Nitidine (chloride)

Nitidine is an alkaloid originally isolated from Z. nitidium that has antimalarial, anti-inflammatory, and anticancer activities. It is active against the F32 chloroquine-sensitive and FcB1 and FcM2 chloroquine-resistant strains of P. falciparum (IC50s = 0.52, 0.8, and 0.49 µM, respectively) and reduces parasitemia in a mouse model of P. vinckei infection with an ED50 value of 18.9 mg/kg per day. It decreases LPS-induced increases in TNF-alpha, IL-1beta, and IL-6 levels and p65 nuclear translocation in RAW 264.7 cells when used at a concentration of 5 µM. Nitidine (5 mg/kg) decreases serum levels of IL-10, TNF-alpha, and IL-6 and reduces mortality in a mouse model of LPS-induced endotoxemia. It inhibits proliferation of B16 melanoma, MCF-7 and Hs 578T breast, and DU145 and MPC3 prostate cancer cells with IC50 values ranging from 2.65 to 370 ng/ml. Nitidine (0.1-10 µM) induces apoptosis and decreases STAT3 phosphorylation in HSC-3 and HSC-4 oral cancer cells, as well as reduces tumor growth in an HSC-3 mouse xenograft model when administered at a dose of 10 mg/kg per day for 24 days.Formal Name: 2,3-dimethoxy-12-methyl-[1,3]benzodioxolo[5,6-c]phenanthridinium, monochloride. CAS Number: 13063-04-2. Synonyms: NSC 146397. Molecular Formula: C21H18NO4 . Cl. Formula Weight: 383.8. Purity: >98%. Formulation: (Request formulation change), A solid. Solubility: DMF: .25 mg/ml, DMSO: .5 mg/ml. lambdamax: 221, 236, 271, 293, 329, 384 nm. SMILES: COC1=C(OC)C=C2C(C=[N+](C)C3=C(C=C(OCO4)C4=C5)C5=CC=C32)=C1.[Cl-]. InChi Code: InChI=1S/C21H18NO4.ClH/c1-22-10-13-7-17(23-2)18(24-3)8-15(13)14-5-4-12-6-19-20(26-11-25-19)9-16(12)21(14)22,/h4-10H,11H2,1-3H3,1H/q+1,/p-1. InChi Key: QLDAACVSUMUMOR-UHFFFAOYSA-M. Origin: Plant/Zanthoxylum nitidum.