Pindolol

Identification

Summary

Pindolol is a beta adrenoceptor antagonist used to treat hypertension, edema, ventricular tachycardias, and atrial fibrillation.

Brand Names

Viskazide, Visken

Generic Name

Pindolol

DrugBank Accession Number

DB00960

Background

Pindolol is a first generation non-selective beta blocker used in the treatment of hypertension.⁹ Early research into the use of pindolol found it had chronotropic effects, and so further investigation focused on the treatment of arrhythmia.⁶ Research into pindolol's use in the treatment of hypertension began in the early 1970s.⁷

Pindolol was granted FDA approval on 3 September 1982.⁸

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 248.3208
Monoisotopic: 248.152477894
Chemical Formula: C₁₄H₂₀N₂O₂

Synonyms

1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol
1-(1H-indol-4-yloxy)-3-(propan-2-ylamino)-propan-2-ol
1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]propan-2-ol
4-(2-hydroxy-3-isopropylaminopropoxy)-indole
Pindolol
Pindololum

External IDs

BRN 1536506
CCRIS 9215
DL-LB-46
HSDB 6539
LB 46
LB-46

Pharmacology

Indication

Pindolol is indicated in the management of hypertension.⁹ In Canada, it is also indicated in the prophylaxis of angina.¹⁰

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Associated Conditions

Contraindications & Blackbox Warnings

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Pharmacodynamics

Pindolol is a nonselective beta blocker indicated in the management of hypertension⁹ and prophylaxis of angina.¹⁰ It has a short duration of action as it is given twice daily, and a wide therapeutic window as doses can range from 10-60 mg/day.⁹ Patients should be counselled regarding the risk of cardiac failure, exacerbating ischemic heart disease with sudden withdrawal, nonallergic bronchospasm, masking hypoglycemia in diabetics, and masking hyperthyroidism.⁹

Mechanism of action

The beta-1 adrenoceptor is a G-protein-coupled receptor.¹ Agonism of the beta-1 adrenoceptor allows the Gs subunit to upregulate adenylyl cyclase, converting ATP to cyclic AMP (cAMP).¹ Increased concentrations of cAMP activate cAMP-dependant kinase A, phosphorylating calcium channels, raising intracellular calcium, increasing calcium exchange through the sarcoplasmic reticulum, and increasing cardiac inotropy.¹ cAMP-dependant kinase A also phosphorylates myosin light chains, increasing smooth muscle contractility.¹ Increased smooth muscle contractility in the kidney releases renin.¹

Pindolol is a non-selective beta blocker.³ Blocking beta-1 adrenergic receptors in the heart results in decreased heart rate and blood pressure.³ By blocking beta-1 receptors in the juxtaglomerular apparatus, pindolol inhibits the release of renin, which inhibits angiotensin II and aldosterone release.^1,2 Reduced angiotensin II inhibits vasoconstriction and reduced aldosterone inhibits water retention.^1,2

Beta-2 adrenoceptors located in the kidneys and peripheral blood vessels use a similar mechanism to activate cAMP-dependant kinase A to increase smooth muscle contractility.⁴ Blocking of the beta-2 adrenoceptor relaxes smooth muscle, leading to vasodilation.⁴

Target	Actions	Organism
ABeta-1 adrenergic receptor	partial agonist	Humans
ABeta-2 adrenergic receptor	partial agonist	Humans
U5-hydroxytryptamine receptor 1A	antagonist inhibitor ligand	Humans
U5-hydroxytryptamine receptor 1B	other/unknown ligand	Humans
UBeta-3 adrenergic receptor	agonist	Humans
UBeta adrenergic receptor	inhibitor	Humans

Absorption

The mean oral bioavailability of pindolol is 87-92%.¹⁰ A 5 mg oral dose reaches a C_max of 33.1 ± 5.2 ng/mL, with a T_max of 1-2 hours.¹⁰

Volume of distribution

The volume of distribution of pindolol is approximately 2-3 L/kg.^9,10

Protein binding

Pindolol is 40% bound to proteins in plasma.⁹ Pindolol mainly binds more strongly to alpha-1-acid glycoprotein than it does to serum albumin.⁵

Metabolism

30-40% of a dose of pindolol is not metabolized.¹⁰ The remainder is hydroxylated and subsequently undergoes glucuronidation or sulfate conjugation.¹⁰

Hover over products below to view reaction partners

Pindolol
- Pindolol Glucuronide
- 3-Hydroxy Pindolol
  - Pindolol 3-glucuronide
  - Pindolol Sulfate

Route of elimination

80% of an oral dose is eliminated in the urine,¹⁰ with 25-40% of the dose as the unchanged parent compound.⁹ 6-9% of an intravenous dose is eliminated in the feces.⁹ Overall, 60-65% of a dose is eliminated as glucuronide and sulfate metabolites.⁹

Half-life

The half life of pindolol varies from 3-4 hours¹⁰ but can be as high as 30 hours in patients with cirrhosis of the liver.⁹

Clearance

In otherwise healthy patients, the systemic clearance of pindolol is 400-500 mL/min.¹⁰ In patients with cirrhosis, the clearance of pindolol varies from 50-300 mL/min.⁹

Adverse Effects

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Toxicity

Patients experiencing an overdose may experience excessive bradycardia, cardiac failure, hypotension, and bronchospasm.⁹ Initiate treatment with symptomatic and supportive measures.⁹

Pathways

Pathway	Category
Pindolol Action Pathway	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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1,2-Benzodiazepine	The risk or severity of adverse effects can be increased when Pindolol is combined with 1,2-Benzodiazepine.
Abacavir	Pindolol may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abatacept	The metabolism of Pindolol can be increased when combined with Abatacept.
Abiraterone	The metabolism of Pindolol can be decreased when combined with Abiraterone.
Acarbose	The therapeutic efficacy of Acarbose can be increased when used in combination with Pindolol.
Acebutolol	The metabolism of Pindolol can be decreased when combined with Acebutolol.
Aceclofenac	Aceclofenac may decrease the antihypertensive activities of Pindolol.
Acemetacin	Acemetacin may decrease the antihypertensive activities of Pindolol.
Acenocoumarol	The risk or severity of adverse effects can be increased when Pindolol is combined with Acenocoumarol.
Acetaminophen	Acetaminophen may decrease the excretion rate of Pindolol which could result in a higher serum level.

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Food Interactions

Avoid alcohol. Alcohol may aggravate signs and symptoms of overdose.
Take with or without food. Food does not significantly affect absorption.

Products

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Product Images

International/Other Brands

Betapindol / Blockin L / Blocklin L / Calvisken / Decreten / Durapindol / Glauco-Visken / Pectobloc / Pinbetol / Prinodolol / Pynastin

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Pindolol-10 Tab 10mg	Tablet	10 mg	Oral	Pro Doc Limitee	1989-12-31	2020-03-09
Pindolol-15 Tab 15mg	Tablet	15 mg	Oral	Pro Doc Limitee	1989-12-31	2012-07-23
Pindolol-5 Tab 5mg	Tablet	5 mg	Oral	Pro Doc Limitee	1989-12-31	2020-03-09
Visken	Tablet	5 mg/1	Oral	Novartis Pharmaceuticals Corporation	1982-09-03	2019-09-10
Visken	Tablet	5 mg	Oral	Xediton Pharmaceuticals Inc	1978-12-31	Not applicable
Visken	Tablet	10 mg	Oral	Xediton Pharmaceuticals Inc	1978-12-31	Not applicable
Visken	Tablet	10 mg/1	Oral	Novartis Pharmaceuticals Corporation	1982-09-03	2019-09-10
Visken	Tablet	15 mg	Oral	Tribute Pharmaceuticals	1978-12-31	2017-07-13

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-pindol Tab 10mg	Tablet	10 mg	Oral	Apotex Corporation	1988-12-31	Not applicable
Apo-pindol Tab 15mg	Tablet	15 mg	Oral	Apotex Corporation	1988-12-31	Not applicable
Apo-pindol Tab 5mg	Tablet	5 mg	Oral	Apotex Corporation	1988-12-31	Not applicable
Dom-pindolol	Tablet	5 mg	Oral	Dominion Pharmacal	1998-09-17	2018-10-10
Dom-pindolol	Tablet	15 mg	Oral	Dominion Pharmacal	1998-09-17	Not applicable
Dom-pindolol	Tablet	10 mg	Oral	Dominion Pharmacal	1998-09-17	2018-10-10
Gen-pindolol Tab 15mg	Tablet	15 mg	Oral	Genpharm Ulc	1994-12-31	2010-08-04
Mylan-pindolol	Tablet	5 mg	Oral	Mylan Pharmaceuticals	1994-12-31	2012-10-19
Mylan-pindolol	Tablet	10 mg	Oral	Mylan Pharmaceuticals	1994-12-31	2012-10-19
Nu-pindol Tab 10mg	Tablet	10 mg	Oral	Nu Pharm Inc	1990-12-31	2012-09-04

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Viskazide	Pindolol (10 mg) + Hydrochlorothiazide (50 mg)	Tablet	Oral	Xediton Pharmaceuticals Inc	1983-12-31	Not applicable
Viskazide	Pindolol (10 mg) + Hydrochlorothiazide (25 mg)	Tablet	Oral	Xediton Pharmaceuticals Inc	1983-12-31	Not applicable

Chemical Identifiers

UNII: BJ4HF6IU1D
CAS number: 13523-86-9
InChI Key: JZQKKSLKJUAGIC-UHFFFAOYSA-N
InChI: 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
IUPAC Name: 1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
SMILES: CC(C)NCC(O)COC1=CC=CC2=C1C=CN2

References

Synthesis Reference

US3471515

General References

Alhayek S, Preuss CV: Beta 1 Receptors . [Article]
Blumenfeld JD, Sealey JE, Mann SJ, Bragat A, Marion R, Pecker MS, Sotelo J, August P, Pickering TG, Laragh JH: Beta-adrenergic receptor blockade as a therapeutic approach for suppressing the renin-angiotensin-aldosterone system in normotensive and hypertensive subjects. Am J Hypertens. 1999 May;12(5):451-9. doi: 10.1016/s0895-7061(99)00005-9. [Article]
Clark BJ, Menninger K, Bertholet A: Pindolol--the pharmacology of a partial agonist. Br J Clin Pharmacol. 1982;13(Suppl 2):149S-158S. doi: 10.1111/j.1365-2125.1982.tb01904.x. [Article]
Ferguson SS, Feldman RD: beta-adrenoceptors as molecular targets in the treatment of hypertension. Can J Cardiol. 2014 May;30(5 Suppl):S3-8. doi: 10.1016/j.cjca.2014.01.017. Epub 2014 Feb 12. [Article]
Belpaire FM, Bogaert MG, Rosseneu M: Binding of beta-adrenoceptor blocking drugs to human serum albumin, to alpha 1-acid glycoprotein and to human serum. Eur J Clin Pharmacol. 1982;22(3):253-6. doi: 10.1007/BF00545224. [Article]
Robak J, Gryglewski R: Influence of INPEA, pindolol and propranolol on the chronotropic and metabolic responses to -adrenergic stimulation in intact rats. Biochem Pharmacol. 1971 Oct;20(10):2749-58. doi: 10.1016/0006-2952(71)90184-5. [Article]
Walter I, Kusus T, Lydtin H: [Clinical test of a new beta-receptor blockader in labile hypertension]. Verh Dtsch Ges Inn Med. 1971;77:940-3. [Article]
FDA Approved Drug Products: Visken (Pindolol) Oral Tablets [Link]
Dailymed: Pindolol Oral Tablet [Link]
Health Canada Approved Drug Products: Apo-Pindolol (Pindolol) Oral Tablet [Link]

External Links

Human Metabolome Database: HMDB0015095
KEGG Drug: D00513
KEGG Compound: C07445
PubChem Compound: 4828
PubChem Substance: 46508362
ChemSpider: 4662
BindingDB: 50019443
RxNav: 8332
ChEBI: 8214
ChEMBL: CHEMBL500
Therapeutic Targets Database: DAP000025
PharmGKB: PA450966
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
PDRhealth: PDRhealth Drug Page
Wikipedia: Pindolol

MSDS

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Enrolling by Invitation	Other	Cardiac Failure / Cardiovascular Disease (CVD) / Heart Failure / Heart Failure With Preserved Ejection Fraction (HFpEF) / Heart Failure, Diastolic	2
4	Recruiting	Treatment	Healthy Subjects (HS)	1
2	Completed	Treatment	Antidepressant Treatment Response / Major Depressive Disorder (MDD)	1
2, 3	Terminated	Treatment	Unipolar Depression	1
1	Completed	Basic Science	Amphetamine-Related Disorders / Moods Disorders / Substance Related Disorders	1
1	Unknown Status	Treatment	Healthy Subjects (HS)	1
Not Available	Completed	Not Available	Coronavirus Disease 2019 (COVID‑19) / COVID / High Blood Pressure (Hypertension)	1
Not Available	Completed	Basic Science	Healthy Subjects (HS)	1
Not Available	Terminated	Treatment	High Blood Pressure (Hypertension) / Microvascular Angina	1
Not Available	Terminated	Treatment	Major Depressive Disorder (MDD)	1

Pharmacoeconomics

Manufacturers

Genpharm pharmaceuticals inc
Ivax pharmaceuticals inc sub teva pharmaceuticals usa
Mutual pharmaceutical co inc
Mylan pharmaceuticals inc
Nostrum laboratories inc
Purepac pharmaceutical co
Sandoz inc
Teva pharmaceuticals usa inc
Watson laboratories inc
Novartis pharmaceuticals corp

Packagers

Advanced Pharmaceutical Services Inc.
Ivax Pharmaceuticals
Major Pharmaceuticals
Merckle GmbH
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Novartis AG
Novopharm Ltd.
Pharmaceutical Utilization Management Program VA Inc.
Physicians Total Care Inc.
Qualitest
Sandhills Packaging Inc.

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet	Oral	10 mg/1
Tablet	Oral	5 mg/1
Tablet	Oral	10 mg / tab
Tablet	Oral	15 mg / tab
Tablet	Oral	5 mg / tab
Tablet	Oral	10 mg
Tablet	Oral
Solution / drops	Oral	5 mg/ml
Tablet	Oral	15 MG
Tablet	Oral	5 MG

Prices

Unit description	Cost	Unit
Visken 15 mg Tablet	1.52USD	tablet
Visken 10 mg Tablet	1.05USD	tablet
Pindolol 10 mg tablet	1.0USD	tablet
Pindolol 5 mg tablet	0.73USD	tablet
Apo-Pindol 15 mg Tablet	0.61USD	tablet
Gen-Pindolol 15 mg Tablet	0.61USD	tablet
Novo-Pindol 15 mg Tablet	0.61USD	tablet
Nu-Pindol 15 mg Tablet	0.61USD	tablet
Pms-Pindolol 15 mg Tablet	0.61USD	tablet
Sandoz Pindolol 15 mg Tablet	0.61USD	tablet
Visken 5 mg Tablet	0.61USD	tablet
Apo-Pindol 10 mg Tablet	0.42USD	tablet
Gen-Pindolol 10 mg Tablet	0.42USD	tablet
Novo-Pindol 10 mg Tablet	0.42USD	tablet
Nu-Pindol 10 mg Tablet	0.42USD	tablet
Pms-Pindolol 10 mg Tablet	0.42USD	tablet
Sandoz Pindolol 10 mg Tablet	0.42USD	tablet
Apo-Pindol 5 mg Tablet	0.24USD	tablet
Gen-Pindolol 5 mg Tablet	0.24USD	tablet
Novo-Pindol 5 mg Tablet	0.24USD	tablet
Nu-Pindol 5 mg Tablet	0.24USD	tablet
Pms-Pindolol 5 mg Tablet	0.24USD	tablet
Sandoz Pindolol 5 mg Tablet	0.24USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	171 °C	PhysProp
water solubility	Practically Insoluble	FDA Label
logP	1.75	SANGSTER (1994)
Caco2 permeability	-4.78	ADME Research, USCD
pKa	9.25	SANGSTER (1994)

Predicted Properties

Property	Value	Source
Water Solubility	0.861 mg/mL	ALOGPS
logP	2.17	ALOGPS
logP	1.69	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	9.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	57.28 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	71.46 m³·mol^-1	ChemAxon
Polarizability	28.27 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9951
Blood Brain Barrier	+	0.6929
Caco-2 permeable	+	0.8867
P-glycoprotein substrate	Substrate	0.6667
P-glycoprotein inhibitor I	Non-inhibitor	0.9272
P-glycoprotein inhibitor II	Non-inhibitor	0.9423
Renal organic cation transporter	Non-inhibitor	0.8179
CYP450 2C9 substrate	Non-substrate	0.8315
CYP450 2D6 substrate	Substrate	0.8919
CYP450 3A4 substrate	Non-substrate	0.708
CYP450 1A2 substrate	Non-inhibitor	0.7809
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Inhibitor	0.5
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.831
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.8331
Ames test	Non AMES toxic	0.9218
Carcinogenicity	Non-carcinogens	0.9367
Biodegradation	Not ready biodegradable	0.9843
Rat acute toxicity	2.9438 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9404
hERG inhibition (predictor II)	Non-inhibitor	0.5774

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

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Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01b9-2900000000-e773b852c7d4839b531d
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01c3-1900000000-97bebf43acd96bd5cf5b
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01ba-0920000000-9c68ad2e49235b630737
LC-MS/MS Spectrum - LC-ESI-ITFT , positive	LC-MS/MS	splash10-01b9-0900000000-e0edd57b20d4dcecb440
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0002-1690000000-c5bffa0f5938ebc6de4b

Targets

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Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	2.4	N/A	N/A	A28612
Kd (nM)	2.6	N/A	N/A	A28612
Ki (nM)	0.52	N/A	N/A	A29238
Ki (nM)	1.94	N/A	N/A	A28610
Ki (nM)	2.6	N/A	N/A	A15544

Details1. Beta-1 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Partial agonist

General Function: Receptor signaling protein activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name: ADRB1
Uniprot ID: P08588
Uniprot Name: Beta-1 adrenergic receptor
Molecular Weight: 51322.1 Da

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Joseph SS, Lynham JA, Molenaar P, Grace AA, Colledge WH, Kaumann AJ: Intrinsic sympathomimetic activity of (-)-pindolol mediated through a (-)-propranolol-resistant site of the beta1-adrenoceptor in human atrium and recombinant receptors. Naunyn Schmiedebergs Arch Pharmacol. 2003 Dec;368(6):496-503. Epub 2003 Nov 8. [Article]
Doggrell SA: Effects of (+/-)- (+)- and (-)-metoprolol, (+/-)- (+)- and (-)-pindolol, (+/-)-mepindolol and (+/-)-bopindolol on the rat left atria and portal vein. Gen Pharmacol. 1991;22(6):1169-77. [Article]
Berendsen HH, Broekkamp CL, Van Delft AM: Antagonism of 8-OH-DPAT-induced behaviour in rats. Eur J Pharmacol. 1990 Oct 2;187(1):97-103. [Article]
Watkins DJ, Lawrence AJ, Lewis SJ, Jarrott B: Loss of [125I]-pindolol binding to beta-adrenoceptors on rat nodose ganglion after chronic isoprenaline treatment. J Auton Nerv Syst. 1996 Aug 27;60(1-2):12-6. [Article]
Brodde OE, Michel MC, Wang XL, Zerkowski HR: Chronic beta-adrenoceptor antagonist treatment modulates human cardiac and vascular beta-adrenoceptor density in a subtype-selective fashion. J Hypertens Suppl. 1988 Dec;6(4):S497-500. [Article]

Details2. Beta-2 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Partial agonist

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name: ADRB2
Uniprot ID: P07550
Uniprot Name: Beta-2 adrenergic receptor
Molecular Weight: 46458.32 Da

References

Rubenstein LA, Zauhar RJ, Lanzara RG: Molecular dynamics of a biophysical model for beta2-adrenergic and G protein-coupled receptor activation. J Mol Graph Model. 2006 Dec;25(4):396-409. Epub 2006 Mar 30. [Article]
Dejgaard A, Liggett SB, Christensen NJ, Cryer PE, Hilsted J: Adrenergic receptors are a fallible index of adrenergic denervation hypersensitivity. Scand J Clin Lab Invest. 1991 Dec;51(8):659-66. [Article]
Wheeldon NM, Newnham DM, Fraser GC, McDevitt DG, Lipworth BJ: The effect of pindolol on creatine kinase is not due to beta 2-adrenoceptor partial agonist activity. Br J Clin Pharmacol. 1991 Jun;31(6):723-4. [Article]
Doggrell SA: Effects of (+/-)- (+)- and (-)-metoprolol, (+/-)- (+)- and (-)-pindolol, (+/-)-mepindolol and (+/-)-bopindolol on the rat left atria and portal vein. Gen Pharmacol. 1991;22(6):1169-77. [Article]
Doggrell SA: Relaxant and beta 2-adrenoceptor blocking activities of (+/- )-, (+)- and (-)-pindolol on the rat isolated aorta. J Pharm Pharmacol. 1990 Jun;42(6):444-6. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	27	N/A	N/A	A29240
Ki (nM)	110	N/A	N/A	A29239 / A27481
Ki (nM)	15	N/A	N/A	A28438
Ki (nM)	17.78	N/A	N/A	A27484
Ki (nM)	22.4	N/A	N/A	A29238
Ki (nM)	24	N/A	N/A	A29240
Ki (nM)	28	N/A	N/A	A28736
Ki (nM)	28.18	N/A	N/A	A27484
Ki (nM)	33.11	N/A	N/A	A27484
Ki (nM)	33.3	N/A	N/A	A28440
Ki (nM)	37.15	N/A	N/A	A27484
Ki (nM)	61.1	N/A	N/A	A28440
Ki (nM)	61.65	N/A	N/A	A27484
Ki (nM)	81.1	N/A	N/A	A29238

Details3. 5-hydroxytryptamine receptor 1A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist
Inhibitor
Ligand

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances. Ligand binding causes a conformation change that triggers...
Gene Name: HTR1A
Uniprot ID: P08908
Uniprot Name: 5-hydroxytryptamine receptor 1A
Molecular Weight: 46106.335 Da

References

Smeraldi E, Benedetti F, Barbini B, Campori E, Colombo C: Sustained antidepressant effect of sleep deprivation combined with pindolol in bipolar depression. A placebo-controlled trial. Neuropsychopharmacology. 1999 Apr;20(4):380-5. [Article]
Haddjeri N, de Montigny C, Blier P: Modulation of the firing activity of rat serotonin and noradrenaline neurons by (+/-)pindolol. Biol Psychiatry. 1999 May 1;45(9):1163-9. [Article]
Gobert A, Millan MJ: Modulation of dialysate levels of dopamine, noradrenaline, and serotonin (5-HT) in the frontal cortex of freely-moving rats by (-)-pindolol alone and in association with 5-HT reuptake inhibitors: comparative roles of beta-adrenergic, 5-HT1A, and 5-HT1B receptors. Neuropsychopharmacology. 1999 Aug;21(2):268-84. [Article]
Andree B, Thorberg SO, Halldin C, Farde L: Pindolol binding to 5-HT1A receptors in the human brain confirmed with positron emission tomography. Psychopharmacology (Berl). 1999 Jun;144(3):303-5. [Article]
Fornal CA, Martin FJ, Metzler CW, Jacobs BL: Pindolol suppresses serotonergic neuronal activity and does not block the inhibition of serotonergic neurons produced by 8-hydroxy-2-(di-n-propylamino)tetralin in awake cats. J Pharmacol Exp Ther. 1999 Oct;291(1):229-38. [Article]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Wada Y, Hirao N, Shiraishi J, Nakamura M, Koshino Y: Pindolol potentiates the effect of fluoxetine on hippocampal seizures in rats. Neurosci Lett. 1999 May 21;267(1):61-4. doi: 10.1016/s0304-3940(99)00321-3. [Article]
Sandell J, Halldin C, Hall H, Thorberg SO, Werner T, Sohn D, Sedvall G, Farde L: Radiosynthesis and autoradiographic evaluation of [11C]NAD-299, a radioligand for visualization of the 5-HT1A receptor. Nucl Med Biol. 1999 Feb;26(2):159-64. doi: 10.1016/s0969-8051(98)00091-2. [Article]
Hayes ES, Adaikan PG, Ratnam SS, Ng SC: 5-HT4 receptors in isolated human corpus cavernosum? Int J Impot Res. 1999 Aug;11(4):219-25. doi: 10.1038/sj.ijir.3900425. [Article]
Clemett DA, Kendall DA, Cockett MI, Marsden CA, Fone KC: Pindolol-insensitive [3H]-5-hydroxytryptamine binding in the rat hypothalamus; identity with 5-hydroxytryptamine7 receptors. Br J Pharmacol. 1999 May;127(1):236-42. doi: 10.1038/sj.bjp.0702503. [Article]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	>10000	N/A	N/A	A28614
Ki (nM)	2600	N/A	N/A	A28614
Ki (nM)	4100	N/A	N/A	A27491

Details4. 5-hydroxytryptamine receptor 1B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Other/unknown
Ligand

General Function: Serotonin receptor activity
Specific Function: G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for ergot alkaloid derivatives, various anxiolytic and antidepressant drugs and other psychoactive subst...
Gene Name: HTR1B
Uniprot ID: P28222
Uniprot Name: 5-hydroxytryptamine receptor 1B
Molecular Weight: 43567.535 Da

References

Dawson LA, Nguyen HQ: The role of 5-HT(1A) and 5-HT(1B/1D) receptors on the modulation of acute fluoxetine-induced changes in extracellular 5-HT: the mechanism of action of (+/-)pindolol. Neuropharmacology. 2000 Apr 3;39(6):1044-52. [Article]
Ariani K, Hamblin MW, Tan GL, Stratford CA, Ciaranello RD: G protein dependent alterations in [125I]iodocyanopindolol and +/- cyanopindolol binding at 5-HT1B binding sites in rat brain membranes. Neurochem Res. 1989 Sep;14(9):835-43. [Article]
Leonhardt S, Herrick-Davis K, Titeler M: Detection of a novel serotonin receptor subtype (5-HT1E) in human brain: interaction with a GTP-binding protein. J Neurochem. 1989 Aug;53(2):465-71. [Article]
Herrick-Davis K, Titeler M, Leonhardt S, Struble R, Price D: Serotonin 5-HT1D receptors in human prefrontal cortex and caudate: interaction with a GTP binding protein. J Neurochem. 1988 Dec;51(6):1906-12. [Article]
Terron JA, Lopez-Munoz FJ, Hong E, Villalon CM: 2-(2-Aminoethyl)-quinoline (D-1997): a novel agonist at 5-hydroxytryptamine1-like receptors in the canine basilar artery. Arch Int Pharmacodyn Ther. 1994 Jan-Feb;327(1):56-68. [Article]
Clemett DA, Kendall DA, Cockett MI, Marsden CA, Fone KC: Pindolol-insensitive [3H]-5-hydroxytryptamine binding in the rat hypothalamus; identity with 5-hydroxytryptamine7 receptors. Br J Pharmacol. 1999 May;127(1):236-42. doi: 10.1038/sj.bjp.0702503. [Article]

Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	166	N/A	N/A	A28612
Ki (nM)	44.1	N/A	N/A	A15544

Details5. Beta-3 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Agonist

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. Beta-3 is involved in the regulation of lipolysis and thermogenesis.
Gene Name: ADRB3
Uniprot ID: P13945
Uniprot Name: Beta-3 adrenergic receptor
Molecular Weight: 43518.615 Da

References

Hoffmann C, Leitz MR, Oberdorf-Maass S, Lohse MJ, Klotz KN: Comparative pharmacology of human beta-adrenergic receptor subtypes--characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol. 2004 Feb;369(2):151-9. Epub 2004 Jan 17. [Article]
Feve B, Emorine LJ, Lasnier F, Blin N, Baude B, Nahmias C, Strosberg AD, Pairault J: Atypical beta-adrenergic receptor in 3T3-F442A adipocytes. Pharmacological and molecular relationship with the human beta 3-adrenergic receptor. J Biol Chem. 1991 Oct 25;266(30):20329-36. [Article]

Details6. Beta adrenergic receptor (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Receptor signaling protein activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...

Components:

Name	UniProt ID
Beta-1 adrenergic receptor	P08588
Beta-2 adrenergic receptor	P07550
Beta-3 adrenergic receptor	P13945

References

Aellig WH: [Clinicopharmacological studies with pindolol following intravenous and oral administration]. Adv Clin Pharmacol. 1976;11:9-13. [Article]
Fornal CA, Martin FJ, Mendlin A, Metzler CW, Bjorvatn B, Jacobs BL: Pindolol increases extracellular 5-HT while inhibiting serotonergic neuronal activity. Eur J Pharmacol. 1999 Jul 21;377(2-3):187-91. doi: 10.1016/s0014-2999(99)00430-6. [Article]
Klein WW, Brandt D, Fluch N, Goebel R, Holzer H, Poch G: [Hemodynamic long-term effects of a beta-receptor blockader (Pindolol) in primary essential hypertension]. Adv Clin Pharmacol. 1976;11:79-85. [Article]
Ohnhaus EE, Munch U, Meier J: [Comparative study on the elimination of pindolol (visken) and antipyrin in patients with liver diseases]. Schweiz Med Wochenschr. 1976 Dec 4;106(49):1748-50. [Article]
Varma DR, Shen H, Deng XF, Peri KG, Chemtob S, Mulay S: Inverse agonist activities of beta-adrenoceptor antagonists in rat myocardium. Br J Pharmacol. 1999 Jun;127(4):895-902. [Article]

Enzymes

Details1. UDP-glucuronosyltransferases (UGTs) (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid binding
Specific Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...

Components:

Name	UniProt ID
UDP-glucuronosyltransferase 1-1	P22309
UDP-glucuronosyltransferase 1-10	Q9HAW8
UDP-glucuronosyltransferase 1-3	P35503
UDP-glucuronosyltransferase 1-4	P22310
UDP-glucuronosyltransferase 1-6	P19224
UDP-glucuronosyltransferase 1-7	Q9HAW7
UDP-glucuronosyltransferase 1-8	Q9HAW9
UDP-glucuronosyltransferase 1-9	O60656
UDP-glucuronosyltransferase 2B15	P54855
UDP-glucuronosyltransferase 2B4	P06133
UDP-glucuronosyltransferase 2B7	P16662

References

Health Canada Approved Drug Products: Apo-Pindolol (Pindolol) Oral Tablet [Link]
Dailymed: Pindolol Oral Tablet [Link]

Details2. Sulfotransferase (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Sulfotransferase activity
Specific Function: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.

Components:

Name	UniProt ID
Bile salt sulfotransferase	Q06520
Sulfotransferase 1A1	P50225
Sulfotransferase 1A2	P50226
Sulfotransferase 1A3	P0DMM9
Sulfotransferase 1A4	P0DMN0
Sulfotransferase 1C2	O00338
Sulfotransferase 1C3	Q6IMI6
Sulfotransferase 1C4	O75897
Sulfotransferase 4A1	Q9BR01
Sulfotransferase 6B1	Q6IMI4
Sulfotransferase family cytosolic 1B member 1	O43704

References

Dailymed: Pindolol Oral Tablet [Link]
Health Canada Approved Drug Products: Apo-Pindolol (Pindolol) Oral Tablet [Link]

Details3. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Smith DA, Jones BC: Speculations on the substrate structure-activity relationship (SSAR) of cytochrome P450 enzymes. Biochem Pharmacol. 1992 Dec 1;44(11):2089-98. [Article]
Ferrari S, Leemann T, Dayer P: The role of lipophilicity in the inhibition of polymorphic cytochrome P450IID6 oxidation by beta-blocking agents in vitro. Life Sci. 1991;48(23):2259-65. [Article]

Carriers

Details1. alpha1-acid glycoprotein (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Not Available
Specific Function: Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:

Name	UniProt ID
Alpha-1-acid glycoprotein 1	P02763
Alpha-1-acid glycoprotein 2	P19652

References

Belpaire FM, Bogaert MG, Rosseneu M: Binding of beta-adrenoceptor blocking drugs to human serum albumin, to alpha 1-acid glycoprotein and to human serum. Eur J Clin Pharmacol. 1982;22(3):253-6. doi: 10.1007/BF00545224. [Article]

Transporters

Details1. Solute carrier family 22 member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Quaternary ammonium group transmembrane transporter activity
Specific Function: Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name: SLC22A2
Uniprot ID: O15244
Uniprot Name: Solute carrier family 22 member 2
Molecular Weight: 62579.99 Da

References

Ciarimboli G, Schroter R, Neugebauer U, Vollenbroker B, Gabriels G, Brzica H, Sabolic I, Pietig G, Pavenstadt H, Schlatter E, Edemir B: Kidney transplantation down-regulates expression of organic cation transporters, which translocate beta-blockers and fluoroquinolones. Mol Pharm. 2013 Jun 3;10(6):2370-80. doi: 10.1021/mp4000234. Epub 2013 May 3. [Article]

Drug created on June 13, 2005 13:24 / Updated on September 19, 2021 19:53

Pindolol

Identification

Structure for Pindolol (DB00960)

Pharmacology

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Enzymes

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Transporters

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