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Home> Encyclopedia >Anti-Allergic Agents>Pharmaceutical Intermediates>Pharmaceutical
Desloratadine structure
Desloratadine structure

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+
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

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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

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 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 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==
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