CAS 118-42-3 Hydroxychloroquine - Analytical Products / Alfa Chemistry

CAT	APS118423
CAS	118-42-3
Synonyms	Oxychloroquine, Hydroxychloroquine, Oxychlorochin, Win 1258-2, Ethanol, 2-[[4-[(7-chloro-4-quinolyl)amino]pentyl]ethylamino]- (6CI,8CI), 7-Chloro-4-[4-[ethyl(2-hydroxyethyl)amino]-1-methylbutylamino]quinoline, Racemic Hydroxychloroquine, 7-Chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinoline, 7-Chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline, WIN 1258, Oxichloroquine, 2-[[4-[(7-Chloro-4-quinolinyl)amino]pentyl]ethylamino]ethanol,Ethanol, 2-[[4-[(7-chloro-4-quinolinyl)amino]pentyl]ethylamino]-, (±)-Hydroxychloroquine
IUPAC Name	2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol
Molecular Weight	335.87
Molecular Formula	C18H26ClN3O
Canonical SMILES	CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12
InChI	InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)

Accurate Mass	335.1764
Format	Neat
Subcategory	Endosomal pH regulators, Antimalarials

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Case Study

Hydroxychloroquine Used for the Preparation of siRNA-Loaded Lipid Nanoparticles for Anti-Tumor Therapy

Huang, L., Guo, W., Zhao, T., Feng, Y., Li, Y., An, Q., ... & Xiang, B. (2025). Chemical Engineering Journal, 160172.

Hydroxychloroquine (HCQ), a well-known autophagy inhibitor, has emerged as a crucial adjuvant in cancer nanomedicine. In a novel strategy to combat drug resistance and toxicity associated with CDK4/6 inhibitors, HCQ was co-encapsulated with small interfering RNA (siRNA) targeting CDK4/6 into lipid nanoparticles (LNPs) using advanced microfluidic technology.
The LNPs were synthesized by merging an organic phase-comprising DLin-MC3-DMA, cholesterol, DSPC, and DSPE-PEG 2000 at a molar ratio of 30:28.5:40:1.5-with an aqueous phase containing siRNA (4.96 μmol/L) and HCQ (2 mg/mL) in citric acid-sodium citrate buffer (pH 4.0). The microfluidic mixing process enabled precise control over nanoparticle formation, maintaining an N/P charge ratio of 10. Post-synthesis, the LNP suspension underwent ultrafiltration and buffer exchange to reach physiological pH (7.4). Subsequently, HCQ was actively loaded into the LNPs using a pH gradient at 55 °C, followed by ice cooling. Excess, unencapsulated HCQ was removed by further ultrafiltration.
The resulting HCQ-siRNA-LNP complex demonstrated synergistic anti-tumor effects by combining siRNA-induced CDK4/6 silencing with HCQ-mediated autophagy inhibition. This dual-action platform shows promise in enhancing the efficacy of breast cancer therapy and overcoming conventional treatment barriers. Hydroxychloroquine thus plays a vital role in the preparation of multifunctional LNP systems for next-generation cancer therapeutics.

Hydroxychloroquine Used for the Preparation of Chitosan-ZnO Nanoparticle Complexes for Antibacterial Applications

Manuja, Anju, et al. Carbohydrate Polymer Technologies and Applications 9 (2025): 100647.

Hydroxychloroquine (HC), widely known for its antimalarial and immunomodulatory properties, is being explored for its synergistic antibacterial potential in combination with metal ions and biopolymers. In this study, HC was successfully incorporated into a chitosan-zinc oxide (ZnO) nanoparticle matrix to create a multifunctional nanocomposite (Ch-ZnHC complex) aimed at improving drug delivery and enhancing antibacterial activity.
Chitosan, a biocompatible and biodegradable polysaccharide, served as an effective carrier to mitigate the cytotoxicity of both zinc and hydroxychloroquine. ZnO nanoparticles were synthesized via a microwave-assisted route using zinc sulfate as a precursor, yielding flower-like nanostructures. HC was incorporated at concentrations ranging from 0.0012-0.012 wt%, with ZnO (0.05-0.75 wt%) and chitosan (0.01-1 wt%) forming a stable composite. The mixture was prepared in 0.1% acetic acid, diluted with distilled water, filtered through a 0.22 µm membrane, and stored at 4 °C.
Molecular docking studies demonstrated that the Ch-ZnHC complex effectively inhibits fibronectin-binding proteins in Streptococcus and Staphylococcus species, underscoring its potential as a targeted antibacterial agent. This formulation not only enhances the bioavailability of hydroxychloroquine but also leverages chitosan's mucoadhesive properties and ZnO's intrinsic antimicrobial effects, making it a promising candidate for combating bacterial infections.

Hydroxychloroquine Used for the Conjugation with Silver Nanoparticles for Antiviral Drug Delivery Applications

Mwenze, Nancy Mwikali, et al. Materials Today: Proceedings (2023).

Hydroxychloroquine (HCQ), a well-known antimalarial and immunomodulatory agent, has been investigated for its potential role in targeted drug delivery through conjugation with silver nanoparticles (AgNPs). In this application, AgNPs serve as nanocarriers, enhancing the therapeutic efficacy of HCQ while minimizing its systemic side effects. The unique physicochemical properties of AgNPs-particularly their high surface-area-to-volume ratio and ability to penetrate cellular membranes-make them ideal for biomedical applications, including antiviral therapies.
The AgNPs/HCQ conjugate was synthesized via a simple one-pot method, wherein pre-formed silver nanoparticles were mixed with 50 mg of hydroxychloroquine and stirred vigorously for 20 minutes. The resulting hybrid nanomaterial was stored at room temperature without further purification, indicating a facile and efficient preparation process.
Computational studies further supported the stability and compatibility of HCQ with AgNPs, suggesting favorable interactions that preserve drug activity while potentially improving its pharmacokinetic profile. The small size of the AgNPs also facilitates intracellular delivery, enhancing the bioavailability of HCQ.
This nanoconjugate system is particularly promising in the context of COVID-19 treatment, where controlled release and targeted delivery are crucial for reducing toxicity and improving therapeutic outcomes. The study highlights hydroxychloroquine's versatility beyond its traditional roles, showcasing its applicability in advanced drug delivery platforms.