U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry MIXED
Molecular Formula C19H24N2O3
Molecular Weight 328.4055
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LABETALOL

SMILES

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

InChI

InChIKey=SGUAFYQXFOLMHL-UHFFFAOYSA-N
InChI=1S/C19H24N2O3/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)

HIDE SMILES / InChI
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

CNS Penetrant
2554
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

1984
98
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16225568/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/16225568/
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:
https://pubmed.ncbi.nlm.nih.gov/7433343
unhealthy, 18-81
n = 32
Health Status: unhealthy
Condition: Hypertension
Age Group: 18-81
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/7433343
Disc. AE: Orthostatic hypotension...
AEs leading to
discontinuation/dose reduction:
Orthostatic hypotension
Sources:
https://pubmed.ncbi.nlm.nih.gov/7433343
14 g single, oral (max)
Overdose
Dose: 14 g
Route: oral
Route: single
Dose: 14 g
Co-administed with::
alcohol, p.o
Sources:
https://pubmed.ncbi.nlm.nih.gov/29147632
healthy, 38
n = 1
Health Status: healthy
Age Group: 38
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/29147632
Disc. AE: Acute renal failure...
AEs leading to
discontinuation/dose reduction:
Acute renal failure
Sources:
https://pubmed.ncbi.nlm.nih.gov/29147632
1200 mg 2 times / day multiple, oral (total daily dose)
Recommended
Dose: 1200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
https://www.ebmconsult.com/articles/monograph-labetalol-normodyne-trandate
https://www.pdr.net/drug-summary/Labetalol-Hydrochloride-Injection-labetalol-hydrochloride-1568
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
https://www.ebmconsult.com/articles/monograph-labetalol-normodyne-trandate
https://www.pdr.net/drug-summary/Labetalol-Hydrochloride-Injection-labetalol-hydrochloride-1568
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
https://www.ebmconsult.com/articles/monograph-labetalol-normodyne-trandate
https://www.pdr.net/drug-summary/Labetalol-Hydrochloride-Injection-labetalol-hydrochloride-1568
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Page: p.5
300 mg single, intravenous (total)
Studied dose
Dose: 300 mg
Route: intravenous
Route: single
Dose: 300 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019425s021lbl.pdf
Page: p.14
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019425s021lbl.pdf
Page: p.14
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019425s021lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/7433343
unhealthy, 18-81
n = 32
Health Status: unhealthy
Condition: Hypertension
Age Group: 18-81
Sex: M+F
Population Size: 32
Sources:
https://pubmed.ncbi.nlm.nih.gov/7433343
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:
https://pubmed.ncbi.nlm.nih.gov/29147632
healthy, 38
n = 1
Health Status: healthy
Age Group: 38
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/29147632
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Page: p.5
unhealthy
Health Status: unhealthy
Condition: Hypertension
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Page: p.5
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Ca2+ channels
57
UGT1A6
307

UGT2B4
249

P-gp
1537

UGT enzymes
27

UGT1A1
418

UGT1A9
380

UGT1A4
347

CYP
270
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
Ca2+ channels
60
 likely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 likely
UGT enzymes
27
 likely
UGT1A9
380
 minor
UGT1A4
347
 no
UGT1A6
307
 no
UGT2B4
249
 no
P-gp
1537
 yes
UGT1A1
418
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:6343
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6343
ChemicalBook
CB7735086
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7735086
MolPort
MolPort-003-898-140
https://www.molport.com/shop/molecule-link/MolPort-003-898-140
eMolecules
653717
https://www.emolecules.com/cgi-bin/more?vid=653717
PubMed

PubMed

TitleDatePubMed
Labetalol (AH5158), a competitive alpha- and beta-receptor blocking drug, in the management of hypertension.
1976 Aug
Letter: Emergency treatment of hypertensive crisis following clonidine withdrawal.
1976 May 29
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
Labetalol decreases cerebral perfusion pressure without negatively affecting cerebral blood flow in hypertensive gravidas.
2002
Factors influencing acute ischaemia-induced renal hypertension in rats.
2002 Dec
Cardiac arrest after labetalol and metoclopramide administration in a patient with scleroderma.
2002 Dec
Electrocardiographic changes associated with beta-blocker toxicity.
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
Labetalol for prophylactic treatment of intractable migraine during pregnancy.
2002 Jul-Aug
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
[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
Multiple Bier blocks with labetalol for complex regional pain syndrome refractory to other treatments.
2003 Apr
The effect of remifentanil on seizure duration and acute hemodynamic responses to electroconvulsive therapy.
2003 Apr
Clonidine facilitates controlled hypotension in adolescent children.
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
Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor.
2003 Jun
Was case report a case of unrecognized local anesthetic toxicity?
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
[Posterior reversible encephalopathy syndrome].
2003 Nov-Dec
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
A survey of Canadian practitioners regarding the management of the hypertensive disorders of pregnancy.
2004
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
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection.
2004 Apr 20
Hyponatremic hypertensive syndrome (HHS) in an 18-month old-child presenting as malignant hypertension: a case report.
2004 Apr 27
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

US4328213
2

Sample Use Guides

In Vivo Use Guide
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 Sat Dec 16 17:53:12 UTC 2023
Edited
by admin
on Sat Dec 16 17:53:12 UTC 2023
Record UNII
R5H8897N95
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LABETALOL
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
BENZAMIDE, 2-HYDROXY-5-(1-HYDROXY-2-((1-METHYL-3-PHENYLPROPYL)AMINO)ETHYL)-
Systematic Name English
AH-5158A FREE BASE
Code English
SCH-15719W FREE BASE
Code English
LABETALOL [HSDB]
Common Name English
Labetalol [WHO-DD]
Common Name English
LABETALOL [VANDF]
Common Name English
IBIDOMIDE
Common Name English
labetalol [INN]
Common Name English
LABETALOL [MI]
Common Name English
Classification Tree Code System Code
LIVERTOX NBK547846
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
NDF-RT N0000175556
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
WHO-ATC C07BG01
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
WHO-VATC QC07CG01
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
WHO-VATC QC07BG01
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
WHO-ATC C07CG01
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
WHO-ATC C07AG01
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
WHO-VATC QC07AG01
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
NDF-RT N0000000161
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
NCI_THESAURUS C72900
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL429
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PRIMARY
ECHA (EC/EINECS)
253-258-3
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
WIKIPEDIA
LABETALOL
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
PUBCHEM
3869
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
MERCK INDEX
m6647
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY Merck Index
LACTMED
Labetalol
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
DAILYMED
R5H8897N95
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
MESH
D007741
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PRIMARY
CHEBI
167638
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PRIMARY
IUPHAR
7207
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PRIMARY
SMS_ID
100000083080
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PRIMARY
RXCUI
6185
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PRIMARY RxNorm
INN
3941
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PRIMARY
CAS
36894-69-6
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PRIMARY
EVMPD
SUB08382MIG
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PRIMARY
FDA UNII
R5H8897N95
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
DRUG CENTRAL
1531
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PRIMARY
EPA CompTox
DTXSID2023191
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PRIMARY
HSDB
6537
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PRIMARY
CHEBI
6343
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
NCI_THESAURUS
C29146
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
DRUG BANK
DB00598
Created by admin on Sat Dec 16 17:53:13 UTC 2023 , Edited by admin on Sat Dec 16 17:53:13 UTC 2023
PRIMARY
Related Record Type Details
Structure of DILEVALOL
ACTIVE ISOMER -> PARENT
BETA-1 ADRENERGIC RECEPTOR
TARGET -> INHIBITOR
ALPHA-1A ADRENERGIC RECEPTOR
TARGET -> AGONIST
Structure of LABETALOL HYDROCHLORIDE
SALT/SOLVATE -> PARENT
ALPHA-1A ADRENERGIC RECEPTOR
TARGET -> INHIBITOR
Ki
Related Record Type Details
Structure of 4-PHENYLBUTAN-2-AMINE
METABOLITE -> PARENT
URINE
Related Record Type Details
Structure of LABETALOL
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
NIH
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