Propranolol
beta-adrenergic antagonist, an anxiolytic drug, an anti-arrhythmia drug, a vasodilator agent, an antihypertensive agent. Propranolol is a racemic mixture of 2 enantiomers where the S(-)-enantiomer has approximately 100 times the binding affinity for beta adrenergic receptors. Propranolol is used to treat a number of conditions but most commonly is used for hypertension. Acetylcholinesterase has a greater affinity for the L-isomer than either the racemate or the D-isomer IC50 in the MM range. In contrast the plasma cholinesterases have greater specificity for the D-isomer than the other isomer or racemate. IC50 in the sub micromolar range
General
Type : Naphthalen, Adrenergic-Receptor-ligand, Multitarget, Drug
Chemical_Nomenclature : 1-naphthalen-1-yloxy-3-(propan-2-ylamino)propan-2-ol
Canonical SMILES : CC(C)NCC(COC1=CC=CC2=CC=CC=C21)O
InChI : InChI=1S\/C16H21NO2\/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16\/h3-9,12,14,17-18H,10-11H2,1-2H3
InChIKey : AQHHHDLHHXJYJD-UHFFFAOYSA-N
Other name(s) : beta-Propranolol || Betalong || Propanolol || Euprovasin || Proprasylyt || Reducor
MW : 259.339
Formula : C16H21NO2
CAS_number : 525-66-6
PubChem : 4946
UniChem : AQHHHDLHHXJYJD-UHFFFAOYSA-N
Target
Families : Propranolol ligand of proteins in family
BCHE
Protein :
human-BCHE
References (21)
| Title : From heart to brain: cognitive potential of propranolol and diltiazem through cholinergic enhancement via butyrylcholinesterase inhibition - Dominguez-Fernandez_2025_Front.Pharmacol_16_1694610 |
| Author(s) : Dominguez-Fernandez C , Kumar A , Kumar R , Darreh-Shori T |
| Ref : Front Pharmacol , 16 :1694610 , 2025 |
| Abstract : |
| PubMedSearch : Dominguez-Fernandez_2025_Front.Pharmacol_16_1694610 |
| PubMedID: 41322300 |
| Title : From heart to brain: cognitive potential of propranolol and diltiazem through cholinergic enhancement via butyrylcholinesterase inhibition - Dominguez-Fernandez_2025_Front.Pharmacol_16_1694610 |
| Author(s) : Dominguez-Fernandez C , Kumar A , Kumar R , Darreh-Shori T |
| Ref : Front Pharmacol , 16 :1694610 , 2025 |
| Abstract : |
| PubMedSearch : Dominguez-Fernandez_2025_Front.Pharmacol_16_1694610 |
| PubMedID: 41322300 |
| Title : From heart to brain: cognitive potential of propranolol and diltiazem through cholinergic enhancement via butyrylcholinesterase inhibition - Dominguez-Fernandez_2025_Front.Pharmacol_16_1694610 |
| Author(s) : Dominguez-Fernandez C , Kumar A , Kumar R , Darreh-Shori T |
| Ref : Front Pharmacol , 16 :1694610 , 2025 |
| Abstract : |
| PubMedSearch : Dominguez-Fernandez_2025_Front.Pharmacol_16_1694610 |
| PubMedID: 41322300 |
| Title : Finite-temperature effect in the O-acylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B - Valderrama_2021_J.Mol.Graph.Model_107_107951 |
| Author(s) : Valderrama DIB , Daza MC , Doerr M |
| Ref : J Mol Graph Model , 107 :107951 , 2021 |
| Abstract : |
| PubMedSearch : Valderrama_2021_J.Mol.Graph.Model_107_107951 |
| PubMedID: 34111759 |
| Gene_locus related to this paper: canar-LipB |
| Title : Effect of the acyl-group length on the chemoselectivity of the lipase-catalyzed acylation of propranolol-a computational study - Doerr_2021_J.Mol.Model_27_198 |
| Author(s) : Doerr M , Romero A , Daza MC |
| Ref : J Mol Model , 27 :198 , 2021 |
| Abstract : |
| PubMedSearch : Doerr_2021_J.Mol.Model_27_198 |
| PubMedID: 34115202 |
| Gene_locus related to this paper: canar-LipB |
| Title : Effect of the acyl-group length on the chemoselectivity of the lipase-catalyzed acylation of propranolol-a computational study - Doerr_2021_J.Mol.Model_27_198 |
| Author(s) : Doerr M , Romero A , Daza MC |
| Ref : J Mol Model , 27 :198 , 2021 |
| Abstract : |
| PubMedSearch : Doerr_2021_J.Mol.Model_27_198 |
| PubMedID: 34115202 |
| Gene_locus related to this paper: canar-LipB |
| Title : Effect of the acyl-group length on the chemoselectivity of the lipase-catalyzed acylation of propranolol-a computational study - Doerr_2021_J.Mol.Model_27_198 |
| Author(s) : Doerr M , Romero A , Daza MC |
| Ref : J Mol Model , 27 :198 , 2021 |
| Abstract : |
| PubMedSearch : Doerr_2021_J.Mol.Model_27_198 |
| PubMedID: 34115202 |
| Gene_locus related to this paper: canar-LipB |
| Title : Finite-temperature effect in the O-acylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B - Valderrama_2021_J.Mol.Graph.Model_107_107951 |
| Author(s) : Valderrama DIB , Daza MC , Doerr M |
| Ref : J Mol Graph Model , 107 :107951 , 2021 |
| Abstract : |
| PubMedSearch : Valderrama_2021_J.Mol.Graph.Model_107_107951 |
| PubMedID: 34111759 |
| Gene_locus related to this paper: canar-LipB |
| Title : Finite-temperature effect in the O-acylation of (R,S)-propranolol catalyzed by Candida antarctica lipase B - Valderrama_2021_J.Mol.Graph.Model_107_107951 |
| Author(s) : Valderrama DIB , Daza MC , Doerr M |
| Ref : J Mol Graph Model , 107 :107951 , 2021 |
| Abstract : |
| PubMedSearch : Valderrama_2021_J.Mol.Graph.Model_107_107951 |
| PubMedID: 34111759 |
| Gene_locus related to this paper: canar-LipB |
| Title : Effects of hexamethonium, phenothiazines, propranolol and ephedrine on acetylcholinesterase carbamylation by physostigmine, aldicarb and carbaryl: interaction between the active site and the functionally distinct peripheral sites in acetylcholinesterase - Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97 |
| Author(s) : Singh AK , Spassova D |
| Ref : Comparative Biochemistry & Physiology C Pharmacology Toxicology & Endocrinology , 119 :97 , 1998 |
| Abstract : |
| PubMedSearch : Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97 |
| PubMedID: 9568379 |
| Title : Effects of hexamethonium, phenothiazines, propranolol and ephedrine on acetylcholinesterase carbamylation by physostigmine, aldicarb and carbaryl: interaction between the active site and the functionally distinct peripheral sites in acetylcholinesterase - Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97 |
| Author(s) : Singh AK , Spassova D |
| Ref : Comparative Biochemistry & Physiology C Pharmacology Toxicology & Endocrinology , 119 :97 , 1998 |
| Abstract : |
| PubMedSearch : Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97 |
| PubMedID: 9568379 |
| Title : Effects of hexamethonium, phenothiazines, propranolol and ephedrine on acetylcholinesterase carbamylation by physostigmine, aldicarb and carbaryl: interaction between the active site and the functionally distinct peripheral sites in acetylcholinesterase - Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97 |
| Author(s) : Singh AK , Spassova D |
| Ref : Comparative Biochemistry & Physiology C Pharmacology Toxicology & Endocrinology , 119 :97 , 1998 |
| Abstract : |
| PubMedSearch : Singh_1998_Comp.Biochem.Physiol.C.Pharmacol.Toxicol.Endocrinol_119_97 |
| PubMedID: 9568379 |
| Title : Differential reactivity of active sites in human plasma cholinesterase toward 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide - Ozer_1987_Arch.Biochem.Biophys_255_89 |
| Author(s) : Ozer N , Ozer I |
| Ref : Archives of Biochemistry & Biophysics , 255 :89 , 1987 |
| Abstract : |
| PubMedSearch : Ozer_1987_Arch.Biochem.Biophys_255_89 |
| PubMedID: 3592672 |
| Title : Differential reactivity of active sites in human plasma cholinesterase toward 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide - Ozer_1987_Arch.Biochem.Biophys_255_89 |
| Author(s) : Ozer N , Ozer I |
| Ref : Archives of Biochemistry & Biophysics , 255 :89 , 1987 |
| Abstract : |
| PubMedSearch : Ozer_1987_Arch.Biochem.Biophys_255_89 |
| PubMedID: 3592672 |
| Title : Differential reactivity of active sites in human plasma cholinesterase toward 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide - Ozer_1987_Arch.Biochem.Biophys_255_89 |
| Author(s) : Ozer N , Ozer I |
| Ref : Archives of Biochemistry & Biophysics , 255 :89 , 1987 |
| Abstract : |
| PubMedSearch : Ozer_1987_Arch.Biochem.Biophys_255_89 |
| PubMedID: 3592672 |
| Title : Studies on the inhibition by propranolol of some human erythrocyte membrane enzymes and plasma cholinesterase - Whittaker_1982_Clin.Chim.Acta_119_107 |
| Author(s) : Whittaker M , Wicks RJ , Britten JJ |
| Ref : Clinica Chimica Acta , 119 :107 , 1982 |
| Abstract : |
| PubMedSearch : Whittaker_1982_Clin.Chim.Acta_119_107 |
| PubMedID: 6120772 |
| Title : Studies on the inhibition by propranolol of some human erythrocyte membrane enzymes and plasma cholinesterase - Whittaker_1982_Clin.Chim.Acta_119_107 |
| Author(s) : Whittaker M , Wicks RJ , Britten JJ |
| Ref : Clinica Chimica Acta , 119 :107 , 1982 |
| Abstract : |
| PubMedSearch : Whittaker_1982_Clin.Chim.Acta_119_107 |
| PubMedID: 6120772 |
| Title : Studies on the inhibition by propranolol of some human erythrocyte membrane enzymes and plasma cholinesterase - Whittaker_1982_Clin.Chim.Acta_119_107 |
| Author(s) : Whittaker M , Wicks RJ , Britten JJ |
| Ref : Clinica Chimica Acta , 119 :107 , 1982 |
| Abstract : |
| PubMedSearch : Whittaker_1982_Clin.Chim.Acta_119_107 |
| PubMedID: 6120772 |
| Title : Inhibition of the plasma cholinesterase variants by propranolol - Whittaker_1981_Br.J.Anaesth_53_511 |
| Author(s) : Whittaker M , Britten JJ , Wicks RJ |
| Ref : British Journal of Anaesthesia , 53 :511 , 1981 |
| Abstract : |
| PubMedSearch : Whittaker_1981_Br.J.Anaesth_53_511 |
| PubMedID: 7236476 |
| Title : Inhibition of the plasma cholinesterase variants by propranolol - Whittaker_1981_Br.J.Anaesth_53_511 |
| Author(s) : Whittaker M , Britten JJ , Wicks RJ |
| Ref : British Journal of Anaesthesia , 53 :511 , 1981 |
| Abstract : |
| PubMedSearch : Whittaker_1981_Br.J.Anaesth_53_511 |
| PubMedID: 7236476 |
| Title : Inhibition of the plasma cholinesterase variants by propranolol - Whittaker_1981_Br.J.Anaesth_53_511 |
| Author(s) : Whittaker M , Britten JJ , Wicks RJ |
| Ref : British Journal of Anaesthesia , 53 :511 , 1981 |
| Abstract : |
| PubMedSearch : Whittaker_1981_Br.J.Anaesth_53_511 |
| PubMedID: 7236476 |