PROPRANOLOL

First approved in 1967

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H21NO2
Molecular Weight	259.3434
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)NCC(O)COC1=C2C=CC=CC2=CC=C1

InChI

InChIKey=AQHHHDLHHXJYJD-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H21NO2
Molecular Weight	259.3434
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25198737 https://www.ncbi.nlm.nih.gov/pubmed/2865152

Propranolol is a nonselective, beta-adrenergic receptor-blocking agent possessing no other autonomic nervous system activity. At dosages greater than required for beta blockade, propranolol also exerts a quinidine-like or anesthetic-like membrane action, which affects the cardiac action potential. Among the factors that may be involved in contributing to the antihypertensive action include: (1) decreased cardiac output, (2) inhibition of renin release by the kidneys, and (3) diminution of tonic sympathetic nerve outflow from vasomotor centers in the brain. Although total peripheral resistance may increase initially, it readjusts to or below the pretreatment level with chronic use of propranolol. Effects of propranolol on plasma volume appear to be minor and somewhat variable. In angina pectoris, propranolol generally reduces the oxygen requirement of the heart at any given level of effort by blocking the catecholamine-induced increases in the heart rate, systolic blood pressure, and the velocity and extent of myocardial contraction. Propranolol may increase oxygen requirements by increasing left ventricular fiber length, end diastolic pressure, and systolic ejection period. The net physiologic effect of beta-adrenergic blockade is usually advantageous and is manifested during exercise by delayed onset of pain and increased work capacity. Propranolol exerts its antiarrhythmic effects in concentrations associated with beta-adrenergic blockade, and this appears to be its principal antiarrhythmic mechanism of action. In dosages greater than required for beta blockade, propranolol also exerts a quinidine-like or anesthetic-like membrane action, which affects the cardiac action potential. The significance of the membrane action in the treatment of arrhythmias is uncertain. The mechanism of the anti-migraine effect of propranolol has not been established. Propranolol is indicated in the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Also is indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris; for the prophylaxis of common migraine headache. In addition, is used to improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis. Due to the high penetration across the blood–brain barrier, propranolol causes sleep disturbances such as insomnia and vivid dreams, and nightmares. Dreaming (rapid eye movement sleep, REM) was reduced and increased awakening.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor beta 89 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6121573	Antagonist 2849

Conditions

Condition	Modality	Highest Phase	Product
hypertension 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Approved 8583	INDERAL LA Approved Use Propranolol hydrochloride extended-release capsules are indicated for the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Propranolol hydrochloride extended-release capsules are not indicated for the management of hypertensive emergencies. Due to Coronary Atherosclerosis Propranolol hydrochloride extended-release capsules are indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris. Propranolol hydrochloride extended-release capsules are indicated for the prophylaxis of a common migraine headache. The efficacy of propranolol in the treatment of a migraine attack that has started has not been established, and propranolol is not indicated for such use. Propranolol hydrochloride extended-release capsules improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis. Launch Date 1987
Angina pectoris 110 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Approved 8583	INDERAL LA Approved Use Propranolol hydrochloride extended-release capsules are indicated in the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Propranolol hydrochloride extended-release capsules is not indicated in the management of hypertensive emergencies. Due to Coronary Atherosclerosis Propranolol hydrochloride extended-release capsules are indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris. Propranolol hydrochloride extended-release capsules are indicated for the prophylaxis of common migraine headache. The efficacy of propranolol in the treatment of a migraine attack that has started has not been established, and propranolol is not indicated for such use. Propranolol hydrochloride extended-release capsules improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis. Launch Date 1987
Migraine 107 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Preventing	Approved 8583	INDERAL LA Approved Use Propranolol hydrochloride extended-release capsules are indicated in the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Propranolol hydrochloride extended-release capsules is not indicated in the management of hypertensive emergencies. Due to Coronary Atherosclerosis Propranolol hydrochloride extended-release capsules are indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris. Propranolol hydrochloride extended-release capsules are indicated for the prophylaxis of common migraine headache. The efficacy of propranolol in the treatment of a migraine attack that has started has not been established, and propranolol is not indicated for such use. Propranolol hydrochloride extended-release capsules improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis. Launch Date 1987
Hypertrophic subaortic stenosis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Approved 8583	INDERAL LA Approved Use Propranolol hydrochloride extended-release capsules are indicated in the management of hypertension. It may be used alone or used in combination with other antihypertensive agents, particularly a thiazide diuretic. Propranolol hydrochloride extended-release capsules is not indicated in the management of hypertensive emergencies. Due to Coronary Atherosclerosis Propranolol hydrochloride extended-release capsules are indicated to decrease angina frequency and increase exercise tolerance in patients with angina pectoris. Propranolol hydrochloride extended-release capsules are indicated for the prophylaxis of common migraine headache. The efficacy of propranolol in the treatment of a migraine attack that has started has not been established, and propranolol is not indicated for such use. Propranolol hydrochloride extended-release capsules improve NYHA functional class in symptomatic patients with hypertrophic subaortic stenosis. Launch Date 1987

C_max

Value	Dose	Analyte	Population
147 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9698776/	40 mg single, sublingual dose: 40 mg route of administration: Sublingual experiment type: SINGLE co-administered:	PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
41 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9698776/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
161 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/016418s080,016762s017,017683s008lbl.pdf	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
47 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/016418s080,016762s017,017683s008lbl.pdf	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
26 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/016418s080,016762s017,017683s008lbl.pdf	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	PROPRANOLOL plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
245 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9698776/	40 mg single, sublingual dose: 40 mg route of administration: Sublingual experiment type: SINGLE co-administered:		PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
79 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9698776/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.91 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9698776/	40 mg single, sublingual dose: 40 mg route of administration: Sublingual experiment type: SINGLE co-administered:		PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
2.41 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9698776/	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:		PROPRANOLOL plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193 inhibitor 2438	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 1057 CYP2B6 926 CYP1A1 132 CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060 ALDH1 41 OCT1 620 OCT2 779 BSEP 550 MRP2 499 MRP3 246 MRP4 290 OATP1B1 1079 OATP1B3 961 OATP2B1 157 BCRP 910 NTCP 39 Cav1.2 58 Nav1.5 116	CYP1A2 1197 CYP2C19 1119 CYP1A1 389 CYP2A6 626 CYP2B6 776 CYP2E1 729 CYP2C8 810 CYP4A11 137 OCT2 434 UGT 219 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A9 423 UGT2B4 278 UGT2B7 456 UGT2B10 131 UGT2B15 236 SULT1A1 37 SULT1A3 31 SULT1E1 22 SULT2A1 28 MRP2 252 MRP3 58 MRP4 91 BCRP 697

Drug as perpetrator

Target	Modality	Activity
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/, https://pubmed.ncbi.nlm.nih.gov/23956101/	likely [IC50 >133 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	likely
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	likely
OATP2B1 162	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	likely
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjcifX0%3D	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >1000 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 345	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19421845/	no
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	no
ALDH1 41	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE2NzEifX0%3D	yes [Activation 28.1838 uM]
OCT2 782	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/19251820/, https://pubmed.ncbi.nlm.nih.gov/19002438/	yes [IC50 189 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/8474022/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	yes [IC50 4 uM]
NTCP 40	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10565843/, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1Mjg3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	yes [Inhibition 5.5 uM]
CYP1A1 272	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/8474022/	yes
CYP2D6 2546	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/9342584/	yes
OCT1 656	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/18788725/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205410s000lbl.pdf#page=5 Page: (Label) 5, 7-8	major		yes (co-administration study) Comment: Coadminstration of CYP1A2 inhibitors increased Propranolol plasma concentration. Coadministration of CYP1A2 inducers decreased Propranolol plasma concentration. Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205410s000lbl.pdf#page=5 Page: (Label) 5, 7-8
CYP2D6 1388	substrate 4014 Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205410s000lbl.pdf#page=5 Page: (Label) 5, 7-8	major		yes (co-administration study) Comment: Coadminstration of CYP2D6 inhibitors increased Propranolol plasma concentration. Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205410s000lbl.pdf#page=5 Page: (Label) 5, 7-8
CYP2C19 1119	substrate 4014 Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205410s000lbl.pdf#page=5 Page: (Label) 5, 7-8	minor		yes (co-administration study) Comment: Coadminstration of CYP2C19 inhibitors increased Propranolol plasma concentration. Coadministration of CYP2C19 inducers decreased Propranolol plasma concentration. Sources: https://www.genome.jp/kegg/drug/br08309.html, https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205410s000lbl.pdf#page=5 Page: (Label) 5, 7-8
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	no	R-plopranolol glucuronide 3
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	no	S-plopranolol glucuronide 3
SULT2A1 28	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	no	4-hydroxypropranolol 3
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT2B10 131	substrate 4014 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MTYwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no
UGT2B15 236	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	R-plopranolol glucuronide 3
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	S-plopranolol glucuronide 3
MRP4 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	R-plopranolol glucuronide 3
MRP4 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	S-plopranolol glucuronide 3
OCT2 434	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/19251820/	yes [Km 11.8 uM]
MRP3 58	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	yes [Km 154 uM]	R-plopranolol glucuronide 3
MRP3 58	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	yes [Km 434 uM]	S-plopranolol glucuronide 3
SULT1A1 37	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
SULT1A3 31	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
SULT1E1 22	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
UGT 219	substrate 4014 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/21098645/	yes
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 63	inhibitor 2237 Sources: https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/abs/10.1002/jat.2784, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTQwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19
Nav1.5 119	inhibitor 2237 Sources: https://academic.oup.com/cardiovascres/article/91/1/53/333710, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTgwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/16150441/, https://academic.oup.com/cardiovascres/article/91/1/53/333710

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8499	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8499
ChemicalBook	CB0875381	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0875381
ChemicalBook	CB63039539	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB63039539
eMolecules	735071	https://www.emolecules.com/cgi-bin/more?vid=735071
MolPort	MolPort-001-794-623	https://www.molport.com/shop/molecule-link/MolPort-001-794-623

PubMed

Title	Date	PubMed
Central corticotropin releasing factor (CRF) and adrenergic receptors mediate hemodynamic responses to cocaine.	2001-03-02	11222986
Propranolol rapidly reverses paralysis, hypokalemia, and hypophosphatemia in thyrotoxic periodic paralysis.	2001-03	11228188
Catecholamines increase lung edema clearance in rats with increased left atrial pressure.	2001-03	11181624
Erythroid carbonic anhydrase and hsp70 expression in chick embryonic development: role of cAMP and hypoxia.	2001-03	11171668
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.	2001-02-16	11226401
Enhancement of memory consolidation in chicks by beta(3)-adrenoceptor agonists.	2001-02-16	11226398
Correlation of the electrical and intrinsic optical signals in the chicken spreading depression phenomenon.	2001-02-16	11166945
Interactions between phospholamban and beta-adrenergic drive may lead to cardiomyopathy and early mortality.	2001-02-13	11171800
Modulation of a 40-kDa catecholamine regulated protein by dopamine receptor antagonists.	2001-02-09	11173065
[Availability of antidotes in French emergency medical aid units].	2001-02-03	11229303
Mechanisms of the increased pressor response to vasopressors in the mesenteric bed of nitric oxide-deficient hypertensive rats.	2001-02-02	11166291
Effects of nebivolol on proliferation and apoptosis of human coronary artery smooth muscle and endothelial cells.	2001-02-01	11164853
Comparison of spontaneous and noradrenaline-evoked non-selective cation channels in rabbit portal vein myocytes.	2001-02-01	11158276
Efficacy and safety of out-of-hospital self-administered single-dose oral drug treatment in the management of infrequent, well-tolerated paroxysmal supraventricular tachycardia.	2001-02	11216977
Idiopathic sustained left ventricular tachycardia in pediatric patients.	2001-02	11207998
Periovulatory changes in catfish ovarian oestradiol-17beta, oestrogen-2-hydroxylase and catechol-O-methyltransferase during GnRH analogue-induced ovulation and in vitro induction of oocyte maturation by catecholoestrogens.	2001-02	11182761
Cellular cholesterol efflux is modulated by phospholipid-derived signaling molecules in familial HDL deficiency/Tangier disease fibroblasts.	2001-02	11181755
Pharmacologic therapy for portal hypertension.	2001-02	11177691
Pharmacologic management of atrial fibrillation: current therapeutic strategies.	2001-02	11174354
Epinephrine yields translocation of lymphocytes to the lung.	2001-02	11170785
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells.	2001-02	11160630
beta(2)-adrenoceptor agonists inhibit release of eosinophil-activating cytokines from human airway smooth muscle cells.	2001-02	11159726
Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats.	2001-02	11158985
beta-Adrenoceptor and nNOS-derived NO interactions modulate hypoglycemic pial arteriolar dilation in rats.	2001-02	11158952
Asymmetric synthesis and preliminary evaluation of (R)- and (S)-[11C]bisoprolol, a putative beta1-selective adrenoceptor radioligand.	2001-02	11137886
Ion-exchange fibers and drugs: an equilibrium study.	2001-01-29	11166422
Effect of carvedilol on atrioventricular conduction in the ischemic heart.	2001-01-26	11165226
Potent serotonin (5-HT)(2A) receptor antagonists completely prevent the development of hyperthermia in an animal model of the 5-HT syndrome.	2001-01-26	11164765
Effects of mono-, di- and tri-hydroxybenzoic acids on the nitrosation of propranolol: structure-activity relationship.	2001-01-25	11152975
Colon and anal sphincter contractions evoked by microstimulation of the sacral spinal cord in cats.	2001-01-19	11166684
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.	2001-01-12	11150484
Misrepresentation and miscommunication of teratogenic risk of drugs; analysis of three highly publicized international cases.	2001-01-04	11137372
Role of PAG in the antinociception evoked from the medial or central amygdala in rats.	2001-01-01	11226714
Daily variation of azygos and portal blood flow and the effect of propranolol administration once an evening in cirrhotics.	2001-01	11211903
Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations.	2001-01	11201505
Spectral analysis of circadian rhythms in heart rate variability of dogs.	2001-01	11197557
Abolition of (-)-CGP 12177-evoked cardiostimulation in double beta1/beta2-adrenoceptor knockout mice. Obligatory role of beta1-adrenoceptors for putative beta4-adrenoceptor pharmacology.	2001-01	11191841
Successful use of propranolol in migraine associated with electroconvulsive therapy.	2001-01	11168610
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.	2001-01	11159692
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes.	2001-01	11156573
Oxygen consumption in patients with hyperthyroidism before and after treatment with beta-blockade versus thyrostatic treatment: a prospective randomized study.	2001-01	11141226
Amiodarone is safe and highly effective therapy for supraventricular tachycardia in infants.	2001-01	11136494
Ventricular activation during sympathetic imbalance and its computational reconstruction.	2001-01	11133921
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium.	2001-01	11133877
Reactive oxygen species mediate alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes.	2001-01	11133229
[Effects of isoprenaline on apoptosis related gene expression in rat myocardium cells].	2000-11	11218852
[Recovery from pancytopenia and liver dysfunction after administration of thiamazole for hyperthyroidism].	2000-11	11193444
Attenuation of changes in sarcoplasmic reticular gene expression in cardiac hypertrophy by propranolol and verapamil.	2000-10	11129949
[Experimental anti-arrhythmic effects of a new beta-adrenergic receptor blocking agent, dl-l-(tert. butylamino)-3-[(2-propinyloxy)phenoxy]2-propanol hydrochloride (dl Kö 1400-Cl)].	1976-07	11153
Severe bradycardia after neostigmine in a patient taking propranolol to control paroxysmal atrial tachycardia.	1975-02	1115373

Patents

Sample Use Guides

In Vivo Use Guide

Hypertension: The usual initial dosage is 80 mg capsules once daily, whether used alone or added to a diuretic. The dosage may be increased to 120 mg once. Angina Pectoris: Starting with 80 mg capsules once daily, dosage should be gradually increased at three- to seven-day intervals until optimal response is obtained. Although individual patients may respond at any dosage level, the average optimal dosage appears to be 160 mg once daily. Migraine: The initial oral dose is 80 mg capsules once daily. The usual effective dose range is 160 to 240 mg once daily. Hypertrophic Subaortic Stenosis: The usual dosage is 80 to 160 mg capsules once daily.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:31:33 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:33 GMT 2025`
Record UNII	9Y8NXQ24VQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AY-64043-

Preferred Name

English

PROPRANOLOL

Official Name

English

Propranolol [WHO-DD]

Common Name

English

INNOPRAN XL

Common Name

English

(±)-PROPRANOLOL

Common Name

English

REDUCOR

Common Name

English

PROPRANOLOL [VANDF]

Common Name

English

PROPRANOLOL [MI]

Common Name

English

.BETA.-PROPRANOLOL

Common Name

English

DL-PROPRANOLOL

Common Name

English

2-PROPANOL, 1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-

Systematic Name

English

1-((1-METHYLETHYL)AMINO)-3-(1-NAPHTHALENYLOXY)-2-PROPANOL

Systematic Name

English

PROPRASYLYT

Common Name

English

EUPROVASIN

Common Name

English

BETALONG

Common Name

English

propranolol [INN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QC07AA05