A nitrogen mustard derivative of fluphenazine
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Fluphenazine-N-2-chloroethane (hydrochloride)

Item No. 18427

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
10-[3-[4-(2-chloroethyl)-1-piperazinyl]propyl]-2-(trifluoromethyl)-10H-phenothiazine dihydrochloride
CAS Number
3892-78-2
Synonyms
  • Fluphenazine-N-mustard
  • FNM
  • FPCE
  • SKF-7171A
Molecular Formula
C22H25ClF3N3S • 2HCl
Formula Weight
528.9
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
257, 307 nm
SMILES
ClCCN1CCN(CCCN2C(C=CC=C3)=C3SC4=C2C=C(C(F)(F)F)C=C4)CC1.Cl.Cl
InChi Code
InChI=1S/C22H25ClF3N3S.2ClH/c23-8-11-28-14-12-27(13-15-28)9-3-10-29-18-4-1-2-5-20(18)30-21-7-6-17(16-19(21)29)22(24,25)26;;/h1-2,4-7,16H,3,8-15H2;2*1H
InChi Key
OAWAULFIPAZCMH-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

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    50 mg

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    100 mg

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    Product Description

    Fluphenazine-N-2-chloroethane is a derivative of fluphenazine that contains an alkylating chlorethylamine chain, which produces irreversible protein binding.1,2 It is a relatively selective, irreversible antagonist of D2 receptors both in vitro (IC50 = 100 nM) and in vivo, inactivating approximately 90% of D2 receptors in mice within 4 hours of treatment.3,4 Through this action, fluphenazine-B-2-chloroethane can be used to induce catalepsy in mice.3,5 It irreversibly inhibits calmodulin at higher doses (IC50 = 10 µM), which can sensitize cancer cells to TRAIL-induced apoptosis.1,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Winkler, J.D., Thermos, K., and Weiss, B. Differential effects of fluphenazine-N-mustard, on calmodulin activity and on D1 and D2 dopaminergic responses. Psychopharmacology (Berl) 92(3), 285-291 (1987).

    2. Hait, W.N., Glazer, L., Kaiser, C., et al. Pharmacological properties of fluphenazine-mustard, an irreversible calmodulin antagonist. Mol. Pharmacol. 32(3), 404-409 (1987).

    3. Qin, Z.H., Zhou, L.W., Zhang, S.P., et al. D2 dopamine receptor antisense oligodeoxynucleotide inhibits the synthesis of a functional pool of D2 dopamine receptors. Mol. Pharmacol. 48(4), 730-737 (1995).

    4. Thermos, K., Winkler, J.D., and Weiss, B. Comparison of the effects of fluphenazine-N-mustard on dopamine binding sites and on behavior induced by apomorphine in supersensitive mice. Neuropharmacology 26(10), 1473-1480 (1987).

    5. Davidkova, G., Zhou, L.W., Morabito, M., et al. D2 dopamine antisense RNA expression vector, unlike haloperidol, produces long-term inhibition of D2 dopamine-mediated behaviors without causing up-regulation of D2 dopamine receptors. J. Pharmacol. Exp. Ther. 285(3), 1187-1196 (1998).

    6. Hwang, M.K., Min, Y.K., and Kim, S.H. Calmodulin inhibition contributes to sensitize TRAIL-induced apoptosis in human lung cancer H1299 cells. Biochem. Cell Biol. 87(6), 919-926 (2009).