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HCID 5152Erstellt: 4. November 2026

Salmeterol

CS-380 · SN408D · gr33343x · GR 33343 · SAMETEROL · Astmerole · SALMETEROL · BNKY006-SX05

https://huagongshe.com/de/chemical/5152

Molekülstruktur von Salmeterol

Identifikatoren & physikalische Daten

CAS No.89365-50-4
SummenformelC25H37NO4
Durchschnittliche Molmasse415,6 g/mol
Monoisotopische Masse415,27225866 g/mol
SMILESOCc1cc(C(O)CNCCCCCCOCCCCc2ccccc2)ccc1O
InChIKeyGIIZNNXWQWCKIB-UHFFFAOYSA-N
PubChem CID5152
ChEMBLCHEMBL1263
ChEBICHEBI:64064
EC No.618-267-2
DTXSIDDTXSID6023571

Chemische & physikalische Eigenschaften

XLogP3,9
Polarare Oberfläche (TPSA)82
H-Brücken-Donoren4
H-Brücken-Akzeptoren5
Frei drehbare Bindungen16
Schwere Atome30
Formalladung0
Komplexität403
ArzneimittelPharmaceuticals
LogP (Verteilungskoeffizient)log Kow = 4.15 /Estimated/4.2
LöslichkeitSparingly soluble2.26e-03 g/LChloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
Human DrugsBreast FeedingLactationMilk, HumanAnti-Asthmatic AgentsBronchodilator AgentsBeta Adrenergic AgonistsPharmaceuticals
Schmelzpunkt75.5-76.5 °C75.7-76.5 °C75.5 - 76.5 °C75.5-76.5°
Dampfdruck1.9X10-15 mm Hg at 25 °C /Estimated/
Henry-KonstanteHenry's Law constant = 2.5X10-17 atm-cu m/mol at 25 °C /Estimated/
Physical DescriptionSolid
Stability/Shelf LifeSalmeterol xinafoate oral inhalation aerosol or oral inhalation powder (Serevent Diskus) is stable for 2 years or 18 months, respectively, from the date of manufacture.
Dissociation ConstantspKa = 11.2 /Estimated/
Other Experimental PropertiesHydroxyl radical reaction rate constant = 1.8X10-10 cu cm/molec sec at 25 °C /Estimated/White to off white. MW: 603.8. Soluble in methanol, slightly soluble in ethanol, chloroform and isopropanolsparingly soluble in water /Xinafoate salt/
Siedepunkt603.0±55.0 °C(Predicted)
Dichte1.112±0.06 g/cm3(Predicted)
Lagerbedingungen2-8°C
pKa (Säurekonstante)9.99±0.31(Predicted)
AggregatzustandSolid
FarbeWhite to Off-White
InChIInChI=1S/C25H37NO4/c27-20-23-18-22(13-14-24(23)28)25(29)19-26-15-7-1-2-8-16-30-17-9-6-12-21-10-4-3-5-11-21/h3-5,10-11,13-14,18,25-29H,1-2,6-9,12,15-17,19-20H2
InChIKeyGIIZNNXWQWCKIB-UHFFFAOYSA-N
SMILESC(C1C=CC(O)=C(CO)C=1)(O)CNCCCCCCOCCCCC1C=CC=CC=1
CAS Datenbank89365-50-4(CAS DataBase Reference)

Sicherheit & Vorschriften

GHS-EinstufungWarningH302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Regulatorische Informationen1,3-Benzenedimethanol, 4-hydroxy-.alpha.1-6-(4-phenylbutoxy)hexylaminomethyl-: Does not have an individual approval but may be used under an appropriate group standard
FDA-AnforderungenThe Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl salmeterol xinafoate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Salmeterol Xinafoate/
Hazard Classes and CategoriesAcute Tox. 4 (50%)
LagerbedingungenThe commercially available inhalation powder and inhalation device (Serevent Diskus) should be stored at room temperature (20-25 °C) in a dry place away from direct heat and sunlight.Commercially available metered-dose salmeterol xinafoate inhalers should be stored at 2-30 °C with the nozzle end downfreezing should be avoided. /Salmeterol xinafoate/
EntsorgungsverfahrenSRP: 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.
WechselwirkungenSalmeterol should be administered with extreme caution to patients being treated with monoamine oxidase inhibitors or tricyclic antidepressants, or within 2 weeks of discontinuation of such agents, because the action of salmeterol on the vascular system may be potentiated by these agents.

Anwendungen & Verwendung

Verwenden

Salmeterol is a β2-Adrenergic agonist used for relief and control of asthma symptoms.

In clinical studies, inhaled corticosteroids and/or inhaled cromolyn sodium did not alter the safety profile of salmeterol oral inhalation when these drugs were administered concurrently.
The systemic pharmacodynamic effects of inhaled salmeterol were not affected by the co-administration of fluticasone propionate.
UmweltverhaltenTERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 7,800(SRC), determined from a structure estimation method(2), indicates that salmeterol is expected to be immobile in soil(SRC). The estimated pKa of salmeterol is 11.2(3), indicating that this compound will primarily exist as a cation in the environment. Cations adsorb strongly to organic carbon and clay and do not volatilize from moist soil surfaces (SRC). Salmeterol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.9X10-15 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 7,800(SRC), determined from a structure estimation method(2), indicates that salmeterol is expected to adsorb to suspended solids and sediment(SRC). The estimated pKa of salmeterol is 11.2(3), indicating that this compound will primarily exist as a cation in the environment. Cations adsorb strongly to suspended solids and sediment and do not volatilize from the soil(4). According to a classification scheme(5), an estimated BCF of 7.0(SRC), from an estimated log Kow of 4.2(6) and a regression derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), salmeterol, which has an estimated vapor pressure of 1.9X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase salmeterol may be removed from the air by wet and dry deposition(SRC). Salmeterol does not contain chromophores that absorb light at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Unerwünschte WirkungenThe most common adverse reactions of salmeterol (incidence ≥3%) in asthmatics include upper respiratory infection or inflammation, oral candidiasis, pharyngitis, bronchitis, dysphonia, headaches, cough, nausea, and vomiting. In patients with chronic obstructive pulmonary disease, the most common adverse effects include pneumonia, throat irritation, viral respiratory infections, oral candidiasis, dysphonia, headaches, and musculoskeletal pains.
ExpositionspfadeBecause of the small therapeutic dose, systemic levels of salmeterol are low or undetectable after inhalation of recommended doses.
ToxizitätsübersichtThere are reports of sympathomimetic syndrome with hyperlactatemia and metabolic acidosis after the intentional inhalation of salmeterol in a suicide attempt. Patients who overdose commonly present with heart palpitation, chest pain, hypophosphatemia, hypokalemia, lactic acidosis, ST-segment depression, and sinus tachycardia. Patients may also present with angina, hypotension, hypertension, dizziness, nausea, fatigue, malaise, insomnia, and muscle cramps. Overdose with salmeterol can lead to prolongation of the QT interval resulting in ventricular arrhythmias.Salmeterol's long, lipophilic side chain binds to exosites near beta(2)-receptors in the lungs and on bronchiolar smooth muscle, allowing the active portion of the molecule to remain at the receptor site, continually binding and releasing. Beta(2)-receptor stimulation in the lung causes relaxation of bronchial smooth muscle, bronchodilation, and increased bronchial airflow.
Signs and SymptomsSymptoms of overdose include angina (chest pain), dizziness, dry mouth, fatigue, flu-like symptoms, headache, heart irregularities, high or low blood pressure, high blood sugar, insomnia, muscle cramps, nausea, nervousness, rapid heartbeat, seizures, and tremor.
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc for salmeterol can be estimated to be 7,800(SRC). According to a classification scheme(2), this estimated Koc value suggests that salmeterol is expected to be immobile in soil. The estimated pKa of salmeterol is 11.2(3), indicating that this compound will primarily exist in cation form in the environment and cations generally adsorb more strongly to organic carbon and clay than their neutral counterparts(4).
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Data from a large placebo-controlled safety study that was stopped early suggest that salmeterol may be associated with rare serious asthma episodes or asthma-related deaths.Data from this study, called the Salmeterol Multi-center Asthma Research Trial (SMART), further suggest that the risk might be greater in African American patients. These results led to stopping the study prematurely. The data from the SMART study are not adequate to determine whether concurrent use of inhaled corticosteroids provides protection from this risk. Given the similar basic mechanisms of action of beta2-agonists, it is possible that the findings seen in the SMART study may be consistent with a class effect. Findings similar to the SMART study findings were reported in a prior 16-week clinical study performed in the United Kingdom, the Salmeterol Nationwide Surveillance (SNS) study. In the SNS study, the incidence of asthma-related death was numerically, though not statistically, greater in patients with asthma treated with salmeterol (42 ug twice daily) versus albuterol (180 ug 4 times daily) added to usual asthma therapy./SIGNS AND SYMPTOMS/ The expected signs and symptoms with overdosage are those of excessive beta-adrenergic stimulation and/or occurrence or exaggeration of any of the adverse reactions ... e.g., seizures, angina, hypertension or hypotension, tachycardia with rates up to 200 beats/min, arrhythmias, nervousness, headache, tremor, muscle cramps, dry mouth, palpitation, nausea, dizziness, fatigue, malaise, and insomnia. ... Overdosage with salmeterol can lead to clinically significant prolongation of the QTc interval, which can produce ventricular arrhythmias. Other signs of overdosage may include hypokalemia and hyperglycemia.
Artificial Pollution SourcesSalmeterol's production and use as a bronchodilator(1) may result in its release to the environment through various waste streams(SRC).
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)SalmeterolDILI NegativeOralRespiratory (inhalation)DOI:10.1016/j.drudis.2019.09.022
Environmental BioconcentrationAn estimated BCF of 7.0 was calculated for salmeterol(SRC), using an estimated log Kow of 4.2(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
RTECS-Nr.CZ6457000
Gefahrstoffdaten89365-50-4(Hazardous Substances Data)