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Desloratadine

HCID 178786289
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Grundinformationen

CAS
1795024-82-6
Standard-SMILES
Clc1ccc2c(c1)CCc1cccnc1C2=C1CCNCC1
InChIKey
JAUOIFJMECXRGI-UHFFFAOYSA-N
Summenformel
C19H19ClN2
Durchschnittliche Molmasse
310,8 g/mol

Überblick

Desloratadine is loratadine in which the ethoxycarbonyl group attached to the piperidine ring is replaced by hydrogen. The major metabolite of loratidine, desloratadine is an antihistamine which is used for the symptomatic relief of allergic conditions including rhinitis and chronic urticaria. It does not readily enter the central nervous system, so does not cause drowsiness. It has a role as a H1-receptor antagonist, a cholinergic antagonist, a drug metabolite and an anti-allergic agent.

Namen und Bezeichner

Bevorzugter Name
Desloratadine
IUPAC
13-chloro-2-piperidin-4-ylidene-4-azatricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaene
Englischer Name
Desloratadine-d7 (Major)
Summenformel
C19H19ClN2
Molmasse
310.82056

Namen und Synonyme

Desloratadine100643-71-8ClarinexAeriusDescarboethoxyloratadineDesloratidineNeoclaritynAzomyrSch-34117DenosinOpulisAllex
Weitere Namen anzeigen
Allex-d7Aerius-d7AzoMyr-d7Opulis-d7Clarinex-d7Sch 34117-d7NSC 675447-d7Neoclarityn-d7Desloratadine-d7Desloratadine-d7 (Major)
Sch 341178-Chloro-11-piperidin-4-ylidene-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridineDesloratadine ActavisDasselta8-chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridineDesloratadine tevaDesloratadina5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 8-chloro-6,11-dihydro-11-(4-piperidinylidene)-

Datenbank-Bezeichner

CAS
1795024-82-6
ChEMBL
CHEMBL1172
ChEBI
CHEBI:291342

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

XLogP
4,5
Polarare Oberfläche (TPSA)
24,9 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
2
Frei drehbare Bindungen
0
Schwere Atome
22
Formalladung
0
Komplexität
425

Experimentelle und physikochemische Eigenschaften

Drugs · 2 Einträge

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals

LogP · 2 Einträge

3.2

2.56

Solubility · 2 Einträge

3.95e-03 g/L

21.6 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 6 Einträge

Breast Feeding; Lactation; Milk, Human; Antihistamines; Antipruritics; Nonsedating Antihistamines

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Physical DescriptionSolid
Collision Cross Section175.5 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

Physikochemische Eigenschaften

Schmelzpunkt

Sicherheit und Regulatorisches

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GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H302 (90%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P354+P338, P317, P318, P321, P330, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 140 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (90%)

Toxikologische Informationen

Toxicity Summary · 1 Eintrag

Like other H1-blockers, Desloratadine competes with free histamine for binding at H<sub>1</sub>-receptors in the GI tract, uterus, large blood vessels, and bronchial smooth muscle. 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.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Desloratadine

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

R06AX27

R - Respiratory system

QR - Respiratory system

Protein BindingDesloratadine is bound approximately 82 to 87% to plasma proteins, while its active metabolite, 3-hydroxydesloratadine, is bound approximately 85 to 89%.
Pharmacodynamics · 1 Eintrag

Desloratadine is a long-acting second-generation H<sub>1</sub>-receptor antagonist which has a selective and peripheral H1-antagonist action. Histamine is a chemical that causes many of the signs that are part of allergic reactions, such as the swelling of tissues. Histamine is released from histamine-storing cells (mast cells) and attaches to other cells that have receptors for histamine. The attachment of the histamine to the receptors causes the cell to be "activated," releasing other chemicals which produce the effects that we associate with allergies. Desloratadine blocks one type of receptor for histamine (the H1 receptor) and thus prevents activation of cells by histamine. Unlike most other antihistamines, Desloratadine does not enter the brain from the blood and, therefore, does not cause drowsiness.

Mechanism of Action · 1 Eintrag

Like other H1-blockers, Desloratadine competes with free histamine for binding at H<sub>1</sub>-receptors in the GI tract, uterus, large blood vessels, and bronchial smooth muscle. 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.

Biological Half-LifeDesloratadine has a mean plasma elimination half-life of approximately 27 hours.
Metabolism/Metabolites · 3 Einträge

Desloratadine is metabolized to the active metabolite 3-hydroxydesloratadine, which is subsequently glucuronidated.

Desloratadine is a known human metabolite of loratadine and Rupatadine.

Route of Elimination: Desloratadine (a major metabolite of loratadine) is extensively metabolized to 3-hydroxydesloratadine, an active metabolite, which is subsequently glucuronidated. Approximately 87% of a 14C-desloratadine dose was equally recovered in urine and feces. Half Life: 50 hours

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UNII
FVF865388R
EC Number
638-878-8
Nikkaji
J574.133E
147 · 147-151°C
storage temp.
-20 °C · -20°C Freezer
Löslichkeit
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
Aggregatzustand
Solid
Farbe
White to Pale Beige
FDA Pharmacological Classification · 6 Einträge

FVF865388R

DESLORATADINE

Mechanisms of Action [MoA] - Histamine H1 Receptor Antagonists

Established Pharmacologic Class [EPC] - Histamine-1 Receptor Antagonist

Desloratadine is a Histamine-1 Receptor Antagonist. The mechanism of action of desloratadine is as a Histamine H1 Receptor Antagonist.

DESLORATADINE

MeSH Pharmacological Classification · 2 Einträge

Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists.

A class of non-sedating drugs that bind to but do not activate histamine receptors (DRUG INVERSE AGONISM), thereby blocking the actions of histamine or histamine agonists. These antihistamines represent a heterogenous group of compounds with differing chemical structures, adverse effects, distribution, and metabolism. Compared to the early (first generation) antihistamines, these non-sedating antihistamines have greater receptor specificity, lower penetration of BLOOD-BRAIN BARRIER, and are less likely to cause drowsiness or psychomotor impairment.

Absorption, Distribution and Excretion · 2 Einträge

Desloratadine administered orally for ten days to healthy volunteers as a 5 mg tablet once daily resulted in a mean Tmax of approximately 3 hours, a mean steady-state Cmax of 4 ng/ml, and a mean steady-state AUC of 56.9 ng\*hr/ml. A similar profile was observed using 10 ml of an oral solution containing 5 mg of desloratadine. Food was found not to affect desloratadine absorption.

Approximately 87% of a <sup>14</sup>C-desloratadine dose was equally recovered in urine and feces as metabolic products.

Tissue LocationsKidney
Cellular LocationsCytoplasm
Metabolite PathwaysDesloratadine H1-Antihistamine Action

Verwendung und Herstellung

Uses · 2 Einträge

Use (kg; approx.) in Germany (2009): >100

For the relief of symptoms of seasonal allergic rhinitis, perennial (non-seasonal) allergic rhinitis. Desloratidine is also used for the sympomatic treatment of pruritus and urticaria (hives) associated with chronic idiopathic urticaria.