1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol

d-Metoprolol · l-Metoprolol · rac Metoprolol · C07202 · Loresor · Preblok · Spesicor · Beatrolol

Identifikatoren & physikalische Daten

CAS No.	37350-58-6
Summenformel	C15H25NO3
Durchschnittliche Molmasse	267,36 g/mol
Monoisotopische Masse	267,18344366 g/mol
SMILES	COCCc1ccc(OCC(O)CNC(C)C)cc1
InChIKey	IUBSYMUCCVWXPE-UHFFFAOYSA-N
PubChem CID	4171
ChEMBL	CHEMBL13
ChEBI	CHEBI:6904
EC No.	253-483-7
DTXSID	DTXSID2023309
Lokaler Name	1-(Isopropylamino)-3-[4-(2-methoxyethyl)phenoxy]propan-2-ol

Chemische & physikalische Eigenschaften

XLogP	1,9
Polarare Oberfläche (TPSA)	50,7
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	4
Frei drehbare Bindungen	9
Schwere Atome	19
Formalladung	0
Komplexität	215
Stoffklassen	Pharmaceutical
Arzneimittel	DrugPharmaceuticalsPharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Antihypertensive drugs
LogP (Verteilungskoeffizient)	log Kow = 1.881.65
Löslichkeit	Soluble (tartrate form)Solubility (mg/ml) @ 25 °C: water >1000methanol >500chloroform 496acetone 1.1acetonitrile 0.89hexane 0.001UV max (water): 223 nm (E 23400) /Tartrate/Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
Human Drugs	Breast FeedingLactationMilk, HumanAntihypertensive AgentsAdrenergic Beta-AntagonistsAntiarrhythmicsPharmaceuticalsAntianginal medicines
Siedepunkt	398ºC (estimate)398.6±37.0 °C(Predicted)
Physical Description	Solid
Dissociation Constants	9.569.7
Collision Cross Section	172.1 Å² [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID2023309]170.7 Å² [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]171.4 Å² [M+H]+ [CCS Type: DTMethod: single field calibrated]172.7 Å² [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]163.49 Å² [M+H-H2O]+ [CCS Type: TW172.54 Å² [M+H]+
Other Experimental Properties	White crystalline powderfreely soluble in watersoluble in methanolsparingly soluble in ethanolslightly soluble in dichloromethane and 2-propanolpractically insoluble in ethyl acetate, acetone, diethylether and heptane /Metoprolol succinate/White crystalline powder /Metoprolol tartrate/Bitter tastepKa = 9.68very sol in water and freely sol in alc. /Metoprolol tartrate/
Schmelzpunkt	35 °C
Dichte	1.033±0.06 g/cm3(Predicted)
Lagerbedingungen	-20°C Freezer
pKa (Säurekonstante)	pKa 9.56± 0.01(H2O,t =25,I=0.15(KCl))(Approximate)
Aggregatzustand	Solid
Farbe	White to Off-White
CAS Datenbank	51384-51-1
EPA chemische Informationen	2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]- (51384-51-1)

Sicherheit & Vorschriften

GHS-Einstufung	WarningH315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.Danger
Weitere Sicherheitsinformationen	IMAP assessments - 2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-: Environment tier I assessment
FDA-Anforderungen	Metoprolol tartrate, used as a beta adrenergic blocking agent, was approved by FDA for marketing in the United States 12/84.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed drug products, incl metaprolol, metoprolol tartrate, and metoprolol succinate approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /Metaprolol, metoprolol tartrate, and metoprolol succinate/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).
Special Reports	Benfield P et alMetoprolol. An Updated Review of its Pharmacodynamic and Pharmacokinetic Properties, and Therapeutic Efficacy, in Hypertension, Ischaemic Heart Disease and Related Cardiovascular DisordersDrugs 31 (5): 376-429 (1986).
Hazard Classes and Categories	Skin Irrit. 2 (66.7%)Flam. Sol. 1 (33.3%)
Lagerbedingungen	Commercially available preparations of metoprolol tartrate should be protected from light. Metoprolol tartrate tablets should be stored in tight, light-resistant containers at 15-30 °C and metoprolol tartrate injection should be stored at a temperature of 30 °C or less, preferably at 15-30 °C, freezing of the injection should be avoided.

Anwendungen & Verwendung

History

Metoprolol was first made in 1969, patented in 1970, and approved for medical use in 1978. Metoprolol was discovered by Astra Pharmaceuticals. It is a cardioselective beta-adrenoceptor antagonist. It has a higher affinity for beta-1 receptors than for the beta-2 receptor subtype. Receptor-subtype selectivity is diminished at higher doses. Treatment of hypertension is the only indication for metoprolol presently sanctioned by the Food and Drug Administration.

Verwenden

rac Metoprolol is a β1 selective aryloxypropanolamine andrenergic antagonist. Used in the treatment of a variety of cardiovascular disorder.