labetalol Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
aromatic ring -CH(-OH)-CH2-NH-R 1531 36894-69-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • labetalol
  • labetalol hydrochloride
  • albetol
  • ibidomide
  • labetalol HCl
  • SCH 19927
  • SCH-19927
A salicylamide derivative that is a non-cardioselective blocker of BETA-ADRENERGIC RECEPTORS and ALPHA-1 ADRENERGIC RECEPTORS.
  • Molecular weight: 328.41
  • Formula: C19H24N2O3
  • CLOGP: 2.50
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 4
  • TPSA: 95.58
  • ALOGS: -4.75
  • ROTB: 8

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.60 g O
0.60 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 16 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 104.53 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 25 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 4.80 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 23 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.50 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 1, 1984 FDA CNTY LINE PHARMS

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Maternal exposure during pregnancy 582.37 62.20 122 378 14741 2342844
Premature delivery 384.96 62.20 68 432 3132 2354453
Exposure during pregnancy 326.82 62.20 85 415 25134 2332451
Pre-eclampsia 213.65 62.20 37 463 1467 2356118
Premature baby 161.73 62.20 33 467 3171 2354414
Caesarean section 142.45 62.20 31 469 4050 2353535
Hypertension 126.91 62.20 42 458 27319 2330266
Low birth weight baby 121.52 62.20 21 479 808 2356777
Foetal exposure during pregnancy 113.47 62.20 27 473 5225 2352360
Hypotension 100.85 62.20 37 463 32399 2325186
Drug ineffective 84.92 62.20 46 454 101578 2256007
Completed suicide 84.19 62.20 29 471 21005 2336580
Bradycardia 82.70 62.20 24 476 9957 2347628
Blood pressure increased 78.07 62.20 26 474 16960 2340625
Frequent bowel movements 74.48 62.20 16 484 1938 2355647
Premature labour 67.72 62.20 15 485 2091 2355494
Hyperkalaemia 66.18 62.20 18 482 5875 2351710
Cardiac arrest 65.15 62.20 22 478 14908 2342677

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Foetal exposure during pregnancy 385.89 91.57 76 247 6283 1740175
Premature baby 301.76 91.57 55 268 2887 1743571
Low birth weight baby 261.04 91.57 41 282 846 1745612
Hypotension 179.65 91.57 56 267 29598 1716860
Foetal disorder 124.84 91.57 16 307 63 1746395
Completed suicide 115.47 91.57 35 288 16277 1730181
Neutropenia neonatal 114.59 91.57 14 309 33 1746425
Bradycardia 111.76 91.57 31 292 10503 1735955

Pharmacologic Action:

SourceCodeDescription
ATC C07AG01 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS
Alpha and beta blocking agents
ATC C07BG01 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS AND THIAZIDES
Alpha and beta blocking agents and thiazides
ATC C07CG01 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS AND OTHER DIURETICS
Alpha and beta blocking agents and other diuretics
MeSH PA D018663 Adrenergic Agents
MeSH PA D058668 Adrenergic alpha-1 Receptor Antagonists
MeSH PA D000317 Adrenergic alpha-Antagonists
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D000319 Adrenergic beta-Antagonists
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:66991 sympatholytic agent
CHEBI has role CHEBI:37890 alpha-adrenergic antagonist
CHEBI has role CHEBI:35530 beta-adrenergic antagonist
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
FDA EPC N0000175556 beta-Adrenergic Blocker
MeSH PA D013566 Sympathomimetics

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Angina pectoris off-label use 194828000
Pheochromocytoma Adjunct Therapy off-label use
Anuria contraindication 2472002 DOID:2983
Bronchospasm contraindication 4386001
Hypercholesterolemia contraindication 13644009
Secondary angle-closure glaucoma contraindication 21571006
Complete atrioventricular block contraindication 27885002
Hypovolemia contraindication 28560003
Dehydration contraindication 34095006
Depressive disorder contraindication 35489007
Hyperuricemia contraindication 35885006 DOID:1920
Hypokalemia contraindication 43339004
Low blood pressure contraindication 45007003
Sinus bradycardia contraindication 49710005
Systemic lupus erythematosus contraindication 55464009 DOID:9074
Sympathectomy contraindication 57071006
Hepatic failure contraindication 59927004
Hypercalcemia contraindication 66931009 DOID:12678
Hyperparathyroidism contraindication 66999008 DOID:13543
Hypochloremic alkalosis contraindication 70134007
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Pulmonary emphysema contraindication 87433001
Cardiogenic shock contraindication 89138009
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hypomagnesemia contraindication 190855004
Partial atrioventricular block contraindication 195039008
Decompensated cardiac failure contraindication 195111005
Acute pancreatitis contraindication 197456007 DOID:2913
Disease of liver contraindication 235856003 DOID:409
Neonatal hyperbilirubinemia contraindication 281610001
Intraoperative floppy iris syndrome contraindication 418801006
Azotemia contraindication 445009001

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.81 acidic
pKa2 12.65 acidic
pKa3 8.23 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-1 adrenergic receptor GPCR ANTAGONIST Ki 8.23 DRUG MATRIX CHEMBL
Beta-2 adrenergic receptor GPCR ANTAGONIST Ki 7.96 DRUG MATRIX CHEMBL
Sigma non-opioid intracellular receptor 1 Membrane receptor Ki 6.12 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter Ki 5.48 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR Ki 6.65 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 5.71 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 5.89 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.10 DRUG MATRIX
Alpha-1D adrenergic receptor GPCR ANTAGONIST Ki 7.64 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 6.49 DRUG MATRIX
5-hydroxytryptamine receptor 1A GPCR IC50 6.41 CHEMBL
Alpha-1A adrenergic receptor GPCR IC50 7.24 CHEMBL
CAAX prenyl protease 1 Unclassified AC50 5.11 CHEMBL
CAAX prenyl protease 2 Unclassified AC50 4.82 CHEMBL

External reference:

IDSource
4019797 VUID
N0000147886 NUI
C0022860 UMLSCUI
D00600 KEGG_DRUG
1GEV3BAW9J UNII
32780-64-6 SECONDARY_CAS_RN
46547007 SNOMEDCT_US
6185 RXNORM
372750000 SNOMEDCT_US
d00016 MMSL
4019797 VANDF
001839 NDDF
CHEMBL429 ChEMBL_ID
DB00598 DRUGBANK_ID
CHEMBL1200323 ChEMBL_ID
3941 INN_ID
CHEBI:6343 CHEBI
3869 PUBCHEM_CID
CHEMBL1204165 ChEMBL_ID
D007741 MESH_DESCRIPTOR_UI
7207 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9320 INJECTION 5 mg INTRAVENOUS ANDA 12 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9622 INJECTION 5 mg INTRAVENOUS ANDA 12 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9623 INJECTION 5 mg INTRAVENOUS ANDA 12 sections
Labetalol HCl HUMAN PRESCRIPTION DRUG LABEL 1 0185-0010 TABLET, FILM COATED 100 mg ORAL ANDA 12 sections
Labetalol HCl HUMAN PRESCRIPTION DRUG LABEL 1 0185-0117 TABLET, FILM COATED 200 mg ORAL ANDA 12 sections
Labetalol HCl HUMAN PRESCRIPTION DRUG LABEL 1 0185-0118 TABLET, FILM COATED 300 mg ORAL ANDA 12 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-2267 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 12 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0409-2339 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 12 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-0605 TABLET, FILM COATED 100 mg ORAL ANDA 11 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-0606 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-0607 TABLET, FILM COATED 300 mg ORAL ANDA 11 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-4539 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7686 TABLET, FILM COATED 100 mg ORAL ANDA 11 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7687 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0615-7688 TABLET, FILM COATED 300 mg ORAL ANDA 11 sections
Labetalol HCL HUMAN PRESCRIPTION DRUG LABEL 1 0615-8130 TABLET, FILM COATED 100 mg ORAL ANDA 11 sections
Labetalol HCL HUMAN PRESCRIPTION DRUG LABEL 1 0615-8131 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-5928 TABLET, FILM COATED 100 mg ORAL ANDA 11 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-5929 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-5930 TABLET, FILM COATED 300 mg ORAL ANDA 11 sections
Labetalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-641 TABLET, FILM COATED 100 mg ORAL ANDA 12 sections
Labetalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-642 TABLET, FILM COATED 200 mg ORAL ANDA 12 sections
Labetalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-643 TABLET, FILM COATED 300 mg ORAL ANDA 12 sections
LABETALOL HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 16590-994 TABLET, FILM COATED 300 mg ORAL ANDA 11 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 17478-420 INJECTION, SOLUTION 5 mg INTRAVENOUS ANDA 12 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-592 TABLET, FILM COATED 100 mg ORAL ANDA 11 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-988 TABLET, FILM COATED 300 mg ORAL ANDA 11 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-994 TABLET, FILM COATED 200 mg ORAL ANDA 11 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-723 TABLET 100 mg ORAL ANDA 11 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 23155-724 TABLET 200 mg ORAL ANDA 11 sections