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HCID 4171생성일: 2026년 10월 27일

메토프로롤

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

https://huagongshe.com/ko/chemical/4171

메토프로롤 분자 구조식

식별자 및 물리적 특성

CAS No.37350-58-6
분자식C15H25NO3
평균 분자량267.36 g/mol
단동위원소 질량267.18344366 g/mol
SMILESCOCCc1ccc(OCC(O)CNC(C)C)cc1
InChIKeyIUBSYMUCCVWXPE-UHFFFAOYSA-N
PubChem CID4171
ChEMBLCHEMBL13
ChEBICHEBI:6904
EC No.253-483-7
DTXSIDDTXSID2023309
현지명메토프로롤

화학 및 물리적 성질

XLogP1.9
극성 표면적50.7
수소 결합 공여자 수2
수소 결합 수용자 수4
회전 가능 결합 수9
무거운 원자 수19
형식 전하0
복잡도215
물질 분류Pharmaceutical
의약품DrugPharmaceuticalsPharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Antihypertensive drugs
LogP(분배 계수)log Kow = 1.881.65
용해도Soluble (tartrate form)Solubility (mg/ml) @ 25 °C: water >1000methanol >500chloroform 496acetone 1.1acetonitrile 0.89hexane 0.001UV max (water): 223 nm (E 23400) /Tartrate/클로로포름(약간 용해됨), DMSO(약간 용해됨), 메탄올(약간 용해됨)
Human DrugsBreast FeedingLactationMilk, HumanAntihypertensive AgentsAdrenergic Beta-AntagonistsAntiarrhythmicsPharmaceuticalsAntianginal medicines
끓는 점398ºC (estimate)398.6±37.0 °C(Predicted)
Physical DescriptionSolid
Dissociation Constants9.569.7
Collision Cross Section172.1 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID2023309]170.7 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]171.4 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated]172.7 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]163.49 Ų [M+H-H2O]+ [CCS Type: TW172.54 Ų [M+H]+
Other Experimental PropertiesWhite 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/
녹는점35 °C
밀도1.033±0.06 g/cm3(Predicted)
저장 조건-20°C Freezer
pKa(산도 계수)pKa 9.56± 0.01(H2O,t =25,I=0.15(KCl))(Approximate)
물리적 상태고체
색상흰색에서 황백색까지
EPA2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]- (51384-51-1)

안전 및 규제

GHS 분류WarningH315 (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
기타 안전 정보IMAP assessments - 2-Propanol, 1-[4-(2-methoxyethyl)phenoxy]-3-[(1-methylethyl)amino]-: Environment tier I assessment
FDA 요건Metoprolol 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 ReportsBenfield 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 CategoriesSkin Irrit. 2 (66.7%)Flam. Sol. 1 (33.3%)
보관 조건Commercially 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.

용도

역사

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.

용도

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

처리 방법
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.
체내 부담Metoprolol is distributed into milk in a concentration about 3-4 times that of maternal plasma concentrations, but the actual amount distributed into milk appears to be very small.
상호 작용The effect of verapamil coadministration on the hepatic first pass clearance of metoprolol was investigated in dogs. Plasma concentration-time course of metoprolol enantiomers and urinary recovery of oxidative metabolites were determined after a single iv (0.51 mg/kg) and an oral (1.37 mg/kg) dose of deuterium labeled pseudoracemic metoprolol, with or without concomitant administration of racemic verapamil (3 mg/kg). Verapamil inhibited both the systemic and oral clearance of metoprolol by about 50-70%. The first pass effect of metoprolol was completely abolished after coadministration of verapamil, reflecting a marked alteration in the degree of hepatic extraction of metoprolol from intermediate to low. The hepatic clearance of metoprolol was slightly (S)-enantioselective (R/S ratio = 0.89 + or - 0.04) in control dogs. Inhibition of hepatic clearance of metoprolol by verapamil was selective towards (S)-metoprolol, such that the enantioselectivity in hepatic clearance toward (S)-metoprolol disappeared following verapamil coadministration (R/S ratio = 1.01 + or - 0.05). Urinary metabolite profiles indicated that O-demethylation and N-dealkylation were the major pathways of oxidative metabolism in the dog. alpha-Hydroxymetoprolol was a minor metabolite in urine. N-Dealkylation showed a strong preference for (S)-metoprolol, whereas O-demethylation and alpha-hydroxylation exhibited a modest selectivity toward (R)-metoprololhence, the slight (S)-enantioselectivity in the overall hepatic clearance. Comparison of metoprolol metabolite formation clearances in the absence or presence of verapamil coadministration showed that all three oxidative pathways were inhibited by 60-80%. The greater inhibition of hepatic clearance observed with (S)-metoprolol as compared to (R)-metoprolol was attributed to a significant (S)-enantioselective inhibition in the O-demethylation of metoprolol by verapamil.The interaction between metoprolol and bromazepam and lorazepam was studied in 12 healthy male volunteers aged 21-37 years. Metoprolol had no significant effect on the pharmacokinetics of bromazepam or lorazepam. However, bromazepam area under the curve was 35% higher in the presence of metoprolol. Bromazepam enhanced the effect of metoprolol on systolic blood pressure but not on diastolic blood pressure or pulse rate. Lorazepam had no effect on either blood pressure or pulse. Metoprolol did not enhance the effect of bromazepam on the psychomotor tests used in this study. Metoprolol caused a small increase in critical flicker fusion threshold with lorazepam but had no effect on the other tests. Lorazepam (2 mg) was more potent than bromazepam (6 mg) in the doses used in this study. The interaction of metoprolol with bromazepam and lorazepam is unlikely to be of clinical significance. No change in dose is necessary when using these drugs together.In contrast to early work showing inhibition of the absorption of beta adrenergic blocking drugs by antacids, subsequent studies did not confirm a reduction in the bioavailability of either atenolol or propranolol during antacid treatmentindeed, they showed an increase in the plasma concentrations of metoprolol when the drug was coadministered with an antacid.Caffeine and metoprolol have been reported to increase peak salicylic acid concentration following aspirin administration.For more Interactions (Complete) data for METOPROLOL (12 total), please visit the HSDB record page.
HepatotoxicityMetoprolol therapy has been associated with a low rate of mild-to-moderate elevations of serum aminotransferase levels which are usually asymptomatic and transient and resolve even with continuation of therapy. A few instances of clinically apparent, acute liver injury attributable to metoprolol have been reported. In view of its wide scale use, metoprolol induced liver injury is exceedingly rare. The typical liver injury associated with beta-blockers has a latency to onset of 2 to 12 weeks and a hepatocellular pattern of liver enzyme. Symptoms of hypersensitivity (rash, fever, eosinophilia) and autoantibody formation have not been reported. Reported cases due to metoprolol have included cases of acute liver failure, but ultimately all were self-limiting and resolved fairly rapidly once once drug was stopped.
환경 거동TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 62(SRC), determined from a structure estimation method(2), indicates that metoprolol is expected to have high mobility in soil(SRC). Volatilization of metoprolol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-11 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Metoprolol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.9X10-7 mm Hg(SRC), determined from a fragment constant method(4).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 62.24(SRC), determined from a structure estimation method(2), indicates that metoprolol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). An estimated pKa of metoprolol is 9.6(9), indicating that this compound will primarily exist in cation form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(5). According to a classification scheme(6), an estimated BCF of 1.252(SRC), from its log Kow of 1.88(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), metoprolol, which has an estimated vapor pressure of 2.9X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase metoprolol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 0.22 days(SRC), calculated from its rate constant of 1.58X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
유해 작용Common Adverse Events
Milk ConcentrationsMetoprolol is distributed into milk in a concentration about 3-4 times that of maternal plasma concentrations, but the actual amount distributed into milk appears to be very small.
독성 요약Signs and Symptoms of Metoprolol Overdose
Effluent ConcentrationsEffluent from sewage treatment plants (n=29) in Germany 1996-1998 contained metoprolol concentrations of 0.73 ug/l (median), 1.3 ug/l (90th percentile) and 2.2 ug/l (maximum)(1). Removal efficiency for metoprolol from sewage treatment plants was 83%(1). Metoprolol concentrations in sewage effluent in Germany were reported ranging from <0.025 to 2.20 ug/l (2). Mean concentration and loads of metoprolol in the effluent of a municipal sewage treatment plant close to Frankfurt/Main, June 24-30, 1996 were 7.2 ug/l (mean concn influent), 2.08 ug/l (mean concn effluent), 374 g/day (load influent), 108 g/day (load effluent)(3). The percent removal for metoprolol was 67% and the mean flow rate for the plant was 63,190 cu m/day(3).
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc for metoprolol can be estimated to be 62(SRC). According to a classification scheme(2), this estimated Koc value suggests that metoprolol is expected to have high mobility in soil. An estimated pKa of metoprolol is 9.6(3), indicating that this compound will primarily exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts(4).
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ A fatality involving a 26-year-old male who intentionally ingested approximately 10 g of metoprolol is presented. Autopsy findings revealed foreign material in the gastric content with an acute thrombosis of the left anterior descending coronary artery. Microscopic studies showed evidence of an extremely early infarct. Metoprolol concentrations in the blood, liver, gastric content, and urine are reported by both capillary gas chromatography and ultraviolet spectrophotometric analysis./SIGNS AND SYMPTOMS/ Acute beta blocker poisoning is characterized by depression of cardiac conduction and contractility, respiratory depression, coma, seizures, and in some patients, hypoglycemia. Symptoms occur within 1-2 hr of ingestion. /Class II Drugs: Beta-Blockers/
Artificial Pollution SourcesMetoprolol's production and use as an antihypertensive, antianginal, and antiarrhythmic drug(1) may result in its release to the environment through various waste streams(SRC).
Drug Induced Liver InjuryBenchmark Dataset for the Liver Toxicity Knowledge Base (LTKB)metoprololLopressor®Beta blockers5less-DILI-concern drugs
신호 어Warning
유해·위험 문구암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H315