3D Mol Similar

Desloratadine

: Iupac Name：8-chloro-11-piperidin-4-ylidene-5,6-dihydrobenzo[1,2]cyclohepta[2,4-b]pyridine; CAS No.: 100643-71-8; Molecular Weight：310.825; Modify Date.: 2022-11-22 21:49; Introduction: 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. View more+

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1. Names and Identifiers

: 1.1 Name; Desloratadine; 1.2 Synonyms; 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, 8-chloro-6,11-dihydro-11-(4-piperidinylidene)- 8-Chlor-11-piperidin-4-yliden-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin 8-Chloro-11-(4-piperidinylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine 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-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine Aerius Allex AzoMyr Clarinex descarboethoxyloratadine Descarboethoxyoratidine Desloratadine for system suitability Desloratadine(Clarinex) DESLORATIDINE Loratadine Related Compound A (15 mg) (8-chloro-6,11-dihydro-11(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b] pyridine) MFCD00871949 Neoclarityn NSC 675447 Opulis Sch34117 UNII-FVF865388R; View all

1.3 CAS No.: 100643-71-8

1.4 CID: 124087

1.5 EINECS(EC#): 1308068-626-2

1.6 Molecular Formula: C19H19ClN2 (isomer)

1.7 Inchi: InChI=1S/C19H19ClN2/c20-16-5-6-17-15(12-16)4-3-14-2-1-9-22-19(14)18(17)13-7-10-21-11-8-13/h1-2,5-6,9,12,21H,3-4,7-8,10-11H2

1.8 InChIkey: JAUOIFJMECXRGI-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CC2=C(C=CC(=C2)Cl)C(=C3CCNCC3)C4=C1C=CC=N4

1.10 Isomers Smiles: C1CC2=C(C=CC(=C2)Cl)C(=C3CCNCC3)C4=C1C=CC=N4

2. Properties

2.1 Density: 1.221

2.1 Melting point: 150-151oC

2.1 Boiling point: 467.9 oC at 760 mmHg

2.1 Refractive index: 1.625

2.1 Flash Point: 236.8 oC

2.1 Precise Quality: 310.12400

2.1 PSA: 24.92000

2.1 logP: 4.34770

2.1 Solubility: DMSO: >10mg/mL

2.2 Appearance: Beige Solid

2.3 Chemical Properties: Beige Solid

2.4 Color/Form: Powder

2.5 Physical: Solid

2.6 pKa: 10.27±0.20(Predicted)

2.7 Water Solubility: DMSO: >10mg/mL

2.8 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 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.

3.2 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.; View all

3.3 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 25 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H302 (64%): Harmful if swallowed [Warning Acute toxicity, oral]
H317 (32%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H318 (40%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H351 (12%): Suspected of causing cancer [Warning Carcinogenicity]
H361 (44%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H411 (64%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P333+P313, P363, P391, P405, and P501; View all

3.4 Usage: A histamine H1-receptor antagonist. An active metabolite of Loratadine

4. Safety and Handling

4.1 Risk Statements: S16-S23-S36/37/39

4.1 Safety Statements: R11:Highly Flammable.

4.1 Hazard Declaration: H302

4.1 RIDADR: 1993

4.1 Caution Statement: P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P305+P351+P338, P308+P313, P310, P321, P330, P333+P313, P363, P391, P405, P501

4.1 WGK Germany: 3

4.1 RTECS: DE8011000

4.1 Specification: ? Desloratadine (CAS NO.100643-71-8), its Synonyms are 8-Chloro-6,11-dihydro-11-(4-piperidinylidene)-5H-benzo(5,6)cyclohepta(1,2-b)pyridine ; Aerius ; Azomyr ; Clarinex ; Denosin ; Neoclarityn ; 5H-Benzo(5,6)cyclohepta(1,2-b)pyridine, 8-chloro-6,11-dihydro-11-(4-piperidinylidene)- .

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Serious eye damage, Category 1

Reproductive toxicity, Category 2

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H302 Harmful if swallowed H318 Causes serious eye damage H361 Suspected of damaging fertility or the unborn child H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026 P308+P313 IF exposed or concerned: Get medical advice/ attention. P391 Collect spillage.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

100643-71-8Total: 11 Synthesis Route

620-20-2 141 Suppliers

100643-71-8 281 Suppliers

Literatures:
Journal of Medicinal Chemistry, , vol. 34, # 1 p. 457 - 461
Yield: null

79794-75-5 437 Suppliers

100643-71-8 281 Suppliers

Literatures:
Mezei, Tibor; Volk, Balazs; Kiraly, Imre; Simig, Gyula Organic Process Research and Development, 2008 , vol. 12, # 5 p. 855 - 859
Yield: ~95%

38089-93-9 23 Suppliers

100643-71-8 281 Suppliers

Literatures:
Bioorganic and Medicinal Chemistry Letters, , vol. 22, # 8 p. 2701 - 2704
Yield: null

View all

7. Precursor and Product

precursor:

107285-30-3

63463-36-5

130642-50-1

31255-57-9

79794-75-5

100643-73-0

31251-41-9

620-20-2

32998-95-1

38089-93-9

38092-89-6

product :

158876-82-5

117796-52-8

8. Other Information

8.0 Target: Value

8.1 Histamine H1 receptor: 51 nM

8.2 Originator: Sepracor (US)

8.3 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.

8.4 Merck: 14,2922

8.5 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.

8.6 Chemical Properties: Beige Solid

8.7 Uses: A histamine H1-receptor antagonist. An active metabolite of Loratadine

8.8 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.

8.9 Uses: antiinflammatory

8.10 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.

8.11 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.

8.12 Brand name: Clarinex (Schering-Plough).

8.13 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

8.14 Collision Cross Section: 175.5 ?2 [M+H]+ [CCS Type: TW, Method: Major Mix IMS/Tof Calibration Kit (Waters)]

8.15 Livertox Summary: Loratadine and its metabolic derivative desloratadine are second generation antihistamines that are used for the treatment of allergic rhinitis, angioedema and chronic urticaria. Loratadine and desloratadine have been linked to rare, isolated instances of clinically apparent acute liver injury.

8.16 Drug Classes: Antihistamines

8.17 Mesh: 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. (See all compounds classified as Histamine H1 Antagonists, Non-Sedating.)|Drugs that bind to but do not activate CHOLINERGIC RECEPTORS, thereby blocking the actions of ACETYLCHOLINE or cholinergic agonists. (See all compounds classified as Cholinergic Antagonists.)

8.18 Absorption: Desloratadine administered orally for ten days to healthy volunteers as a 5 mg tablet once daily resulted in a mean T_max of approximately 3 hours, a mean steady-state C_max 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 ¹⁴C-desloratadine dose was equally recovered in urine and feces as metabolic products.

8.19 Metabolism: Desloratadine is metabolized to the active metabolite 3-hydroxydesloratadine, which is subsequently glucuronidated.|Desloratadine is a known human metabolite of Rupatadine and loratadine.

8.20 Biological Half Life: Desloratadine has a mean plasma elimination half-life of approximately 27 hours.

8.21 Mesh Entry Terms: Aerius

8.22 Use Classification: Human drugs -> Azomyr -> EMA Drug Category|Antihistamines for systemic use -> Human pharmacotherapeutic group|Human drugs -> Aerius -> EMA Drug Category|Human drugs -> Neoclarityn -> EMA Drug Category|Human drugs -> Aerinaze -> EMA Drug Category|Nasal preparations -> Human pharmacotherapeutic group|Human drugs -> Desloratadine Actavis -> EMA Drug Category|Human drugs -> Desloratadine Teva -> EMA Drug Category|Human drugs -> Dasselta -> EMA Drug Category|Human drugs -> Desloratadine ratiopharm -> EMA Drug Category|Human drugs -> Allex -> EMA Drug Category|Human drugs -> Opulis -> EMA Drug Category|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9. Computational chemical data

Molecular Weight: 310.825g/mol
Molecular Formula: C₁₉H₁₉ClN₂
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 310.1236763
Monoisotopic Mass: 310.1236763
Complexity: 425
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 24.9
Heavy Atom Count: 22
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceB7AAAEAAAAAAAAAAAAAAAAAAAAAAA8WIAABgAAAAABwAAAHAIQAAAADArBHiQ8gJLIEACgAzRnRACCgCAxByAI2KA4ZpgIIOLBk5GEIAhgkADIyAcQgMAOhAAAIAAQAAAIAABAACAAAAAAAAAAAA==

10. Question & Answer

What are the differences between Loratadine, Desloratadine, and Desloratadine Citrate? May 27 2023
Loratadine, Desloratadine, and Desloratadine Citrate are commonly used medications for the treatment of allergic rhinitis, urticaria, pruritic skin diseases, and other allergic skin diseases. So, what..
What is Desloratadine and how does it work? Apr 17 2022
Desloratadine, also known as AERIUS/DENOSIN, is a third-generation antihistamine that belongs to the long-acting tricyclic class of histamine antagonists. It selectively acts on the H1 receptors. Data..
What is Desloratadine and its uses? Jan 19 2022
Desloratadine, also known as AERIUS or DENOSIN, is a third-generation long-acting histamine antagonist that selectively acts on the H1 receptor. Data from receptor binding studies show that it intera..
What is the main function of Desloratadine and how does it work? Oct 20 2021
Before using any medication, it is important to understand its main function in order to know how to take it effectively for treating one's illness. Just like many people who want to know the main fu..

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Desloratadine