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
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
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 | ( + / - ) |
DescriptionCurator'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
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 |
---|---|---|---|
Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6121573 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | INDERAL LA Approved UsePropranolol 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 Date5.43023989E11 |
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Primary | INDERAL LA Approved UsePropranolol 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 Date5.43023989E11 |
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Preventing | INDERAL LA Approved UsePropranolol 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 Date5.43023989E11 |
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Primary | INDERAL LA Approved UsePropranolol 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 Date5.43023989E11 |
Cmax
Value | Dose | Co-administered | 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 |
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 |
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 |
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 |
T1/2
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 |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
likely [IC50 >133 uM] | ||||
likely | ||||
likely | ||||
likely | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >1000 uM] | ||||
no [IC50 >133 uM] | ||||
no [IC50 >133 uM] | ||||
no | ||||
no | ||||
no | ||||
yes [Activation 28.1838 uM] | ||||
yes [IC50 189 uM] | ||||
yes [IC50 4 uM] | ||||
yes [Inhibition 5.5 uM] | ||||
yes | ||||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
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. Page: (Label) 5, 7-8 |
||
Page: (Label) 5, 7-8 |
major | yes (co-administration study) Comment: Coadminstration of CYP2D6 inhibitors increased Propranolol plasma concentration. Page: (Label) 5, 7-8 |
||
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. Page: (Label) 5, 7-8 |
||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
weak | ||||
weak | ||||
weak | ||||
weak | ||||
yes [Km 11.8 uM] | ||||
yes [Km 154 uM] | ||||
yes [Km 434 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Severe bradycardia after neostigmine in a patient taking propranolol to control paroxysmal atrial tachycardia. | 1975 Feb |
|
[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 |
|
[Effects of isoprenaline on apoptosis related gene expression in rat myocardium cells]. | 2000 Nov |
|
[Recovery from pancytopenia and liver dysfunction after administration of thiamazole for hyperthyroidism]. | 2000 Nov |
|
Attenuation of changes in sarcoplasmic reticular gene expression in cardiac hypertrophy by propranolol and verapamil. | 2000 Oct |
|
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 |
|
Idiopathic sustained left ventricular tachycardia in pediatric patients. | 2001 Feb |
|
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 |
|
Cellular cholesterol efflux is modulated by phospholipid-derived signaling molecules in familial HDL deficiency/Tangier disease fibroblasts. | 2001 Feb |
|
Epinephrine yields translocation of lymphocytes to the lung. | 2001 Feb |
|
Characterization of a novel cationic drug transporter in human retinal pigment epithelial cells. | 2001 Feb |
|
beta(2)-adrenoceptor agonists inhibit release of eosinophil-activating cytokines from human airway smooth muscle cells. | 2001 Feb |
|
Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats. | 2001 Feb |
|
beta-Adrenoceptor and nNOS-derived NO interactions modulate hypoglycemic pial arteriolar dilation in rats. | 2001 Feb |
|
Asymmetric synthesis and preliminary evaluation of (R)- and (S)-[11C]bisoprolol, a putative beta1-selective adrenoceptor radioligand. | 2001 Feb |
|
Effects of nebivolol on proliferation and apoptosis of human coronary artery smooth muscle and endothelial cells. | 2001 Feb 1 |
|
Comparison of spontaneous and noradrenaline-evoked non-selective cation channels in rabbit portal vein myocytes. | 2001 Feb 1 |
|
Interactions between phospholamban and beta-adrenergic drive may lead to cardiomyopathy and early mortality. | 2001 Feb 13 |
|
Correlation of the electrical and intrinsic optical signals in the chicken spreading depression phenomenon. | 2001 Feb 16 |
|
Mechanisms of the increased pressor response to vasopressors in the mesenteric bed of nitric oxide-deficient hypertensive rats. | 2001 Feb 2 |
|
[Availability of antidotes in French emergency medical aid units]. | 2001 Feb 3 |
|
Modulation of a 40-kDa catecholamine regulated protein by dopamine receptor antagonists. | 2001 Feb 9 |
|
Daily variation of azygos and portal blood flow and the effect of propranolol administration once an evening in cirrhotics. | 2001 Jan |
|
Evidence for the binding of beta-adrenoceptor blockers to microsomal Na+/K+-ATPase in guinea pig heart preparations. | 2001 Jan |
|
Spectral analysis of circadian rhythms in heart rate variability of dogs. | 2001 Jan |
|
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 |
|
Successful use of propranolol in migraine associated with electroconvulsive therapy. | 2001 Jan |
|
beta(1)-Adrenoceptors compensate for beta(3)-adrenoceptors in ileum from beta(3)-adrenoceptor knock-out mice. | 2001 Jan |
|
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes. | 2001 Jan |
|
Oxygen consumption in patients with hyperthyroidism before and after treatment with beta-blockade versus thyrostatic treatment: a prospective randomized study. | 2001 Jan |
|
Amiodarone is safe and highly effective therapy for supraventricular tachycardia in infants. | 2001 Jan |
|
Ventricular activation during sympathetic imbalance and its computational reconstruction. | 2001 Jan |
|
Adrenergic receptor activated ion transport in human fetal retinal pigment epithelium. | 2001 Jan |
|
Reactive oxygen species mediate alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes. | 2001 Jan |
|
alpha-Adrenoceptor stimulation-mediated negative inotropism and enhanced Na(+)/Ca(2+) exchange in mouse ventricle. | 2001 Jan |
|
Evaluation of a vincristine resistant Caco-2 cell line for use in a calcein AM extrusion screening assay for P-glycoprotein interaction. | 2001 Jan |
|
Role of PAG in the antinociception evoked from the medial or central amygdala in rats. | 2001 Jan 1 |
|
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 |
|
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI. | 2001 Jan 12 |
|
Colon and anal sphincter contractions evoked by microstimulation of the sacral spinal cord in cats. | 2001 Jan 19 |
|
Effects of mono-, di- and tri-hydroxybenzoic acids on the nitrosation of propranolol: structure-activity relationship. | 2001 Jan 25 |
|
Effect of carvedilol on atrioventricular conduction in the ischemic heart. | 2001 Jan 26 |
|
Potent serotonin (5-HT)(2A) receptor antagonists completely prevent the development of hyperthermia in an animal model of the 5-HT syndrome. | 2001 Jan 26 |
|
Ion-exchange fibers and drugs: an equilibrium study. | 2001 Jan 29 |
|
Structural basis for enantiomer binding and separation of a common beta-blocker: crystal structure of cellobiohydrolase Cel7A with bound (S)-propranolol at 1.9 A resolution. | 2001 Jan 5 |
|
Misrepresentation and miscommunication of teratogenic risk of drugs; analysis of three highly publicized international cases. | 2001 Jan-Feb |
|
Evidence of alpha-adrenoceptor-mediated chronotropic action in children. | 2001 Jan-Feb |
|
Propranolol rapidly reverses paralysis, hypokalemia, and hypophosphatemia in thyrotoxic periodic paralysis. | 2001 Mar |
|
Catecholamines increase lung edema clearance in rats with increased left atrial pressure. | 2001 Mar |
|
Central corticotropin releasing factor (CRF) and adrenergic receptors mediate hemodynamic responses to cocaine. | 2001 Mar 2 |
Sample Use Guides
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20732454
Curator's Comment: Propranolol dose-dependently inhibited growth factor-induced proliferation of cultured human umbilical vein endothelial cells (HUVECs) through a G₀/G₁ phase cell cycle arrest. This was correlated to decreased cyclin D1, cyclin D3, and cyclin-dependent kinase CDK6 protein levels, while increases in the CDK inhibitors p15(INK4B), p21(WAF1/Cip1) and p27(Kip1) were observed.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:59:32 UTC 2023
by
admin
on
Wed Jul 05 23:59:32 UTC 2023
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Record UNII |
9Y8NXQ24VQ
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Record Status |
Validated (UNII)
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Record Version |
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WHO-VATC |
QC07AA05
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WHO-ATC |
C07FA05
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NDF-RT |
N0000175556
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LIVERTOX |
NBK548218
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FDA ORPHAN DRUG |
266708
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NCI_THESAURUS |
C29576
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EU-Orphan Drug |
EU/3/16/1805
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WHO-VATC |
QC07FA05
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WHO-VATC |
QC07BA05
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FDA ORPHAN DRUG |
703319
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WHO-ESSENTIAL MEDICINES LIST |
7.2
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NDF-RT |
N0000000161
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WHO-ATC |
C07BA05
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WHO-ATC |
C07FX01
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FDA ORPHAN DRUG |
475715
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WHO-ATC |
C07AA05
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FDA ORPHAN DRUG |
484315
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DB00571
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564
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525-66-6
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CHEMBL27
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M9223
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PROPRANOLOL
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1940
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235-867-6
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13013-17-7
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4946
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Propranolol
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D011433
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C62073
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2303
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SUB10119MIG
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8787
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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METABOLIC ENZYME -> SUBSTRATE |
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
COMPETITIVE INHIBITOR
Ki
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TARGET -> INHIBITOR |
Ki
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
In vitro studies have indicated that the aromatic hydroxylation of propranolol is catalyzed mainly by polymorphic CYP2D6.
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
MAJOR
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METABOLITE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
In vitro studies have indicated that the aromatic hydroxylation of propranolol is catalyzed mainly by polymorphic CYP2D6. Side-chain oxidation is mediated mainly by CYP1A2 and to some extent by CYP2D6.
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METABOLITE -> PARENT |
URINE
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METABOLITE ACTIVE -> PARENT |
Metabolite to parent drug ratio in non-uraemic human plasma after chronic administration of parent drug.
METABOLITE TO PARENT DRUG RATIO
PLASMA; URINE
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METABOLITE ACTIVE -> PARENT |
MAJOR
URINE
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METABOLITE -> PARENT |
URINE
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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