DT-Web

DB08808 - Bupranolol


Identification
Name Bupranolol
Accession Number DB08808
Type small molecule
Description Bupranolol is a non-selective beta blocker without intrinsic sympathomimetic activity (ISA), but with strong membrane stabilizing activity. Its potency is similar to "propranolol":http://www.drugbank.ca/drugs/DB00571.
Structure
MOL SDF PDB SMILES InChI
Categories (*)
Molecular Weight 271.783
Groups approved
Monoisotopic Weight 271.13390666
Pharmacology
Indication Used to manage hypertension and tachycardia. Also used to treat glaucoma.
Mechanism of action Bupranolol competes with sympathomimetic neurotransmitters such as catecholamines for binding at beta(1)-adrenergic receptors in the heart, inhibiting sympathetic stimulation. This results in a reduction in resting heart rate, cardiac output, systolic and diastolic blood pressure, and reflex orthostatic hypotension.
Absorption Quickly and completely absorbed from the gut with less than 10% oral bioavailability.
Protein binding 76%
Biotransformation Over 90% undergo first-pass metabolism. The main metabolite is carboxybupranolol, 4-chloro-3-[3-(1,1-dimethylethylamino)-2-hydroxy-propyloxy]benzoic acid, of which 88% are eliminated renally within 24 hours.
Route of elimination Not Available
Toxicity Symptoms of overdose include bradycardia, cardiac failure, hypotension, and brochospasm.
Affected organisms
  • Humans and other mammals
Interactions
Drug Interactions Not Available
Food Interactions Not Available

Targets


Beta-1 adrenergic receptor
Name Beta-1 adrenergic receptor
Gene Name ADRB1
Pharmacological action yes
Actions antagonist
References
  • Zelaszczyk D, Kozlowska H, Baranowska U, Baranowska M, Reutelsterz A, Kiec-Kononowicz K, Malinowska B, Schlicker E: Four close bupranolol analogues are antagonists at the low-affinity state of beta1-adrenoceptors. J Physiol Pharmacol. 2009 Mar;60(1):51-60. - Pubmed
DTHybrid score 0.8463
Beta-2 adrenergic receptor
Name Beta-2 adrenergic receptor
Gene Name ADRB2
Pharmacological action unknown
Actions antagonist
References
  • Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. - Pubmed
DTHybrid score 0.8484
Beta-3 adrenergic receptor
Name Beta-3 adrenergic receptor
Gene Name ADRB3
Pharmacological action unknown
Actions antagonist
References
  • Lenard NR, Gettys TW, Dunn AJ: Activation of beta2- and beta3-adrenergic receptors increases brain tryptophan. J Pharmacol Exp Ther. 2003 May;305(2):653-9. Epub 2003 Jan 24. - Pubmed
  • Matsushita M, Horinouchi T, Tanaka Y, Tsuru H, Koike K: Characterization of beta 3-adrenoceptor-mediated relaxation in rat abdominal aorta smooth muscle. Eur J Pharmacol. 2003 Dec 15;482(1-3):235-44. - Pubmed
DTHybrid score 0.4271

Predictions


Id Partner name Gene Name Score
4119 Cytochrome P450 2D6 CYP2D6 0.1188
320 5-hydroxytryptamine 1A receptor HTR1A 0.073
556 Alpha-1A adrenergic receptor ADRA1A 0.0678
1588 Multidrug resistance protein 1 ABCB1 0.0607
885 5-hydroxytryptamine 1B receptor HTR1B 0.0527
318 Alpha-2A adrenergic receptor ADRA2A 0.0526
4200 Cytochrome P450 1A2 CYP1A2 0.0462
4512 Cytochrome P450 3A4 CYP3A4 0.0452
1820 Beta-nerve growth factor NGF 0.0449
6144 Solute carrier family 22 member 2 SLC22A2 0.0422
6024 Cytochrome P450 1A1 CYP1A1 0.0421
629 Alpha-2B adrenergic receptor ADRA2B 0.0416
4146 Phosphatidylinositol 3-kinase regulatory subunit gamma PIK3R3 0.0408
4145 Phosphatidylinositol 3-kinase regulatory subunit beta PIK3R2 0.0408
378 Alpha-2C adrenergic receptor ADRA2C 0.0384
3923 Cholinesterase BCHE 0.0377
540 Sodium-dependent noradrenaline transporter SLC6A2 0.0372
1281 Phosphatidylinositol 3-kinase regulatory subunit alpha PIK3R1 0.0345
1181 Alpha-1-acid glycoprotein 1 ORM1 0.0343
632 Alpha-1B adrenergic receptor ADRA1B 0.0335
828 Phenylalanine-4-hydroxylase PAH 0.0319
3109 Phenylalanine-4-hydroxylase phhA 0.0319
777 Tumor necrosis factor TNF 0.0293
6016 Cytochrome P450 2C19 CYP2C19 0.0283
101 Potassium voltage-gated channel subfamily H member 2 KCNH2 0.0262
789 Alpha-1D adrenergic receptor ADRA1D 0.026
2300 Lysozyme E 0.0243
3633 Lysozyme R 0.0243
5597 Lysozyme 17 0.0243
1176 Mitogen-activated protein kinase 1 MAPK1 0.023
6145 Solute carrier family 22 member 1 SLC22A1 0.0229
3941 Amine oxidase [flavin-containing] A MAOA 0.0228
3810 Catechol O-methyltransferase COMT 0.0211
824 Sodium-dependent serotonin transporter SLC6A4 0.0189
713 Sodium-dependent dopamine transporter SLC6A3 0.0182
6164 POU domain, class 5, transcription factor 1 POU5F1 0.0164
6040 6-phosphogluconate dehydrogenase, decarboxylating PGD 0.016
131 Synaptic vesicular amine transporter SLC18A2 0.0153
3876 Aromatic-L-amino-acid decarboxylase DDC 0.0146
6147 Solute carrier family 22 member 3 SLC22A3 0.0128
118 Organic cation/carnitine transporter 2 SLC22A5 0.0124
6107 Cytochrome P450 3A7 CYP3A7 0.0124
4292 Acyl-[acyl-carrier-protein]--UDP-N-acetylglucosamine O-acyltransferase lpxA 0.0124
4757 Cytochrome P450 2C9 CYP2C9 0.0123
3939 Amine oxidase [flavin-containing] B MAOB 0.0122
3076 Antigen 85-C fbpC 0.0122
4118 Cytochrome P450 3A5 CYP3A5 0.0117
6151 Monocarboxylate transporter 10 SLC16A10 0.0108
5718 Cytochrome P450 2A6 CYP2A6 0.0103
6139 Solute carrier organic anion transporter family member 1A2 SLCO1A2 0.0095
587 Serum albumin ALB 0.0093
6847 Lactase-phlorizin hydrolase LCT 0.0093
23 D(1A) dopamine receptor DRD1 0.0064
6022 UDP-glucuronosyltransferase 1-1 UGT1A1 0.0063
1374 Natriuretic peptides B NPPB 0.0061
1827 Gap junction alpha-1 protein GJA1 0.0061
1908 Vascular cell adhesion protein 1 VCAM1 0.0061
194 NADH dehydrogenase [ubiquinone] 1 subunit C2 NDUFC2 0.005
4924 Cytochrome P450 2C8 CYP2C8 0.005
183 Vascular endothelial growth factor A VEGFA 0.0045
1360 Sphingomyelin phosphodiesterase SMPD1 0.0036
6013 Cytochrome P450 2E1 CYP2E1 0.0036
502 5-hydroxytryptamine 2A receptor HTR2A 0.0036
492 Histamine H1 receptor HRH1 0.0035
3947 Xanthine dehydrogenase/oxidase XDH 0.0032
1256 5-hydroxytryptamine 6 receptor HTR6 0.003
6025 UDP-glucuronosyltransferase 1-4 UGT1A4 0.0029
124 Histamine H2 receptor HRH2 0.0028
465 Calmodulin CALM1 0.0028
716 5-hydroxytryptamine 7 receptor HTR7 0.0028
6432 Transporter snf 0.0027
4160 Voltage-dependent calcium channel subunit alpha-2/delta-2 CACNA2D2 0.0027
436 5-hydroxytryptamine 2B receptor HTR2B 0.0026
432 D(4) dopamine receptor DRD4 0.0025
964 Voltage-dependent T-type calcium channel subunit alpha-1H CACNA1H 0.0025
638 D(3) dopamine receptor DRD3 0.0024
20 Prostaglandin G/H synthase 1 PTGS1 0.0024
233 Potassium channel subfamily K member 2 KCNK2 0.0023
590 5-hydroxytryptamine 2C receptor HTR2C 0.0023
831 D(2) dopamine receptor DRD2 0.002
4114 Voltage-dependent L-type calcium channel subunit beta-3 CACNB3 0.0019
4112 Voltage-dependent L-type calcium channel subunit beta-4 CACNB4 0.0019
6106 Cytochrome P450 2C18 CYP2C18 0.0019
274 Muscarinic acetylcholine receptor M5 CHRM5 0.0019
833 Organic cation/carnitine transporter 1 SLC22A4 0.0019
450 Muscarinic acetylcholine receptor M4 CHRM4 0.0018
4113 Voltage-dependent L-type calcium channel subunit alpha-1F CACNA1F 0.0018
333 Voltage-dependent L-type calcium channel subunit beta-1 CACNB1 0.0017
158 Sodium channel protein type 1 subunit alpha SCN1A 0.0017
51 Muscarinic acetylcholine receptor M3 CHRM3 0.0016
617 Muscarinic acetylcholine receptor M2 CHRM2 0.0016
103 Muscarinic acetylcholine receptor M1 CHRM1 0.0015
4110 Voltage-dependent L-type calcium channel subunit beta-2 CACNB2 0.0015
4115 Voltage-dependent L-type calcium channel subunit alpha-1D CACNA1D 0.0015
4111 Voltage-dependent L-type calcium channel subunit alpha-1S CACNA1S 0.0015
478 Voltage-dependent L-type calcium channel subunit alpha-1C CACNA1C 0.0014
6030 Cytochrome P450 2B6 CYP2B6 0.0014
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