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Substance Name: Proguanil [INN:BAN]
RN: 500-92-5
UNII: S61K3P7B2V
InChIKey: SSOLNOMRVKKSON-UHFFFAOYSA-N

Note

  • A biguanide compound which metabolizes in the body to form cycloguanil, an anti-malaria agent.

Molecular Formula

  • C11-H16-Cl-N5

Molecular Weight

  • 253.7354
 

Classification Codes

  • Anti-Infective Agents
  • Antimalarials
  • Antimetabolites
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Noxae
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Chloroguanide
  • Proguanil [INN:BAN]

MeSH Heading

  • Proguanil

Synonyms

  • 1-(p-Chlorophenyl)-5-isopropylbiguanide
  • 1-Isopropyl-5-(4-chlorophenyl)biguanide
  • 4-12-00-01198 (Beilstein Handbook Reference)
  • Bigumal
  • BRN 2811599
  • Chlorguanid
  • Chlorguanide
  • Chloroguanide
  • EINECS 207-915-6
  • N1-p-Chlorophenyl-N5-isopropylbiguanide
  • Paludrin
  • Proguanil
  • Proguanile
  • Proguanile [DCIT]
  • Proguanilum
  • Proguanilum [INN-Latin]
  • UNII-S61K3P7B2V

Systematic Names

  • Biguanide, 1-(p-chlorophenyl)-5-isopropyl-
  • Imidodicarbonimidic diamide, N-(4-chlorophenyl)-N'-(1-methylethyl)-
  • Proguanil

Mixture Name

  • Malarone

Registry Numbers

CAS Registry Number

  • 500-92-5

FDA UNII

  • S61K3P7B2V

Other Registry Number

  • 46920-30-3

Related Registry Number

  • 637-32-1 (hydrochloride)

System Generated Number

  • 0000500925

Structure Descriptors

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)

InChIKey

SSOLNOMRVKKSON-UHFFFAOYSA-N

Smiles

CC(C)NC(=N)NC(=N)Nc1ccc(cc1)Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LDLo intravenous 60mg/kg (60mg/kg)   Compilation of LD50 Values of New Drugs.
chicken LDLo oral 400mg/kg (400mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LD50 intravenous 22mg/kg (22mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 4, Pg. 14, 1949.
mouse LDLo intraperitoneal 25mg/kg (25mg/kg)   Compilation of LD50 Values of New Drugs.
mouse LDLo oral 50mg/kg (50mg/kg)   Compilation of LD50 Values of New Drugs.
rabbit LD50 intraperitoneal 50mg/kg (50mg/kg)   Compilation of LD50 Values of New Drugs.
rabbit LD50 oral 150mg/kg (150mg/kg)   Compilation of LD50 Values of New Drugs.
rat LD50 intraperitoneal 15mg/kg (15mg/kg)   "International Congress of Chemotherapy, Proceedings of the 3rd Congress, 1963," Kuemmerle, H.P., and Prezios, P., Stuttgart, Fed. Rep. Ger., Georg Thieme Verlag, 1964Vol. -, Pg. 367, 1964.
rat LDLo intravenous 40mg/kg (40mg/kg)   Compilation of LD50 Values of New Drugs.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 129 deg C   EXP
log P (octanol-water) 2.53 (none)   EXP
Water Solubility 156 mg/L 25 EST
Vapor Pressure 7.40E-07 mm Hg 25 EST
Henry's Law Constant 2.51E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 1.57E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.