PROPRANOLOL

First approved in 1967

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H21NO2
Molecular Weight	259.344
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)NCC(COc1cccc2ccccc21)O

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	259.344
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:: 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 95 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6121573	Antagonist 2577	hypertension Angina pectoris Hypertrophic subaortic stenosis

Conditions

Condition	Modality	Targets	Highest Phase	Product
hypertension 6 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Adrenergic receptor beta	Approved 7997	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 543024000000
Angina pectoris 90 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Adrenergic receptor beta	Approved 7997	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 543024000000
Migraine 98 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Preventing		Approved 7997	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 543024000000
Hypertrophic subaortic stenosis 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Adrenergic receptor beta	Approved 7997	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 543024000000

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
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
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

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 1470 inhibitor 1172	substrate 865 inhibitor 1318	substrate 1038 inhibitor 1421	inhibitor 1360

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 89 CYP1A2 1268 CYP2C8 761 CYP2B6 679 CYP2A6 594 CYP2C19 1215 CYP2E1 761 ALDH1 33 OCT1 473 OCT2 582 BSEP 363 MRP2 341 MRP3 148 MRP4 194 OATP1B1 698 OATP1B3 613 OATP2B1 107 BCRP 574 NTCP 31 Cav1.2 45 Nav1.5 89	SULT2A1 17 MRP2 172 MRP3 46 CYP1A2 892 CYP2C19 830 CYP1A1 302 CYP2A6 452 CYP2B6 575 CYP2E1 567 CYP2C8 586 CYP4A11 90 OCT2 304 UGT 160 UGT1A1 358 UGT1A3 358 UGT1A4 295 UGT1A6 258 UGT1A9 327 UGT2B4 213 UGT2B7 329 UGT2B10 112 UGT2B15 165 SULT1A1 20 SULT1A3 19 SULT1E1 8 MRP4 73 BCRP 461

Drug as perpetrator

Target	Modality	Activity
MRP2 421	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/, https://pubmed.ncbi.nlm.nih.gov/23956101/	likely [IC50 >133 uM]
OATP1B1 713	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	likely
OATP1B3 622	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	likely
OATP2B1 107	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	likely
CYP2A6 625	inhibitor 2614 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2C19 1277	inhibitor 2614 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2C9 1362	inhibitor 2614 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2E1 841	inhibitor 2614 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP3A4 1462	inhibitor 2614 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjcifX0%3D	no [IC50 >10 uM]
BSEP 364	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >1000 uM]
MRP3 200	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 226	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
BCRP 639	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/19421845/	no
CYP2B6 845	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2C8 810	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	no
ALDH1 33	inhibitor 2614 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE2NzEifX0%3D	yes [Activation 28.1838 uM]
OCT2 583	inhibitor 2614 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 1406	inhibitor 2614 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 32	inhibitor 2614 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 188	inhibitor 2614 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/8474022/	yes
CYP2D6 1455	inhibitor 2614 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/9342584/	yes
OCT1 488	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/18788725/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 892	substrate 2752 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 1038	substrate 2752 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 830	substrate 2752 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 302	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2A6 452	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2B6 575	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2C8 586	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2C9 865	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2E1 567	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP3A4 1470	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP4A11 90	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
MRP2 172	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	no	R-plopranolol glucuronide 3
MRP2 172	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	no	S-plopranolol glucuronide 3
SULT2A1 17	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	no	4-hydroxypropranolol 3
UGT1A1 358	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A3 358	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A4 295	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A6 258	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT2B10 112	substrate 2752 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MTYwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no
UGT2B15 165	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
BCRP 461	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	R-plopranolol glucuronide 3
BCRP 461	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	S-plopranolol glucuronide 3
MRP4 73	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	R-plopranolol glucuronide 3
MRP4 73	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	S-plopranolol glucuronide 3
OCT2 304	substrate 2752 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 46	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	yes [Km 154 uM]	R-plopranolol glucuronide 3
MRP3 46	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	yes [Km 434 uM]	S-plopranolol glucuronide 3
SULT1A1 20	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
SULT1A3 19	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
SULT1E1 8	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
UGT 160	substrate 2752 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/21098645/	yes
UGT1A9 327	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes
UGT2B4 213	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes
UGT2B7 329	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 48	inhibitor 1374 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 91	inhibitor 1374 Sources: https://academic.oup.com/cardiovascres/article/91/1/53/333710, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTgwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19
hERG 1392	inhibitor 1374 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
MolPort	MolPort-001-794-623	https://www.molport.com/shop/molecule-link/MolPort-001-794-623

PubMed

Title	Date	PubMed
Severe bradycardia after neostigmine in a patient taking propranolol to control paroxysmal atrial tachycardia.	1975 Feb	1115373
[Effects of isoprenaline on apoptosis related gene expression in rat myocardium cells].	2000 Nov	11218852
[Recovery from pancytopenia and liver dysfunction after administration of thiamazole for hyperthyroidism].	2000 Nov	11193444
Attenuation of changes in sarcoplasmic reticular gene expression in cardiac hypertrophy by propranolol and verapamil.	2000 Oct	11129949
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 Feb	11216977
Idiopathic sustained left ventricular tachycardia in pediatric patients.	2001 Feb	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 Feb	11182761
Cellular cholesterol efflux is modulated by phospholipid-derived signaling molecules in familial HDL deficiency/Tangier disease fibroblasts.	2001 Feb	11181755
Pharmacologic therapy for portal hypertension.	2001 Feb	11177691
Epinephrine yields translocation of lymphocytes to the lung.	2001 Feb	11170785
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells.	2001 Feb	11160630
beta(2)-adrenoceptor agonists inhibit release of eosinophil-activating cytokines from human airway smooth muscle cells.	2001 Feb	11159726
Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats.	2001 Feb	11158985
beta-Adrenoceptor and nNOS-derived NO interactions modulate hypoglycemic pial arteriolar dilation in rats.	2001 Feb	11158952
Asymmetric synthesis and preliminary evaluation of (R)- and (S)-[11C]bisoprolol, a putative beta1-selective adrenoceptor radioligand.	2001 Feb	11137886
Effects of nebivolol on proliferation and apoptosis of human coronary artery smooth muscle and endothelial cells.	2001 Feb 1	11164853
Comparison of spontaneous and noradrenaline-evoked non-selective cation channels in rabbit portal vein myocytes.	2001 Feb 1	11158276
Interactions between phospholamban and beta-adrenergic drive may lead to cardiomyopathy and early mortality.	2001 Feb 13	11171800
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.	2001 Feb 16	11226401
Enhancement of memory consolidation in chicks by beta(3)-adrenoceptor agonists.	2001 Feb 16	11226398
Correlation of the electrical and intrinsic optical signals in the chicken spreading depression phenomenon.	2001 Feb 16	11166945
Mechanisms of the increased pressor response to vasopressors in the mesenteric bed of nitric oxide-deficient hypertensive rats.	2001 Feb 2	11166291
[Availability of antidotes in French emergency medical aid units].	2001 Feb 3	11229303
Modulation of a 40-kDa catecholamine regulated protein by dopamine receptor antagonists.	2001 Feb 9	11173065
Daily variation of azygos and portal blood flow and the effect of propranolol administration once an evening in cirrhotics.	2001 Jan	11211903
Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations.	2001 Jan	11201505
Spectral analysis of circadian rhythms in heart rate variability of dogs.	2001 Jan	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 Jan	11191841
Successful use of propranolol in migraine associated with electroconvulsive therapy.	2001 Jan	11168610
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.	2001 Jan	11159692
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes.	2001 Jan	11156573
Oxygen consumption in patients with hyperthyroidism before and after treatment with beta-blockade versus thyrostatic treatment: a prospective randomized study.	2001 Jan	11141226
Amiodarone is safe and highly effective therapy for supraventricular tachycardia in infants.	2001 Jan	11136494
Ventricular activation during sympathetic imbalance and its computational reconstruction.	2001 Jan	11133921
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium.	2001 Jan	11133877
Reactive oxygen species mediate alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes.	2001 Jan	11133229
alpha-Adrenoceptor stimulation-mediated negative inotropism and enhanced Na(+)/Ca(2+) exchange in mouse ventricle.	2001 Jan	11123227
Evaluation of a vincristine resistant Caco-2 cell line for use in a calcein AM extrusion screening assay for P-glycoprotein interaction.	2001 Jan	11113639
Role of PAG in the antinociception evoked from the medial or central amygdala in rats.	2001 Jan 1	11226714
Activation of extracellular signal-regulated kinases, NF-kappa B, and cyclic adenosine 5'-monophosphate response element-binding protein in lung neutrophils occurs by differing mechanisms after hemorrhage or endotoxemia.	2001 Jan 1	11123332
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.	2001 Jan 12	11150484
Colon and anal sphincter contractions evoked by microstimulation of the sacral spinal cord in cats.	2001 Jan 19	11166684
Effect of carvedilol on atrioventricular conduction in the ischemic heart.	2001 Jan 26	11165226
Ion-exchange fibers and drugs: an equilibrium study.	2001 Jan 29	11166422
Misrepresentation and miscommunication of teratogenic risk of drugs; analysis of three highly publicized international cases.	2001 Jan-Feb	11137372
Evidence of alpha-adrenoceptor-mediated chronotropic action in children.	2001 Jan-Feb	11123125
Propranolol rapidly reverses paralysis, hypokalemia, and hypophosphatemia in thyrotoxic periodic paralysis.	2001 Mar	11228188
Catecholamines increase lung edema clearance in rats with increased left atrial pressure.	2001 Mar	11181624
Erythroid carbonic anhydrase and hsp70 expression in chick embryonic development: role of cAMP and hypoxia.	2001 Mar	11171668
Central corticotropin releasing factor (CRF) and adrenergic receptors mediate hemodynamic responses to cocaine.	2001 Mar 2	11222986

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.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Jun 26 16:14:15 UTC 2021` Edited by `admin` on `Sat Jun 26 16:14:15 UTC 2021`
Record UNII	9Y8NXQ24VQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PROPRANOLOL

Official Name

English

INNOPRAN XL

Common Name

English

(+/-)-PROPRANOLOL

Common Name

English

REDUCOR

Common Name

English

PROPRANOLOL [VANDF]

Common Name

English

AY-64043-

Code

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

PROPRANOLOL [WHO-DD]

Common 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