An antihistamine with anticholinergic and antiserotonergic activities
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Azatadine (maleate)

Item No. 29758

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
6,11-dihydro-11-(1-methyl-4-piperidinylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine, (2Z)-2-butenedioate
CAS Number
3978-86-7
Molecular Formula
C20H22N2 • 2C4H4O4
Formula Weight
522.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 20mg/mLDMSO: 20mg/mLEthanol: 5mg/mLPBS (pH 7.2): 10mg/mL
SMILES
CN(CC/1)CCC1=C2C(N=CC=C3)=C3CCC4=C\2C=CC=C4.OC(/C=C\C(O)=O)=O.OC(/C=C\C(O)=O)=O
InChi Code
InChI=1S/C20H22N2.2C4H4O4/c1-22-13-10-16(11-14-22)19-18-7-3-2-5-15(18)8-9-17-6-4-12-21-20(17)19;2*5-3(6)1-2-4(7)8/h2-7,12H,8-11,13-14H2,1H3;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-
InChi Key
SGHXFFAHXTZRQM-SPIKMXEPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Azatadine is an antihistamine with anticholinergic and antiserotonergic activities.1,2 It is a histamine H1 receptor antagonist (Ki = 3.9 nM).3,4 Azatadine inhibits histamine- and acetylcholine-induced contractions in isolated guinea pig ilium and contractions induced by serotonin (5-HT; Item No. 14332) in isolated rat uterus (EC50s = 6.5, 10, and 14 nM, respectively).2 It delays the onset of dyspnea induced by aerosolized histamine, 5-HT, or acetylcholine in guinea pigs. Azatadine prevents histamine-induced lethality in guinea pigs and paw edema in mice (ED50s = 9 and 68 μg/kg, respectively).1 It increases survival in guinea pig and mouse models of anaphylactic shock with 50% protective dose (PD50) values of 0.024 and 0.019 mg/kg, respectively.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Barnett, A., Iorio, L.C., Kreutner, W., et al. Evaluation of the CNS properties of SCH 29851, a potential non-sedating antihistamine. Agents Actions 43(3-4), 149-156 (1994).

    2. Tozzi, S., Roth, F.E., and Tabachnick, I.I.A. The pharmacology of azatadine, a potential antiallergy drug. Agents Actions 4(4), 264-270 (1974).

    3. Piwinski, J.J., Wong, J.K., Green, M.J., et al. Dual antagonists of platelet activating factor and histamine. Identification of structural requirements for dual activity of N-Acyl-4-(5,6-dihydro-llH-benzo[5,6]cyclohepta-[1,2-b]pyridin-11-y1idene)piperidines. J. Med. Chem. 34(1), 457-461 (1991).

    4. Baroody, F.M., and Naclerio, R.M. Antiallergic effects of H1-receptor antagonists. Allergy 55(Suppl 64), 17-27 (2000).