DT-Web

DB00816 - Orciprenaline


Identification
Name Orciprenaline
Accession Number DB00816 (APRD00210)
Type small molecule
Description A beta-adrenergic agonist used in the treatment of asthma and bronchospasms. [PubChem]
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 211.2576
Groups approved
Monoisotopic Weight 211.120843415
Pharmacology
Indication For the treatment of bronchospasm, chronic bronchitis, asthma, and emphysema.
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%)
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.
Route of elimination 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
Interactions
Drug Interactions
Drug Mechanism of interaction
Acebutolol Antagonism
Alseroxylon Increased arterial pressure
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of orciprenaline.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of orciprenaline.
Atenolol Antagonism
Betaxolol Beta-Blockers (Beta1 Selective) like betaxolol may diminish the bronchodilatory effect of Beta2-Agonists like orciprenaline. Therapy should be monitored.
Bevantolol Antagonism
Bisoprolol Antagonism
Carteolol Antagonism
Carvedilol Antagonism
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of orciprenaline.
Deserpidine Increased arterial pressure
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of orciprenaline.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of orciprenaline.
Esmolol Antagonism
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of orciprenaline.
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 of orciprenaline.
Nadolol Antagonism
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of orciprenaline.
Oxprenolol Antagonism
Pargyline Increased arterial pressure
Penbutolol Antagonism
Phenelzine Increased arterial pressure
Pindolol Antagonism
Practolol Antagonism
Propranolol Antagonism
Protriptyline The tricyclic antidepressant, protriptyline, increases the sympathomimetic effect of orciprenaline.
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Sotalol Antagonism
Timolol Antagonism
Tranylcypromine Increased arterial pressure
Trimipramine The tricyclic antidepressant, trimipramine, increases the sympathomimetic effect of orciprenaline.
Food Interactions
  • Take without regard to meals.
  • Avoid high doses of caffeine.

Targets


Beta-2 adrenergic receptor
Name Beta-2 adrenergic receptor
Gene Name ADRB2
Pharmacological action yes
Actions agonist
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
  • Gelmont DM, Balmes JR, Yee A: Hypokalemia induced by inhaled bronchodilators. Chest. 1988 Oct;94(4):763-6. - Pubmed
  • Fitch KD: The use of anti-asthmatic drugs. Do they affect sports performance? Sports Med. 1986 Mar-Apr;3(2):136-50. - 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
  • 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
  • Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. - Pubmed
DTHybrid score 0.4603

Predictions


Id Partner name Gene Name Score
193 Beta-1 adrenergic receptor ADRB1 0.2195
1517 Beta-3 adrenergic receptor ADRB3 0.0648
4119 Cytochrome P450 2D6 CYP2D6 0.0544
556 Alpha-1A adrenergic receptor ADRA1A 0.0293
3923 Cholinesterase BCHE 0.028
320 5-hydroxytryptamine 1A receptor HTR1A 0.0245
1588 Multidrug resistance protein 1 ABCB1 0.0209
4512 Cytochrome P450 3A4 CYP3A4 0.0204
2300 Lysozyme E 0.0191
3633 Lysozyme R 0.0191
5597 Lysozyme 17 0.0191
318 Alpha-2A adrenergic receptor ADRA2A 0.0186
6144 Solute carrier family 22 member 2 SLC22A2 0.0169
6040 6-phosphogluconate dehydrogenase, decarboxylating PGD 0.016
6016 Cytochrome P450 2C19 CYP2C19 0.0147
885 5-hydroxytryptamine 1B receptor HTR1B 0.0137
4200 Cytochrome P450 1A2 CYP1A2 0.0125
629 Alpha-2B adrenergic receptor ADRA2B 0.0113
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.0109
3810 Catechol O-methyltransferase COMT 0.0101
632 Alpha-1B adrenergic receptor ADRA1B 0.01
6145 Solute carrier family 22 member 1 SLC22A1 0.01
378 Alpha-2C adrenergic receptor ADRA2C 0.0096
5718 Cytochrome P450 2A6 CYP2A6 0.0094
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0089
4757 Cytochrome P450 2C9 CYP2C9 0.0088
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0086
6024 Cytochrome P450 1A1 CYP1A1 0.0081
1820 Beta-nerve growth factor NGF 0.0081
4146 Phosphatidylinositol 3-kinase regulatory subunit gamma PIK3R3 0.0074
4145 Phosphatidylinositol 3-kinase regulatory subunit beta PIK3R2 0.0074
828 Phenylalanine-4-hydroxylase PAH 0.0071
3109 Phenylalanine-4-hydroxylase phhA 0.0071
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0063
1281 Phosphatidylinositol 3-kinase regulatory subunit alpha PIK3R1 0.006
789 Alpha-1D adrenergic receptor ADRA1D 0.0057
824 Sodium-dependent serotonin transporter SLC6A4 0.0057
777 Tumor necrosis factor TNF 0.0054
6107 Cytochrome P450 3A7 CYP3A7 0.0051
713 Sodium-dependent dopamine transporter SLC6A3 0.0051
3941 Amine oxidase [flavin-containing] A MAOA 0.0051
6147 Solute carrier family 22 member 3 SLC22A3 0.005
4118 Cytochrome P450 3A5 CYP3A5 0.0049
1176 Mitogen-activated protein kinase 1 MAPK1 0.004
118 Organic cation/carnitine transporter 2 SLC22A5 0.0038
4924 Cytochrome P450 2C8 CYP2C8 0.0036
1374 Natriuretic peptides B NPPB 0.0029
6164 POU domain, class 5, transcription factor 1 POU5F1 0.0029
1827 Gap junction alpha-1 protein GJA1 0.0029
1908 Vascular cell adhesion protein 1 VCAM1 0.0029
131 Synaptic vesicular amine transporter SLC18A2 0.0028
465 Calmodulin CALM1 0.0028
3876 Aromatic-L-amino-acid decarboxylase DDC 0.0026
194 NADH dehydrogenase [ubiquinone] 1 subunit C2 NDUFC2 0.0024
183 Vascular endothelial growth factor A VEGFA 0.0022
3939 Amine oxidase [flavin-containing] B MAOB 0.0022
6151 Monocarboxylate transporter 10 SLC16A10 0.0019
1360 Sphingomyelin phosphodiesterase SMPD1 0.0018
6013 Cytochrome P450 2E1 CYP2E1 0.0018
502 5-hydroxytryptamine 2A receptor HTR2A 0.0017
492 Histamine H1 receptor HRH1 0.0017
3947 Xanthine dehydrogenase/oxidase XDH 0.0015
1256 5-hydroxytryptamine 6 receptor HTR6 0.0015
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0014
124 Histamine H2 receptor HRH2 0.0013
716 5-hydroxytryptamine 7 receptor HTR7 0.0013
6432 Transporter snf 0.0013
436 5-hydroxytryptamine 2B receptor HTR2B 0.0012
432 D(4) dopamine receptor DRD4 0.0012
638 D(3) dopamine receptor DRD3 0.0012
20 Prostaglandin G/H synthase 1 PTGS1 0.0012
590 5-hydroxytryptamine 2C receptor HTR2C 0.0011
23 D(1A) dopamine receptor DRD1 0.001
831 D(2) dopamine receptor DRD2 0.001
6106 Cytochrome P450 2C18 CYP2C18 0.0009
274 Muscarinic acetylcholine receptor M5 CHRM5 0.0009
833 Organic cation/carnitine transporter 1 SLC22A4 0.0009
450 Muscarinic acetylcholine receptor M4 CHRM4 0.0009
51 Muscarinic acetylcholine receptor M3 CHRM3 0.0008
617 Muscarinic acetylcholine receptor M2 CHRM2 0.0008
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0007
6030 Cytochrome P450 2B6 CYP2B6 0.0007
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