Identification

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Name
Labetalol
Accession Number
DB00598  (APRD01062)
Type
Small Molecule
Groups
Approved
Description

Labetalol is a racemic mixture of 2 diastereoisomers where dilevalol, the R,R' stereoisomer, makes up 25% of the mixture.8 Labetalol is formulated as an injection or tablets to treat hypertension.7,8

Labetalol was granted FDA approval on 1 August 1984.6

Structure
Thumb
Synonyms
  • 3-Carboxamido-4-hydroxy-alpha-((1-methyl-3-phenylpropylamino)methyl)benzyl alcohol
  • 5-(1-Hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide
  • Labétalol
  • Labetalol
  • Labetalolum
  • Labetolol
Product Ingredients
IngredientUNIICASInChI Key
Labetalol hydrochloride1GEV3BAW9J32780-64-6WQVZLXWQESQGIF-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Labetalol HClInjection, solution5 mg/1mLIntravenousCantrell Drug Company2012-05-182015-01-14Us
Labetalol HydrochlorideTablet, film coated200 mg/1OralAlvogen Inc.2018-03-01Not applicableUs
Labetalol HydrochlorideTablet100 mg/1OralREMEDYREPACK INC.2016-11-30Not applicableUs
Labetalol HydrochlorideTablet200 mg/1OralA-S Medication Solutions2014-12-01Not applicableUs50090 242820180913 8702 1paanpz
Labetalol HydrochlorideTablet, film coated100 mg/1OralAlvogen Inc.2018-03-01Not applicableUs
Labetalol HydrochlorideTablet300 mg/1OralCounty Line Pharmaceuticals LLC2014-12-012020-11-01Us
Labetalol HydrochlorideTablet, film coated300 mg/1OralMutual Pharmaceutical2007-01-03Not applicableUs
Labetalol HydrochlorideTablet300 mg/1Oralbryant ranch prepack2014-12-01Not applicableUs
Labetalol HydrochlorideTablet200 mg/1OralWellSpring Pharma Services Inc.2014-12-012017-11-29Us
Labetalol HydrochlorideTablet100 mg/1OralA-S Medication Solutions2014-12-01Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-labetalol TabletsTabletOralApotex Corporation2001-06-01Not applicableCanada
Apo-labetalol TabletsTabletOralApotex Corporation2001-03-16Not applicableCanada
LabetalolTablet, film coated200 mg/1OralSun Pharmaceutical Industries Limited1999-07-292018-04-23Us
LabetalolTablet, film coated100 mg/1OralMarlex Pharmaceuticals Inc2018-04-01Not applicableUs
LabetalolTablet, film coated100 mg/1OralSun Pharmaceutical Industries Limited1999-07-292018-04-23Us
LabetalolInjection, solution5 mg/1mLIntravenousSagent Pharmaceuticals2010-02-172015-09-30Us
LabetalolTablet, film coated300 mg/1OralMarlex Pharmaceuticals Inc2018-04-01Not applicableUs
LabetalolTablet, film coated300 mg/1OralSun Pharmaceutical Industries Limited1999-07-292018-04-23Us
LabetalolTablet, film coated200 mg/1OralMarlex Pharmaceuticals Inc2018-04-01Not applicableUs
Labetalol HClTablet, film coated200 mg/1OralBlue Point Laboratories2014-02-26Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Labetalol HClLabetalol hydrochloride (5 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2012-05-182015-01-14Us
International/Other Brands
Albetol (Leiras) / Latol (Standard) / Normadate (GlaxoSmithKline) / Normodyne (Schering)
Categories
UNII
R5H8897N95
CAS number
36894-69-6
Weight
Average: 328.4055
Monoisotopic: 328.178692644
Chemical Formula
C19H24N2O3
InChI Key
SGUAFYQXFOLMHL-UHFFFAOYSA-N
InChI
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)
IUPAC Name
2-hydroxy-5-{1-hydroxy-2-[(4-phenylbutan-2-yl)amino]ethyl}benzamide
SMILES
CC(CCC1=CC=CC=C1)NCC(O)C1=CC(C(N)=O)=C(O)C=C1

Pharmacology

Indication

Labetalol injections are indicated to control blood pressure in severe hypertension.7 Labetalol tablets are indicated alone or in combination with antihypertensives like thiazides and loop diuretics to manage hypertension.8

Associated Conditions
Pharmacodynamics

Labetalol antagonizes various adrenergic receptors to decrease blood pressure.5,3,4,7 The duration of action is long as it is generally given twice daily, and the therapeutic window is wide as patients usually take 200-400mg twice daily.8 Patients susceptible to bronchospasms should not use labetalol unless they are unresponsive to or intolerant of other antihypertensives.8

Mechanism of action

Labetalol non-selectively antagonizes beta-adrenergic receptors, and selectively antagonizes alpha-1-adrenergic receptors.5 Following oral administration, labetalol has 3 times the beta-blocking ability than alpha-blocking ability.5 This increases to 6.9 times following intravenous administration.5 Antagonism of alpha-1-adrenergic receptors leads to vasodilation and decreased vascular resistance.3 This leads to a decrease in blood pressure that is most pronounced while standing.4 Antagonism of beta-1-adrenergic receptors leads to a slight decrease in heart rate.7 Antagonism of beta-2-adrenergic receptors leads to some of the side effects of labetalol such as bronchospasms, however this may be slightly attenuated by alpha-1-adrenergic antagonism.4 Labetalol leads to sustained vasodilation over the long term without a significant decrease in cardiac output or stroke volume, and a minimal decrease in heart rate.3,4

TargetActionsOrganism
ABeta-1 adrenergic receptor
antagonist
Humans
ABeta-2 adrenergic receptor
antagonist
Humans
AAlpha-1 adrenergic receptors
antagonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

100mg and 200mg oral doses of labetalol have a Tmax of 20 minutes to 2 hours.2 Bioavailability may be as low as 11% or as high as 86% and may increase in older patients or when taken with food.2

Volume of distribution

In normotensive patients, the volume of distribution is 805L.2 In hypertensive patients, the volume of distribution is between 188-747L with an average of 392L.2

Protein binding

Labetalol is approximately 50% protein bound in serum.2,7,8

Metabolism

The metabolism of labetalol has not been fully described in the literature but studies in sheep show an N-dealkylation to 3-amino-1-phenyl butane.1 This metabolite may be further metabolized to benzylacetone and 3-amino-(4-hydroxyphenyl)butane.1 Labetalol in humans is mainly metabolized to glucuronide metabolites such as the O-phenyl-glucuronide and the N-glucuronide.2,7,8

Route of elimination

Radiolabelled doses of labetalol are 55-60% recovered in the urine and 12-27% recovered in the feces.2

Half life

Labetalol has a half life of 1.7-6.1 hours.2

Clearance

Labetalol has a plasma clearance of approximately 1500mL/min and a whole blood clearance of 1100mL/min.2

Toxicity

The oral LD50 in mice is 600mg/kg and in rats is >2g/kg.7,8 The intravenous LD50 in mice and rats is 50-60mg/kg.7,8

Patients experiencing an overdose may present with excessive hypotension and bradycardia.7,8 Patients should be placed on their back with their legs raised to maintain perfusion of the brain.7,8 Oral overdoses may be treated with gastric lavage or emesis, bradycardia may be treated with atropine or epinephrine, cardiac failure may be treated with digitalis and a diuretic, hypotension may be treated with vasopressors, bronchospasms may be treated with epinephrine or a beta2 agonist, and seizures may be treated with diazepam.7,8

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Labetalol Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidineThe metabolism of Labetalol can be decreased when combined with 1-(2-Phenylethyl)-4-phenyl-4-acetoxypiperidine.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Labetalol.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Labetalol.
1,10-Phenanthroline1,10-Phenanthroline may increase the bradycardic activities of Labetalol.
2,4-thiazolidinedioneThe therapeutic efficacy of 2,4-thiazolidinedione can be increased when used in combination with Labetalol.
2,5-Dimethoxy-4-ethylamphetamineThe therapeutic efficacy of Labetalol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe therapeutic efficacy of Labetalol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
25-desacetylrifapentineThe metabolism of Labetalol can be increased when combined with 25-desacetylrifapentine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Labetalol is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,5-diiodothyropropionic acidThe risk or severity of adverse effects can be increased when Labetalol is combined with 3,5-diiodothyropropionic acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take without regard to meals.

References

Synthesis Reference

U.S. Patent 4,012,444.

General References
  1. Yeleswaram K, Rurak DW, Kwan E, Hall C, Doroudian A, Abbott FS, Axelson JE: Disposition, metabolism, and pharmacodynamics of labetalol in adult sheep. Drug Metab Dispos. 1993 Mar-Apr;21(2):284-92. [PubMed:8097698]
  2. McNeil JJ, Louis WJ: Clinical pharmacokinetics of labetalol. Clin Pharmacokinet. 1984 Mar-Apr;9(2):157-67. doi: 10.2165/00003088-198409020-00003. [PubMed:6370541]
  3. Opie LH: Role of vasodilation in the antihypertensive and antianginal effects of labetalol: implications for therapy of combined hypertension and angina. Cardiovasc Drugs Ther. 1988 Sep;2(3):369-76. [PubMed:3154919]
  4. Carter BL: Labetalol. Drug Intell Clin Pharm. 1983 Oct;17(10):704-12. [PubMed:6354658]
  5. MacCarthy EP, Bloomfield SS: Labetalol: a review of its pharmacology, pharmacokinetics, clinical uses and adverse effects. Pharmacotherapy. 1983 Jul-Aug;3(4):193-219. [PubMed:6310529]
  6. FDA Approved Drug Products: Normodyne Labetalol Hydrochloride Injection (Discontinued) [Link]
  7. FDA Approved Drug Products: Labetalol Hydrochloride Injection [Link]
  8. FDA Approved Drug Products: Labetalol Hydrochloride Tablet [Link]
External Links
Human Metabolome Database
HMDB0014736
KEGG Drug
D08106
KEGG Compound
C07063
PubChem Compound
3869
PubChem Substance
46505511
ChemSpider
3734
BindingDB
25758
ChEBI
6343
ChEMBL
CHEMBL429
Therapeutic Targets Database
DAP000038
PharmGKB
PA164743150
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Labetalol
ATC Codes
C07BG01 — Labetalol and thiazidesC07CG01 — Labetalol and other diureticsC07AG01 — Labetalol
AHFS Codes
  • 24:24.00 — Beta-adrenergic Blocking Agents
FDA label
Download (401 KB)
MSDS
Download (53.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedSupportive CareControlled Hypotension for Nasal Surgeries1
0RecruitingPreventionChronic Hypertension Complicating Pregnancy (Diagnosis) / Preeclampsia1
0RecruitingPreventionObesity, Morbid / Preeclampsia1
1, 2CompletedTreatmentCraniotomy / High Blood Pressure (Hypertension)1
1, 2WithdrawnTreatmentHigh Blood Pressure (Hypertension) / Pregnancy Toxemias / Proteinuria1
2CompletedTreatmentChronic Rhinosinusitis1
2CompletedTreatmentCocaine-Related Disorders1
2CompletedTreatmentHydralazine Adverse Reaction / Pre-eclampsia Superimposed Pre-existing Hypertension / Pregnancy associated hypertension / Prophylaxis of preeclampsia1
2CompletedTreatmentIntracerebral Hemorrhage1
2CompletedTreatmentStroke, Acute1
2CompletedTreatmentTobacco Use Disorders1
2RecruitingTreatmentBloodpressure / Heart Rate1
2RecruitingTreatmentIntracerebral Hemorrhage1
2, 3RecruitingTreatmentSevere Pre-Eclampsia, Antepartum1
2, 3WithdrawnPreventionChronic Hypertension / Gestational Hypertension / Preeclampsia / Pregnancy associated hypertension / Superimposed Preeclampsia1
3CompletedTreatmentPregnancy associated hypertension1
3Not Yet RecruitingTreatmentPostnatal Hypertension1
4CompletedPreventionSurgery, Laparoscopic1
4CompletedTreatmentBronchoscopy1
4CompletedTreatmentHypertension in Pregnancy / Preeclampsia2
4CompletedTreatmentHypertensive Urgency1
4RecruitingPreventionHypertension, Pregnancy-Induced / Prophylaxis of preeclampsia1
4RecruitingSupportive CareDeliberate Hypotension / Sinus Endoscopic Surgery / Tissue Perfusion1
4RecruitingTreatmentChronic Hypertension in Obstetric Context / Preeclampsia With Severe Features1
4RecruitingTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentPreeclampsia With Severe Features1
Not AvailableCompletedTreatmentCVA (Cerebrovascular Accident) / Intracerebral Hemorrhage / Intracranial Hemorrhages1
Not AvailableCompletedTreatmentSevere Postpartum Hypertension1
Not AvailableRecruitingNot AvailableAcute Bacterial Exacerbation of Chronic Bronchitis (ABECB) / Acute Bacterial Sinusitis (ABS) / Acute Decompensated Heart Failure (ADHF) / Acute Pyelonephritis / Adenovirus / Adjunct to general anesthesia therapy / Adrenal Insufficiency / Airway Swelling / Anaesthesia therapy / Anxiety / Anxiolysis / Arterial Hypotension / Autism, Early Infantile / Autistic Disorder / Bartonellosis / Benzodiazepine Withdrawal / Benzodiazepines / Bipolar Disorder (BD) / Bloodstream Infections / Bone and Joint Infections / Bradycardia / Brain Swelling / Bronchospasm / Brucellosis / Cardiac Arrest / Cardiac Dysrhythmia / Central Nervous System Infections / Cholera / Chronic Bacterial Prostatitis / Chronic Kidney Disease (CKD) / Community Acquired Pneumonia (CAP) / Complicated Urinary Tract Infections / Convulsions / Cytomegalovirus Retinitis / Drug hypersensitivity reaction / Early-onset Schizophrenia Spectrum Disorders / Endocarditis / Epilepsies / Fibrinolytic Bleeding / Flu caused by Influenza / Gastroparesis / Gram-negative Infection / Gynaecological infection / Headaches / Heart Failure / Heavy Menstrual Bleeding / Hemophilia / Herpes Simplex Virus / High Blood Pressure (Hypertension) / High Cholesterol / Hospital-acquired bacterial pneumonia / Hyperaldosteronism / Hyperlipidemias / Hypokalaemia / Infantile Hemangiomas / Infection caused by staphylococci / Infection NOS / Inflammatory Conditions / Inflammatory Reaction / Influenza Treatment or Prophylaxis / Inhalational Anthrax (Post-Exposure) / Intra-Abdominal Infections / Life-threatening Fungal Infections / Lower Respiratory Tract Infection (LRTI) / Meningitis, Bacterial / Methicillin Resistant Staphylococcus Aureus (MRSA) / Migraine / Muscle Spasms / Nausea / Neuromuscular Blockade / Neutropenias / Oedema / Opioid Addiction / Pain NOS / Plague / Pneumonia / Prophylaxis / Psittacosis / Pulmonary Arterial Hypertension (PAH) / Q Fever / Reflux / Relapsing Fever / Rocky Mountain Spotted Fever / Schizophrenic Disorders / Sedation therapy / Seizures / Sepsis / Skeletal Muscle Spasms / Skin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections / Sleeplessness / Stable Angina (SA) / Thromboprophylaxis / Thrombotic events / Toxic effect of hydrocyanic acid and cyanides / Trachoma / Treatment-resistant Schizophrenia / Tularemia / Typhus Fever / Uncomplicated Skin and Skin Structure Infections / Uncomplicated Urinary Tract Infections / Urinary Tract Infections (UTIs) / Vomiting / Withdrawal1
Not AvailableRecruitingTreatmentAcute Coronary Syndromes (ACS)1
Not AvailableUnknown StatusPreventionIntubation, Endotracheal / Patients Who Are Intubated for General Anesthesia1
Not AvailableWithdrawnTreatmentHigh Blood Pressure (Hypertension)1

Pharmacoeconomics

Manufacturers
  • Apothecon inc div bristol myers squibb
  • Bedford laboratories div ben venue laboratories inc
  • Claris lifesciences ltd
  • Hospira inc
  • Taylor pharmaceuticals
  • Sagent strides llc
  • Schering corp sub schering plough corp
  • Prometheus laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Mutual pharmaceutical co inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
Packagers
  • Akorn Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Cardinal Health
  • Comprehensive Consultant Services Inc.
  • Diversified Healthcare Services Inc.
  • Eon Labs
  • Goldline Laboratories Inc.
  • Heartland Repack Services LLC
  • Hospira Inc.
  • Ivax Pharmaceuticals
  • Kaiser Foundation Hospital
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Neuman Distributors Inc.
  • Novex Pharma
  • Nucare Pharmaceuticals Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Prometheus Laboratories Inc.
  • Rebel Distributors Corp.
  • Sagent Pharmaceuticals
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • United Research Laboratories Inc.
  • Vangard Labs Inc.
  • Watson Pharmaceuticals
  • Wellspring Pharmaceutical
Dosage forms
FormRouteStrength
PowderNot applicable1 kg/1kg
InjectionIntravenous5 mg/1mL
Tablet, coatedOral100 mg/1
Tablet, coatedOral200 mg/1
Tablet, coatedOral300 mg/1
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral200 mg/1
Tablet, film coatedOral300 mg/1
SolutionIntravenous
Injection, solutionIntravenous5 mg/1mL
TabletOral100 mg/1
TabletOral200 mg/1
TabletOral300 mg/1
LiquidIntravenous
TabletOral
Prices
Unit descriptionCostUnit
Labetalol Hydrochloride 5 mg/ml1.36USD ml
Trandate 300 mg tablet1.28USD tablet
Trandate 5 mg/ml vial1.25USD ml
Trandate 200 mg tablet1.08USD tablet
Labetalol hcl 300 mg tablet1.02USD tablet
Normodyne 200 mg tablet1.0USD tablet
Labetalol hcl 200 mg tablet0.76USD tablet
Trandate 100 mg tablet0.68USD tablet
Labetalol hcl 100 mg tablet0.53USD tablet
Trandate 200 mg Tablet0.47USD tablet
Trandate 100 mg Tablet0.27USD tablet
Labetalol hcl 5 mg/ml vial0.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)188 °CU.S. Patent 4,012,444.
boiling point (°C)552.7http://www.chemspider.com/Chemical-Structure.3734.html
pKa9.3https://pubchem.ncbi.nlm.nih.gov/compound/Labetalol#section=Caco2-Permeability
Predicted Properties
PropertyValueSource
Water Solubility0.00578 mg/mLALOGPS
logP1.73ALOGPS
logP1.89ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area95.58 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.72 m3·mol-1ChemAxon
Polarizability36.83 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9943
Blood Brain Barrier-0.8313
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7073
P-glycoprotein inhibitor INon-inhibitor0.8908
P-glycoprotein inhibitor IINon-inhibitor0.9269
Renal organic cation transporterNon-inhibitor0.8457
CYP450 2C9 substrateNon-substrate0.7448
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.6202
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8995
CYP450 3A4 inhibitorNon-inhibitor0.8256
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8383
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9189
BiodegradationNot ready biodegradable0.945
Rat acute toxicity2.1174 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9501
hERG inhibition (predictor II)Non-inhibitor0.7398
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-03dl-7900000000-e18d52bcb93357c4a7e2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-004i-0319000000-cd3fa186952809ae3558
MS/MS Spectrum - , positiveLC-MS/MSsplash10-03di-0519000000-0a8da4acfa8cd259fb3f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03dl-4928000000-117458013dbd49aaf54b

Taxonomy

Description
This compound belongs to the class of organic compounds known as salicylamides. These are carboxamide derivatives of salicylic acid. Salicylic acid is the ortho-hydroxylated derivative of benzoic acid.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzoic acids and derivatives
Direct Parent
Salicylamides
Alternative Parents
Benzamides / Benzoyl derivatives / Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Secondary alcohols / Primary carboxylic acid amides / Amino acids and derivatives / 1,2-aminoalcohols / Dialkylamines
show 4 more
Substituents
Salicylamide / Benzamide / Benzoyl / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Aralkylamine / Vinylogous acid / Amino acid or derivatives / 1,2-aminoalcohol / Secondary alcohol
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
benzamides, secondary amino compound (CHEBI:6343)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor signaling protein activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. Riva E, Mennini T, Latini R: The alpha- and beta-adrenoceptor blocking activities of labetalol and its RR-SR (50:50) stereoisomers. Br J Pharmacol. 1991 Dec;104(4):823-8. [PubMed:1687367]
  2. Monopoli A, Bamonte F, Forlani A, Ongini E, Parravicini L: Effects of the R, R-isomer of labetalol, SCH 19927, in isolated tissues and in spontaneously hypertensive rats during a repeated treatment. Arch Int Pharmacodyn Ther. 1984 Dec;272(2):256-63. [PubMed:6151824]
  3. Sassard J, Zech PY, Pozet N, Cuisinaud G, Vincent M: [Comparative effects of an alpha 1 and beta 1-2 blocker (labetalol) and a beta-1 blocker (atenolol) in the hypertensive patient]. J Pharmacol. 1983;14 Suppl 2:121-9. [PubMed:6355664]
  4. Nakagawa Y, Takeda K, Sakurai H, Mitomi A, Imai S: [Antihypertensive effects of labetalol in three types of hypertensive models of rats (author's transl)]. Nihon Yakurigaku Zasshi. 1981 Apr;77(4):435-45. [PubMed:7286847]
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  6. Pujos E, Cren-Olive C, Paisse O, Flament-Waton MM, Grenier-Loustalot MF: Comparison of the analysis of beta-blockers by different techniques. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Dec 1;877(31):4007-14. doi: 10.1016/j.jchromb.2009.10.014. Epub 2009 Oct 17. [PubMed:19879818]
  7. Rosendorff C: Beta-blocking agents with vasodilator activity. J Hypertens Suppl. 1993 Jun;11(4):S37-40. [PubMed:8104240]
  8. van Zwieten PA: An overview of the pharmacodynamic properties and therapeutic potential of combined alpha- and beta-adrenoceptor antagonists. Drugs. 1993 Apr;45(4):509-17. [PubMed:7684671]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein homodimerization activity
Specific Function
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
References
  1. Doggrell SA: The effects of labetalol and dilevalol on isolated cardiovascular preparations of the guinea-pig and rat. J Pharm Pharmacol. 1992 Dec;44(12):1001-6. [PubMed:1361547]
  2. Doggrell SA: Relaxant and beta 2-adrenoceptor blocking activities of labetalol, dilevalol, amosulalol and KF-4317 on the rat isolated aorta. J Pharm Pharmacol. 1988 Nov;40(11):812-5. [PubMed:2907566]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  4. Sassard J, Zech PY, Pozet N, Cuisinaud G, Vincent M: [Comparative effects of an alpha 1 and beta 1-2 blocker (labetalol) and a beta-1 blocker (atenolol) in the hypertensive patient]. J Pharmacol. 1983;14 Suppl 2:121-9. [PubMed:6355664]
  5. Pujos E, Cren-Olive C, Paisse O, Flament-Waton MM, Grenier-Loustalot MF: Comparison of the analysis of beta-blockers by different techniques. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Dec 1;877(31):4007-14. doi: 10.1016/j.jchromb.2009.10.014. Epub 2009 Oct 17. [PubMed:19879818]
  6. Rosendorff C: Beta-blocking agents with vasodilator activity. J Hypertens Suppl. 1993 Jun;11(4):S37-40. [PubMed:8104240]
  7. van Zwieten PA: An overview of the pharmacodynamic properties and therapeutic potential of combined alpha- and beta-adrenoceptor antagonists. Drugs. 1993 Apr;45(4):509-17. [PubMed:7684671]
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:
References
  1. Bernstein JS, Ebert TJ, Stowe DF, Schmeling WT, Nelson MA, Woods MP: Partial attenuation of hemodynamic responses to rapid sequence induction and intubation with labetalol. J Clin Anesth. 1989;1(6):444-51. [PubMed:2696507]
  2. Nakamura T, Maruyama K, Ohnuki T, Hattori K, Watanabe K, Nagatomo T: Tamsulosin: assessment of affinityof (3)H-P razosin binding to two alpha-1- adrenoceptor subtypes in the canine aorta. Pharmacology. 1999 Nov;59(5):234-8. [PubMed:10529655]
  3. Sassard J, Zech PY, Pozet N, Cuisinaud G, Vincent M: [Comparative effects of an alpha 1 and beta 1-2 blocker (labetalol) and a beta-1 blocker (atenolol) in the hypertensive patient]. J Pharmacol. 1983;14 Suppl 2:121-9. [PubMed:6355664]
  4. Pedersen ME, Cockcroft JR: The vasodilatory beta-blockers. Curr Hypertens Rep. 2007 Aug;9(4):269-77. [PubMed:17686376]
  5. Shiraishi K, Moriya M, Miyake N, Takayanagi I: Alpha 1-adrenoceptor blocking activities of bevantolol hydrochloride(NC-1400) and labetalol in rat isolated thoracic aorta--do they distinguish between subtypes? Gen Pharmacol. 1992 Sep;23(5):843-5. [PubMed:1358746]
  6. Rosendorff C: Beta-blocking agents with vasodilator activity. J Hypertens Suppl. 1993 Jun;11(4):S37-40. [PubMed:8104240]
  7. van Zwieten PA: An overview of the pharmacodynamic properties and therapeutic potential of combined alpha- and beta-adrenoceptor antagonists. Drugs. 1993 Apr;45(4):509-17. [PubMed:7684671]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Hermann DJ, Krol TF, Dukes GE, Hussey EK, Danis M, Han YH, Powell JR, Hak LJ: Comparison of verapamil, diltiazem, and labetalol on the bioavailability and metabolism of imipramine. J Clin Pharmacol. 1992 Feb;32(2):176-83. [PubMed:1613128]
  2. Shin J, Johnson JA: Pharmacogenetics of beta-blockers. Pharmacotherapy. 2007 Jun;27(6):874-87. doi: 10.1592/phco.27.6.874. [PubMed:17542770]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Jeong H, Choi S, Song JW, Chen H, Fischer JH: Regulation of UDP-glucuronosyltransferase (UGT) 1A1 by progesterone and its impact on labetalol elimination. Xenobiotica. 2008 Jan;38(1):62-75. doi: 10.1080/00498250701744633 . [PubMed:18098064]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Glucuronosyltransferase activity
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name
UGT2B7
Uniprot ID
P16662
Uniprot Name
UDP-glucuronosyltransferase 2B7
Molecular Weight
60694.12 Da
References
  1. Jeong H, Choi S, Song JW, Chen H, Fischer JH: Regulation of UDP-glucuronosyltransferase (UGT) 1A1 by progesterone and its impact on labetalol elimination. Xenobiotica. 2008 Jan;38(1):62-75. doi: 10.1080/00498250701744633 . [PubMed:18098064]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Retinoic acid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
Gene Name
UGT1A9
Uniprot ID
O60656
Uniprot Name
UDP-glucuronosyltransferase 1-9
Molecular Weight
59940.495 Da
References
  1. Jeong H, Choi S, Song JW, Chen H, Fischer JH: Regulation of UDP-glucuronosyltransferase (UGT) 1A1 by progesterone and its impact on labetalol elimination. Xenobiotica. 2008 Jan;38(1):62-75. doi: 10.1080/00498250701744633 . [PubMed:18098064]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Martinez-Gomez MA, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of basic drug-human serum protein interactions by capillary electrophoresis. Electrophoresis. 2006 Sep;27(17):3410-9. doi: 10.1002/elps.200600102. [PubMed:16944456]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Martinez-Gomez MA, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of basic drug-human serum protein interactions by capillary electrophoresis. Electrophoresis. 2006 Sep;27(17):3410-9. doi: 10.1002/elps.200600102. [PubMed:16944456]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Efflux transmembrane transporter activity
Specific Function
Drug efflux transporter present in a number of stem cells that acts as a regulator of cellular differentiation. Able to mediate efflux from cells of the rhodamine dye and of the therapeutic drug do...
Gene Name
ABCB5
Uniprot ID
Q2M3G0
Uniprot Name
ATP-binding cassette sub-family B member 5
Molecular Weight
138639.48 Da
References
  1. Wessler JD, Grip LT, Mendell J, Giugliano RP: The P-glycoprotein transport system and cardiovascular drugs. J Am Coll Cardiol. 2013 Jun 25;61(25):2495-502. doi: 10.1016/j.jacc.2013.02.058. Epub 2013 Apr 3. [PubMed:23563132]

Drug created on June 13, 2005 07:24 / Updated on October 17, 2019 18:08