[2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine

• ChemBase ID: 836
• Molecular Formular: C14H20N2O2
• Molecular Mass: 248.3208
• Monoisotopic Mass: 248.15247789
• SMILES: O(CC(O)CNC(C)C)c1c2c([nH]cc2)ccc1
• Canonical SMILES: OC(COc1cccc2c1cc[nH]2)CNC(C)C
• 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
• InChIKey: JZQKKSLKJUAGIC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine; 1-(1H-indol-4-yloxy)-3-[(propan-2-yl)amino]propan-2-ol
• IUPAC Traditional name: [2-hydroxy-3-(1H-indol-4-yloxy)propyl](propan-2-yl)amine; pindolol; 1-(1H-indol-4-yloxy)-3-(isopropylamino)propan-2-ol
• Brand Name: Blockin L; Blocklin L; Calvisken; Cardilate; Decreten; Durapindol; Glauco-Visken; Pectobloc; Pinbetol; Pynastin; Visken
• Synonyms: Prindolol; Visken; (+/-)-4-[2-Hydroxy-3-(isopropylamino)propoxy]indole; Apo-pindol; Decreten; Pectobloc; Betapindol; Prinodolol; Pindolol; 1-(1H-Indol-4-yloxy)-3-(isopropylamino)-2-propanol; 1-(1H-Indol-4-yloxy)-3-[(1-methylethyl)amino]-2-propanol; Pindolol

Database IDs

• CAS Number: 13523-86-9
• EC Number: 236-867-9
• MDL Number: MFCD00010530
• PubChem SID: 160964299; 46508362; 24277795
• PubChem CID: 4828
• CHEBI ID: 8214
• ATC CODE: C07AA03
• CHEMBL: 500
• Chemspider ID: 4662
• DrugBank ID: DB00960
• IUPHAR ligand ID: 91
• KEGG ID: D00513
• Unique Ingredient Identifier: BJ4HF6IU1D
• Wikipedia Title: Pindolol
• Medline Plus: a684032

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.086726
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.5002506
• LogD (pH = 7.4): -0.5322574
• Log P: 1.6929811
• Molar Refractivity: 71.462 cm^3
• Polarizability: 29.42685 Å^3
• Polar Surface Area: 57.28 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.17
• LOG S: -2.46
• Solubility (Water): 8.61e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble20 mg/mL; 0.1 M NaOH: soluble0.2 mg/mL; 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.2 mg/mL; 7880 mg/L; DMSO; H2O: insoluble; Methanol
• Apperance: White Solid; white to off-white powder
• Melting Point: 165-167°C; 167-171 °C(lit.)
• Hydrophobicity(logP): 1.9

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: UB6660000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others
• Admin Routes: oral, iv
• Bioavailability: 50% to 95%
• Excretion: Renal
• Half Life: 3–4 hours
• Metabolism: Hepatic
• Legal Status: Rx-only
• Pregnancy Category: B (US); C (Australia)
• Gene Information: human ... ADRB1(153), HTR1A(3350)
• Mechanism of Action: 5HT1A serotonin receptor antagonist; Non-cardioselective beta-Adrenoceptor antagonist; Partial agonist; Possesses intrinsic sympathomimetic actions (ISA), but little membrane-stabilizing activity; Sympatholytic-Beta; Vasodilator

Product Information

• Purity: ≥98% (TLC)
• Salt Data: Free Base
• Application(s): Used in treatment of Angina pectoris and hypertension; Vasodilator

DETAILS

DrugBank - DB00960

• Drug Groups: approved
• Description: 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)
• Indication: For the management of hypertension, edema, ventricular tachycardias, and atrial fibrillation.
• Pharmacology: Pindolol is a non-selective beta-adrenergic antagonist (beta-blocker) which possesses intrinsic sympathomimetic activity (ISA) in therapeutic dosage ranges but does not possess quinidine-like membrane stabilizing activity. Pindolol impairs AV node conduction and decreases sinus rate and may also increase plasma triglycerides and decrease HDL-cholesterol levels. Pindolol is nonpolar and hydrophobic, with low to moderate lipid solubility. Pindolol has little to no intrinsic sympathomimetic activity and, unlike some other beta-adrenergic blocking agents, pindolol has little direct myocardial depressant activity and does not have an anesthetic-like membrane-stabilizing action.
• Toxicity: LD₅₀=263 mg/kg (orally in rats). Signs of overdose include excessive bradycardia, cardiac failure, hypotension, and bronchospasm.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. In man, 35% to 40% is excreted unchanged in the urine and 60% to 65% is metabolized primarily to hydroxy-metabolites which are excreted as glucuronides and ethereal sulfates.
• Absorption: Rapidly and reproducibly absorbed (bioavailability greater than 95%).
• Half Life: 3 to 4 hours
• Protein Binding: 40%
• Elimination: Pindolol undergoes extensive metabolism in animals and man. In man, 35% to 40% is excreted unchanged in the urine and 60% to 65% is metabolized primarily to hydroxy-metabolites which are excreted as glucuronides and ethereal sulfates. About 6% to 9% of an administered intravenous dose is excreted by the bile into the feces.
• Distribution: * 2 L/kg
• Clearance: * 50-300 mL/min [cirrhotic patients]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - P0778

Biochem/physiol Actions
β1-adrenoceptor antagonist; putative 5-HT1A serotonin receptor agonist; vasodilator.
Features and Benefits
Shelf-life of the powder is at least five years.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. P0778.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - P468000

Mixed β-adrenergic blocker and serotonin 5HT1A-receptor antagonist. Antihypertensive; antianginal; antiarrhythmic; antiglaucoma.

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