labetalol ๐Ÿถ Veterinary Use | 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 ยตM/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
Exposure during pregnancy 155.30 15.32 123 5873 136219 56149852
Pre-eclampsia 120.27 15.32 42 5954 8444 56277627
Caesarean section 107.21 15.32 46 5950 16045 56270026
Premature delivery 95.74 15.32 50 5946 27010 56259061
Premature baby 93.21 15.32 44 5952 19161 56266910
Maternal exposure during pregnancy 69.68 15.32 93 5903 189460 56096611
Foetal growth restriction 63.27 15.32 25 5971 7074 56278997
Hypertension 61.11 15.32 100 5896 244178 56041893
Patent ductus arteriosus 50.05 15.32 18 5978 3933 56282138
Premature labour 45.00 15.32 23 5973 11859 56274212
Haemangioma congenital 43.55 15.32 10 5986 436 56285635
Pregnancy 42.23 15.32 32 5964 33001 56253070
Foetal exposure during pregnancy 35.14 15.32 29 5967 33794 56252277
Hypotension 29.39 15.32 75 5921 250433 56035638
Low birth weight baby 29.31 15.32 14 5982 6244 56279827
Maternal drugs affecting foetus 28.85 15.32 13 5983 5080 56280991
Rheumatoid arthritis 27.58 15.32 4 5992 382600 55903471
HELLP syndrome 27.19 15.32 8 5988 928 56285143
Foetal death 25.13 15.32 14 5982 8573 56277498
Post transplant lymphoproliferative disorder 23.56 15.32 11 5985 4661 56281410
Gestational diabetes 23.19 15.32 13 5983 8051 56278020
Phaeochromocytoma 22.41 15.32 6 5990 493 56285578
Exomphalos 21.80 15.32 6 5990 547 56285524
Ultrasound uterus abnormal 20.93 15.32 4 5992 70 56286001
Dilatation intrahepatic duct acquired 20.84 15.32 6 5990 644 56285427
Blood pressure increased 19.69 15.32 46 5950 145130 56140941
Hyperkalaemia 18.68 15.32 25 5971 50840 56235231
Drug intolerance 18.54 15.32 3 5993 264815 56021256
Cardiac arrest 17.15 15.32 32 5964 86282 56199789
Abortion spontaneous 16.83 15.32 22 5974 43731 56242340
Red blood cell schistocytes present 15.71 15.32 4 5992 270 56285801
Kidney transplant rejection 15.50 15.32 8 5988 4205 56281866
Neuromuscular blockade 15.34 15.32 4 5992 297 56285774

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
Premature baby 116.35 18.67 51 3470 18015 31675808
Foetal exposure during pregnancy 74.78 18.67 50 3471 40826 31652997
Low birth weight baby 73.35 18.67 28 3493 6942 31686881
Foetal disorder 72.24 18.67 17 3504 793 31693030
Neutropenia neonatal 64.45 18.67 15 3506 666 31693157
Foetal growth restriction 46.22 18.67 17 3504 3798 31690025
Congenital oesophageal anomaly 44.58 18.67 8 3513 93 31693730
Polyhydramnios 31.91 18.67 7 3514 237 31693586
Patent ductus arteriosus 30.63 18.67 12 3509 3181 31690642
Hypertension 29.82 18.67 52 3469 128048 31565775
Maternal exposure during pregnancy 29.46 18.67 13 3508 4643 31689180
Anhedonia 29.33 18.67 15 3506 7427 31686396
Neonatal respiratory distress 26.40 18.67 7 3514 532 31693291
Newborn persistent pulmonary hypertension 24.91 18.67 5 3516 109 31693714
Nephrogenic systemic fibrosis 24.88 18.67 11 3510 3944 31689879
Emotional distress 24.86 18.67 17 3504 14339 31679484
Injury 24.29 18.67 19 3502 19690 31674133
Fear 22.64 18.67 14 3507 9960 31683863
Neonatal cholestasis 22.41 18.67 4 3517 45 31693778
Ventricular septal defect 22.40 18.67 10 3511 3667 31690156
Cardiac arrest 21.80 18.67 37 3484 89025 31604798
Pyelocaliectasis 21.40 18.67 7 3514 1104 31692719
Renal injury 19.35 18.67 13 3508 10652 31683171

FDA Adverse Event Reporting System (Geriatric)

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
Exposure during pregnancy 137.82 15.17 95 7231 87622 70833496
Pre-eclampsia 96.35 15.17 33 7293 6452 70914666
Caesarean section 87.76 15.17 36 7290 11571 70909547
Hypertension 77.97 15.17 122 7204 295911 70625207
Premature labour 47.80 15.17 21 7305 7979 70913139
Maternal exposure during pregnancy 42.72 15.17 56 7270 115289 70805829
Hypotension 36.67 15.17 108 7218 404273 70516845
Cardiac arrest 32.78 15.17 59 7267 159775 70761343
Pregnancy 30.93 15.17 23 7303 23758 70897360
Kidney transplant rejection 28.95 15.17 16 7310 9945 70911173
Premature delivery 26.36 15.17 20 7306 21284 70899834
Phaeochromocytoma 25.87 15.17 7 7319 618 70920500
Foetal death 23.75 15.17 12 7314 6227 70914891
Anhedonia 23.70 15.17 16 7310 14197 70906921
Renal injury 21.91 15.17 16 7310 16078 70905040
Bradycardia 21.80 15.17 43 7283 124572 70796546
Foetal growth restriction 21.79 15.17 8 7318 1911 70919207
Nephrogenic systemic fibrosis 21.18 15.17 11 7315 6041 70915077
Mental status changes 20.84 15.17 29 7297 63072 70858046
Myocardial infarction 20.69 15.17 51 7275 171594 70749524
Dilatation intrahepatic duct acquired 20.60 15.17 6 7320 693 70920425
HELLP syndrome 20.47 15.17 6 7320 708 70920410
Fear 20.32 15.17 17 7309 20794 70900324
Cerebrovascular accident 19.87 15.17 45 7281 143425 70777693
Renal failure 19.52 15.17 53 7273 189017 70732101
Abortion spontaneous 18.67 15.17 18 7308 26461 70894657
Blood pressure increased 18.62 15.17 52 7274 188465 70732653
Skin induration 18.54 15.17 9 7317 4286 70916832
Rheumatoid arthritis 18.11 15.17 4 7322 291801 70629317
Premature baby 17.28 15.17 8 7318 3431 70917687
Red blood cell schistocytes present 17.24 15.17 5 7321 569 70920549
Cardiac failure congestive 17.12 15.17 41 7285 135416 70785702
Emotional distress 16.86 15.17 20 7306 37168 70883950
Angioedema 16.82 15.17 27 7299 66583 70854535
Cerebral haemorrhage 16.67 15.17 24 7302 53840 70867278
Coronary artery disease 16.63 15.17 26 7300 62710 70858408
Malignant hypertension 15.94 15.17 6 7320 1535 70919583
Post transplant lymphoproliferative disorder 15.53 15.17 11 7315 10534 70910584

FDA Adverse Event Reporting System (Pediatric)

None

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
FDA MoA N0000000161 Adrenergic beta-Antagonists
FDA EPC N0000175556 beta-Adrenergic Blocker
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
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D013566 Sympathomimetics
CHEBI has role CHEBI:35530 beta-adrenergic blockers
CHEBI has role CHEBI:35674 antihypertensive drugs
CHEBI has role CHEBI:37890 alpha-adrenergic receptor blockaders
CHEBI has role CHEBI:66991 sympatholytic drug

Drug Use | Suggest Off label Use Form| |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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
Alpha-1A adrenergic receptor GPCR IC50 7.24 CHEMBL
5-hydroxytryptamine receptor 1A GPCR IC50 6.41 CHEMBL
CAAX prenyl protease 1 Enzyme AC50 5.11 CHEMBL
CAAX prenyl protease 2 Enzyme AC50 4.82 CHEMBL

External reference:

IDSource
4019797 VUID
N0000147886 NUI
D00600 KEGG_DRUG
32780-64-6 SECONDARY_CAS_RN
4018799 VANDF
4019797 VANDF
C0022860 UMLSCUI
CHEBI:6343 CHEBI
CHEMBL429 ChEMBL_ID
DB00598 DRUGBANK_ID
CHEMBL1200323 ChEMBL_ID
D007741 MESH_DESCRIPTOR_UI
3869 PUBCHEM_CID
7207 IUPHAR_LIGAND_ID
3941 INN_ID
R5H8897N95 UNII
202693 RXNORM
11828 MMSL
201477 MMSL
4950 MMSL
d00016 MMSL
001839 NDDF
004368 NDDF
372750000 SNOMEDCT_US
46547007 SNOMEDCT_US
50627005 SNOMEDCT_US
CHEMBL1204165 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9320 INJECTION 5 mg INTRAVENOUS ANDA 24 sections
Labetalol HCl in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9363 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol HCl in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9363 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol HCl in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9364 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol HCl in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9364 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol HCl in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9365 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol HCl in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9365 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol HCl in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0143-9366 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol HCl in Dextrose HUMAN PRESCRIPTION DRUG LABEL 1 0143-9366 INJECTION 1 mg INTRAVENOUS NDA 24 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9622 INJECTION 5 mg INTRAVENOUS ANDA 23 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9623 INJECTION 5 mg INTRAVENOUS ANDA 23 sections
Labetalol HCl HUMAN PRESCRIPTION DRUG LABEL 1 0185-0010 TABLET, FILM COATED 100 mg ORAL ANDA 23 sections
Labetalol HCl HUMAN PRESCRIPTION DRUG LABEL 1 0185-0117 TABLET, FILM COATED 200 mg ORAL ANDA 23 sections
Labetalol HCl HUMAN PRESCRIPTION DRUG LABEL 1 0185-0118 TABLET, FILM COATED 300 mg ORAL ANDA 23 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 22 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-0606 TABLET, FILM COATED 200 mg ORAL ANDA 22 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0591-0607 TABLET, FILM COATED 300 mg ORAL ANDA 22 sections
Labetalol HCL HUMAN PRESCRIPTION DRUG LABEL 1 0615-8130 TABLET, FILM COATED 100 mg ORAL ANDA 22 sections
Labetalol HCL HUMAN PRESCRIPTION DRUG LABEL 1 0615-8131 TABLET, FILM COATED 200 mg ORAL ANDA 22 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0641-6252 INJECTION 5 mg INTRAVENOUS NDA 26 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-5928 TABLET, FILM COATED 100 mg ORAL ANDA 22 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-5929 TABLET, FILM COATED 200 mg ORAL ANDA 22 sections
Labetalol hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-5930 TABLET, FILM COATED 300 mg ORAL ANDA 22 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7109 TABLET, FILM COATED 100 mg ORAL ANDA 19 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7110 TABLET, FILM COATED 200 mg ORAL ANDA 19 sections
Labetalol Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7111 TABLET, FILM COATED 300 mg ORAL ANDA 19 sections
Labetalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-641 TABLET, FILM COATED 100 mg ORAL ANDA 23 sections
Labetalol HUMAN PRESCRIPTION DRUG LABEL 1 10135-642 TABLET, FILM COATED 200 mg ORAL ANDA 23 sections