| 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 |
|
| Name |
Orciprenaline |
| Drug Type |
|
| Description |
A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem] |
| Synonyms |
- Metaproterenol
- Metaproterenol Sulfate
- Orciprenalina [INN-Spanish]
- Orciprenaline Sulfate
- Orciprenalinum [INN-Latin]
|
| Brand Names |
- Alotec
- Alupent
- Metaprel
- Metaproterenol Polistirex
- Novasmasol
- 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 |
 |
| 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  |
| KEGG Compound |
C07144  |
| PubChem Compound |
4086  |
| PubChem Substance |
9353  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA450390  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available |
| RxList Link |
http://www.rxlist.com/cgi/generic2/metaproterenol.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Orciprenaline  |
| 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 | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 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 |
|
| 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 |
|
| Patient Information |
Show  |
| Contraindications |
Show  |
| Interactions |
Show  |
| 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 |
- Drugs.com

- Wikipedia

- RxList

|
| Organisms Affected |
|
| Targets |
- Beta-2 adrenergic receptor
|
|
Drug Target 1
[top]
|
| Target 1 ID |
766 |
| Target 1 Name |
Beta-2 adrenergic receptor |
| Target 1 Synonyms |
- Beta-2 adrenoceptor
- 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 |
|
| 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  |
| Target 1 UniProtKB/Swiss-Prot ID |
P07550  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
ADRB2_HUMAN  |
| 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  |
| Target 1 GenAtlas ID |
ADRB2  |
| Target 1 HGNC ID |
HGNC:286  |
| Target 1 Chromosome Location |
5 |
| Target 1 Locus |
5q31-q32 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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.
- 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 |
- 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
]
- 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
]
- Fitch KD: The use of anti-asthmatic drugs. Do they affect sports performance? Sports Med. 1986 Mar-Apr;3(2):136-50. [PubMed
]
- Gelmont DM, Balmes JR, Yee A: Hypokalemia induced by inhaled bronchodilators. Chest. 1988 Oct;94(4):763-6. [PubMed
]
- 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
]
|