Proguanil Hydrochloride
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MedKoo CAT#: 318580

CAS#: 637-32-1 (HCl)

Description: 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

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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: 0.00
Molecular Weight: 290.190
Elemental Analysis: C, 45.53; H, 5.90; Cl, 24.43; N, 24.13

Price and Availability

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10mg USD 300 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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO, not in water 0.0 100.00

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: 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.
PubMed PMID: 26434663.


2: 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. PubMed PMID: 21787658.


3: 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. PubMed PMID: 18628561.


4: Looareesuwan S, Wilairatana P, Glanarongran R, Indravijit KA, Supeeranontha L,
Chinnapha S, Scott TR, Chulay JD. Atovaquone and proguanil hydrochloride followed
by primaquine for treatment of Plasmodium vivax malaria in Thailand. Trans R Soc
Trop Med Hyg. 1999 Nov-Dec;93(6):637-40. PubMed PMID: 10717754.


5: van der Berg JD, Duvenage CS, Roskell NS, Scott TR. Safety and efficacy of
atovaquone and proguanil hydrochloride for the prophylaxis of Plasmodium
falciparum malaria in South Africa. Clin Ther. 1999 Apr;21(4):741-9. PubMed PMID:
10363739.


6: Kremsner PG, Looareesuwan S, Chulay JD. Atovaquone and proguanil hydrochloride
for treatment of malaria. J Travel Med. 1999 May;6 Suppl 1:S18-20. Review. PubMed
PMID: 23573548.


7: Pudney M, Gutteridge W, Zeman A, Dickins M, Woolley JL. Atovaquone and
proguanil hydrochloride: a review of nonclinical studies. J Travel Med. 1999
May;6 Suppl 1:S8-12. Review. PubMed PMID: 23573546.


8: Shanks GD. New options for the prevention and treatment of malaria: focus on
the role of atovaquone and proguanil hydrochloride. J Travel Med. 1999 May;6
Suppl 1:S1. PubMed PMID: 23573544.


9: Houben MH, Hoorntje SJ. Pancytopenia due to Paludrine (proguanil
hydrochloride). Nephron. 1995;71(3):368. PubMed PMID: 8569995.


10: GUNTHER CE. Proguanil hydrochloride (paludrine) in the prevention and
treatment of malaria in New Guinea. Trans R Soc Trop Med Hyg. 1951
Feb;44(4):473-8. PubMed PMID: 14817823.


11: 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. PubMed PMID: 15335195.


12: 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. PubMed PMID: 12649236; PubMed Central PMCID: PMC151974.


13: Atovaquone and proguanil hydrochloride. Am J Health Syst Pharm. 2000 Dec
1;57(23):2165-6. PubMed PMID: 11127694.


14: Anabwani G, Canfield CJ, Hutchinson DB. Combination atovaquone and proguanil
hydrochloride vs. halofantrine for treatment of acute Plasmodium falciparum
malaria in children. Pediatr Infect Dis J. 1999 May;18(5):456-61. PubMed PMID:
10353520.


15: Looareesuwan S, Chulay JD, Canfield CJ, Hutchinson DB. Malarone (atovaquone
and proguanil hydrochloride): a review of its clinical development for treatment
of malaria. Malarone Clinical Trials Study Group. Am J Trop Med Hyg. 1999
Apr;60(4):533-41. Review. PubMed PMID: 10348225.


16: Shanks GD, Kremsner PG, Sukwa TY, van der Berg JD, Shapiro TA, Scott TR,
Chulay JD; Malarone Clinical Trials Study Group. Atovaquone and proguanil
hydrochloride for prophylaxis of malaria. J Travel Med. 1999 May;6 Suppl 1:S21-7.
Review. PubMed PMID: 23573549.


17: Beerahee M. Clinical pharmacology of atovaquone and proguanil hydrochloride.
J Travel Med. 1999 May;6 Suppl 1:S13-7. Review. PubMed PMID: 23573547.


18: Kolawole JA, Mustapha A, Abdul-Aguye I, Ochekpe N. Effect of temperature on
chlorproguanil and proguanil hydrochloride solutions: a chemical stability study.
J Pharm Biomed Anal. 1996 Apr;14(6):685-93. PubMed PMID: 8807543.


19: Jamaludin A, Mohamad M, Navaratnam V, Yeoh PY, Wernsdorfer WH. Multiple-dose
pharmacokinetic study of proguanil and cycloguanil following 12-hourly
administration of 100 mg proguanil hydrochloride. Trop Med Parasitol. 1990
Sep;41(3):268-72. PubMed PMID: 2255843.


20: Nevill CG, Watkins WM, Carter JY, Munafu CG. Comparison of mosquito nets,
proguanil hydrochloride, and placebo to prevent malaria. BMJ. 1988 Aug
6;297(6645):401-3. PubMed PMID: 3044515; PubMed Central PMCID: PMC1834306.