PROPRANOLOL

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 87 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6121573	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
hypertension 5 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Approved 8429	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 106 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Primary	Approved 8429	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 103 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/018553s037lbl.pdf	Preventing	Approved 8429	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 8429	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
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 1737 inhibitor 1587	substrate 1037 inhibitor 1767	substrate 1217 inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911 CYP2B6 810 CYP1A1 110 CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882 ALDH1 40 OCT1 512 OCT2 647 BSEP 402 MRP2 383 MRP3 157 MRP4 204 OATP1B1 788 OATP1B3 706 OATP2B1 123 BCRP 699 NTCP 34 Cav1.2 45 Nav1.5 97	CYP1A2 1054 CYP2C19 991 CYP1A1 349 CYP2A6 543 CYP2B6 664 CYP2E1 667 CYP2C8 693 CYP4A11 119 OCT2 355 UGT 192 UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A9 380 UGT2B4 249 UGT2B7 389 UGT2B10 127 UGT2B15 203 SULT1A1 29 SULT1A3 27 SULT1E1 17 SULT2A1 24 MRP2 205 MRP3 50 MRP4 77 BCRP 561

Drug as perpetrator

Target	Modality	Activity
MRP2 475	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18457386/, https://pubmed.ncbi.nlm.nih.gov/23956101/	likely [IC50 >133 uM]
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	likely
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	likely
OATP2B1 126	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	likely
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no [IC50 >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjcifX0%3D	no [IC50 >10 uM]
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/, https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >1000 uM]
MRP3 207	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
MRP4 238	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23956101/	no [IC50 >133 uM]
BCRP 773	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19421845/	no
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/17101742/	no
CYP2C8 965	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/	no
ALDH1 40	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNTc3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE2NzEifX0%3D	yes [Activation 28.1838 uM]
OCT2 648	inhibitor 3277 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 1692	inhibitor 3277 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 35	inhibitor 3277 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 218	inhibitor 3277 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/8474022/	yes
CYP2D6 1891	inhibitor 3277 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/9342584/	yes
OCT1 543	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/18788725/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1054	substrate 3367 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 1217	substrate 3367 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 991	substrate 3367 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 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2A6 543	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2C8 693	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
CYP4A11 119	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/10945865/	no
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	no	R-plopranolol glucuronide 3
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	no	S-plopranolol glucuronide 3
SULT2A1 24	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	no	4-hydroxypropranolol 3
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
UGT2B10 127	substrate 3367 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MTYwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19	no
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	no
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	R-plopranolol glucuronide 3
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	S-plopranolol glucuronide 3
MRP4 77	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	R-plopranolol glucuronide 3
MRP4 77	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	weak	S-plopranolol glucuronide 3
OCT2 355	substrate 3367 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 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	yes [Km 154 uM]	R-plopranolol glucuronide 3
MRP3 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/28850245/	yes [Km 434 uM]	S-plopranolol glucuronide 3
SULT1A1 29	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
SULT1A3 27	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
SULT1E1 17	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/15748705/	yes	4-hydroxypropranolol 3
UGT 192	substrate 3367 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000525666, https://pubmed.ncbi.nlm.nih.gov/21098645/	yes
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/18936551/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
Cav1.2 49	inhibitor 1626 Sources: https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/abs/10.1002/jat.2784, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTQwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19
Nav1.5 100	inhibitor 1626 Sources: https://academic.oup.com/cardiovascres/article/91/1/53/333710, https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxOTgwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3In19
hERG 1647	inhibitor 1626 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
MolPort	MolPort-001-794-623	https://www.molport.com/shop/molecule-link/MolPort-001-794-623
eMolecules	735071	https://www.emolecules.com/cgi-bin/more?vid=735071

PubMed

Title	Date	PubMed
Metabolic responses to catecholamines.	1976	1032269
[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 Jul	11153
Comparison of atenolol with propranolol in the treatment of angina pectoris with special reference to once daily administration of atenolol.	1978 Sep	101223
Heart hypertrophy induced by levothyroxine aggravates ischemic lesions and reperfusion arrhythmias in rats.	1997 Jan	10072899
Neurotransmitter-mediated open-field behavioral action of CGRP.	1999	10075105
Sexual dysfunction related to antihypertensive agents: results from the animal model.	1999 Apr	10356671
Lipolysis is an important determinant of isoproterenol-induced myocardial necrosis.	1999 Sep-Oct	10533957
Dystonia in a patient treated with propranolol and gabapentin.	2000 Apr	10768633
Functional, biochemical and molecular biological evidence for a possible beta(3)-adrenoceptor in human near-term myometrium.	2000 Aug	10952688
[Effects of nitrates and beta-blockers on platelet aggregation in patients with coronary heart disease].	2000 Feb	10808734
Platelet alpha2-adrenoceptor alterations in patients with essential hypertension are normalized after treatment with doxazosin but not propranolol.	2000 Feb	10694191
Leukocytoclastic vasculitis: is propranolol implicated?	2000 Jul	10907976
Role of aortic nitric oxide synthase 3 (eNOS) in the systemic vasodilation of portal hypertension.	2000 Jul	10889169
Beta-blockade in adriamycin-induced cardiomyopathy.	2000 Jun	10908085
Effects of prolonged propranolol treatment on left ventricular remodeling and oxidative stress after myocardial infarction in rats.	2000 May	10813385
Norepinephrine induces vascular endothelial growth factor gene expression in brown adipocytes through a beta -adrenoreceptor/cAMP/protein kinase A pathway involving Src but independently of Erk1/2.	2000 May 5	10788502
Akathisia and exacerbation of psychopathology: a preliminary report.	2000 May-Jun	10895402
Beta-adrenergic modulation of NNK-induced lung carcinogenesis in hamsters.	2000 Nov	11079726
Impaired memory consolidation in rats produced with beta-adrenergic blockade.	2000 Nov	11031131
Functional assessment of skeletal muscle ventricles after pumping for up to four years in circulation.	2000 Oct	11081886
Catecholamines suppress leptin release from in vitro differentiated subcutaneous human adipocytes in primary culture via beta1- and beta2-adrenergic receptors.	2000 Sep	11022189
Protein phosphatase activity is increased in a rat model of long-term beta-adrenergic stimulation.	2000 Sep	10997724
Cellular cholesterol efflux is modulated by phospholipid-derived signaling molecules in familial HDL deficiency/Tangier disease fibroblasts.	2001 Feb	11181755
Pharmacologic management of atrial fibrillation: current therapeutic strategies.	2001 Feb	11174354
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
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
[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
Spectral analysis of circadian rhythms in heart rate variability of dogs.	2001 Jan	11197557
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice.	2001 Jan	11159692
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
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
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.	2001 Jan 12	11150484
Effects of mono-, di- and tri-hydroxybenzoic acids on the nitrosation of propranolol: structure-activity relationship.	2001 Jan 25	11152975
Ion-exchange fibers and drugs: an equilibrium study.	2001 Jan 29	11166422
Propranolol rapidly reverses paralysis, hypokalemia, and hypophosphatemia in thyrotoxic periodic paralysis.	2001 Mar	11228188
Erythroid carbonic anhydrase and hsp70 expression in chick embryonic development: role of cAMP and hypoxia.	2001 Mar	11171668

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 `Fri Dec 15 16:34:05 GMT 2023` Edited by `admin` on `Fri Dec 15 16:34:05 GMT 2023`
Record UNII	9Y8NXQ24VQ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

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

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