Pindolol

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H20N2O2
Molecular Weight	248.3208
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=JZQKKSLKJUAGIC-UHFFFAOYSA-N

InChI=1S/C14H20N2O2/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

HIDE SMILES / InChI

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
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=05dfb38c-b832-4ae0-b28b-d271008e670b
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1a (5-HT1a) receptor 177 Target ID: CHEMBL214 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2429847	Antagonist 2849		6.4 nM [Ki]
Adrenergic receptor beta 89 Target ID: CHEMBL2094118 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2879589	Antagonist 2849		9.25 null [pKd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018285s034lbl.pdf	Primary		Approved 8583	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
Hypertension 575 Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=05dfb38c-b832-4ae0-b28b-d271008e670b	Primary		Approved 8583	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

C_max

Value	Dose	Co-administered	Analyte	Population
250 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2880722/	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

Value	Dose	Co-administered	Analyte	Population
1200 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2880722/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2880722/	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

Dose	Population	Adverse 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018285s034lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018285s034lbl.pdf	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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/018285s034lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 2507 substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052 CYP 303 OCT transporters 2 MATE proteins 2

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 2546	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00960	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://go.drugbank.com/drugs/DB00960	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19248229/	yes
CYP 303	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/6146340/	yes	yes (co-administration study) Comment: cimetidine coadministration increases pindolol plasma levels Sources: https://pubmed.ncbi.nlm.nih.gov/6146340/
MATE proteins 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/1563208/	yes	yes (co-administration study) Comment: cimetidine increased AUC by 1.4 fold and Cmax by 1.3 fold Sources: https://pubmed.ncbi.nlm.nih.gov/1563208/
OCT transporters 2	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/1563208/	yes	yes (co-administration study) Comment: cimetidine increased AUC by 1.4 fold and Cmax by 1.3 fold Sources: https://pubmed.ncbi.nlm.nih.gov/1563208/

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:8214	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:8214
ChemicalBook	CB3105373	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3105373
eMolecules	494631	https://www.emolecules.com/cgi-bin/more?vid=494631
MolPort	MolPort-001-792-503	https://www.molport.com/shop/molecule-link/MolPort-001-792-503

PubMed

Title	Date	PubMed
Anxiolytic-like effects of baicalein and baicalin in the Vogel conflict test in mice.	2003-03-19	12620506
EEG effects of buspirone and pindolol: a method of examining 5-HT1A receptor function in humans.	2003-03	12589521
Effects on sleep architecture of pindolol, paroxetine and their combination in healthy volunteers.	2003-03	12536263
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	12564698
Evidence against beta 3-adrenoceptors or low affinity state of beta 1-adrenoceptors mediating relaxation in rat isolated aorta.	2003-01	12522078
Evidence that the anorexia induced by lipopolysaccharide is mediated by the 5-HT2C receptor.	2003-01	12479973
Pharmacological management for agitation and aggression in people with acquired brain injury.	2003	12535468
Serotonin regulates hippocampal glucocorticoid receptor expression via a 5-HT7 receptor.	2002-12-15	12480134
Indorenate produces antidepressant-like actions in the rat forced swimming test via 5-HT1A receptors.	2002-12	12474119
The role of in vivo molecular imaging with PET and SPECT in the elucidation of psychiatric drug action and new drug development.	2002-12	12468013
Involvement of 5-HT7 receptors in serotonergic effects on spike afterpotentials in presumed jaw-closing motoneurons of rats.	2002-11-08	12414103
Spin trapping study of reactive oxygen species formation during bopindolol peroxidation.	2002-10-15	12209459
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	12181435
[Pharmacology of beta blockers and their significance for therapy of hypertension].	2002-08	12229254
[Reactions between dialkylamine drugs, 2,3-dichloro-1,4-naphthoquinone and acetaldehyde].	2002-08	12227191
Serotonergic control of cerebellar mossy fiber activity by modulation of signal transfer by rat pontine nuclei neurons.	2002-08	12163509
Enantioselectivity in the steady-state pharmacokinetics and transplacental distribution of pindolol at delivery in pregnancy-induced hypertension.	2002-08	12125040
Melatonin potentiates 5-HT(1A) receptor activation in rat hypothalamus and results in hypothermia.	2002-08	12121481
Altered expression of autonomic neurotransmitter receptors and proliferative responses in lymphocytes from a chronic mild stress model of depression: effects of fluoxetine.	2002-08	12096882
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	12065723
Synthesis and evaluation of (S)-[18F]-fluoroethylcarazolol for in vivo beta-adrenoceptor imaging in the brain.	2002-07	11918968
5-HT1A receptor blockade and the motivational profile of ethanol.	2002-06-28	12072158
The neuropharmacology of serotonin and noradrenaline in depression.	2002-06	12369606
[Effect of (+/-)-pindolol on the central 5-HT1A receptor by the use of in vivo microdialysis and hippocampal slice preparations].	2002-06	12166089
Management of treatment resistant obsessive-compulsive disorder. Algorithms for pharmacotherapy.	2002-06	12032425
Familial left ventricular hypertrabeculation in two blind brothers.	2002-05-29	12031765
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	12016018
Determination of bopindolol in pharmaceuticals by capillary isotachophoresis.	2002-05-15	12008130
Somatodendritic action of pindolol to attenuate the paroxetine-induced decrease in serotonin release from the rat ventral hippocampus: a microdialysis study.	2002-05	12012024
Direct determination of pindolol enantiomers in human serum by column-switching LC-MS/MS using a phenylcarbamate-beta-cyclodextrin chiral column.	2002-04-01	11861113
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	11888550
Imaging the neurochemical brain in health and disease.	2002-03-02	11871642
Influence of monoamine oxidase A and serotonin receptor 2A polymorphisms in SSRI antidepressant activity.	2002-03	12057029
Pharmacokinetic scaling of pindolol in healthy volunteers after single dose oral administration.	2002-03	12040882
Copper(II) complexes of the beta-blocker pindolol: properties, structure, biological activity.	2002-03	11860026
Methiothepin attenuates gastric secretion and motility effects of vagal stimulants at the dorsal vagal complex.	2002-02-01	11834248
Screening drugs for metabolic stability using pulsed ultrafiltration mass spectrometry.	2002-02	11860340
Studies on the expression and function of beta-3-adrenoceptors in the colon of rats with acetic acid-induced colitis.	2002-02	11803250
Synthesis and evaluation of radiolabeled antagonists for imaging of beta-adrenoceptors in the brain with PET.	2002-02	11738481
Comparison of the affinity of beta-blockers for two states of the beta 1-adrenoceptor in ferret ventricular myocardium.	2002-01	11815381
PET-examination and metabolite evaluation in monkey of [(11)C]NAD-299, a radioligand for visualisation of the 5-HT(1A) receptor.	2002-01	11786274
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	11767310
Imaging of beta-adrenoceptors in the human thorax using (S)-[(11)C]CGP12388 and positron emission tomography.	2001-12-21	11755150
Further characterization of beta3-adrenoceptors in the guinea pig gastric fundus: stereoselectivity, beta-adrenoceptor alkylation, and structure-activity relationship.	2001-12	11824942
Pindolol augmentation of selective serotonin reuptake inhibitors: PET evidence that the dose used in clinical trials is too low.	2001-12	11729033
No association between dopamine D(2) and D(4) receptor gene variants and antidepressant activity of two selective serotonin reuptake inhibitors.	2001-11-30	11728608
Flesinoxan, a 5-HT1A receptor agonist/alpha 1-adrenoceptor antagonist, lowers intraocular pressure in NZW rabbits.	2001-08	11840354
Management of treatment-refractory panic disorder.	2001	12397890
Partial agonistic properties of (+/-)-pindolol at atypical beta-adrenoceptors in the guinea pig gastric fundus.	2001	11729357
Effects of prindolol on isoproterenol-induced subendocardial ischaemia in dogs with multiple chronic coronary artery occlusion.	1975-07	1182733

Patents

Sample Use Guides

In Vivo Use Guide

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 19:29:55 GMT 2025` Edited by `admin` on `Mon Mar 31 19:29:55 GMT 2025`
Record UNII	BJ4HF6IU1D
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Pindolol

Official Name

English

BLOCKLIN-L

Preferred Name

English

NSC-757276

Code

English

4-(2-HYDROXY-3-ISOPROPYLAMINOPROPOXY)INDOLE

Systematic Name

English

PINDOLOL [JAN]

Common Name

English

PECTOBLOC

Brand Name

English

DL-LB-46

Common Name

English

(RS)-PINDOLOL

Common Name

English

DL-PINDOLOL

Common Name

English

2-PROPANOL, 1-(1H-INDOL-4-YLOXY)-3-(1-METHYLETHYL)AMINO-

Systematic Name

English

PINDOLOL [MI]

Common Name

English

PYNASTIN

Common Name

English

PINDOLOL [HSDB]

Common Name

English

PINDOLOL [EP MONOGRAPH]

Common Name

English

PINDOLOL [USAN]

Common Name

English

LB-46

Code

English

DECRETEN

Common Name

English

4-(3-ISOPROPYLAMINO-2-HYDROXYPROPOXY)INDOLE

Systematic Name

English

VISKAZIDE COMPONENT PINDOLOL

Common Name

English

1-((1-METHYLETHYL)AMINO)-3-(4-INDOLYLOXY)-2-PROPANOL

Systematic Name

English

CARVISKEN

Brand Name

English

PINDOLOL [VANDF]

Common Name

English

PINBETOL

Common Name

English

(±)-PINDOLOL

Common Name

English

PRINODOLOL

Common Name

English

1-(Indol-4-yloxy)-3-(isopropylamino)-2-propanol

Systematic Name

English

PINDOLOL [USP MONOGRAPH]

Common Name

English

CALVISKEN

Brand Name

English

PINDOLOL [MART.]

Common Name

English

GLAUCO-VISKEN

Common Name

English

APO-PINDOL

Common Name

English

N-(2-HYDROXY-3-(1H-INDOL-4-YLOXY)PROPYL)-N-ISOPROPYLAMINE

Systematic Name

English

PINDOLOL [USP-RS]

Common Name

English

pindolol [INN]

Common Name

English

PINDOLOL [ORANGE BOOK]

Common Name

English

DL-4-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)INDOLE

Common Name

English

Pindolol [WHO-DD]

Common Name

English

(±)-4-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)INDOLE

Systematic Name

English

DURAPINDOL

Common Name

English

VISKEN

Brand Name

English

BETAPINDOL

Common Name

English

(±)-LB-46

Code

English

2-PROPANOL, 1-(INDOL-4-YLOXY)-3-(ISOPROPYLAMINO)-

Systematic Name

English

Classification Tree Code System Code

WHO-VATC

QC07AA03