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Details

Stereochemistry MIXED
Molecular Formula C19H24N2O3.ClH
Molecular Weight 364.866
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LABETALOL HYDROCHLORIDE

SMILES

Cl.CC(CCC1=CC=CC=C1)NCC(O)C2=CC=C(O)C(=C2)C(N)=O

InChI

InChIKey=WQVZLXWQESQGIF-UHFFFAOYSA-N
InChI=1S/C19H24N2O3.ClH/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24;/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24);1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H24N2O3
Molecular Weight 328.4055
Charge 0
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including http://www.rxlist.com/trandate-drug.htm

Labetalol is a blocker of both alpha- and beta-adrenergic receptors that is used as an antihypertensive. It may be used alone or in combination with other antihypertensive agents, especially thiazide and loop diuretics. The capacity of labetalol HCl to block alpha receptors in man has been demonstrated by attenuation of the pressor effect of phenylephrine and by a significant reduction of the pressor response caused by immersing the hand in ice-cold water ("cold-pressor test"). Labetalol HCl's beta1-receptor blockade in man was demonstrated by a small decrease in the resting heart rate, attenuation of tachycardia produced by isoproterenol or exercise, and by attenuation of the reflex tachycardia to the hypotension produced by amyl nitrite. Beta2-receptor blockade was demonstrated by inhibition of the isoproterenol-induced fall in diastolic blood pressure. Both the alpha- and beta-blocking actions of orally administered labetalol HCl contribute to a decrease in blood pressure in hypertensive patients. Labetalol HCl consistently, in dose-related fashion, blunted increases in exercise-induced blood pressure and heart rate, and in their double product. The pulmonary circulation during exercise was not affected by labetalol HCl dosing. Single oral doses of labetalol HCl administered to patients with coronary artery disease had no significant effect on sinus rate, intraventricular conduction, or QRS duration. The atrioventricular (A-V) conduction time was modestly prolonged in two of seven patients. In another study, IV labetalol HCl slightly prolonged A-V nodal conduction time and atrial effective refractory period with only small changes in heart rate. The metabolism of labetalol is mainly through conjugation to glucuronide metabolites. These metabolites are present in plasma and are excreted in the urine and, via the bile, into the feces. Approximately 55% to 60% of a dose appears in the urine as conjugates or unchanged labetalol within the first 24 hours of dosing. Labetalol has been shown to cross the placental barrier in humans. Only negligible amounts of the drug crossed the blood-brain barrier in animal studies. Labetalol is approximately 50% protein bound. Neither hemodialysis nor peritoneal dialysis removes a significant amount of labetalol HCl from the general circulation.

CNS Activity

Curator's Comment: Labetalol has been shown to cross the placental barrier in humans. Only negligible amounts of the drug crossed the blood-brain barrier in animal studies.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
LABETALOL HYDROCHLORIDE

Approved Use

Labetalol hydrochloride tablets, USP are indicated in the management of hypertension. Labetalol hydrochloride tablets, USP may be used alone or in combination with other antihypertensive agents, especially thiazide and loop diuretics.

Launch Date

5.8656961E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
72.4 ng/mL
100 mg 2 times / 2 days steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LABETALOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
571 ng × h/mL
100 mg 2 times / 2 days steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
LABETALOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3000 mg single, oral (max)
Highest studied dose
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unhealthy, 18-81
n = 32
Health Status: unhealthy
Condition: Hypertension
Age Group: 18-81
Sex: M+F
Population Size: 32
Sources:
Disc. AE: Orthostatic hypotension...
AEs leading to
discontinuation/dose reduction:
Orthostatic hypotension
Sources:
14 g single, oral (max)
Overdose
Dose: 14 g
Route: oral
Route: single
Dose: 14 g
Co-administed with::
alcohol, p.o
Sources:
healthy, 38
n = 1
Health Status: healthy
Age Group: 38
Sex: F
Population Size: 1
Sources:
Disc. AE: Acute renal failure...
AEs leading to
discontinuation/dose reduction:
Acute renal failure
Sources:
1200 mg 2 times / day multiple, oral (total daily dose)
Recommended
unhealthy
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources: Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.5
Disc. AE: Cardiac failure...
Other AEs: Hepatocellular injury, Congestive heart failure...
AEs leading to
discontinuation/dose reduction:
Cardiac failure
Other AEs:
Hepatocellular injury (severe, rare)
Congestive heart failure
Sources: Page: p.5
300 mg single, intravenous (total)
Studied dose
Dose: 300 mg
Route: intravenous
Route: single
Dose: 300 mg
Sources: Page: p.14
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.14
AEs

AEs

AESignificanceDosePopulation
Orthostatic hypotension Disc. AE
3000 mg single, oral (max)
Highest studied dose
Dose: 3000 mg
Route: oral
Route: single
Dose: 3000 mg
Sources:
unhealthy, 18-81
n = 32
Health Status: unhealthy
Condition: Hypertension
Age Group: 18-81
Sex: M+F
Population Size: 32
Sources:
Acute renal failure Disc. AE
14 g single, oral (max)
Overdose
Dose: 14 g
Route: oral
Route: single
Dose: 14 g
Co-administed with::
alcohol, p.o
Sources:
healthy, 38
n = 1
Health Status: healthy
Age Group: 38
Sex: F
Population Size: 1
Sources:
Congestive heart failure
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources: Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.5
Cardiac failure Disc. AE
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources: Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.5
Hepatocellular injury severe, rare
400 mg 2 times / day multiple, oral (max)
Recommended
Dose: 400 mg, 2 times / day
Route: oral
Route: multiple
Dose: 400 mg, 2 times / day
Sources: Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources: Page: p.5
PubMed

PubMed

TitleDatePubMed
Labetalol (AH5158), a competitive alpha- and beta-receptor blocking drug, in the management of hypertension.
1976 Aug
Pharmacological basis for antihypertensive effects of intravenous labetalol.
1977 Jan
Hemodynamic collapse following labetalol administration in preeclampsia.
1992 Feb
Hypersensitivity immune reaction as a mechanism for dilevalol-associated hepatitis.
1992 Jul-Aug
Liddle syndrome in a newborn infant.
2002 Aug
Postpartum eclampsia.
2002 Aug 1
Cardiac arrest after labetalol and metoclopramide administration in a patient with scleroderma.
2002 Dec
Partial agonistic activity of labetalol, the arylethanolamine, on beta 3-adrenoceptors in the guinea-pig gastric fundus.
2002 Feb
[Nuclear medicine diagnosis of pheochromocytoma with metaiodobenzylguanidine].
2002 Jul
Shy-Drager syndrome and severe unexplained intraoperative hypotension responsive to vasopressin.
2002 Jul
Labetalol-induced hyperkalemia in renal transplant recipients.
2002 Jul-Aug
Effects of hemoconcentration and sympathetic activation on serum lipid responses to brief mental stress.
2002 Jul-Aug
Hepatic sinusoidal vasodilators improve transplanted cell engraftment and ameliorate microcirculatory perturbations in the liver.
2002 Jun
Vanillylamide-based propanolamine derivative displays alpha/beta-adrenoceptor blocking and vasodilating properties.
2002 Jun
Labetalol-induced hepatitis in a patient with chronic hepatitis B infection.
2002 Mar-Apr
Acute and chronic hypertensive headache and hypertensive encephalopathy.
2002 May
The effect of antihypertensive drugs on the fetus.
2002 May
[beta-Adrenergic receptor blockers--a group of chiral drugs: different effects of each enantiomer].
2002 May
Early anti-remodeling effect of labetalol in the congestive heart failure model induced by aortic constriction in the guinea pig.
2002 May
Spectrofluorometric determination of labetolol in pharmaceutical preparations and spiked human urine through the formation of coumarin derivative.
2002 Nov 7
Comprehensive management of hypertensive emergencies and urgencies.
2002 Nov-Dec
[Influence of labetalol on the resistance of human fetoplacental vessels in perfusion in vitro].
2002 Sep
Short-term treatment of severe hypertension of pregnancy: prospective comparison of nicardipine and labetalol.
2002 Sep
[Influence of different pharmacological agents in the ex vivo proliferation of mesothelial cells obtained from the peritoneal effluent of patients treated with peritoneal dialysis].
2003
Scleroderma renal crisis sine scleroderma during pregnancy.
2003
Refractory hypotension during caesarean section following pre-operative administration of anti-hypertensive agents.
2003 Apr
Left ventricular diastolic function in pregnancy-induced hypertension.
2003 Apr
Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine.
2003 Apr
The effect of remifentanil on seizure duration and acute hemodynamic responses to electroconvulsive therapy.
2003 Apr
Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers.
2003 Aug
Labetalol treatment enhances the attenuation of tobacco withdrawal symptoms by nicotine in abstinent smokers.
2003 Dec
Managing hypertension in patients with stroke. Are you prepared for labetalol infusion?
2003 Jun
Community-based thrombolytic therapy of acute ischemic stroke in Helsinki.
2003 Jun
Remifentanil for intraoperative analgesia during the endoscopic surgical treatment of pituitary lesions.
2003 Mar
Acute myocardial infarction as a complication of clonidine withdrawal.
2003 Nov
Enantioselective determination of arotinolol in human plasma by HPLC using teicoplanin chiral stationary phase.
2003 Oct
Fatality from administration of labetalol and crushed extended-release nifedipine.
2003 Oct
Clinical review: the management of hypertensive crises.
2003 Oct
Hydralazine for treatment of severe hypertension in pregnancy: meta-analysis.
2003 Oct 25
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].
2003 Oct-Dec
Very low-dose spinal anesthesia for cesarean section in a morbidly obese preeclamptic patient and its potential implications.
2004 Apr
Dexmedetomidine for awake carotid endarterectomy: efficacy, hemodynamic profile, and side effects.
2004 Apr
In vitro effects of antihypertensive drugs on thromboxane agonist (U46619)-induced vasoconstriction in human internal mammary artery.
2004 Aug
Chiral separation of labetalol stereoisomers in human plasma by capillary electrophoresis.
2004 Feb 20
Periprocedural hypertension: current concepts in management for the vascular surgeon.
2004 Jul-Aug
[Protective effect of alpha beta-blockers on hypertensive target-organ damage].
2004 Mar
Polymeric alkenoxy amino acid surfactants: II. Chiral separations of beta-blockers with multiple stereogenic centers.
2004 Mar
Effect of beta-adrenergic antagonists on bioluminescence control in three species of brittlestars (Echinodermata: Ophiuroidea).
2004 May
[Surgery to save body-packers].
2004 May
Severe hypertension and massive proteinuria in a newborn with renal artery stenosis.
2004 May
Patents

Patents

Sample Use Guides

The recommended initial dosage is 100 mg twice daily whether used alone or added to a diuretic regimen. After 2 or 3 days, using standing blood pressure as an indicator, dosage may be titrated in increments of 100 mg b.i.d. every 2 or 3 days. The usual maintenance dosage of labetalol HCl is between 200 and 400 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: The effects of the alpha-beta-adrenergic antagonist labetalol on the activation of human platelets by adrenaline and other aggregating stimuli have been investigated. Labetalol inhibited platelet aggregation and secretion induced by collagen and the second phase of aggregation caused by ADP, platelet activating factor, adrenaline and ionophore A23187.
Unknown
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:40:36 UTC 2023
Edited
by admin
on Wed Jul 05 23:40:36 UTC 2023
Record UNII
1GEV3BAW9J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LABETALOL HYDROCHLORIDE
EP   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN  
Official Name English
LABETALOL HYDROCHLORIDE [JAN]
Common Name English
TRANDATE
Brand Name English
IBIDOMIDE HYDROCHLORIDE
Common Name English
NORMODYNE
Brand Name English
LABETALOL HYDROCHLORIDE [MART.]
Common Name English
5-[1-Hydroxy-2-[(1-methyl-3-phenylpropyl)amino]ethyl]salicylamide monohydrochloride
Systematic Name English
LABETALOL HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
LABETALOL HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
Labetalol hydrochloride [WHO-DD]
Common Name English
LABETALOL HYDROCHLORIDE COMPONENT OF NORMOZIDE
Common Name English
LABETALOL HCL
Common Name English
AH 5158A
Code English
SCH 15719W
Code English
AH-5158A
Code English
LABETALOL HYDROCHLORIDE [MI]
Common Name English
LABETALOL HYDROCHLORIDE [VANDF]
Common Name English
SCH-15719W
Code English
BENZAMIDE, 2-HYDROXY-5-(1-HYDROXY-2-((1-METHYL-3-PHENYLPROPYL)AMINO)ETHYL)-, MONOHYDROCHLORIDE
Systematic Name English
AH-5158A HYDROCHLORIDE
Code English
LABETALOL HYDROCHLORIDE [ORANGE BOOK]
Common Name English
NSC-290312
Code English
SCH-15719W HYDROCHLORIDE
Code English
LABETALOL HYDROCHLORIDE [USAN]
Common Name English
LABETALOL HYDROCHLORIDE [USP-RS]
Common Name English
NORMOZIDE COMPONENT LABETALOL HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29713
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
Code System Code Type Description
MERCK INDEX
M6647
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY Merck Index
RXCUI
202693
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY RxNorm
DAILYMED
1GEV3BAW9J
Created by admin on Wed Jul 05 23:40:36 UTC 2023 , Edited by admin on Wed Jul 05 23:40:36 UTC 2023
PRIMARY
NCI_THESAURUS
C63578
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY
ECHA (EC/EINECS)
251-211-1
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY
CAS
32780-64-6
Created by admin on Wed Jul 05 23:40:36 UTC 2023 , Edited by admin on Wed Jul 05 23:40:36 UTC 2023
PRIMARY
DRUG BANK
DBSALT000320
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID0044654
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PRIMARY
NSC
290312
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL429
Created by admin on Wed Jul 05 23:40:36 UTC 2023 , Edited by admin on Wed Jul 05 23:40:36 UTC 2023
PRIMARY
PUBCHEM
71412
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PRIMARY
FDA UNII
1GEV3BAW9J
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY
RS_ITEM_NUM
1356654
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY
EVMPD
SUB02844MIG
Created by admin on Wed Jul 05 23:40:36 UTC 2023 , Edited by admin on Wed Jul 05 23:40:36 UTC 2023
PRIMARY
SMS_ID
100000089827
Created by admin on Wed Jul 05 23:40:37 UTC 2023 , Edited by admin on Wed Jul 05 23:40:37 UTC 2023
PRIMARY
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