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MedKoo Cat#: 318580 | Name: Proguanil Hydrochloride
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Description:

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

Proguanil Hydrochloride is a biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.Upon hydrolysis, proguanil is converted to its active cyclic triazine metabolite, cycloguanil, by a cytochrome P450 dependent reaction. Cycloguanil selectively inhibits the bifunctional dihydrofolate reductase-thymidylate synthase of plasmodium parasite, thereby disrupting deoxythymidylate synthesis and ultimately blocking DNA and protein synthesis in the parasite.

Chemical Structure

Proguanil Hydrochloride
Proguanil Hydrochloride
CAS#637-32-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 318580

Name: Proguanil Hydrochloride

CAS#: 637-32-1 (HCl)

Chemical Formula: C11H17Cl2N5

Exact Mass: 0.0000

Molecular Weight: 290.19

Elemental Analysis: C, 45.53; H, 5.90; Cl, 24.43; N, 24.13

Price and Availability

Size Price Availability Quantity
10mg USD 450.00 2 Weeks
50mg USD 850.00 2 Weeks
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Related CAS #
500-92-5 (free base) 637-32-1 (HCl)
Synonym
Proguanil Hydrochloride; Paludrine; Chloroguanide hydrochloride; Proguanil HCl; Chloroquanil; Zeneca Brand of Chloroguanide Hydrochloride; Chloroguanide Hydrochloride; Hydrochloride, Chloroguanide; Hydrochloride, Proguanil;
IUPAC/Chemical Name
(1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;hydrochloride
InChi Key
SARMGXPVOFNNNG-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H16ClN5.ClH/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);1H
SMILES Code
CC(C)N=C(N)N=C(N)NC1=CC=C(C=C1)Cl.Cl
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
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Solvent mg/mL mM
Solubility
Soluble in DMSO, not in water 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 290.19 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: 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. 2: Yin M, Zhang HB, Tao Y, Yao JM, Liu H, Win HH, Huo LL, Jiang B, Chen JX. Optimization of an Evaluation Method for Anti-Babesia microti Drug Efficacy. Acta Trop. 2022 Jan;225:106179. doi: 10.1016/j.actatropica.2021.106179. Epub 2021 Oct 8. PMID: 34627758. 3: Elmehankar MS, Elhenawy AA, Aboukamar WA, Elzoheiry MA, Nabih N. Histopathological and ultrastructural assessment of atovaquone-proguanil hydrochloride combination in chronic murine toxoplasmosis. Ultrastruct Pathol. 2021 Nov 2;45(6):376-383. doi: 10.1080/01913123.2021.1984349. Epub 2021 Oct 1. PMID: 34595988. 4: Anderson S, Windscheffel J, Gunning K. Covid Media Misguidance: A Case Report Highlighting the Influence of Media on Patient Medication Decision Making. Innov Pharm. 2021 Jan 8;12(1):10.24926/iip.v12i1.3555. doi: 10.24926/iip.v12i1.3555. PMID: 34007686; PMCID: PMC8102979. 5: Lee SH, Kwak D, Kim KT. The first clinical cases of Haemoproteus infection in a snowy owl (Bubo scandiacus) and a goshawk (Accipiter gentilis) at a zoo in the Republic of Korea. J Vet Med Sci. 2018 Aug 10;80(8):1255-1258. doi: 10.1292/jvms.18-0072. Epub 2018 Jun 22. PMID: 29937458; PMCID: PMC6115260. 6: Plöger GF, Abrahamsson B, Cristofoletti R, Groot DW, Langguth P, Mehta MU, Parr A, Polli JE, Shah VP, Tajiri T, Dressman JB. Biowaiver Monographs for Immediate Release Solid Oral Dosage Forms: Proguanil Hydrochloride. J Pharm Sci. 2018 Jul;107(7):1761-1772. doi: 10.1016/j.xphs.2018.03.009. Epub 2018 Mar 20. PMID: 29571740. 7: Darade A, Pathak S, Sharma S, Patravale V. Atovaquone oral bioavailability enhancement using electrospraying technology. Eur J Pharm Sci. 2018 Jan 1;111:195-204. doi: 10.1016/j.ejps.2017.09.051. Epub 2017 Sep 30. PMID: 28974387. 8: Erhardt J, Frank M. Rezidivierende Fieberschübe 6 Monate nach Afrikareise - Fall 4 / 2015 [13-year old girl with fever 6 months after returning from sub- Saharan Africa]. Dtsch Med Wochenschr. 2015 Oct;140(21):1614. German. doi: 10.1055/s-0041-103556. Epub 2015 Oct 21. PMID: 26488102. 9: Dinter D, Gajski G, Domijan AM, Garaj-Vrhovac V. Cytogenetic and oxidative status of human lymphocytes after exposure to clinically relevant concentrations of antimalarial drugs atovaquone and proguanil hydrochloride in vitro. Fundam Clin Pharmacol. 2015 Dec;29(6):575-85. doi: 10.1111/fcp.12153. Epub 2015 Oct 5. PMID: 26434663. 10: Gajski G, Dinter D, Garaj-Vrhovac V. In vitro effect of the antimalarial drug proguanil hydrochloride on viability and DNA damage in human peripheral blood lymphocytes. Environ Toxicol Pharmacol. 2010 Nov;30(3):257-63. doi: 10.1016/j.etap.2010.07.001. Epub 2010 Jul 16. PMID: 21787658. 11: Remich SA, Otieno W, Polhemus ME, Ogutu B, Walsh DS. Bullous erythema multiforme after treatment with Malarone, a combination antimalarial composed of atovaquone and proguanil hydrochloride. Trop Doct. 2008 Jul;38(3):190-1. doi: 10.1258/td.2007.070192. PMID: 18628561. 12: Boggild AK, Parise ME, Lewis LS, Kain KC. Atovaquone-proguanil: report from the CDC expert meeting on malaria chemoprophylaxis (II). Am J Trop Med Hyg. 2007 Feb;76(2):208-23. PMID: 17297027. 13: Happi CT, Gbotosho GO, Folarin OA, Milner D, Sarr O, Sowunmi A, Kyle DE, Milhous WK, Wirth DF, Oduola AM. Confirmation of emergence of mutations associated with atovaquone-proguanil resistance in unexposed Plasmodium falciparum isolates from Africa. Malar J. 2006 Oct 4;5:82. doi: 10.1186/1475-2875-5-82. PMID: 17020611; PMCID: PMC1594577. 14: Soto J, Toledo J, Luzz M, Gutierrez P, Berman J, Duparc S. Randomized, double-blind, placebo-controlled study of Malarone for malaria prophylaxis in non-immune Colombian soldiers. Am J Trop Med Hyg. 2006 Sep;75(3):430-3. PMID: 16968916. 15: Patel SN, Kain KC. Atovaquone/proguanil for the prophylaxis and treatment of malaria. Expert Rev Anti Infect Ther. 2005 Dec;3(6):849-61. doi: 10.1586/14787210.3.6.849. PMID: 16307498. 16: Uchiyama H, Okamoto A, Sato K, Yamada T, Murakami S, Yoneda S, Kajita Y, Tegoshi T, Arizono N. Quinine-resistant severe falciparum malaria effectively treated with atovaquone and proguanil hydrochloride combination therapy. Intern Med. 2004 Jul;43(7):624-7. doi: 10.2169/internalmedicine.43.624. PMID: 15335195. 17: Anteyi EA, Liman HM, Gbaji A. Malaria prophylaxis in post renal transplant recipients in the tropics: is it necessary? Cent Afr J Med. 2003 May- Jun;49(5-6):63-6. PMID: 15214285. 18: Emberger M, Lechner AM, Zelger B. Stevens-Johnson syndrome associated with Malarone antimalarial prophylaxis. Clin Infect Dis. 2003 Jul 1;37(1):e5-7. doi: 10.1086/375073. Epub 2003 Jun 18. PMID: 12830430. 19: Färnert A, Lindberg J, Gil P, Swedberg G, Berqvist Y, Thapar MM, Lindegårdh N, Berezcky S, Björkman A. Evidence of Plasmodium falciparum malaria resistant to atovaquone and proguanil hydrochloride: case reports. BMJ. 2003 Mar 22;326(7390):628-9. doi: 10.1136/bmj.326.7390.628. PMID: 12649236; PMCID: PMC151974. 20: Butcher GA, Sinden RE. Persistence of atovaquone in human sera following treatment: inhibition of Plasmodium falciparum development in vivo and in vitro. Am J Trop Med Hyg. 2003 Jan;68(1):111-4. PMID: 12556158.