Proguanil

• CAT Number: I013690
• CAS Number: 500-92-5
• Molecular Formula: C₁₁H₁₆ClN₅
• Molecular Weight: 253.73
• Purity: ≥95%
• Target: Parasite
• Solubility: DMSO: ≥ 33 mg/mL
• IUPAC Name: (1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine
• InChI: InChI=1S/C11H16ClN5/c1-7(2)15-10(13)17-11(14)16-9-5-3-8(12)4-6-9/h3-7H,1-2H3,(H5,13,14,15,16,17)
• InChIKey: SSOLNOMRVKKSON-UHFFFAOYSA-N
• SMILES: CC(C)N=C(N)N=C(N)NC1=CC=C(C=C1)Cl

Proguanil (CAt: I013690) is an antimalarial drug used for the prevention and treatment of malaria. It is a prodrug that is metabolized in the body to its active form, cycloguanil. Proguanil exerts its antimalarial activity by inhibiting the enzyme dihydrofolate reductase (DHFR), which is essential for the replication of the malaria parasite. By inhibiting DHFR, proguanil disrupts the synthesis of DNA and RNA in the parasite, ultimately leading to its death. Proguanil is often used in combination with other antimalarial drugs, such as atovaquone, to enhance its effectiveness and combat drug resistance. It is an important component of malaria control and prevention strategies worldwide.

Reference

1. Pudney M, et al. Atovaquone and proguanil hydrochloride: a review of nonclinical studies. J Travel Med. 1999 May;6 Suppl 1:S8-12.
2. Srivastava IK, et al. A mechanism for the synergistic antimalarial action of atovaquone and proguanil. Antimicrob Agents Chemother. 1999 Jun;43(6):1334-9.
3. Lochner M, et al. The antimalarial drug proguanil is an antagonist at 5-HT3 receptors. J Pharmacol Exp Ther. 2014 Dec;351(3):674-84.
4. Stephen AO, et al. Prolonged administration of proguanil induces reproductive toxicity in male rats. J Toxicol Sci. 2011 Oct;36(5):587-99.
5. Iguchi A, et al. The in vitro interactions and in vivo efficacy of atovaquone and proguanil against Babesia gibsoni infection in dogs. Vet Parasitol. 2013 Nov 8;197(3-4):527-33.