13523-86-9 Usage
Chemical Properties
White Solid
Originator
Betadren, Lagap
Uses
Different sources of media describe the Uses of 13523-86-9 differently. You can refer to the following data:
1. Mixed β-adrenergic blocker and serotonin 5HT1A-receptor antagonist. Antihypertensive; antianginal; antiarrhythmic; antiglaucoma.
2. Pindolol, like nadolol, is a nonselective β-adrenoblocker. It possesses antianginal, antihypotensive, and antiarrythmic action. It is used for arterial hypertension, angina stress (preventing attacks), supraventricular tachycardia, tachsystolic form of atrial fibrillation, and
superventricular extrasystole.
Definition
ChEBI: A member of the class of indols which is the 2-hydroxy-3-(isopropylamino)propyl ether derivative of 1H-indol-4-ol.
Manufacturing Process
4-Hydroxyindole is obtained by debenzylation of 4-benzyloxyindole with hydrogen in the presence of a 5% palladium catalyst on aluminium oxide.10.0 g of 4-hydroxyindole and subsequently 7.4 ml of epichlorohydrin are added while stirring in an atmosphere of nitrogen to a solution of 2.73 g of sodium hydroxide in 65 ml of water. Stirring is effected at room temperaturefor a further 15 h, the reaction mixture is extracted 4 times with 50 ml of methylene chloride and the combined organic layers which have been dried over magnesium sulfate are evaporated at reduced pressure. So 3-chloro-1(4-indolyloxy)-2-propanol is obtained.The 3-chloro-1-(4-indolyloxy)-2-propanol is dissolved in 50 ml of toluene and 50 ml of isopropylamine and heated to the boil for 45 h. Evaporation to dryness is effected in a vacuum, the residue is shaken out thrice between ethyl acetate and a 1 N tartaric acid solution and a 5 N sodium hydroxide solution is then added to the combined tartaric acid phases until an alkaline reaction is obtained. The alkaline solution is shaken out thrice with 50 ml of methylene chloride, the extracts are dried over magnesium sulfate and the solvent evaporated in vacuum. The residue is crystallized from ethyl acetate/ether to give the 4-(2-hydroxy-3-isopropylaminopropoxy)indole.
Brand name
Visken (Novartis).
Therapeutic Function
Beta-adrenergic blocker
Biological Activity
5-HT 1A/1B ? receptor antagonist, with roughly equal affinity for each subtype. A partial agonist at mouse and human β 3 -adrenoceptors.
Biochem/physiol Actions
β1-adrenoceptor antagonist; putative 5-HT1A serotonin receptor agonist; vasodilator.
Clinical Use
Beta-blocker:
Hypertension
Angina
Drug interactions
Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: NSAIDs antagonise hypotensive effect.
Anti-arrhythmics: increased risk of myocardial
depression and bradycardia; increased risk of
bradycardia, myocardial depression and AV block
with amiodarone; increased risk of myocardial
depression and bradycardia with flecainide.
Antidepressants: enhanced hypotensive effect with
MAOIs.
Antihypertensives; enhanced hypotensive effect;
increased risk of withdrawal hypertension with
clonidine; increased risk of first dose hypotensive
effect with post-synaptic alpha-blockers such as
prazosin.
Antimalarials: increased risk of bradycardia with
mefloquine.
Antipsychotics: enhanced hypotensive effect with
phenothiazines.
Calcium-channel blockers: increased risk of
bradycardia and AV block with diltiazem;
hypotension and heart failure possible with
nifedipine and nisoldipine; asystole, severe
hypotension and heart failure with verapamil.
Cytotoxics: possible increased risk of bradycardia
with crizotinib.
Diuretics: enhanced hypotensive effect.
Fingolimod: possibly increased risk of bradycardia.
Moxisylyte: possible severe postural hypotension.
Sympathomimetics: severe hypertension with
adrenaline and noradrenaline and possibly with
dobutamine.
Metabolic pathway
Several metabolites of pindolol formed in vitro are
detected after a 24 h incubation of human hepatocytes
in both pure culture and co-culture by adding rat liver
epithelial cells. The hepatocytes are able to oxidize
the isopropyl amine moiety and the pyrrole ring of the
indole moiety and conjugate pindolol as sulfates and
glucuronides.
Metabolism
Pindolol (Visken) is extensively absorbed from the
gastrointestinal tract. First-pass metabolism is estimated
at about 15%, and its plasma half-life is on the order of
3 to 4 hours.The binding of pindolol to plasma proteins
is approximately 50%.The metabolic fate of pindolol is
not completely understood, although 50% of an administered
dose is recovered, primarily in the urine, as unchanged
drug.
Check Digit Verification of cas no
The CAS Registry Mumber 13523-86-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,5,2 and 3 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 13523-86:
(7*1)+(6*3)+(5*5)+(4*2)+(3*3)+(2*8)+(1*6)=89
89 % 10 = 9
So 13523-86-9 is a valid CAS Registry Number.
InChI:InChI=1/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/p+1/t11-/m1/s1
13523-86-9Relevant articles and documents
Synthetic method of pindolol medicine intermediate (I)-4-(2-hydroxyl-3-isopropyl amino propoxy)indole
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Paragraph 0015-0016, (2017/03/08)
The invention relates to a synthetic method of pindolol medicine intermediate (I)-4-(2-hydroxyl-3-isopropyl amino propoxy)indole. The synthetic method comprises the following steps: adding 0.17 mol of 4-Hydroxyindole, 0.18 mol of sodium sulfite and 230 to 260 ml of sodium chloride solution into a reaction vessel with a stirrer and a thermometer, controlling a stirring speed at 110 to 130 rpm, dropwise adding 0.176 to 0.179 mol of (I) epoxy amine propane, then continuously stirring for 16 to 18 h, extracting by virtue of cyclohexane, merging extraction solutions, dehydrating by virtue of phosphorus pentoxide, steaming out a solvent, adding 230 to 260 ml of acetonitrile and 90 to 130 ml of isopropylamine into the remainder, increasing the temperature of the solution to 90 to 95 DEG C, performing the reaction for 26 to 29 h, concentrating and steaming, extracting for 6 to 8 times by virtue of trichloro ethylene, merging the trichloro ethylene layers, adding a sodium hydrogen sulfite solution, adjusting the pH of the solution to 9 to 10, extracting the solution by virtue of methylbenzene, dehydrating by virtue of a dehydrating agent, decompressing and concentrating, adding the remainder into chlorobenzene, increasing the temperature of the solution to 40 to 45 DEG C, concentrating a filtrate, precipitating crystals, and re-crystallizing for 7 to 9 times in the chlorobenzene to obtain (I)-4(2-hydroxyl-3-isopropyl amino propoxy)indole.
THERAPY FOR COMPLICATIONS OF DIABETES
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, (2009/07/02)
A method for enhancing glycemic control and/or insulin sensitivity in a human subject having diabetic nephropathy and/or metabolic syndrome comprises administering to the subject a selective endothelin A (ETA) receptor antagonist in a glycemic control and/or insulin sensitivity enhancing effective amount. A method for treating a complex of comorbidities in an elderly diabetic human subject comprises administering to the subject a selective ETA receptor antagonist in combination or as adjunctive therapy with at least one additional agent that is (i) other than a selective ETA receptor antagonist and (ii) effective in treatment of diabetes and/or at least one of said comorbidities other than hypertension. A therapeutic combination useful in such a method comprises a selective ETA receptor antagonist and at least one antidiabetic, anti-obesity or antidyslipidemic agent other than a selective ETA receptor antagonist.
FLUORESCENCE BASED DETECTION OF SUBSTANCES
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, (2009/09/28)
A method for the fluorescent detection of a substance, the method comprising providing particles comprising a metal or a metal oxide core, wherein one or more optionally fluorescently tagged antibodies or human specific peptide nucleic acid (PNA) oligomers for binding to a substance is/are bound, directly or indirectly, to the surface of the metal or metal oxide; contacting a substrate, which may or may not have the substance on its surface, with the particles for a time sufficient to allow the antibody/PNA oligomer to bind with the substance; removing those particles which have not bound to the substrate; if the antibodies or PNA oligomers are not fluorescently tagged, contacting the substrate with one or more fluorophores that selectively bind with the antibody and/or substance, then optionally washing the substrate to remove unbound fluorophores; and illuminating the substrate with appropriate radiation to show the fluorophores on the substrate.
