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 155.26 15.88 120 5601 120895 50478508
Caesarean section 102.59 15.88 45 5676 15594 50583809
Pre-eclampsia 101.14 15.88 37 5684 8007 50591396
Premature delivery 93.44 15.88 48 5673 23615 50575788
Premature baby 86.58 15.88 42 5679 18295 50581108
Maternal exposure during pregnancy 69.84 15.88 88 5633 159690 50439713
Foetal growth restriction 56.55 15.88 23 5698 6604 50592799
Patent ductus arteriosus 49.60 15.88 18 5703 3802 50595601
Premature labour 44.47 15.88 23 5698 11453 50587950
Pregnancy 43.69 15.88 32 5689 29545 50569858
Haemangioma congenital 43.12 15.88 10 5711 429 50598974
Foetal exposure during pregnancy 30.38 15.88 25 5696 27334 50572069
Low birth weight baby 29.34 15.88 14 5707 5867 50593536
Hypotension 28.48 15.88 74 5647 235395 50364008
Maternal drugs affecting foetus 28.15 15.88 13 5708 5064 50594339
HELLP syndrome 26.86 15.88 8 5713 911 50598492
Post transplant lymphoproliferative disorder 24.04 15.88 11 5710 4193 50595210
Gestational diabetes 23.41 15.88 13 5708 7452 50591951
Ultrasound uterus abnormal 22.77 15.88 4 5717 40 50599363
Phaeochromocytoma 22.44 15.88 6 5715 462 50598941
Foetal death 22.30 15.88 13 5708 8167 50591236
Exomphalos 21.45 15.88 6 5715 547 50598856
Dilatation intrahepatic duct acquired 20.54 15.88 6 5715 639 50598764
Hypertension 20.21 15.88 61 5660 211142 50388261
Hyperkalaemia 18.61 15.88 25 5696 48064 50551339
Abortion spontaneous 16.60 15.88 22 5699 41750 50557653
Cardiac arrest 16.51 15.88 32 5689 83619 50515784
Blood pressure increased 16.22 15.88 42 5679 133090 50466313
Frequent bowel movements 16.04 15.88 13 5708 13905 50585498

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 110.02 18.47 49 3377 17231 29553870
Foetal disorder 72.10 18.47 17 3409 766 29570335
Low birth weight baby 70.07 18.47 27 3399 6581 29564520
Foetal exposure during pregnancy 66.52 18.47 44 3382 33823 29537278
Neutropenia neonatal 64.36 18.47 15 3411 642 29570459
Foetal growth restriction 45.74 18.47 17 3409 3749 29567352
Congenital oesophageal anomaly 44.24 18.47 8 3418 93 29571008
Polyhydramnios 31.62 18.47 7 3419 237 29570864
Maternal exposure during pregnancy 30.45 18.47 13 3413 4110 29566991
Patent ductus arteriosus 30.37 18.47 12 3414 3119 29567982
Anhedonia 29.21 18.47 15 3411 7185 29563916
Neonatal respiratory distress 26.38 18.47 7 3419 511 29570590
Newborn persistent pulmonary hypertension 24.79 18.47 5 3421 107 29570994
Emotional distress 24.72 18.47 17 3409 13878 29557223
Nephrogenic systemic fibrosis 24.47 18.47 11 3415 3931 29567170
Injury 24.16 18.47 19 3407 19027 29552074
Hypertension 22.80 18.47 45 3381 116569 29454532
Fear 22.73 18.47 14 3412 9490 29561611
Ventricular septal defect 22.39 18.47 10 3416 3519 29567582
Neonatal cholestasis 22.24 18.47 4 3422 45 29571056
Cardiac arrest 21.75 18.47 37 3389 85554 29485547
Pyelocaliectasis 21.12 18.47 7 3419 1102 29569999
Renal injury 19.38 18.47 13 3413 10189 29560912

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 136.07 15.45 92 6970 77583 64414087
Caesarean section 83.38 15.45 35 7027 11239 64480431
Pre-eclampsia 80.48 15.45 29 7033 6202 64485468
Premature labour 47.60 15.45 21 7041 7599 64484071
Maternal exposure during pregnancy 43.44 15.45 53 7009 95831 64395839
Hypotension 35.81 15.45 107 6955 380867 64110803
Hypertension 33.58 15.45 82 6980 259179 64232491
Pregnancy 32.43 15.45 23 7039 20842 64470828
Cardiac arrest 31.87 15.45 59 7003 154005 64337665
Kidney transplant rejection 28.77 15.45 16 7046 9495 64482175
Phaeochromocytoma 25.88 15.45 7 7055 582 64491088
Premature delivery 25.50 15.45 19 7043 18570 64473100
Anhedonia 23.38 15.45 16 7046 13690 64477980
Foetal growth restriction 22.14 15.45 8 7054 1722 64489948
Renal injury 21.68 15.45 16 7046 15413 64476257
Nephrogenic systemic fibrosis 20.85 15.45 11 7051 5881 64485789
Foetal death 20.79 15.45 11 7051 5919 64485751
Bradycardia 20.44 15.45 42 7020 118177 64373493
Dilatation intrahepatic duct acquired 20.29 15.45 6 7056 688 64490982
HELLP syndrome 20.25 15.45 6 7056 693 64490977
Mental status changes 20.24 15.45 29 7033 61133 64430537
Fear 19.92 15.45 17 7045 20154 64471516
Cerebrovascular accident 19.37 15.45 45 7017 137538 64354132
Renal failure 18.91 15.45 53 7009 181635 64310035
Myocardial infarction 18.88 15.45 50 7012 165771 64325899
Abortion spontaneous 18.57 15.45 18 7044 25125 64466545
Skin induration 18.28 15.45 9 7053 4166 64487504
Premature baby 17.21 15.45 8 7054 3264 64488406
Red blood cell schistocytes present 17.16 15.45 5 7057 545 64491125
Angioedema 17.15 15.45 27 7035 61794 64429876
Blood pressure increased 16.66 15.45 49 7013 172503 64319167
Cerebral haemorrhage 16.57 15.45 24 7038 51066 64440604
Cardiac failure congestive 16.54 15.45 41 7021 130539 64361131
Emotional distress 16.43 15.45 20 7042 36018 64455652
Coronary artery disease 16.22 15.45 26 7036 60407 64431263
Malignant hypertension 15.96 15.45 6 7056 1442 64490228
Post transplant lymphoproliferative disorder 15.95 15.45 11 7051 9533 64482137

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