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1-(1H-indol-4-yloxy)-3-((1-methyl-ethyl)amino)-2-propanol
lb46 · LB-46 · Visken · Vasken · dl-lb46 · Decreten · Pinbetol · Pynastin
Identifikatoren & physikalische Daten
| CAS No. | 13523-86-9 |
|---|---|
| Summenformel | C14H20N2O2 |
| Durchschnittliche Molmasse | 248,32 g/mol |
| Monoisotopische Masse | 248,15247788 g/mol |
| SMILES | CC(C)NCC(O)COc1cccc2[nH]ccc12 |
| InChIKey | JZQKKSLKJUAGIC-UHFFFAOYSA-N |
| PubChem CID | 4828 |
| ChEMBL | CHEMBL500 |
| ChEBI | CHEBI:8214 |
| EC No. | 236-867-9 |
| DTXSID | DTXSID8023476 |
| Lokaler Name | 1-(1H-indol-4-yloxy)-3-((1-methyl-ethyl)amino)-2-propanol |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 57,3 |
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 248 |
| Arzneimittel | Pharmaceuticals |
| LogP (Verteilungskoeffizient) | log Kow = 1.751.9 |
| Geruch | Faint odor |
| Color/Form | Crystals from ethanolWhite to off-white crystalline powder |
| Löslichkeit | Practically InsolublePractically insoluble in water and slightly soluble in alcohol8.61e-01 g/L>37.2 [ug/mL] (The mean of the results at pH 7.4)0.1 M NaOH: 0.2 mg/mL33mg/L(22.5 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanAntihypertensive AgentsAdrenergic Beta-AntagonistsAntiarrhythmicsFDA approved drugs -> Active ingredientPharmaceuticals |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| Schmelzpunkt | 171-173 °C167 - 171 °C167-171 °C(lit.) |
| Physical Description | Solid |
| Dissociation Constants | 9.549.25 |
| Collision Cross Section | 159.1 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]152.36 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]157.6 Ų [M+H]+ [CCS Type: TW |
| Siedepunkt | 391.39°C (rough estimate) |
| Dichte | 1.0606 (rough estimate) |
| Brechungsindex | 1.5110 (estimate) |
| Lagerbedingungen | 2-8°C |
| Aggregatzustand | powder |
| pKa (Säurekonstante) | pKa 9.26 (Uncertain) |
| Farbe | white to off-white |
| Merck | 13,7525 |
| Hauptanwendungen | pharmaceutical (small molecule) |
| 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 |
| SMILES | C(OC1=CC=CC2=C1C=CN2)C(O)CNC(C)C |
| CAS Datenbank | 13523-86-9(CAS DataBase Reference) |
| NIST chemische Informationen | Pindolol(13523-86-9) |
| EPA chemische Informationen | 2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]- (13523-86-9) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (90.7%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 43 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH301: Toxic if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatorische Informationen | Pindolol: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 2-Propanol, 1-(1H-indol-4-yloxy)-3-[(1-methylethyl)amino]-: Environment tier I assessment |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl pindolol, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act.Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392). |
| Hazard Classes and Categories | Acute Tox. 4 (90.7%)Acute toxicity (Oral) - Category 3 |
| Lagerbedingungen | Pindolol tablets should be protected from light and stored in well-closed containers. |
| Entsorgungsverfahren | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| Körperbelastung | /Pindolol/ ... is distributed into milk. |
| Wechselwirkungen | Concomitant administration of pindolol with reserpine may increase the incidence of hypotension and bradycardia as compared with pindolol alone, because of reserpine's catecholamine-depleting activity. Pindolol also is additive with and may potentiate the hypotensive actions of other hypotensive agents (e.g., hydralazine, hydrochlorothiazide).Slight transient decreases in serum digoxin concentrations have occurred when pindolol and digoxin were used concurrentlyhowever, this effect is not considered clinically important.Pindolol has been shown to increase serum thioridazine levels when both drugs are co-administered. Pindolol levels may also be increased with this combination. |
| Hepatotoxicity | Mild-to-moderate elevations in serum aminotransferase levels occur in less than 2% of patients on pindolol and are usually transient and asymptomatic, resolving even with continuation of therapy. Despite its wide spread use, pindolol has not been convincingly linked to instances of clinically apparent liver injury. Other beta-blockers have been implicated in rare instances of clinically apparent liver injury with a latency to onset ranging from 4 to 24 weeks, a hepatocellular pattern of serum enzyme elevations, and a mild, self-limiting course without evidence of hypersensitivity or autoimmune reactions. |
| Milk Concentrations | /Pindolol/ ... is distributed into milk. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ A 250 mg overdose /of pindolol/ resulted in coma without hypotension ... No deaths were reported before 1985. The partial agonist activity of pindolol may contribute to the relative safety of this drug in overdose./HUMAN EXPOSURE STUDIES/ Limited information is available on acute pindolol toxicity. In general, overdosage of pindolol may be expected to produce effects that are mainly extensions of pharmacologic effects, including symptomatic bradycardia, hypotension, bronchospasm, and acute cardiac failure. In one hypertensive patient who ingested 500 mg of pindolol, blood pressure increased and heart rate was at least 80 beats/minrecovery was uneventful. In another individual, 250 mg of pindolol was ingested with 150 mg of diazepam and 50 mg of nitrazepam, resulting in coma and hypotensionthe patient recovered in 24 hr. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)PindololvNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015 |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In chronic oral toxicologic studies (1-2 years) in mice, rats, and dogs, Pindolol did not produce any significant toxic effects. In 2-year oral carcinogenicity studies in rats and mice in doses as high as 59 mg/kg/day and 124 mg/kg/day ...Pindolol did not produce any neoplastic, preneoplastic, or nonneoplastic pathologic lesions./LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ In fertility and general reproductive performance studies in rats, Pindolol caused no adverse effects at a dose of 10 mg/kg. In the male fertility and general reproductive performance test in rats, definite toxicity characterized by mortality and decreased weight gain was observed in the group given 100 mg/kg/day. At 30 mg/kg/day, decreased mating was associated with testicular atrophy and/or decreased spermatogenesis ... There appeared to be an increase in prenatal mortality in males given 100 mg/kg but development of offspring was not impaired. If females administered Pindolol prior to mating through day 21 of lactation, mating behavior was decreased at 100 mg/kg and 30 mg/kg. At these dosages there also was increased mortality of offspring. Prenatal mortality was increased at 10 mg/kg but there was not a clear response relationship in this experiment. There was an increased resorption rate at 100 mg/kg observed in females necropsied on the 15th day of gestation. |
| Antidote and Emergency Treatment | Glucagon increases cAMP levels via noncatecholamine mechanisms and can exert potent chronotropic and inotropic effects. This likely explains its use as an antidote in beta-blocker and calcium channel blocker overdose. /Class II drugs: Beta Blockers/Most overdoses are mild and respond to supportive care. Observe mild overdose cases at least 4 hours for the development of signs of poisoning. Hypotension: Multiple intravenous boluses of adrenaline may lead to a rise in blood pressure after dopamine, glucagon, sodium bicarbonate, and calcium have not been successful. Amrinone ... is a positive inotropic agent with intrinsic vasodilator activity that may be as effective as glucagon in reversing depressed myocardial function. /Class II drugs: Beta Blockers/Emergency and supportive measures. 1. Maintain an open airway and assist ventilation if necessary. 2. Treat coma, seizures, hypotension, hyperkalemia, and hypoglycemia if they occur. 3. Treat bradycardia with atropine, ... IVisoproterenol ...or cardiac pacing. 4. Treat bronchospasm with nebulized bronchodilators. 5. Continuously monitor the vital signs and ECG for at least 6 hours after ingestion. /Beta-adrenergic blockers/Specific drugs and antidotes. 1. Bradycardia and hypotension resistant to... /normal/ measures should be treated with glucagon, ... . Epinephrine (intravenous) infusion ... and titrating to effect. 2. Wide complex conduction defects caused by membrane-depressant poisoning may respond to sodium bicarbonate, ... , as given for tricyclic antidepressant overdose. 3. Torsades de pointes polymorphous ventricular tachycardia associated with QT prolongation resulting from sotalol poisoning can be treated with isoproterenol infusion, magnesium, or overdrive pacing. Correction of hypokalemia may also be useful. /Beta-adrenergic blockers/For more Antidote and Emergency Treatment (Complete) data for PINDOLOL (6 total), please visit the HSDB record page. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | 3249 |
| Zollcode | 2933995300 |
| RTECS-Nr. | UB6660000 |
| R-Sätze (R) | 22-36/37/38 |
| Toxizität | LD50 oral in rabbit: 650mg/kg |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | 6.1(b)Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| Gefahrstoffdaten | 13523-86-9(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
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.