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

Stem definitionDrug idCAS RN
beta-adrenoreceptor antagonists 2176 13523-86-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pindolol
  • betapindol
  • pinbetol
  • prinodolol
  • dl-Pindolol
  • durapindol
  • LB-46
A moderately lipophilic beta blocker (ADRENERGIC BETA-ANTAGONISTS). It is non-cardioselective and has intrinsic sympathomimetic actions, but little membrane-stabilizing activity. (From Martindale, The Extra Pharmocopoeia, 30th ed, p638)
  • Molecular weight: 248.33
  • Formula: C14H20N2O2
  • CLOGP: 1.67
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 3
  • TPSA: 57.28
  • ALOGS: -2.46
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
15 mg O
15 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.03 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Hosey CM, Chan R, Benet LZ
S (Water solubility) 7.90 mg/mL Hosey CM, Chan R, Benet LZ
EoM (Fraction excreted unchanged in urine) 54 % Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 88 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.20 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 7.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.58 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 3, 1982 FDA

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
Oesophagitis 61.92 33.76 17 557 13634 46671854
Atrioventricular block complete 61.41 33.76 15 559 7612 46677876
Neutrophil count abnormal 54.04 33.76 11 563 2439 46683049
White blood cell count abnormal 51.16 33.76 12 562 5120 46680368
Rhabdomyolysis 50.36 33.76 19 555 41890 46643598
Urinary tract infection 47.99 33.76 31 543 220235 46465253
Haemoglobin abnormal 47.72 33.76 11 563 4352 46681136
Chromaturia 34.25 33.76 11 563 15008 46670480

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

Pharmacologic Action:

SourceCodeDescription
ATC C07AA03 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS
Beta blocking agents, non-selective
ATC C07CA03 CARDIOVASCULAR SYSTEM
BETA BLOCKING AGENTS
BETA BLOCKING AGENTS AND OTHER DIURETICS
Beta blocking agents, non-selective, and other diuretics
FDA MoA N0000000161 Adrenergic beta-Antagonists
FDA EPC N0000175556 beta-Adrenergic Blocker
MeSH PA D018663 Adrenergic Agents
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 D018490 Serotonin Agents
MeSH PA D012702 Serotonin Antagonists
MeSH PA D014665 Vasodilator Agents
CHEBI has role CHEBI:35530 beta-adrenoceptor antagonists
CHEBI has role CHEBI:35620 vasodilator
CHEBI has role CHEBI:35674 antihypertensive
CHEBI has role CHEBI:39456 antiglaucoma agent
CHEBI has role CHEBI:48279 serotonin antagonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Angina pectoris off-label use 194828000
Bronchospasm contraindication 4386001
Complete atrioventricular block contraindication 27885002
Depressive disorder contraindication 35489007
Anaphylaxis contraindication 39579001
Sinus bradycardia contraindication 49710005
Diabetes mellitus contraindication 73211009 DOID:9351
Pulmonary emphysema contraindication 87433001
Cardiogenic shock contraindication 89138009
Kidney disease contraindication 90708001 DOID:557
Myasthenia gravis contraindication 91637004 DOID:437
Partial atrioventricular block contraindication 195039008
Decompensated cardiac failure contraindication 195111005
Disease of liver contraindication 235856003 DOID:409
Raynaud's phenomenon contraindication 266261006
Pregnancy, function contraindication 289908002
Severe chronic obstructive pulmonary disease contraindication 313299006
Right ventricular failure contraindication 367363000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.41 acidic
pKa2 9.19 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-2 adrenergic receptor GPCR PARTIAL AGONIST Ki 9 WOMBAT-PK CHEMBL
Beta-1 adrenergic receptor GPCR PARTIAL AGONIST Ki 9.40 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2A GPCR AGONIST Ki 5 IUPHAR
5-hydroxytryptamine receptor 2C GPCR Ki 4.27 CHEMBL
Beta-3 adrenergic receptor GPCR Kd 6.78 CHEMBL
5-hydroxytryptamine receptor 1B GPCR Ki 7.10 WOMBAT-PK
5-hydroxytryptamine receptor 1D GPCR Ki 5.21 PDSP
5-hydroxytryptamine receptor 1A GPCR Ki 8.10 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR AGONIST Ki 5.70 IUPHAR
Serotonin 2 (5-HT2) receptor GPCR Ki 4.53 CHEMBL
Serotonin 1 (5-HT1) receptor GPCR Ki 7 CHEMBL
5-hydroxytryptamine receptor 1B GPCR Ki 7.10 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 7.70 CHEMBL

External reference:

IDSource
4018760 VUID
N0000147063 NUI
D00513 KEGG_DRUG
4018760 VANDF
C0728922 UMLSCUI
CHEBI:8214 CHEBI
CHEMBL500 ChEMBL_ID
D010869 MESH_DESCRIPTOR_UI
DB00960 DRUGBANK_ID
4828 PUBCHEM_CID
91 IUPHAR_LIGAND_ID
2698 INN_ID
BJ4HF6IU1D UNII
8332 RXNORM
1482 MMSL
5302 MMSL
d00137 MMSL
001857 NDDF
18381001 SNOMEDCT_US
387102009 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 0378-0052 TABLET 5 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 0378-0127 TABLET 10 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 29033-028 TABLET 5 mg ORAL ANDA 14 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 29033-029 TABLET 10 mg ORAL ANDA 14 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 57664-655 TABLET 5 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 57664-656 TABLET 10 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 62559-560 TABLET 5 mg ORAL ANDA 19 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 62559-561 TABLET 10 mg ORAL ANDA 19 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 68151-1320 TABLET 5 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 68151-3005 TABLET 10 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 70710-1063 TABLET 5 mg ORAL ANDA 17 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 70710-1064 TABLET 10 mg ORAL ANDA 17 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 70771-1134 TABLET 5 mg ORAL ANDA 1 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 70771-1135 TABLET 10 mg ORAL ANDA 1 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 72789-099 TABLET 10 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 72789-100 TABLET 5 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 76385-131 TABLET 5 mg ORAL ANDA 21 sections
Pindolol HUMAN PRESCRIPTION DRUG LABEL 1 76385-132 TABLET 10 mg ORAL ANDA 21 sections