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Proguanil hydrochloride

CAT: 0931-T4382-01Size: 1 mL - 10 mM (in DMSO)Dry Ice: NoHazardous: No
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CAT#:0931-T4382-01Size:1 mL - 10 mM (in DMSO)
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CAS Number
637-32-1
Target
Dehydrogenase, Parasite, DNA/RNA Synthesis, Antifolate
Related Pathways
Metabolism, Microbiology/Virology, Cell Cycle/Checkpoint, DNA Damage/DNA Repair
Purity
0.9903
Bioactivity
Proguanil hydrochloride (Chloroquanil) is a biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.Upon hydrolysis, Proguanil hydrochloride 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.
Smiles
Cl.Clc1ccc(NC(=N)NC(=N)NC(C)C)cc1
Molecular Formula
C11H17Cl2N5
Molecular Weight
290.19
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Proguanil Hydrochloride

Proguanil Hydrochloride is the hydrochloride salt form of proguanil, a synthetic biguanide derivative of pyrimidine and an folate antagonist with antimalarial property. 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 (DHFR-TS) of plasmodium parasite, thereby disrupting deoxythymidylate synthesis and ultimately blocking DNA and protein synthesis in the parasite.

CAS Number637-32-1
PubChem CID9570076
IUPAC Name(1E)-1-[amino-(4-chloroanilino)methylidene]-2-propan-2-ylguanidine;hydrochloride
Molecular FormulaC11H17Cl2N5
Molecular Weight290.19
Topological Polar Surface Area88.8
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count1
Rotatable Bond Count4
Heavy Atom Count18
Formal Charge0
Complexity292
SMILES
CC(C)N=C(N)/N=C(\N)/NC1=CC=C(C=C1)Cl.Cl
InChI
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
InChIKey
SARMGXPVOFNNNG-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Proguanil Hydrochloride
CAS: 637-32-1
CID: 9570076
Formula: C11H17Cl2N5
MW: 290.19
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight290.19
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count1
Rotatable Bond Count4
Exact Mass289.0861010
Monoisotopic Mass289.0861010
Topological Polar Surface Area88.8 Ų
Heavy Atom Count18
Formal Charge0
Complexity292
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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