1-3-(4-chlorophenyl)carbamimidamido-N-(propan-2-yl)methanimidamide hydrochloride

• ChemBase ID: 154740
• Molecular Formular: C11H17Cl2N5
• Molecular Mass: 290.19218
• Monoisotopic Mass: 289.08610093
• SMILES: CC(C)NC(=N)NC(=N)Nc1ccc(cc1)Cl.Cl
• Canonical SMILES: CC(NC(=N)NC(=N)Nc1ccc(cc1)Cl)C.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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-3-(4-chlorophenyl)carbamimidamido-N-(propan-2-yl)methanimidamide hydrochloride
• IUPAC Traditional name: proguanil hydrochloride
• Synonyms: N-(4-Chlorophenyl)-N'-(1-methylethyl)-imidodicarbonimidic Diamide Hydrochloride; 1-(p-Chlorophenyl)-5-isopropylbiguanide Hydrochloride; Bigumal; Chlorguanid; Chloroguanide; Paludrin; Proguanil; M-4888; Chlorguanide Hydrochloride; Chlorguanide; N1-(4-Chlorophenyl)-N5-isopropylbiguanide; Proguanil hydrochloride

Database IDs

• CAS Number: 637-32-1
• EC Number: 211-283-7
• MDL Number: MFCD01732193
• PubChem SID: 162248878
• PubChem CID: 9570076

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 5
• LogD (pH = 5.5): -2.2630687
• LogD (pH = 7.4): -0.7753296
• Log P: 2.3811002
• Molar Refractivity: 91.6532 cm^3
• Polarizability: 26.265787 Å^3
• Polar Surface Area: 83.79 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: acetonitrile: water: ~1 mg/mL (60/40); DMSO; Methanol
• Apperance: solid; White Solid
• Melting Point: 249-251°C

Safety Information

• Storage Condition: -20°C Freezer; desiccated
• RTECS: DU1750000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (HPLC)
• Empirical Formula (Hill Notation): C11H16ClN5·HCl

DETAILS

Sigma Aldrich - G7048

Biochem/physiol Actions
Chlorguanide (proguanil) is combined with atovaquone for malaria prophylaxis. The two compounds act synergistically to inhibit the plasmodial dihydrofolate reductase (DHFR) and interrupt the electron transport chain.1 Mutations in DHFR account for the development of resistant strains.2

Toronto Research Chemicals - C329500

Antimalarial.

REFERENCES

• Schmidt., et al.: J. Pharmacol. Exp. Ther., 90, 233 (1947)
• Cortese, J., et al.: J. Infect. Dis., 186, 999 (1947)
• Lim, P., et al.: Antimicrob. Agents Chemother., 47, 87 (1947)
• Sidhu, A., et al.: Mol. Microbiol., 57, 913 (1947)