U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C14H20N2O2.ClH
Molecular Weight 284.782
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Pindolol hydrochloride

SMILES

Cl.CC(C)NCC(O)COC1=C2C=CNC2=CC=C1

InChI

InChIKey=MAUPDHMFNIUWSK-UHFFFAOYSA-N
InChI=1S/C14H20N2O2.ClH/c1-10(2)16-8-11(17)9-18-14-5-3-4-13-12(14)6-7-15-13;/h3-7,10-11,15-17H,8-9H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C14H20N2O2
Molecular Weight 248.3208
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: Description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/2879589 http://www.ncbi.nlm.nih.gov/pubmed/6125094 https://www.ncbi.nlm.nih.gov/pubmed/9536453 https://www.ncbi.nlm.nih.gov/pubmed/2429847 http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018285s034lbl.pdf

Pindolol was developed at Sandoz at 1960s. Pindolol is a nonselective beta-adrenergic antagonist (beta-blocker) which possesses intrinsic sympathomimetic activity (partial agonist activity) in therapeutic dosage ranges but does not possess quinidine-like membrane stabilizing activity. The partial beta-adrenergic agonistic activity of pindolol in the heart appears to be completely restricted to the sinoatrial pacemaker. In standard pharmacologic tests in man and animals, Pindolol attenuates increases in heart rate, systolic blood pressure, and cardiac output resulting from exercise and isoproterenol administration, thus confirming its beta-blocking properties. In addition to beta-adrenergic activity pindolol demonstrates mixed agonist-antagonist activity at central 5-HT receptors. Although in accordance with the hypothesis that pindolol increases the antidepressant effects of selective serotonin reuptake inhibitors by antagonism of 5-HT at inhibitory 5-HT1A autoreceptors, pindolol possesses partial agonist activity at 5-HT1A receptors. Pindolol tablets are indicated in the management of hypertension.

Originator

Sources: Innovation in the Pharmaceutical Industry: The Process of Drug Discovery and Development. Takuji Hara. Edward Elgar Publishing, 2003. ISBN 1843760509 p.76

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
6.4 nM [Ki]
9.25 null [pKd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
VISKEN

Approved Use

Pindolol tablets are indicated in the management of hypertension. It may be used alone or concomitantly with other antihypertensive agents, particularly with a thiazide-type diuretic.

Launch Date

1982
Primary
PINDOLOL

Approved Use

Pindolol tablets are indicated in the management of hypertension. It may be used alone or concomitantly with other antihypertensive agents, particularly with a thiazide-type diuretic.

Launch Date

1992
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
250 nM
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PINDOLOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1200 nM × h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PINDOLOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.1 h
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PINDOLOL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Other AEs: Bizarre dreams, Dizziness...
Other AEs:
Bizarre dreams (5%)
Dizziness (9%)
Fatigue (8%)
Hallucinations (<1%)
Insomnia (10%)
Nervousness (7%)
Weakness (4%)
Paresthesia (3%)
Dyspnea (5%)
Edema (6%)
Heart failure (<1%)
Palpitations (<1%)
Chest pain (3%)
Joint pain (7%)
Muscle cramps (3%)
Muscle pain (10%)
Abdominal discomfort (4%)
Nausea (5%)
Pruritus (1%)
Rash (<1%)
Anxiety (uncertain, <2%)
Lethargy (uncertain, <2%)
Visual disturbances (uncertain, <2%)
Hyperhidrosis (uncertain, <2%)
Bradycardia (uncertain, <2%)
Claudication (uncertain, <2%)
Cold extremities (uncertain, <2%)
Heart block (uncertain, <2%)
Syncope (uncertain, <2%)
Tachycardia (uncertain, <2%)
Weight gain (uncertain, <2%)
Hypotension (uncertain, <2%)
Diarrhea (uncertain, <2%)
Vomiting (uncertain, <2%)
Wheezing (uncertain, <2%)
Impotence (uncertain, <2%)
Pollakiuria (uncertain, <2%)
Eye discomfort (uncertain, <2%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Pruritus 1%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Insomnia 10%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Muscle pain 10%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Chest pain 3%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Muscle cramps 3%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Paresthesia 3%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Abdominal discomfort 4%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Weakness 4%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Bizarre dreams 5%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Dyspnea 5%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Nausea 5%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Edema 6%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Joint pain 7%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Nervousness 7%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Fatigue 8%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Dizziness 9%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Hallucinations <1%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Heart failure <1%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Palpitations <1%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Rash <1%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Anxiety uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Bradycardia uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Claudication uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Cold extremities uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Diarrhea uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Eye discomfort uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Heart block uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Hyperhidrosis uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Hypotension uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Impotence uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Lethargy uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Pollakiuria uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Syncope uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Tachycardia uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Visual disturbances uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Vomiting uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Weight gain uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Wheezing uncertain, <2%
5 mg 2 times / day steady, oral
Recommended
Dose: 5 mg, 2 times / day
Route: oral
Route: steady
Dose: 5 mg, 2 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
yes
yes
yes (co-administration study)
Comment: cimetidine coadministration increases pindolol plasma levels
yes
yes (co-administration study)
Comment: cimetidine increased AUC by 1.4 fold and Cmax by 1.3 fold
yes
yes (co-administration study)
Comment: cimetidine increased AUC by 1.4 fold and Cmax by 1.3 fold
PubMed

PubMed

TitleDatePubMed
Anxiolytic-like effects of baicalein and baicalin in the Vogel conflict test in mice.
2003-03-19
EEG effects of buspirone and pindolol: a method of examining 5-HT1A receptor function in humans.
2003-03
Effects on sleep architecture of pindolol, paroxetine and their combination in healthy volunteers.
2003-03
Chiral separation of amines with N-benzoxycarbonylglycyl-L-proline as selector in non-aqueous capillary electrophoresis using methanol and 1,2-dichloroethane in the background electrolyte.
2003-01-17
Evidence against beta 3-adrenoceptors or low affinity state of beta 1-adrenoceptors mediating relaxation in rat isolated aorta.
2003-01
Evidence that the anorexia induced by lipopolysaccharide is mediated by the 5-HT2C receptor.
2003-01
Pharmacological management for agitation and aggression in people with acquired brain injury.
2003
Serotonin regulates hippocampal glucocorticoid receptor expression via a 5-HT7 receptor.
2002-12-15
Indorenate produces antidepressant-like actions in the rat forced swimming test via 5-HT1A receptors.
2002-12
The role of in vivo molecular imaging with PET and SPECT in the elucidation of psychiatric drug action and new drug development.
2002-12
Involvement of 5-HT7 receptors in serotonergic effects on spike afterpotentials in presumed jaw-closing motoneurons of rats.
2002-11-08
Spin trapping study of reactive oxygen species formation during bopindolol peroxidation.
2002-10-15
Antibody capture assay reveals bell-shaped concentration-response isotherms for h5-HT(1A) receptor-mediated Galpha(i3) activation: conformational selection by high-efficacy agonists, and relationship to trafficking of receptor signaling.
2002-09
[Pharmacology of beta blockers and their significance for therapy of hypertension].
2002-08
[Reactions between dialkylamine drugs, 2,3-dichloro-1,4-naphthoquinone and acetaldehyde].
2002-08
Serotonergic control of cerebellar mossy fiber activity by modulation of signal transfer by rat pontine nuclei neurons.
2002-08
Enantioselectivity in the steady-state pharmacokinetics and transplacental distribution of pindolol at delivery in pregnancy-induced hypertension.
2002-08
Melatonin potentiates 5-HT(1A) receptor activation in rat hypothalamus and results in hypothermia.
2002-08
Altered expression of autonomic neurotransmitter receptors and proliferative responses in lymphocytes from a chronic mild stress model of depression: effects of fluoxetine.
2002-08
Reconsideration of 5-hydroxytryptamine (5-HT)(7) receptor distribution using [(3)H]5-carboxamidotryptamine and [(3)H]8-hydroxy-2-(di-n-propylamino)tetraline: analysis in brain of 5-HT(1A) knockout and 5-HT(1A/1B) double-knockout mice.
2002-07
Synthesis and evaluation of (S)-[18F]-fluoroethylcarazolol for in vivo beta-adrenoceptor imaging in the brain.
2002-07
5-HT1A receptor blockade and the motivational profile of ethanol.
2002-06-28
The neuropharmacology of serotonin and noradrenaline in depression.
2002-06
[Effect of (+/-)-pindolol on the central 5-HT1A receptor by the use of in vivo microdialysis and hippocampal slice preparations].
2002-06
Management of treatment resistant obsessive-compulsive disorder. Algorithms for pharmacotherapy.
2002-06
Familial left ventricular hypertrabeculation in two blind brothers.
2002-05-29
Simultaneous determination of eight beta-blockers by gradient high-performance liquid chromatography with combined ultraviolet and fluorescence detection in corneal permeability studies in vitro.
2002-05-25
Determination of bopindolol in pharmaceuticals by capillary isotachophoresis.
2002-05-15
Somatodendritic action of pindolol to attenuate the paroxetine-induced decrease in serotonin release from the rat ventral hippocampus: a microdialysis study.
2002-05
Direct determination of pindolol enantiomers in human serum by column-switching LC-MS/MS using a phenylcarbamate-beta-cyclodextrin chiral column.
2002-04-01
Specific labelling of serotonin 5-HT(1B) receptors in rat frontal cortex with the novel, phenylpiperazine derivative, [3H]GR125,743. A pharmacological characterization.
2002-04
Imaging the neurochemical brain in health and disease.
2002-03-02
Influence of monoamine oxidase A and serotonin receptor 2A polymorphisms in SSRI antidepressant activity.
2002-03
Pharmacokinetic scaling of pindolol in healthy volunteers after single dose oral administration.
2002-03
Copper(II) complexes of the beta-blocker pindolol: properties, structure, biological activity.
2002-03
Methiothepin attenuates gastric secretion and motility effects of vagal stimulants at the dorsal vagal complex.
2002-02-01
Screening drugs for metabolic stability using pulsed ultrafiltration mass spectrometry.
2002-02
Studies on the expression and function of beta-3-adrenoceptors in the colon of rats with acetic acid-induced colitis.
2002-02
Synthesis and evaluation of radiolabeled antagonists for imaging of beta-adrenoceptors in the brain with PET.
2002-02
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.
2002-01
PET-examination and metabolite evaluation in monkey of [(11)C]NAD-299, a radioligand for visualisation of the 5-HT(1A) receptor.
2002-01
Influence of various biological matrices (plasma, blood microdialysate) on chromatographic performance in the determination of beta-blockers using an alkyl-diol silica precolumn for sample clean-up.
2001-12-25
Imaging of beta-adrenoceptors in the human thorax using (S)-[(11)C]CGP12388 and positron emission tomography.
2001-12-21
Further characterization of beta3-adrenoceptors in the guinea pig gastric fundus: stereoselectivity, beta-adrenoceptor alkylation, and structure-activity relationship.
2001-12
Pindolol augmentation of selective serotonin reuptake inhibitors: PET evidence that the dose used in clinical trials is too low.
2001-12
No association between dopamine D(2) and D(4) receptor gene variants and antidepressant activity of two selective serotonin reuptake inhibitors.
2001-11-30
Flesinoxan, a 5-HT1A receptor agonist/alpha 1-adrenoceptor antagonist, lowers intraocular pressure in NZW rabbits.
2001-08
Management of treatment-refractory panic disorder.
2001
Partial agonistic properties of (+/-)-pindolol at atypical beta-adrenoceptors in the guinea pig gastric fundus.
2001
Effects of prindolol on isoproterenol-induced subendocardial ischaemia in dogs with multiple chronic coronary artery occlusion.
1975-07
Patents

Sample Use Guides

The recommended initial dose of pindolol tablets is 5 mg b.i.d. alone or in combination with other antihypertensive agents. An antihypertensive response usually occurs within the first week of treatment. Maximal response, however, may take as long as or occasionally longer than 2 weeks. If a satisfactory reduction in blood pressure does not occur within 3 to 4 weeks, the dose may be adjusted in increments of 10 mg/day at these intervals up to a maximum of 60 mg/day.
Route of Administration: Oral
In Vitro Use Guide
Pindolol (1-10 uM) blocked the catecholamine-induced augmentation of late after-discharge (LAD) (postganglionic branches or ganglion cells of the paravertebral sympathetic chain of the bullfrog were used in vitro)
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:20:55 GMT 2025
Edited
by admin
on Mon Mar 31 23:20:55 GMT 2025
Record UNII
2XEX32G2GD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LB-46-HYDROCHLORIDE
Preferred Name English
Pindolol hydrochloride
Common Name English
2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-, hydrochloride
Systematic Name English
DL-PINDOLOL HYDROCHLORIDE
Common Name English
(±)-Pindolol hydrochloride
Common Name English
2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-, monohydrochloride
Systematic Name English
2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-, hydrochloride (1:1)
Systematic Name English
Code System Code Type Description
ECHA (EC/EINECS)
252-931-9
Created by admin on Mon Mar 31 23:20:55 GMT 2025 , Edited by admin on Mon Mar 31 23:20:55 GMT 2025
PRIMARY
CAS
28813-39-0
Created by admin on Mon Mar 31 23:20:55 GMT 2025 , Edited by admin on Mon Mar 31 23:20:55 GMT 2025
PRIMARY
CAS
34203-14-0
Created by admin on Mon Mar 31 23:20:55 GMT 2025 , Edited by admin on Mon Mar 31 23:20:55 GMT 2025
SUPERSEDED
ECHA (EC/EINECS)
257-080-7
Created by admin on Mon Mar 31 23:20:55 GMT 2025 , Edited by admin on Mon Mar 31 23:20:55 GMT 2025
ALTERNATIVE
CAS
36236-36-9
Created by admin on Mon Mar 31 23:20:55 GMT 2025 , Edited by admin on Mon Mar 31 23:20:55 GMT 2025
NON-SPECIFIC STOICHIOMETRY
FDA UNII
2XEX32G2GD
Created by admin on Mon Mar 31 23:20:55 GMT 2025 , Edited by admin on Mon Mar 31 23:20:55 GMT 2025
PRIMARY
PUBCHEM
162634
Created by admin on Mon Mar 31 23:20:55 GMT 2025 , Edited by admin on Mon Mar 31 23:20:55 GMT 2025
PRIMARY