bupranolol   Click here for help

GtoPdb Ligand ID: 550

Synonyms: Betadrenol® | BRN 2272923 | Ophtorenin® | SK&F 16805-A
Approved drug
bupranolol is an approved drug
Compound class: Synthetic organic
Comment: Bupranolol is a β-adrenoceptor antagonist (beta blocker) with a similar potency to propranolol.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 2
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 41.49
Molecular weight 271.13
XLogP 3.24
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES OC(COc1cc(C)ccc1Cl)CNC(C)(C)C
Isomeric SMILES OC(COc1cc(C)ccc1Cl)CNC(C)(C)C
InChI InChI=1S/C14H22ClNO2/c1-10-5-6-12(15)13(7-10)18-9-11(17)8-16-14(2,3)4/h5-7,11,16-17H,8-9H2,1-4H3
1. Baker JG. (2005)
The selectivity of beta-adrenoceptor antagonists at the human beta1, beta2 and beta3 adrenoceptors.
Br J Pharmacol, 144 (3): 317-22. [PMID:15655528]
2. Blin N, Camoin L, Maigret B, Strosberg AD. (1993)
Structural and conformational features determining selective signal transduction in the beta 3-adrenergic receptor.
Mol Pharmacol, 44 (6): 1094-104. [PMID:7903415]
3. Candelore MR, Deng L, Tota L, Guan XM, Amend A, Liu Y, Newbold R, Cascieri MA, Weber AE. (1999)
Potent and selective human beta(3)-adrenergic receptor antagonists.
J Pharmacol Exp Ther, 290 (2): 649-55. [PMID:10411574]
4. Louis SN, Nero TL, Iakovidis D, Jackman GP, Louis WJ. (1999)
LK 204-545, a highly selective beta1-adrenoceptor antagonist at human beta-adrenoceptors.
Eur J Pharmacol, 367 (2-3): 431-5. [PMID:10079020]
5. Méjean A, Guillaume JL, Strosberg AD. (1995)
Carazolol: a potent, selective beta 3-adrenoceptor agonist.
Eur J Pharmacol, 291 (3): 359-66. [PMID:8719421]
6. Obara K, Shigematsu M, Takahasi H, Iiboshi Y, Yoshioka K, Kasuya Y, Tanaka Y. (2020)
Pharmacological properties of β-adrenoceptors mediating rat superior mesenteric artery relaxation and the effects of chemical sympathetic denervation.
Life Sci, 241: 117155. [PMID:31837330]