StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project：[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
Zurück
HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HCID 3957Erstellt: 4. November 2026

Loratadine

LORATIDINE · CLARITIN · Ethyl 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate · 1-Piperidinecarboxylic acid · 4-(8-chloro-5,6-dihydro-11h-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic acid ethyl ester · Loranox · CLARATYNE · Loratadine Powder

https://huagongshe.com/de/chemical/3957

Molekülstruktur von Loratadine

Identifikatoren & physikalische Daten

CAS No.79794-75-5
SummenformelC22H23ClN2O2
Durchschnittliche Molmasse382,9 g/mol
Monoisotopische Masse382,1448057 g/mol
SMILESCCOC(=O)N1CCC(=C2c3ccc(Cl)cc3CCc3cccnc32)CC1
InChIKeyJCCNYMKQOSZNPW-UHFFFAOYSA-N
PubChem CID3957
ChEMBLCHEMBL998
ChEBICHEBI:6538
EC No.616-734-5
DTXSIDDTXSID2023224

Chemische & physikalische Eigenschaften

XLogP5,2
Polarare Oberfläche (TPSA)42,4
H-Brücken-Donoren0
H-Brücken-Akzeptoren3
Frei drehbare Bindungen2
Schwere Atome27
Formalladung0
Komplexität569
StoffklassenPharmaceutical
ArzneimittelPharmaceuticalsPharmaceuticals -> Listed in ZINC15
LogP (Verteilungskoeffizient)Log P= 5.20 at pH 7.44.4
Color/FormCrystals from acetonitrile
Löslichkeit<1 mg/ml at 25°CDMSO: 26 mg/mL, solubleIt is soluble in DMSO (50 mg/ml), ethanol (77 mg/ml at 25°C), water (<1 mg/ml at 25°C), chloroform, and methanol.
Human DrugsBreast FeedingLactationMilk, HumanAntihistaminesAntipruriticsNonsedating AntihistaminesFDA approved drugs -> Active ingredientPharmaceuticalsAntiallergics and medicines used in anaphylaxis
Schmelzpunkt134-136 °C134 - 136 °C134-136°C
Physical DescriptionSolid
Collision Cross Section187.4 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID2023224]185.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]187.4 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)]192.04 Ų [M]+ [CCS Type: TW
Siedepunkt531.3±50.0 °C(Predicted)
Dichte1.261±0.06 g/cm3(Predicted)
Lagerbedingungen2-8°C
Aggregatzustandpowder
pKa (Säurekonstante)4.27±0.20(Predicted)
Farbewhite
Merck14,5578
BCS Class2
StabilitätStable, but may be heat sensitive - refrigerate. Incompatible with strong oxidizing agents.
InChI1S/C22H23ClN2O2/c1-2-27-22(26)25-12-9-15(10-13-25)20-19-8-7-18(23)14-17(19)6-5-16-4-3-11-24-21(16)20/h3-4,7-8,11,14H,2,5-6,9-10,12-13H2,1H3
InChIKeyJCCNYMKQOSZNPW-UHFFFAOYSA-N
SMILESCCOC(=O)N1CC\C(CC1)=C2/c3ccc(Cl)cc3CCc4cccnc24
CAS Datenbank79794-75-5(CAS DataBase Reference)
EPA chemische Informationen1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-, ethyl ester (79794-75-5)

Sicherheit & Vorschriften

GHS-EinstufungThis chemical does not meet GHS hazard criteria for 0.9% (1 of 111) of reports.WarningH315 (48.6%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 111 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.This chemical does not meet GHS hazard criteria for 2.3% (2 of 86) of reports.
Regulatorische InformationenREACH registered substance: 1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo(5,6)cyclohepta(1,2-b)pyridin-11-ylidene)-, ethyl ester (EC: 935-907-9)1-Piperidinecarboxylic acid, 4-(8-chloro-5,6-dihydro-11H-benzo5,6cyclohepta1,2-bpyridin-11-ylidene)-, ethyl ester: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
FDA-AnforderungenManufacturers, 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 ReportsRosa FReprod Toxicol 9 (6): 583 (1995). New medical entities widely used in fertile women: post marketing surveillance priorities.Bergman HDSouth Pharm J 86: 17-21 (1994). Major new drugs: review of 1993. The pharmacology, pharmacokinetics, uses, efficacy and adverse effects of /new drug products are reviewed/.Haria M, et alDrugs 48: 617-37 (1994). Loratadine: reapprasial of its pharmacological properties and therapeutic use in allergic disorders.Corey JPOtolaryngol Head Neck Surg 109 (3 pt 2): 584-92 (1993). Advances in the pharmacotherapy of allergic rhinitis: second generation H1 receptor antagonists.For more Special Reports (Complete) data for LORATADINE (7 total), please visit the HSDB record page.

Anwendungen & Verwendung

Beschreibung

Loratadine is a non-sedating antihistamine indicated for use in allergic rhinitis and chronic urticaria. Its major advantage over other non-sedating antihistamines such as astemizole and terfenadine is its very fast onset of action. Loratadine is claimed not to cross the blood-brain barrier.

Verwenden

Loratadine, is used as a peripheral histamine H1 receptor agonist. It is also used as an orally active antiallergic agent. It is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and Dyestuff.

Hazard Classes and CategoriesSkin Irrit. 2 (66.3%)Skin Irrit. 2 (48.6%)
LagerbedingungenProtect Unit-of-Use packaging and Unit Dose-Hospital Pack from excessive moisture. Store between 2 deg and 30 °C (36 deg and 86 °F).
EntsorgungsverfahrenSRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
TreatmentTreatment of overdosage would reasonably consist of emesis (ipecac syrup), except in patients with impaired consciousness, followed by the administration of activated charcoal to absorb any remaining drug. If vomiting is unsuccessful, or contraindicated, gastric lavage should be performed with normal saline. Saline cathartics may also be of value for rapid dilution of bowel contents. Loratadine is not eliminated by hemodialysis. It is not known if loratadine is eliminated by peritoneal dialysis. (L1712)
WechselwirkungenConcurrent use may potentiate the CNS depressant effects of either these medications /alcohol or other CNS depression-producing medications/ or antihistaminesalso, concurrent use of maprotiline or tricyclic antidepressants may potentiate the anticholinergic effects of either antihistamines or these medications. /Antihistamines/Anticholinergic effects may be potentiated when these medications /anticholinergics or other medications with anticholinergic activity/ are used concurrently with antihistaminespatients should be advised to report occurrence of gastrointestinal problems promptly since paralytic ileus may occur with concurrent therapy. /Antihistamines/Concurrent use of monoamine oxidase (MAO) inhibitors with antihistamines may prolong the intensify the anticholinergic and CNS depressant effects of antihistaminesconcurrent use is not recommended. /Antihistamines/Concurrent use /of ototoxic medications/ with antihistamines may mask the symptoms of ototoxicity such as tinnitus, dizziness, or vertigo. /Antihistamines/For more Interactions (Complete) data for LORATADINE (6 total), please visit the HSDB record page.
Gesundheitliche AuswirkungenLoratadine causes sedation and psychomotor impairment.
Unerwünschte WirkungenAlthough loratadine is a relatively safe and effective medication for treating allergic rhinitis, its primary adverse effects include headaches, dizziness, and gastrointestinal distress (diarrhea, abdominal pain, nausea, and vomiting). Loratadine may also cause sedation (a rare adverse effect), mydriasis, and xerostomia. These effects are primarily due to the drug's anticholinergic propertiesanticholinergic adverse effects are minimal at therapeutic dosage. In a patient undergoing long-term loratadine treatment, a rare case of bilateral cystoid macular edema has been described, which resolved after discontinuation of loratadine. The potential pathophysiology remains unclear. It may involve dysfunction of H1-receptor–expressing retinal neurons and associated signal transduction, toxicity affecting Müller cells or retinal pigment epithelium cells, and intracellular fluid accumulation.
ExpositionspfadeRapidly absorbed following oral administration (40% bioavailability)
ToxizitätsübersichtSigns and Symptoms of OverdoseLoratadine competes with free histamine and exhibits specific, selective peripheral H<sub>1</sub> antagonistic activity. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms (eg. nasal congestion, watery eyes) brought on by histamine. Loratadine has low affinity for cholinergic receptors and does not exhibit any appreciable alpha-adrenergic blocking activity in-vitro. Loratadine also appears to suppress the release of histamine and leukotrienes from animal mast cells, and the release of leukotrienes from human lung fragments, although the clinical importance of this is unknown.
Signs and SymptomsSomnolence, tachycardia, and headache. Psychomotor impairment, and antimuscarinic effects such as urinary retention, dry mouth, blurred vision, and gastrointestinal disturbances are the most common side effects.
Ongoing Test StatusThe following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=79794-75-5]
Human Toxicity ExcerptsSomnolence, tachycardia, and headache have been reported with overdoses greater than 10 mg (40 to 180 mg).The second generation H1 antagonists (eg, terfenadine, astemizole, loratadine) have no effect on muscarinic receptors.
Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)LoratadinevNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015
Non-Human Toxicity ExcerptsIn mutagenicity studies, there was no evidence of mutagenic potential in reverse (Ames) or forward point mutation (CHO-HGPRT) assays, or in the assay for DNA damage (rat Primary Hepatocyte Unscheduled DNA Assay) or in two assays for chromosomal aberrations (Human Peripheral Blood Lymphocyte Clastogenesis Assay and the Mouse Bone Marrow Erythrocyte Micronucleus Assay). In the Mouse Lymphoma Assay, a positive finding occurred in the nonactivated but not the activated phase of the study.In an 18 month oncogenicity study in mice and a 2 year study in rats, loratadine was administered in the diet at doses up to 40 mg/kg (mice) and 25 mg/kg (rats). In the carcinogenicity studies, pharmacokinetic assessments were carried out to determine animal exposure to the drug. AUC data demonstrated that the exposure of mice given 40 mg/kg of loratadine was 3.6 (loratadine) and 18 (active metabolite) times higher than a human given 10 mg/kg. Exposure of rats given 25 mg/kg of loratadine was 28 (loratadine) and 67 (active metabolite) times higher than a human given 10 mg/day. Male mice given 40 mg/kg had a significantly higher incidence of hepatocellular tumors (combined adenomas and carcinomas) than concurrent controls. In rats, a significantly higher incidence of hepatocellular tumors (combined adenomas and carcinomas) was observed in males given 10 mg/kg and males and females given 25 mg/kg. The clinical significant of these findings during long-term use of Claritin tablets is not known. /Claritin/Loratadine administration produced hepatic microsomal enzyme induction in the mouse at 40 mg/kg and rat at 25 mg/kg, but not at lower doses.There was no evidence of animal teratogenicity in studies performed in rats and rabbits at oral doses up to 96 mg/kg (75 times and 150 times, respectively, the recommended daily human dose on a mg/sq m basis).Decreased fertility in male rats, shown by lower female conception rates, occurred at approximately 64 mg/kg and was reversible with cessation of dosing. Loratadine had no effect on male or female fertility or reproduction in the rat at doses of approximately 24 mg/kg.
Wassergefährdungsklasse (WGK)2
UN-Transportnummer3077
Zollcode29333990
R-Sätze (R)36/37/38
GefahrensymboleXi
Sicherheitshinweise (S)22-24/25-36-26
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten79794-75-5(Hazardous Substances Data)