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Chemical Compound Review:

CHEMBL1211 8-(5-aminopentan-2-ylamino)- 6-methoxy-1H...

Synonyms: AG-G-03801, SureCN5639040, CTK1G9522, AC1L57TD, WR 199507, ...

Bowman, Z.S. et al., Vasquez-Vivar, J. et al., Vásquez-Vivar, J. et al., Bowman, Z.S. et al.

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Disease relevance of 5-Hydroxyprimaquine

Primaquine-induced hemolytic anemia: role of membrane lipid peroxidation and cytoskeletal protein alterations in the hemotoxicity of 5-hydroxyprimaquine [1].

High impact information on 5-Hydroxyprimaquine

Previous studies have suggested that a phenolic metabolite, 5-hydroxyprimaquine (5-HPQ), mediates primaquine hemotoxicity by generating reactive oxygen species (ROS) within erythrocytes that overwhelm antioxidant defenses [1].
Primaquine-induced hemolytic anemia: role of splenic macrophages in the fate of 5-hydroxyprimaquine-treated rat erythrocytes [2].
ESR detection of free radical intermediates during autoxidation of 5-hydroxyprimaquine [3].
5-Hydroxyprimaquine underwent fast autoxidation under mild conditions (pH 7.4-8.5, 25 degrees C, and presence of 1 mM diethylenetriamine pentaacetic acid); each mol of the drug consumed 0.75 mol of oxygen and formed 0.5 mol of hydrogen peroxide [3].

Anatomical context of 5-Hydroxyprimaquine

In both cases, the most effective metabolites in oxidizing hemoglobin and depleting non-protein sulfhydryl groups from erythrocytes were the quinone-imine derivatives of the ring-hydroxylated metabolites, 5-hydroxyprimaquine and 5-hydroxydemethyl-primaquine [4].

References

Primaquine-induced hemolytic anemia: role of membrane lipid peroxidation and cytoskeletal protein alterations in the hemotoxicity of 5-hydroxyprimaquine. Bowman, Z.S., Morrow, J.D., Jollow, D.J., McMillan, D.C. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
Primaquine-induced hemolytic anemia: role of splenic macrophages in the fate of 5-hydroxyprimaquine-treated rat erythrocytes. Bowman, Z.S., Jollow, D.J., McMillan, D.C. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
ESR detection of free radical intermediates during autoxidation of 5-hydroxyprimaquine. Vasquez-Vivar, J., Augusto, O. Free Radic. Res. Commun. (1990) [Pubmed]
Oxidative activity of primaquine metabolites on rat erythrocytes in vitro and in vivo. Vásquez-Vivar, J., Augusto, O. Biochem. Pharmacol. (1994) [Pubmed]

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