cys341 in the carboxyl tail leads to an uncoupled nonpalmitoylated form of the receptor. J Biol Chem. 1989 May 5;264(13):7564-9. [PubMed Link Image]
  4. Emorine LJ, Marullo S, Delavier-Klutchko C, Kaveri SV, Durieu-Trautmann O, Strosberg AD: Structure of the gene for human beta 2-adrenergic receptor: expression and promoter characterization. Proc Natl Acad Sci U S A. 1987 Oct;84(20):6995-9. [PubMed Link Image]
  5. Chung FZ, Wang CD, Potter PC, Venter JC, Fraser CM: Site-directed mutagenesis and continuous expression of human beta-adrenergic receptors. Identification of a conserved aspartate residue involved in agonist binding and receptor activation. J Biol Chem. 1988 Mar 25;263(9):4052-5. [PubMed Link Image]
  6. Kobilka BK, Dixon RA, Frielle T, Dohlman HG, Bolanowski MA, Sigal IS, Yang-Feng TL, Francke U, Caron MG, Lefkowitz RJ: cDNA for the human beta 2-adrenergic receptor: a protein with multiple membrane-spanning domains and encoded by a gene whose chromosomal location is shared with that of the receptor for platelet-derived growth factor. Proc Natl Acad Sci U S A. 1987 Jan;84(1):46-50. [PubMed Link Image]
  7. Chung FZ, Lentes KU, Gocayne J, Fitzgerald M, Robinson D, Kerlavage AR, Fraser CM, Venter JC: Cloning and sequence analysis of the human brain beta-adrenergic receptor. Evolutionary relationship to rodent and avian beta-receptors and porcine muscarinic receptors. FEBS Lett. 1987 Jan 26;211(2):200-6. [PubMed Link Image]
  8. Schofield PR, Rhee LM, Peralta EG: Primary structure of the human beta-adrenergic receptor gene. Nucleic Acids Res. 1987 Apr 24;15(8):3636. [PubMed Link Image]
  9. Kobilka BK, Frielle T, Dohlman HG, Bolanowski MA, Dixon RA, Keller P, Caron MG, Lefkowitz RJ: Delineation of the intronless nature of the genes for the human and hamster beta 2-adrenergic receptor and their putative promoter regions. J Biol Chem. 1987 May 25;262(15):7321-7. [PubMed Link Image]
  10. Turki J, Pak J, Green SA, Martin RJ, Liggett SB: Genetic polymorphisms of the beta 2-adrenergic receptor in nocturnal and nonnocturnal asthma. Evidence that Gly16 correlates with the nocturnal phenotype. J Clin Invest. 1995 Apr;95(4):1635-41. [PubMed Link Image]
  11. 7915137 Green SA, Turki J, Innis M, Liggett SB: Amino-terminal polymorphisms of the human beta 2-adrenergic receptor impart distinct agonist-promoted regulatory properties. Biochemistry. 1994 Aug 16;33(32):9414-9.
  12. 8383511 Reihsaus E, Innis M, MacIntyre N, Liggett SB: Mutations in the gene encoding for the beta 2-adrenergic receptor in normal and asthmatic subjects. Am J Respir Cell Mol Biol. 1993 Mar;8(3):334-9.
Target 1 Drug 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 Link Image]
  2. 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 Link Image]
  3. Fitch KD: The use of anti-asthmatic drugs. Do they affect sports performance? Sports Med. 1986 Mar-Apr;3(2):136-50. [PubMed Link Image]
  4. Gelmont DM, Balmes JR, Yee A: Hypokalemia induced by inhaled bronchodilators. Chest. 1988 Oct;94(4):763-6. [PubMed Link Image]
  5. 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 Link Image]

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