CAS 79794-75-5|Claritin|Loratadine|Alavert|ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate|loratadine|Loratidine|ethyl 4-(8-ch...

General Information

Structure

Molecular Formula

C₂₂H₂₃ClN₂O₂

Molecular Mass

382.88322

Exact Mass

382.14480567

Charge

InChI

InChI=1S/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

InChIKey

JCCNYMKQOSZNPW-UHFFFAOYSA-N

Canonic Smiles

CCOC(=O)N1CCC(=C2c3ccc(cc3CCc3c2nccc3)Cl)CC1

Isomeric Smiles

Clc1cc2c(C(=C3CCN(CC3)C(=O)OCC)c3ncccc3CC2)cc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

4.5269837

LogD (pH = 7.4)

4.5542197

Log P

4.5545793

Molar Refractivity

116.9769

Polarizability

41.254913

Polar Surface Area

42.43

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

4.8

LOG S

-4.46

Solubility (Water)

1.34e-02 g/l

Data Source

Names and Identifiers

Synonyms

ClaritinLoratadineAlavertLoratidineethyl 4-(8-chloro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-11(6H)-ylidene)piperidine-1-carboxylateLoratadine4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene-1-piperidinecarboxylic acid ethyl esterLoratadinum [Latin]Loratadina [Spanish]Claritin, Sch-29851,4-(8-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)-1-piperidinecarboxylic Acid Ethyl Esterethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylateClaritineClaritin-DClarityneClaritynFristaminLoratadine

IUPAC name

ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-ylidene}piperidine-1-carboxylate ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}piperidine-1-carboxylate ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}piperidine-1-carboxylate ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3(8),4,6,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

IUPAC Traditional name

loratadine ethyl 4-{13-chloro-4-azatricyclo[9.4.0.0³,⁸]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}piperidine-1-carboxylate

Brand Name

LorantisZeosHistaloranClaratyneLoracertLoratyneAlerprivLorfastBiloinaClaritynTadineBonalergSanelorAlarinLoritineLoranoxOptiminBedix LoratadinaLoradifLomilanTalorat DyLergyRoletraLertamineFristaminSensibitAerotinaClaritineLoradexClaritin ReditabsLowadinaLisinoRestamineNularefPolaratyneRinomexClaritinVelodanLesidasVersalClarinase ReperabsSinhistan DyClarinaseAlavertLoraverSohotinLorastineClaritin-DAllertidinRhinaseCiveranPylorClarityne

Names and Identifiers

Registration numbers

MDL Number

MFCD00672869

CAS Number

79794-75-5

PubChem SID

2427852516096380146507853

PubChem CID

3957

Registration numbers

Properties

Product Information

Salt Data

Free Base

Empirical Formula (Hill Notation)

C22H23N2O2Cl

Purity

≥98% (HPLC)

95%

98%

Certificate of Analysis

Download link

Other pharmacol. mechanisms under investigation

Used in the treatment of rhinitis and skin disorders

Pharmacology Properties

Target

Histamine receptors

Gene Information

human ... CYP3A4(1576), HRH1(3269), KCNH1(3756), KCNH2(3757), PTAFR(5724)rat ... Hrh1(24448)

Mechanism of Action

Histamine H1-receptor antagonist

Safety Information

Storage Condition

-20°C

-20°C Freezer

Personal Protective Equipment

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

MSDS Link

Download link

2-8°C

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

Molecule Details

DrugBank

DB00455

Drug Groups

approved

Description

Loratadine is a derivative of azatadine and a second-generation histamine H1 receptor antagonist used in the treatment of allergic rhinitis and urticaria. Unlike most classical antihistamines (histamine H1 antagonists) it lacks central nervous system depressing effects such as drowsiness. [PubChem]

Indication

A self-medication that is used alone or in combination with pseudoephedrine sulfate for the symptomatic relief of seasonal allergic rhinitis. Also used for the symptomatic relief of pruritus, erythema, and urticaria associated with chronic idiopathic urticaria in patients (not for children under 6 unless directed by a clincian).

Pharmacology

Loratadine is a long acting second generation antihistamine that is similar in structure to cyproheptadine and azatadine. The pharmacology of loratadine is similar to other antihistamines, but unlike other H₁-blockers, loratidine is shown to exhibit competitive, specific, and selective antagonism of H₁ receptors. The exact mechanism of this interaction is unknown, but disposition of the drug suggests that loratadine's prolonged antagonism of histamine may be due to the drug's slow dissociation from the receptor or the formation of the active metabolite, desloratadine. Loratadine does not penetrate the CNS effectively and has a low affinity for CNS H₁-receptors.

Toxicity

somnolence, tachycardia, and headache LD₅₀=mg/kg (orally in rat)

Affected Organisms

Humans and other mammals

Biotransformation

Hepatic

Absorption

Rapidly absorbed following oral administration (40% bioavailability)

Half Life

8.4 hours

Protein Binding

97-99%

References

• See S: Desloratadine for allergic rhinitis. Am Fam Physician. 2003 Nov 15;68(10):2015-6. [Pubmed]

• Menardo JL, Horak F, Danzig MR, Czarlewski W: A review of loratadine in the treatment of patients with allergic bronchial asthma. Clin Ther. 1997 Nov-Dec;19(6):1278-93; discussion 1523-4. [Pubmed]

• Howarth PH: Histamine and asthma: an appraisal based on specific H1-receptor antagonism. Clin Exp Allergy. 1990 Aug;20 Suppl 2:31-41. [Pubmed]

• Baroody FM, Naclerio RM: Antiallergic effects of H1-receptor antagonists. Allergy. 2000;55 Suppl 64:17-27. [Pubmed]

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1358

Research Area: Inflammation
Biological Activity:
Loratadine is a selective inverse peripheral histamine H1-receptor agonist with an IC50 of >32 μM. [1] Histamine is responsible for many features of allergic reactions. Loratadine (Alavert, Claritin) is a second-generation antihistamine agent closely structurally related to tricyclic antidepressants such as imipramine, and distantly related to the atypical antipsychotic quetiapine, used to treat allergies. [2]

Sigma Aldrich

L9664

Biochem/physiol Actions
Non-sedating histamine H1-receptor antagonist.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. L9664.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

L469575

A nonsedating-type histamine H1-receptor.

Molecule Details

References

PubChem Literature

From Data Sources

• See S: Desloratadine for allergic rhinitis. Am Fam Physician. 2003 Nov 15;68(10):2015-6. Pubmed

• Howarth PH: Histamine and asthma: an appraisal based on specific H1-receptor antagonism. Clin Exp Allergy. 1990 Aug;20 Suppl 2:31-41. Pubmed

• Menardo JL, Horak F, Danzig MR, Czarlewski W: A review of loratadine in the treatment of patients with allergic bronchial asthma. Clin Ther. 1997 Nov-Dec;19(6):1278-93; discussion 1523-4. Pubmed

• Baroody FM, Naclerio RM: Antiallergic effects of H1-receptor antagonists. Allergy. 2000;55 Suppl 64:17-27. Pubmed

• http://www.rxlist.com/claritin-drug.htm

• Bruttmann, G., et al.: J. Allergy Clin. Immunol., 83, 411 (1989)

• Haria, M., et al.: Drugs, 48, 617 (1994)

• Molet, S. et al., Clin. Exp. Allergy, 1997, 27, 1167-1174, (desloratadine, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 413

• McClellan, K. et al., Drugs, 2001, 61, 789-796, (desloratadine, rev)

• Johnson, R. et al., J. Chromatogr., B: Biomed. Appl., 1994, 657, 125, (gc)

• Roman, I.J. et al., Clin. Rev. Allergy, 1993, 11, 89, (pharmacol, rev)

• Letari, O. et al., Eur. J. Pharmacol., 1994, 266, 219, (pharmacol)

• Caballero, R. et al., Br. J. Pharmacol., 1997, 122, 796-798, (desloratadine, pharmacol)

• Batenhorst, R.L. et al., Eur. J. Clin. Pharmacol., 1986, 31, 247, (pharmacol)

• Bradley, C.M. et al., Eur. J. Clin. Pharmacol., 1987, 32, 419, (pharmacol)

• Haria, M. et al., Drugs, 1994, 48, 617, (rev)

• Barnett, A. et al., Chron. Drug Discovery, 1993, 3, 83, (rev)

• Pat. Coop. Treaty (WIPO), 1985, Schering, 85 03 707; CA, 104, 116091a, (desloratadine, synth, pharmacol)

• Schumacher, D.P. et al., J.O.C., 1989, 54, 2242, (synth, pmr)

• Piwinski, J.J. et al., J.O.C., 1990, 55, 3341, (metab)

• Villani, F.J. et al., Arzneim.-Forsch., 1986, 36, 1311, (synth)

• Barnett, A. et al., Agents Actions, 1984, 14, 590, (pharmacol)

• Kreutner, W. et al., Allergy (Copenhagen), 1987, 42, 57, (pharmacol)

• Piwinski, J.J. et al., J. Med. Chem., 1991, 34, 457, (activity)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8869, (synonyms)

• Hilbert, J. et al., J. Clin. Pharmacol., 1987, 27, 530; 694; 1988, 28, 234, (pharmacol)

• Clissold, S.P. et al., Drugs, 1989, 37, 42, (rev)

References

Bioactivity

PubChem BioAssay

Bioactivity