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 205.61 14.01 165 7936 155382 63325539
Pre-eclampsia 173.92 14.01 59 8042 9074 63471847
Caesarean section 154.90 14.01 64 8037 16968 63463953
Premature baby 136.42 14.01 62 8039 20673 63460248
Premature delivery 125.41 14.01 66 8035 30215 63450706
Maternal exposure during pregnancy 93.35 14.01 127 7974 219935 63260986
Foetal growth restriction 77.62 14.01 31 8070 7522 63473399
Premature labour 59.67 14.01 30 8071 12474 63468447
Patent ductus arteriosus 49.14 14.01 19 8082 4231 63476690
Low birth weight baby 45.86 14.01 21 8080 7108 63473813
Foetal exposure during pregnancy 44.38 14.01 35 8066 31927 63448994
Pregnancy 42.05 14.01 36 8065 36800 63444121
Haemangioma congenital 41.62 14.01 10 8091 442 63480479
HELLP syndrome 37.69 14.01 11 8090 1033 63479888
Foetal death 34.59 14.01 20 8081 10960 63469961
Maternal drugs affecting foetus 32.34 14.01 15 8086 5227 63475694
Hyperkalaemia 32.02 14.01 37 8064 54166 63426755
Hypotension 30.53 14.01 90 8011 272514 63208407
Nephrogenic systemic fibrosis 27.99 14.01 13 8088 4543 63476378
Blood pressure increased 27.97 14.01 63 8038 161999 63318922
Drug intolerance 26.31 14.01 4 8097 308657 63172264
Phaeochromocytoma 25.69 14.01 7 8094 512 63480409
Cerebral haemorrhage 23.43 14.01 24 8077 30705 63450216
Gestational diabetes 23.06 14.01 14 8087 8382 63472539
Kidney transplant rejection 22.61 14.01 11 8090 4260 63476661
Pulmonary oedema 22.16 14.01 31 8070 54842 63426079
Hypertension 21.27 14.01 81 8020 279222 63201699
Cerebrovascular accident 20.91 14.01 44 8057 107980 63372941
Post transplant lymphoproliferative disorder 20.90 14.01 11 8090 5020 63475901
Exomphalos 20.69 14.01 6 8095 551 63480370
Proteinuria 20.41 14.01 18 8083 19127 63461794
Ultrasound uterus abnormal 20.21 14.01 4 8097 70 63480851
Dilatation intrahepatic duct acquired 19.46 14.01 6 8095 680 63480241
Neuromuscular blockade 19.43 14.01 5 8096 293 63480628
Skin induration 19.19 14.01 9 8092 3214 63477707
Placental insufficiency 18.66 14.01 7 8094 1434 63479487
Cardiac failure congestive 18.30 14.01 38 8063 92395 63388526
Intestinal malrotation 18.23 14.01 5 8096 375 63480546
Blood pressure inadequately controlled 18.21 14.01 10 8091 4968 63475953
Abortion spontaneous 18.08 14.01 26 8075 47169 63433752
Mental status changes 16.93 14.01 23 8078 39576 63441345
Bradycardia 16.77 14.01 32 8069 73195 63407726
Thymus hypoplasia 16.62 14.01 3 8098 31 63480890
Foetal cardiac disorder 16.62 14.01 3 8098 31 63480890
Off label use 16.33 14.01 39 8062 674423 62806498
Rheumatoid arthritis 16.31 14.01 6 8095 253813 63227108
Drug withdrawal syndrome neonatal 16.17 14.01 7 8094 2074 63478847
Arthropathy 16.05 14.01 5 8096 234787 63246134
Skin hypertrophy 15.77 14.01 8 8093 3383 63477538
Infusion related reaction 15.45 14.01 6 8095 245515 63235406
Phaeochromocytoma crisis 15.31 14.01 4 8097 249 63480672
Cardiac arrest 14.87 14.01 35 8066 92510 63388411
Red blood cell schistocytes present 14.87 14.01 4 8097 279 63480642
Nipple pain 14.53 14.01 4 8097 304 63480617
Decerebration 14.29 14.01 3 8098 71 63480850
Gingival hypertrophy 14.24 14.01 6 8095 1665 63479256
Treatment failure 14.03 14.01 4 8097 199039 63281882

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 151.97 17.58 67 4691 19566 34932607
Low birth weight baby 98.67 17.58 38 4720 7867 34944306
Foetal exposure during pregnancy 85.10 17.58 57 4701 38044 34914129
Anhedonia 68.84 17.58 29 4729 7556 34944617
Foetal disorder 68.46 17.58 17 4741 809 34951364
Neutropenia neonatal 60.75 17.58 15 4743 697 34951476
Foetal growth restriction 55.70 17.58 21 4737 4096 34948077
Injury 53.62 17.58 34 4724 20653 34931520
Fear 48.09 17.58 25 4733 10451 34941722
Congenital oesophageal anomaly 42.95 17.58 8 4750 93 34952080
Emotional distress 42.21 17.58 26 4732 15000 34937173
Renal injury 35.65 17.58 21 4737 11174 34940999
Nephrogenic systemic fibrosis 35.29 17.58 15 4743 3990 34948183
Maternal exposure during pregnancy 32.33 17.58 15 4743 4903 34947270
Patent ductus arteriosus 31.01 17.58 13 4745 3341 34948832
Polyhydramnios 30.47 17.58 7 4751 238 34951935
Exposure during pregnancy 26.47 17.58 16 4742 8918 34943255
Anxiety 26.43 17.58 48 4710 99380 34852793
Neonatal respiratory distress 24.02 17.58 7 4751 613 34951560
Cardiac arrest 23.77 17.58 45 4713 96114 34856059
Newborn persistent pulmonary hypertension 23.36 17.58 5 4753 122 34952051
Mental status changes 22.79 17.58 27 4731 38056 34914117
Unevaluable event 22.71 17.58 25 4733 32565 34919608
Hypertension 22.34 17.58 54 4704 136389 34815784
Neonatal cholestasis 21.59 17.58 4 4754 45 34952128
Hypotension 20.98 17.58 72 4686 221577 34730596
Skin fibrosis 20.38 17.58 7 4751 1045 34951128
Pyelocaliectasis 19.89 17.58 7 4751 1123 34951050
Ventricular septal defect 19.66 17.58 10 4748 3991 34948182
Renal failure 19.61 17.58 50 4708 130507 34821666
Skin induration 18.76 17.58 8 4750 2143 34950030

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 185.99 14.55 129 9669 101003 79633587
Pre-eclampsia 157.91 14.55 51 9747 6990 79727600
Caesarean section 122.19 14.55 49 9749 12486 79722104
Maternal exposure during pregnancy 71.58 14.55 86 9712 136452 79598138
Premature delivery 57.82 14.55 36 9762 23431 79711159
Premature labour 55.77 14.55 25 9773 8365 79726225
Anhedonia 55.77 14.55 30 9768 14868 79719722
Nephrogenic systemic fibrosis 43.01 14.55 19 9779 6141 79728449
Hypotension 42.89 14.55 135 9663 440182 79294408
Fear 42.57 14.55 29 9769 21957 79712633
Foetal growth restriction 38.11 14.55 13 9785 2106 79732484
Renal injury 36.80 14.55 24 9774 16903 79717687
Kidney transplant rejection 36.59 14.55 20 9778 10226 79724364
Hypertension 34.52 14.55 104 9694 330888 79403702
Cardiac arrest 33.87 14.55 69 9729 172027 79562563
Skin induration 31.73 14.55 14 9784 4511 79730079
HELLP syndrome 31.69 14.55 9 9789 797 79733793
Mental status changes 31.54 14.55 40 9758 66919 79667671
Pregnancy 31.00 14.55 26 9772 26825 79707765
Renal failure 29.86 14.55 72 9726 200896 79533694
Blood pressure increased 29.58 14.55 74 9724 211286 79523304
Foetal death 29.55 14.55 16 9782 8028 79726562
Emotional distress 29.24 14.55 30 9768 39939 79694651
Phaeochromocytoma 28.73 14.55 8 9790 659 79733931
Injury 28.43 14.55 41 9757 77455 79657135
Cerebral haemorrhage 28.03 14.55 35 9763 57638 79676952
Skin hypertrophy 27.48 14.55 13 9785 4915 79729675
Cerebrovascular accident 26.77 14.55 59 9739 155233 79579357
Myocardial infarction 26.32 14.55 65 9733 184064 79550526
Bradycardia 25.07 14.55 53 9745 135504 79599086
Anxiety 24.87 14.55 77 9721 248435 79486155
Premature baby 24.28 14.55 11 9787 3769 79730821
Unevaluable event 22.75 14.55 31 9767 55554 79679036
Cardiac failure congestive 20.05 14.55 50 9748 142352 79592238
Off label use 20 14.55 52 9746 907163 78827427
Dilatation intrahepatic duct acquired 19.25 14.55 6 9792 732 79733858
Blood pressure inadequately controlled 19.18 14.55 11 9787 6166 79728424
Skin fibrosis 18.54 14.55 7 9791 1517 79733073
Drug intolerance 18.14 14.55 5 9793 264114 79470476
Abortion spontaneous 17.79 14.55 20 9778 29487 79705103
Hypertensive encephalopathy 17.56 14.55 6 9792 976 79733614
Placental insufficiency 16.77 14.55 6 9792 1117 79733473
Neuromuscular blockade 16.33 14.55 5 9793 575 79734015
Red blood cell schistocytes present 16.25 14.55 5 9793 584 79734006
Proteinuria 16.23 14.55 20 9778 32482 79702108
Completed suicide 15.87 14.55 66 9732 245701 79488889
Unresponsive to stimuli 15.54 14.55 26 9772 55762 79678828
Coronary artery disease 14.99 14.55 28 9770 65446 79669144
Skin tightness 14.95 14.55 9 9789 5513 79729077
Stillbirth 14.90 14.55 8 9790 3947 79730643
Malignant hypertension 14.63 14.55 6 9792 1616 79732974
Pulmonary oedema 14.60 14.55 33 9765 88221 79646369

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 0409-0125 INJECTION, SOLUTION 5 mg INTRAVENOUS 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 0409-2267 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