Labetalol Hydrochloride

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 Search

SMILES

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

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/98/74787_Labetalol%20Hydrochloride_Prntlbl.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adrenergic receptor 35 Target ID: CHEMBL2331074 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6355664	Antagonist 2849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/anda/98/74787_Labetalol%20Hydrochloride_Prntlbl.pdf	Primary		Approved 8583	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 1988

C_max

Value	Dose	Co-administered	Analyte	Population
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

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse events
3000 mg single, oral Highest studied dose Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7433343	unhealthy, 18-81 Health Status: unhealthy Age Group: 18-81 Sex: M+F 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 Overdose Dose: 14 g Route: oral Route: single Dose: 14 g Sources: https://pubmed.ncbi.nlm.nih.gov/29147632	healthy, 38 Health Status: healthy Age Group: 38 Sex: F 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 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 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 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf	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
300 mg single, intravenous Studied dose Dose: 300 mg Route: intravenous Route: single Dose: 300 mg Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019425s021lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019425s021lbl.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/019425s021lbl.pdf

AEs

AE	Significance	Dose	Population
Orthostatic hypotension	Disc. AE	3000 mg single, oral Highest studied dose Dose: 3000 mg Route: oral Route: single Dose: 3000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7433343	unhealthy, 18-81 Health Status: unhealthy Age Group: 18-81 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/7433343
Acute renal failure	Disc. AE	14 g single, oral Overdose Dose: 14 g Route: oral Route: single Dose: 14 g Sources: https://pubmed.ncbi.nlm.nih.gov/29147632	healthy, 38 Health Status: healthy Age Group: 38 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/29147632
Congestive heart failure		400 mg 2 times / day multiple, oral 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Cardiac failure	Disc. AE	400 mg 2 times / day multiple, oral 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf
Hepatocellular injury	severe, rare	400 mg 2 times / day multiple, oral 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	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/018716s026lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
Ca2+ channels 59	UGT1A6 343 UGT2B4 278 P-gp 2052 UGT enzymes 27 UGT1A1 479 UGT1A9 423 UGT1A4 399 CYP 303

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
Ca2+ channels 62	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/98/75133_Labetalol%20Hydrochloride.pdf Page: 5.0	likely

Drug as victim

Target	Modality	Activity
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/98/74989_Labetalol%20Hydrochloride.pdf	likely
UGT enzymes 27	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/anda/98/75133_Labetalol%20Hydrochloride.pdf Page: 5.0	likely
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18098064/	minor
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18098064/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18098064/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18098064/	no
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24735251/	yes
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/18098064/	yes

Sourcing

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

PubMed

Title	Date	PubMed
Periprocedural hypertension: current concepts in management for the vascular surgeon.	2004-08-13	15306955
In vitro effects of antihypertensive drugs on thromboxane agonist (U46619)-induced vasoconstriction in human internal mammary artery.	2004-08	15169740
Effect of beta-adrenergic antagonists on bioluminescence control in three species of brittlestars (Echinodermata: Ophiuroidea).	2004-05	15313447
[Surgery to save body-packers].	2004-05	15158240
Severe hypertension and massive proteinuria in a newborn with renal artery stenosis.	2004-05	14986083
[Posterior reversible encephalopathy syndrome].	2004-04-30	15114789
Hyponatremic hypertensive syndrome (HHS) in an 18-month old-child presenting as malignant hypertension: a case report.	2004-04-27	15113447
Simultaneous determination of thirteen beta-blockers and one metabolite by gradient high-performance liquid chromatography with photodiode-array UV detection.	2004-04-20	15066710
Very low-dose spinal anesthesia for cesarean section in a morbidly obese preeclamptic patient and its potential implications.	2004-04	15321413
Dexmedetomidine for awake carotid endarterectomy: efficacy, hemodynamic profile, and side effects.	2004-04	15021281
[Protective effect of alpha beta-blockers on hypertensive target-organ damage].	2004-03	15171441
Polymeric alkenoxy amino acid surfactants: II. Chiral separations of beta-blockers with multiple stereogenic centers.	2004-03	15004846
Chiral separation of labetalol stereoisomers in human plasma by capillary electrophoresis.	2004-02-20	14971505
[Toxicologic analysis of some adrenergic-beta blockers in the diagnosis of intoxications].	2004-02-20	14971294
A survey of Canadian practitioners regarding the management of the hypertensive disorders of pregnancy.	2004	15117601
Labetalol treatment enhances the attenuation of tobacco withdrawal symptoms by nicotine in abstinent smokers.	2003-12	14668079
Acute myocardial infarction as a complication of clonidine withdrawal.	2003-11	14654180
Hydralazine for treatment of severe hypertension in pregnancy: meta-analysis.	2003-10-25	14576246
Enantioselective determination of arotinolol in human plasma by HPLC using teicoplanin chiral stationary phase.	2003-10	14598329
Fatality from administration of labetalol and crushed extended-release nifedipine.	2003-10	14519033
Clinical review: the management of hypertensive crises.	2003-10	12974970
Improvement of peak shape and separation performance of beta-blockers in conventional reversed-phase columns using solvent modifiers.	2003-08	12908951
Managing hypertension in patients with stroke. Are you prepared for labetalol infusion?	2003-06	12830778
Agonist actions of "beta-blockers" provide evidence for two agonist activation sites or conformations of the human beta1-adrenoceptor.	2003-06	12761341
Was case report a case of unrecognized local anesthetic toxicity?	2003-06	12761032
Community-based thrombolytic therapy of acute ischemic stroke in Helsinki.	2003-06	12738891
Refractory hypotension during caesarean section following pre-operative administration of anti-hypertensive agents.	2003-04	15321504
Left ventricular diastolic function in pregnancy-induced hypertension.	2003-04	12784777
Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine.	2003-04	12727538
Multiple Bier blocks with labetalol for complex regional pain syndrome refractory to other treatments.	2003-04	12691679
The effect of remifentanil on seizure duration and acute hemodynamic responses to electroconvulsive therapy.	2003-04	12651657
Clonidine facilitates controlled hypotension in adolescent children.	2003-04	12651645
Remifentanil for intraoperative analgesia during the endoscopic surgical treatment of pituitary lesions.	2003-03	12792580
[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	12891939
Scleroderma renal crisis sine scleroderma during pregnancy.	2003	12635948
Labetalol for prophylactic treatment of intractable migraine during pregnancy.	2002-12-17	12482217
Factors influencing acute ischaemia-induced renal hypertension in rats.	2002-12	12473871
Cardiac arrest after labetalol and metoclopramide administration in a patient with scleroderma.	2002-12	12456435
Electrocardiographic changes associated with beta-blocker toxicity.	2002-12	12447337
Comprehensive management of hypertensive emergencies and urgencies.	2002-11-21	12441013
Spectrofluorometric determination of labetolol in pharmaceutical preparations and spiked human urine through the formation of coumarin derivative.	2002-11-07	12408909
[Influence of labetalol on the resistance of human fetoplacental vessels in perfusion in vitro].	2002-09	12602277
[Nuclear medicine diagnosis of pheochromocytoma with metaiodobenzylguanidine].	2002-07	12584993
Partial agonistic activity of labetalol, the arylethanolamine, on beta 3-adrenoceptors in the guinea-pig gastric fundus.	2002-02	12423424
Labetalol decreases cerebral perfusion pressure without negatively affecting cerebral blood flow in hypertensive gravidas.	2002	12517326
Hypersensitivity immune reaction as a mechanism for dilevalol-associated hepatitis.	1992-07-01	1504402
Hemodynamic collapse following labetalol administration in preeclampsia.	1992-02	1316047
Pharmacological basis for antihypertensive effects of intravenous labetalol.	1977-01	12778
Labetalol (AH5158), a competitive alpha- and beta-receptor blocking drug, in the management of hypertension.	1976-08	14627
Letter: Emergency treatment of hypertensive crisis following clonidine withdrawal.	1976-05-29	1268685

Patents

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

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:22:12 GMT 2025` Edited by `admin` on `Mon Mar 31 18:22:12 GMT 2025`
Record UNII	1GEV3BAW9J
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Labetalol Hydrochloride

Official Name

English

NORMOZIDE COMPONENT LABETALOL HYDROCHLORIDE

Preferred 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 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

Classification Tree Code System Code

NCI_THESAURUS

C29713