The natural polymer chitosan is the second most abundant biopolymer on earth after chitin and has been extensively explored for preparation of versatile drug delivery systems. The presence of two distinct reactive functional groups (an amino group at C2, and a primary and secondary hydroxyl group at C3 and C6) of chitosan are involved in the transformation of expedient derivatives such as acylated, alkylated, carboxylated, quaternized and esterified chitosan. Amongst these, quaternized chitosan is preferred in pharmaceutical industries owing to its prominent features including superior water solubility, augmented antimicrobial actions, modified wound healing, pH-sensitive targeting, biocompatibility, and biodegradability. It has been explored in a large realm of pharmaceuticals, cosmeceuticals, and the biomedical arena. Immense classy drug delivery systems containing quaternized chitosan have been intended for tissue engineering, wound healing, gene, and vaccine delivery. This review article outlines synthetic techniques, basic characteristics, inherent properties, biomedical applications, and ubiquitous challenges associated to quaternized chitosan