Skip Navigation
ChemIDplus A TOXNET DATABASE LiteBrowseAdvanced

Substance Name: Proguanil hydrochloride [USAN:USP]
RN: 637-32-1
UNII: R71Y86M0WT
InChIKey: SARMGXPVOFNNNG-UHFFFAOYSA-N

Note

  • A biguanide compound which has little antimalarial activity until metabolized in the body to the active antimalarial agent cycloguanil. The usefulness of proguanil is limited by the rapid development of drug resistance by the malarial parasite. The hydrochloride is used for the casual prophylaxis of falciparum malaria, to suppress other forms of malaria, and to reduce transmission of infection (From Martindale, The Extra Pharmacopoeia, 30th ed, p405)

Molecular Formula

  • C11-H16-Cl-N5.Cl-H

Molecular Weight

  • 290.1963
 

Classification Codes

  • Drug / Therapeutic Agent
  • Prophylaxis and Treatment of Malaria
  • Reproductive Effect
* denotes mobile formatted website

Links to Resources


Search for this InChIKey on the Web

Names and Synonyms

Name of Substance

  • Proguanil hydrochloride [USAN:USP]

MeSH Heading

  • Chloroguanide

Synonyms

  • 1-(p-Chlorophenyl)-5-isopropylbiguanide hydrochloride
  • 3359 RP
  • 336U50
  • Bigumalum
  • Chlorguanide hydrochloride
  • Chloroguanide hydrochloride
  • Chloroguanidine hydrochloride
  • Chloroquanil
  • Diguanyl
  • Drinupal hydrochloride
  • EINECS 211-283-7
  • Guanatol hydrochloride
  • GW AH7673A
  • M 4888
  • N-(4-Chlorophenyl)-N(sup5)-isopropyldiguanide hydrochloride
  • N-4-Chlorophenyl-N(sup 5)-isopropyldiguanide hydrochloride
  • NSC 12977
  • NSC 26614
  • Paludrin
  • Paludrine
  • Palusil hydrochloride
  • Proguanil HCl
  • Proguanil hydrochloride
  • SN 12,837
  • Tirian hydrochloride
  • UNII-R71Y86M0WT

Systematic Names

  • 1-(p-Chlorophenyl)-5-isopropylbiguanide hydrochloride
  • Biguanide, 1-(p-chlorophenyl)-5-isopropyl-, monohydrochloride
  • Imidodicarbonimidic diamide, N-(4-chlorophenyl)-N'-(1-methylethyl)-, monohydrochloride (9CI)
  • Proguanil hydrochloride

Registry Numbers

CAS Registry Number

  • 637-32-1

FDA UNII

  • R71Y86M0WT

Related Registry Number

  • 500-92-5 (Parent)

System Generated Number

  • 0000637321

Molecular Formulas

Molecular Formula

  • C11-H16-Cl-N5.Cl-H

Molecular Formula Fragments

  • C11-H16-Cl-N5
  • Cl-H
  • COMPONENT

Structure Descriptors

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

Smiles

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

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 oral 400mg/kg (400mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 2, Pg. 181, 1947.
guinea pig LD50 intraperitoneal 15mg/kg (15mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 474, 1960.
guinea pig LD50 intravenous 39510ug/kg (39.51mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
mouse LD50 intravenous 23mg/kg (23mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
mouse LD50 oral 27mg/kg (27mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
mouse LD50 subcutaneous 35mg/kg (35mg/kg)   Toxicology and Applied Pharmacology. Vol. 2, Pg. 474, 1960.
rabbit LD50 intravenous 44850ug/kg (44.85mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rabbit LD50 oral 150mg/kg (150mg/kg)   British Journal of Pharmacology and Chemotherapy. Vol. 2, Pg. 181, 1947.
rat LD50 intravenous 33mg/kg (33mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.
rat LD50 oral 58mg/kg (58mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 91, Pg. 157, 1947.