Desloratadine

ChemicalBook > CAS DataBase List > Desloratadine

Product Name: Desloratadine
CAS No.: 100643-71-8
Chemical Name: Desloratadine
Synonyms: DESLORATIDINE;Clarinex;Desloratadine Citrate Disodium;descarboethoxyloratadine;Loratadine Related Compound A (15 mg) (8-chloro-6,11-dihydro-11(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b] pyridine);DesL;Allex;AzoMyr;Opulis;Aerius
CBNumber: CB3462564
Molecular Formula: C19H19ClN2
Formula Weight: 310.82
MOL File: 100643-71-8.mol

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Desloratadine Property

Melting point:: 150-151°C
Boiling point:: 467.9±45.0 °C(Predicted)
Density: 1?+-.0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: DMSO: >10mg/mL
pka: 10.27±0.20(Predicted)
form: powder
color: White to Light orange to Yellow
Merck: 14,2922
BCS Class: 1
InChIKey: JAUOIFJMECXRGI-UHFFFAOYSA-N
CAS DataBase Reference: 100643-71-8(CAS DataBase Reference)

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Safety

WGK Germany: 3
RTECS: DE8011000
HS Code: 2933399090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

H361Suspected of damaging fertility or the unborn child

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P310Immediately call a POISON CENTER or doctor/physician.

P330Rinse mouth.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 1370280
Product name: Loratadine Related Compound A
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 15mg
Price: $1380
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1173042
Product name: Desloratadine
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $436
Updated: 2024/03/01

TCI Chemical

Product number: D3787
Product name: Desloratadine
Purity: >98.0%(HPLC)(T)
Packaging: 100mg
Price: $34
Updated: 2024/03/01

TCI Chemical

Product number: D3787
Product name: Desloratadine
Purity: >98.0%(HPLC)(T)
Packaging: 1g
Price: $200
Updated: 2024/03/01

Cayman Chemical

Product number: 16931
Product name: Desloratadine
Purity: ≥98%
Packaging: 50mg
Price: $49
Updated: 2024/03/01

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Desloratadine Chemical Properties,Usage,Production

Description

Desloratadine is a second generation of tricyclic antihistamine. It is a H1-receptor antagonist which has anti-inflammatory activity. Its affinity to the H1 receptor is higher than most other H1-receptor antagonists. Desloratadine works by blocking a certain natural substance (histamine) which is produced during an allergic reaction. Desloratidine has a long-lasting effect and does not cause drowsiness because it does not readily enter the central nervous system.
Desloratadine is used to treat nasal and non-nasal symptoms (watery eyes, runny nose, itching eyes/nose, sneezing, and itching) of seasonal allergic rhinitis. It is also used to relieve chronic itching caused by hives.

Chemical Properties

Beige Solid

Originator

Sepracor (US)

Uses

Desloratadine has been used to test its effect on embryoid body development in in vitro gastrulation model of P19C5 stem cells. It has also been used as an antihistamine mimic in rats and to treat lung cancer (A549) and glioblastoma (U87) cells in various cellular studies.

Uses

Nonsedating-type histamine H1-receptor antagonist. An active metabolite of Loratadine. Also inhibits generation and release of inflammatory mediators from basophils and mast cells.

Uses

antiinflammatory

Uses

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.

Definition

ChEBI: 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 nd chronic urticaria. It does not readily enter the central nervous system, so does not cause drowsiness.

Indications

Desloratadine (Clarinex) is an active metabolite of loratadine. A 5 mg daily dose has been shown to be effective. There is no evidence that it offers any advantage over loratadine. Fexofenadine (like its parent compound terfenadine) may rarely promote cardiac arrhythmias (24). No significant difference in efficacy has been noted in the nonsedating H1 blockers. Combinations of nonsedating antihistamines in the morning and sedating antihistamines in the evening may be more cost effective than increasing doses of the nonsedating agent.

Manufacturing Process

To a solution of 10.9 g (0.1 mole) of ethylchloroformate in 300 ml of anhydrous benzene is added dropwise, with stirring at room temperature, a solution of 16.2 g (0.05 M) of 11-(N-methyl-4-piperidylidene)-8-chloro-6,11- dihydro-5H-benzo-[5,6]-cyclohepta-[1,2-b]-pyridine in 200 ml of benzene. The solution is stirred and is heated under reflux overnight (16-20 hours). The mixture is cooled and is poured into ice water and the organic layer is separated, washed with water, dried, and then concentrated to dryness. The residue is triturated with petroleum ether and a white solid of 8-chloro-6,11- dihydro-11-(1-ethoxycarbonyl-4-piperidylidene)-5H-benzo[5,6 ]cyclohepta[1,2-b]pyridine having a melting point of 128-130°C is recrystallized from isopropyl ether after decolorization with decolorizing carbon.
To 12 g of sodium hydroxide in 30 ml ethyl alcohol (70%) add 6 g of 8-chloro6,11-dihydro-11-(1-ethoxycarbonyl-4-piperidylidene)-5Hbenzo[5,6]cyclohepta[1,2-b]pyridine and reflux with stirring for 24 hours. After about the first 6-8 hours an additional 30 ml of 70% ethyl alcohol may be added. Remove about 50% of the solvent by distillation in vacuo. Add a small amount of ice water and acidify with glacial acetic acid. Extract with chloroform (6-8 times), since the product precipitates from the acetic acid solution as a thick emulsion which cannot be filtered. Concentrate the chloroform extracts to a small volume and precipitate the product with hexane to give crude 8-chloro-6,11-dihydro-11-(4-piperidylidene)-5Hbenzo[5,6]cyclohepta[1,2-b]pyridine acetic acid salt, m.p. 197-200°C. Recrystallize from benzene-hexane to obtain the product, m.p. 199-200°C. Yield 4.0-4.5 g.

brand name

Clarinex (Schering-Plough).

Therapeutic Function

Antiallergic

General Description

Desloratadine, 8-chloro-6,11-dihydro-11-(4-piperdinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine(Clarinex) is a white to off-white powder that is slightlysoluble in water, but very soluble in ethanol and propyleneglycol. It is the proposed active metabolite loratadine and hasa very similar receptor binding and safety profile. It is indicated for the symptomatic relief of pruritus andreduction in the number and size of hives in chronic idiopathicurticaria patients 6 months of age and older and for therelief of the nasal and nonnasal symptoms of perennial allergicrhinitis (in patients 6 months of age and older) and seasonalallergic rhinitis (in patients 2 years of age and older).
Desloratadine is extensively metabolized to 3-hydroxydesloratadine,also an active metabolite, which is subsequentlyglucuronidated . The cytochrome enzymesresponsible for the formation of 3-hydroxydesloratadinehave not been reported. Coadministration ofdesloratadine with CYP3A4 inhibitors results in marginalincreases in plasma concentrations of desloratadine and3-hydroxydesloratadine, but no significant changes in safetyor efficacy. The mean elimination half-life of desloratadineis about 6 hours, and the drug and its metabolites areeliminated in the urine and feces.

Biochem/physiol Actions

Desloratadine is a selective and nonsedating histamine H1 receptor antagonist, an active metabolite of loratadine (Claritin), used to relieve hay fever and allergy symptoms with less drowsiness than other antihistamines; does not significantly inhibits cardiac K+ channels at clinically achievable blood levels. Free from antimuscarinic/anticholinergic effects.

Clinical Use

Desloratadine was launched as an improved version of Schering-Plough's Claritin? (Loratadine), for the treatment of nasal and non-nasal symptoms of seasonal allergic rhinitis (SAR). Desloratadine can be prepared by a 7-step synthesis starting with a Ritter reaction on 2-cyano-3-picoline and involving successively alkylation with 3- chlorobenzyl chloride, dehydration, Grignard reaction with the piperidine magnesium chloride, intramolecular cyclization in strong acidic medium, and finally demethylation of the piperidine. Desloratadine (the descarboethoxyloratadine) is a biologically active metabolite of the second-generation antihistamine Ioratadine. Desloratadine is a nonsedating competitive histamine H₁ receptor antagonist with increased potency and improved safety as compared to Ioratadine. When compared with other H1 antagonists as an inhibitor of histamine-induced calcium flux in CHO cells, desloratadine was found to be more potent than most H₁ antagonists (such as the widely used terfenadine, fexofenadine, cetirizine, Ioratadine and astemizole) in this assay. Desloratadine is also a potent antagonist of muscarinic M₁ and M₃ receptors (not M₂) indicating anticholinergic activity. These effects may be the explanation for the unexpected decongestant effects of desloratadine reported in clinical trials. Desloratadine appears to be devoid of significant effects on potassium channels and does not appear to suffer from adverse interaction with cytochrome P450 inhibitors. Clinical studies have shown that it does not induce sedation or cardiac arrhythmias and does not potentiate the effects of alcohol. Apparent total body clearance is in the range of 114-201 l/h and the mean elimination half life is 19-34.6 h in human. Desloratadine is available as 5-mg tablets, which is the once-daily recommended dose for adults and children above 12 years. It may be taken without regard to food. The treatment not only improved symptoms of SAR but also improved patient ratings of nasal congestion. The FDA also has issued an "approvable" letter for this agent for the treatment of chronic idiopathic urticaria (ClU).

References

[1] https://www.drugbank.ca
[2] Raif S. Geha, Eli O. Meltzer (2001) Desloratadine: A new, nonsedating, oral antihistamine, The Journal of Allergy and Clinical Immunology,107, 751-762

Desloratadine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Desloratadine manufacturers

Wuhan Haorong Biotechnology Co.,Ltd

Product: Desloratadine 100643-71-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 5000
Release date: 2023-07-27

Shanghai Aosiris new Material Technology Co., LTD

Product: Desloratadine 100643-71-8
Price: US $3.00-1.00/kg
Min. Order: 1kg
Purity: 99.9%
Supply Ability: 10 tons
Release date: 2024-04-03

Hangzhou Hyper Chemicals Limited

Product: Desloratadine 100643-71-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 5000KG
Release date: 2024-04-10

100643-71-8, DesloratadineRelated Search:

Loratadine 2,2,6,6-Tetramethyl-4-piperidinol Triacetonediamine DROPERIDOL Haloperidol Benzo[b]thien-2-ylboronic acid Cetirizine dihydrochloride Desloratadine IMpurity B Desloratadine Epoxide 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine-d 1-Oxide Desloratadine IMpurity 3 8-Chloro-11-fluoro-6,11-dihydro-11-(4-piperidinyl)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine 8-Dechloro-9-chloro Desloratadine Desloratadine Citric Amide Desloratadine-d7 (Major) 8-Deschloro-8-bromo-N-methyl Desloratadine IMp. A (EP): Ethyl 4-[(11RS)-8-Chloro-11-hydroxy-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-yl]piperidine-1-carboxylate Desloratadine N-Carboxylic Acid Methyl Ester

AzoMyr

Neoclarityn

NSC 675447

Opulis

Desloratadine(Clarinex)

5H-Benzo[5,6]cyclohepta[1,2-b]pyridine, 8-chloro-6,11-dihydro- 11-(4-piperidinylidene)-

Desloratadine for system suitability

Loratadine Related Compound A (15 mg) (8-chloro-6,11-dihydro-11(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b] pyridine)

Clarinex (TN)

Clarinex RediTabs

Denosin

Desalex

Descarboethoxyoratidine

Desloratadine (USAN)

Desloratadine [USAN]

Loratadine EP IMpurity D

8-chloro-11-piperidin-4-ylidene-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

8-Chloro-6,11-dihydro-11-(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b] pyridine

Loratadine Impurity D (Desloratadine)(EP )

Loratadine EP Impurity D (Desloratadine) (Rupatadine EP Impurity B)

Rupatadine EP Impurity B (Loratadine EP Impurity D) (Desloratadine)

Loratadine Impurity 4(Loratadine EP Impurity D)

Loratadine EP Impurity D (Desloratadine)

8-chloro-6,11-dihydro-11-(4-piperdinylidene)-5h-benzo[5,6]cyclohepta[1,2-b]pyridine

8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDINYLIDENE)-5H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDINE

AKOS 92131

DESLORATIDINE

SCH-34117

Aerius

Dis-loratadine

Sch-34117, 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine, Clairinex, Aerius

descarboethoxyloratadine

Sch-34117, 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H- benzo[5,6]cyclohepta[1,2-β]pyridine, Clairinex, Aerius

Clarinex(R), 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H- benzo[5,6]cyclohepta[1,2,b]pyridine

Clarinex

Desloratadine Citrate Disodium

Loratadine Related CoMpound A

Loratadine Related Compound A (15 mg) (8-Chloro-6,11-dihydro-11(4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b] pyridine)

13-chloro-2-(piperidin-4-ylidene)-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,11,13-hexaene

Allex

Rupatadine EP Impurity D

Loratadine Impurity D/ Rupatadine Impurity B

Rupatadine EP Impurity B

Loratadine impurity-D(EP)

DESLORATADINE IMPURITY-D, 8-CHLORO-6,11-DIHYDRO-11-(4-PIPERDINYLIDENE)- 5H-BENZO[5,6]CYCLOHEPTA[1,2-B]PYRIDINE.

Desloratadine&gt

Desloratadine for system suitability CRS

Desloratadine CRS

DesL

oratadine

esloratadine

Desloratadine USP/EP/BP

Desloratadine Citrate Disodium USP/EP/BP

Deslloratadine

Loratidine EP Impurity D/ Loratidine Related Compound A (Desloratadine)

desloratadine intermediate

8-chloro-11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine

Desloratadine (Sch34117)