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MedKoo Cat#: 414746 | Name: Proguanil free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Proguanil free base is a biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.

Chemical Structure

Proguanil free base
Proguanil free base
CAS#500-92-5 (free base)

Theoretical Analysis

MedKoo Cat#: 414746

Name: Proguanil free base

CAS#: 500-92-5 (free base)

Chemical Formula: C11H16ClN5

Exact Mass: 253.1094

Molecular Weight: 253.73

Elemental Analysis: Chemical Formula: Exact Mass: Molecular Weight: Elemental Analysis: C, 52.07; H, 6.36; Cl, 13.97; N, 27.60

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 Weeks
50mg USD 800.00 2 Weeks
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Related CAS #
500-92-5 (free base) 637-32-1 (HCl)
Synonym
Proguanil free base; BRN2811599; BRN-2811599; BRN 2811599; Chloroguanide
IUPAC/Chemical Name
Biguanide, 1-(p-chlorophenyl)-5-isopropyl-
InChi Key
SSOLNOMRVKKSON-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
N=C(NC(NC(C)C)=N)NC1=CC=C(Cl)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 253.73 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Ñacata I, Early AM, Boboy J, Neafsey DE, Sáenz FE. Effects of drug pressure and human migration on antimalarial resistance in circulating Plasmodium falciparum malaria parasites in Ecuador. Res Sq [Preprint]. 2024 Aug 16:rs.3.rs-4638168. doi: 10.21203/rs.3.rs-4638168/v1. PMID: 39184096; PMCID: PMC11343295. 2: Drugs and Lactation Database (LactMed®) [Internet]. Bethesda (MD): National Institute of Child Health and Human Development; 2006–. Atovaquone and Proguanil. 2024 Jul 15. PMID: 30000538. 3: Francesconi V, Rizzo M, Pozzi C, Tagliazucchi L, Konchie Simo CU, Saporito G, Landi G, Mangani S, Carbone A, Schenone S, Santarém N, Tavares J, Cordeiro-da- Silva A, Costi MP, Tonelli M. Identification of Innovative Folate Inhibitors Leveraging the Amino Dihydrotriazine Motif from Cycloguanil for Their Potential as Anti-Trypanosoma brucei Agents. ACS Infect Dis. 2024 Aug 9;10(8):2755-2774. doi: 10.1021/acsinfecdis.4c00113. Epub 2024 Jul 2. PMID: 38953453. 4: Kuemmerle A, Gossen D, Marx MW, Lorch U, Szramowska M, Kumar A, Singh D, Singh S, Ramachandruni H, Thankachen B, Kore S, Gaaloul ME, Borghini-Fuhrer I, Chalon S. A randomized, open-label two-period crossover pilot study to evaluate the relative bioavailability in the fed state of atovaquone-proguanil (Atoguanil™) versus atovaquone-proguanil hydrochloride (Malarone®) in healthy adult participants. Naunyn Schmiedebergs Arch Pharmacol. 2024 Jun 25. doi: 10.1007/s00210-024-03245-x. Epub ahead of print. PMID: 38918235. 5: Bae J, Kim JH, Kim S, Huh J, Choi HJ. Late Parasitological Failure and Subsequent Isolated Gametocytemia of Uncomplicated Plasmodium falciparum Malaria in a Returned Traveler From Ghana, 2023. J Korean Med Sci. 2024 Jun 10;39(22):e186. doi: 10.3346/jkms.2024.39.e186. PMID: 38859743; PMCID: PMC11164651. 6: Krause PJ, Rogers R, Shah MK, Kang H, Parsonnet J, Kodama R, Vannier E. Tafenoquine for Relapsing Babesiosis: A Case Series. Clin Infect Dis. 2024 Jul 19;79(1):130-137. doi: 10.1093/cid/ciae238. PMID: 38814096; PMCID: PMC11259219. 7: Liu R, Li G, Li M, Wang B, Zhang D, Xu L, Zhao L, Liao R, Xu Q, Bei Z-C, Song Y. In vitro interaction of naphthoquine with ivermectin, atovaquone, curcumin, and ketotifen in the asexual blood stage of Plasmodium falciparum 3D7. Microbiol Spectr. 2024 Jul 2;12(7):e0063024. doi: 10.1128/spectrum.00630-24. Epub 2024 May 23. PMID: 38780257; PMCID: PMC11218538. 8: Shahid M, Wechsler B, Parameswaran V, Diaz MA. Atovaquone-Proguanil: A Promising Therapy for Persistent Relapsing Babesiosis. Case Rep Infect Dis. 2024 May 14;2024:7168928. doi: 10.1155/2024/7168928. PMID: 38774593; PMCID: PMC11108688. 9: Kaiser J, Gertzen CGW, Bernauer T, Nitsche V, Höfner G, Niessen KV, Seeger T, Paintner FF, Wanner KT, Steinritz D, Worek F, Gohlke H. Identification of ligands binding to MB327-PAM-1, a binding pocket relevant for resensitization of nAChRs. Toxicol Lett. 2024 Jul;398:91-104. doi: 10.1016/j.toxlet.2024.05.013. Epub 2024 May 18. PMID: 38768836. 10: Yongvanitchit K, Kum-Arb U, Limsalakpetch A, Im-Erbsin R, Ubalee R, Spring MD, Vesely BA, Waters N, Pichyangkul S. Superior protection in a relapsing Plasmodium cynomolgi rhesus macaque model by a chemoprophylaxis with sporozoite immunization regimen with atovaquone-proguanil followed by primaquine. Malar J. 2024 Apr 17;23(1):106. doi: 10.1186/s12936-024-04933-y. PMID: 38632607; PMCID: PMC11022453. 11: Kästner M, Hemmer CJ, Reisinger EC. Gastrointestinale Symptome als Ausdruck einer komplizierten Malaria tropica [Gastrointestinal symptoms may reflect complicated falciparum malaria]. Dtsch Med Wochenschr. 2024 Apr;149(8):454-457. German. doi: 10.1055/a-2256-6589. Epub 2024 Apr 2. PMID: 38565119. 12: Gupta N, Curcic M, Srivastava SK. Proguanil Suppresses Breast Tumor Growth In Vitro and In Vivo by Inducing Apoptosis via Mitochondrial Dysfunction. Cancers (Basel). 2024 Feb 22;16(5):872. doi: 10.3390/cancers16050872. PMID: 38473234; PMCID: PMC10931526. 13: Varadarajan R, Patel A, Salah H, Sutaria N, Barrios R, Truong L, Gaber L, El-Zaatari ZM. Myoglobin Cast Nephropathy Diagnosed on Renal Biopsy in a Patient Treated for Malarial Infection. Case Rep Nephrol. 2024 Feb 12;2024:6764335. doi: 10.1155/2024/6764335. PMID: 38375068; PMCID: PMC10876304. 14: García-Guerrero AE, Marvin RG, Blackwell AM, Sigala PA. Biogenesis of cytochromes c and c1 in the electron transport chain of malaria parasites. bioRxiv [Preprint]. 2024 Jun 1:2024.02.01.575742. doi: 10.1101/2024.02.01.575742. PMID: 38352463; PMCID: PMC10862854. 15: Kishore E, Gyabaah F, Deoker A. Polymicrobial Infection in an Immigrant Female at the United States-Mexico Border. Cureus. 2023 Dec 31;15(12):e51400. doi: 10.7759/cureus.51400. PMID: 38293001; PMCID: PMC10826631. 16: Rodriguez-Valero N, Ledesma-Carbayo MJ, Martí-Soler H, Cuadrado Sanchez D, Vladimirov A, Camprubí-Ferrer D, Pinazo MJ, Losada I, Almuedo-Riera A, Romero L, Roman A, Vera I, Roldan-Torralvo M, Ferrer E, de Alba T, Jimenez A, Gómez- Valverde JJ, Muñoz J, Luengo Oroz M. A Smartphone App for Real-Time Assessment of Malaria Prophylaxis Adverse Events. Telemed J E Health. 2024 May;30(5):1436-1442. doi: 10.1089/tmj.2023.0200. Epub 2024 Jan 12. PMID: 38215269. 17: Pierreux J, Bottieau E, Florence E, Maniewski U, Bruggemans A, Malotaux J, Martin C, Cox J, Konopnicki D, Guetens P, Verschueren J, Coppens J, Van Esbroeck M, Mutsaers M, Rosanas-Urgell A. Failure of artemether-lumefantrine therapy in travellers returning to Belgium with Plasmodium falciparum malaria: an observational case series with genomic analysis. J Travel Med. 2024 Apr 6;31(3):taad165. doi: 10.1093/jtm/taad165. PMID: 38157311. 18: Wang C, Zhang T, Wang Y, Wang Y, Pan H, Dong X, Liu S, Cao M, Wang S, Wang M, Li Y, Zhang J, Hu W. Proguanil and chlorhexidine augment the antibacterial activities of clarithromycin and rifampicin against Acinetobacter baumannii. Int J Antimicrob Agents. 2024 Feb;63(2):107065. doi: 10.1016/j.ijantimicag.2023.107065. Epub 2023 Dec 18. PMID: 38122947. 19: Okubo K, Kudo T, Yoshihara S, Nakabayashi Y, Nakauchi K, Tanaka A, Saito M, Tsujisawa A, Goda H, Yamagishi Y, Otake C, Makino K, Takahashi H, Ito K. Physiologically based pharmacokinetic model analysis of the inhibitory effect of vonoprazan on the metabolic activation of proguanil. Drug Metab Pharmacokinet. 2024 Feb;54:100537. doi: 10.1016/j.dmpk.2023.100537. Epub 2023 Nov 7. PMID: 38086197. 20: Pugliese N, Samarelli R, Lombardi R, Schiavone A, Crescenzo G, Circella E, Zizzadoro C, Lai O, Saleh MS, Prioletti M, Camarda A. A Safe and Effective Atovaquone-Proguanil Therapeutic Protocol for the Treatment of Avian Malaria by Plasmodium relictum in Snowy Owl (Bubo scandiacus). Animals (Basel). 2023 Nov 9;13(22):3457. doi: 10.3390/ani13223457. PMID: 38003076; PMCID: PMC10668658.