A dopamine D1 and D2 receptor antagonist
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Pro-drug Form(s)
39903Fluphenazine decanoate
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Fluphenazine (hydrochloride)

Item No. 23555

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[3-[2-(trifluoromethyl)-10H-phenothiazin-10-yl]propyl]-1-piperazineethanol, dihydrochloride
CAS Number
146-56-5
Synonyms
  • SQ 4,918
Molecular Formula
C22H26F3N3OS • 2HCl
Formula Weight
510.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 20 mg/mlEthanol: 5 mg/ml
λmax
259, 311 nm
SMILES
OCCN1CCN(CCCN2C(C=CC=C3)=C3SC4=C2C=C(C(F)(F)F)C=C4)CC1.Cl.Cl
InChi Code
InChI=1S/C22H26F3N3OS.2ClH/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29;;/h1-2,4-7,16,29H,3,8-15H2;2*1H
InChi Key
MBHNWCYEGXQEIT-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 mg

    $37

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    1 g

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    5 g

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    Product Description

    Fluphenazine is a dopamine D1 and D2 receptor antagonist (Kis = 5 and 0.63 nM, respectively) and an active metabolite of fluphenazine decanoate (Item No. 39903).1 It also binds to histamine H1, serotonin 5-HT2A, and 5-HT2B receptors (Kis = 45, 17, and 82 nM, respectively).2 It acts as an inverse agonist at H1 and 5-HT2A receptors.2,3 Fluphenazine is a typical antipsychotic compound. It induces extrapyramidal symptoms in animal models, including monkeys.4 Formulations containing fluphenazine have been used in the management of psychotic disorders.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Meltzer, H.Y., Matsubara, S., and Lee, J.-C. Classification of typical and atypical antipsychotic drugs on the basis of dopamine D-1, D-2 and serotonin2 pKi values. J. Pharmacol. Exp. Ther. 251(1), 238-246 (1989).

    2. Weiner, D.M., Burstein, E.S., Nash, N.R., et al. 5-hydroxytryptamine2A receptor inverse agonists as antipsychotics. J. Pharmacol. Exp. Ther. 299(1), 268-276 (2001).

    3. Appl, H., Holzammer, T., Dove, S., et al. Interactions of recombinant human histamine H1, H2, H3, and H4 receptors with 34 antidepressants and antipsychotics. Naunyn-Schmiedebergs Arch. Pharmacol. 385(2), 145-170 (2012).

    4. Kovacic, B., and Domino, E.F. Fluphenazine-induced acute and tardive dyskinesias in monkeys. Psychopharmacology (Berl.) 84(3), 310-314 (1984).