Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2013-02-09 00:33:19 UTC
HMDB IDHMDB15263
Secondary Accession NumbersNone
Metabolite Identification
Common NameProguanil
DescriptionProguanil is a prophylactic antimalarial drug, which works by stopping the malaria parasite, Plasmodium falciparum and Plasmodium vivax, from reproducing once it is in the red blood cells. It does this by inhibiting the enzyme, dihydrofolate reductase, which is involved in the reproduction of the parasite.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H16ClN5
Average Molecular Weight253.731
Monoisotopic Molecular Weight253.109423244
IUPAC Name(E)-1-({amino[(4-chlorophenyl)amino]methylidene}amino)-N'-(propan-2-yl)methenimidamide
Traditional IUPAC Nameproguanil
CAS Registry Number500-92-5
SMILES
CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1
InChI Identifier
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)
InChI KeySSOLNOMRVKKSON-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassGuanidines
Sub ClassBiguanides
Other Descriptors
  • Chlorobenzenes
  • Organic Compounds
  • biguanides(ChEBI)
  • organochlorine compound(ChEBI)
Substituents
  • Aryl Chloride
  • Organochloride
  • Polyamine
Direct ParentBiguanides
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Antimalarials
  • Antimetabolites
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility2.86e-01 g/LNot Available
LogP1.8Not Available
Predicted Properties
PropertyValueSource
water solubility0.29 g/LALOGPS
logP1.9ALOGPS
logP1.89ChemAxon
logS-3ALOGPS
pKa (strongest acidic)19.77ChemAxon
pKa (strongest basic)10.12ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area88.79ChemAxon
rotatable bond count2ChemAxon
refractivity71.07ChemAxon
polarizability26.84ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01131
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01131
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01131
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4754
KEGG Compound IDC07631
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkProguanil
NuGOwiki LinkHMDB15263
Metagene LinkHMDB15263
METLIN IDNot Available
PubChem Compound4923
PDB IDNot Available
ChEBI ID8455
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
DHFR
Uniprot ID:
P00374
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C9
Uniprot ID:
P11712
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2E1
Uniprot ID:
P05181
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP1A2
Uniprot ID:
P05177