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

Details

Stereochemistry MIXED
Molecular Formula C19H24N2O3
Molecular Weight 328.4062
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LABETALOL

SMILES

CC(CCc1ccccc1)NCC(c2ccc(c(c2)C(=N)O)O)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 328.4062
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
Letter: Emergency treatment of hypertensive crisis following clonidine withdrawal.
1976 May 29
Hemiparesis after single minibolus of labetalol for hypertensive encephalopathy.
1979 Sep 15
Hypersensitivity immune reaction as a mechanism for dilevalol-associated hepatitis.
1992 Jul-Aug
A randomized, double-blind trial of oral nifedipine and intravenous labetalol in hypertensive emergencies of pregnancy.
1999 Oct
Effects of labetalol treatment on the physiological and subjective response to smoked cocaine.
2000 Feb
A comparative study between a calcium channel blocker (Nicardipine) and a combined alpha-beta-blocker (Labetalol) for the control of emergence hypertension during craniotomy for tumor surgery.
2000 Oct
Factor analysis, including antihypertensive medication, of the outcome of pregnancy in pregnancy-associated hypertension.
2001
Quantitative structure-retention and retention-activity relationships of beta-blocking agents by micellar liquid chromatography.
2001 Apr 6
Studies on the photostability and in vitro phototoxicity of Labetalol.
2001 Feb
A case of renovascular hypertension due to bilateral renal artery microaneurysm who succeeded in baby delivery.
2001 Jan
Hypoperfusion without ischemia surrounding acute intracerebral hemorrhage.
2001 Jul
Monitored anesthesia care using remifentanil and propofol for awake craniotomy.
2001 Jul
A new aspect of view in synthesizing new type beta-adrenoceptor blockers with ancillary antioxidant activities.
2001 Jul
Low-dose alpha/beta blockade in the treatment of essential hypertension.
2001 Jun
Norepinephrine release after acute brain death abolishes the cardioprotective effects of ischemic preconditioning in rabbit.
2001 Mar
Evidence of functional myocardial ischemia associated with myocardial dysfunction in brain-dead pigs.
2001 Sep 18
Partial agonistic activity of labetalol, the arylethanolamine, on beta 3-adrenoceptors in the guinea-pig gastric fundus.
2002 Feb
Elevated vascular resistance after labetalol during resection of a pheochromocytoma (brief report).
2002 Feb
Shy-Drager syndrome and severe unexplained intraoperative hypotension responsive to vasopressin.
2002 Jul
Labetalol for prophylactic treatment of intractable migraine during pregnancy.
2002 Jul-Aug
Vanillylamide-based propanolamine derivative displays alpha/beta-adrenoceptor blocking and vasodilating properties.
2002 Jun
Pemoline ingestion in children: a report of five cases and review of the literature.
2002 Mar
Labetalol-induced hepatitis in a patient with chronic hepatitis B infection.
2002 Mar-Apr
Short-term treatment of severe hypertension of pregnancy: prospective comparison of nicardipine and labetalol.
2002 Sep
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
Managing hypertension in patients with stroke. Are you prepared for labetalol infusion?
2003 Jun
Was case report a case of unrecognized local anesthetic toxicity?
2003 Jun
[Posterior reversible encephalopathy syndrome].
2003 Nov-Dec
Enantioselective determination of arotinolol in human plasma by HPLC using teicoplanin chiral stationary phase.
2003 Oct
Clinical review: the management of hypertensive crises.
2003 Oct
Hydralazine for treatment of severe hypertension in pregnancy: meta-analysis.
2003 Oct 25
Very low-dose spinal anesthesia for cesarean section in a morbidly obese preeclamptic patient and its potential implications.
2004 Apr
[Protective effect of alpha beta-blockers on hypertensive target-organ damage].
2004 Mar
[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 Sat Jun 26 03:27:45 UTC 2021
Edited
by admin
on Sat Jun 26 03:27:45 UTC 2021
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 536
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
NDF-RT N0000175556
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
WHO-ATC C07BG01
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
WHO-VATC QC07CG01
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
WHO-VATC QC07BG01
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
WHO-ATC C07CG01
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
WHO-ATC C07AG01
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
WHO-VATC QC07AG01
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
NDF-RT N0000000161
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
NCI_THESAURUS C72900
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL429
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
253-258-3
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
WIKIPEDIA
LABETALOL
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
PUBCHEM
3869
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
MERCK INDEX
M6647
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY Merck Index
LACTMED
Labetalol
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
MESH
D007741
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
IUPHAR
7207
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
RXCUI
6185
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY RxNorm
INN
3941
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
CAS
36894-69-6
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
EVMPD
SUB08382MIG
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
FDA UNII
R5H8897N95
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
DRUG CENTRAL
1531
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
EPA CompTox
36894-69-6
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
HSDB
6537
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
NCI_THESAURUS
C29146
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
DRUG BANK
DB00598
Created by admin on Sat Jun 26 03:27:45 UTC 2021 , Edited by admin on Sat Jun 26 03:27:45 UTC 2021
PRIMARY
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Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC