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Substance Name: Pentamidine [INN:BAN:DCF]
RN: 100-33-4
UNII: 673LC5J4LQ
InChIKey: XDRYMKDFEDOLFX-UHFFFAOYSA-N

Note

  • Antiprotozoal agent effective in trypanosomiasis, leishmaniasis, and some fungal infections; used in treatment of PNEUMOCYSTIS pneumonia in HIV-infected patients. It may cause diabetes mellitus, central nervous system damage, and other toxic effects.

Molecular Formula

  • C19-H24-N4-O2

Molecular Weight

  • 340.425
 

Classification Codes

  • Anti-Infective Agents
  • Antifungal Agents
  • Antiparasitic Agents
  • Antiprotozoal Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Trypanocidal Agents

Names and Synonyms

Name of Substance

  • Pentamidine
  • Pentamidine [INN:BAN:DCF]

MeSH Heading

  • Pentamidine

Synonyms

  • 4,4'-(1,5-Pentanediylbis(oxy))bis-benzenecarboximidamide
  • 4,4'-(Pentamethylenedioxy)dibenzamidine
  • 4,4'-Diamidinodiphenoxypentane
  • 4-10-00-00447 (Beilstein Handbook Reference)
  • BRN 3159790
  • CCRIS 3825
  • EINECS 202-841-0
  • HSDB 7474
  • MB 800 [as isethionate]
  • Nebupent
  • Nebupent (as isethionate)
  • NSC 9921
  • p,p'-(Pentamethylene-dioxy)bis-benzamidine
  • p,p'-(Pentamethylenedioxy)dibenzamidine
  • Pentacarinat
  • Pentacarinat (as isethionate)
  • Pentam 300
  • Pentam 300 (as isethionate)
  • Pentamidina
  • Pentamidina [DCIT]
  • Pentamidine
  • Pentamidinum
  • Pentamidinum [INN-Latin]
  • RP 2512 [as isethionate]
  • UNII-673LC5J4LQ

Systematic Names

  • 4,4'-(Pentamethylenedioxy)dibenzamidine
  • Benzamidine, 4,4'-(pentamethylenedioxy)di-
  • Benzenecarboximidamide, 4,4'-(1,5-pentanediylbis(oxy))bis- (9CI)
  • Pentamidine

Registry Numbers

CAS Registry Number

  • 100-33-4

FDA UNII

  • 673LC5J4LQ

System Generated Number

  • 0000100334

Structure Descriptors

InChI

1S/C19H24N4O2/c20-18(21)14-4-8-16(9-5-14)24-12-2-1-3-13-25-17-10-6-15(7-11-17)19(22)23/h4-11H,1-3,12-13H2,(H3,20,21)(H3,22,23)

InChIKey

XDRYMKDFEDOLFX-UHFFFAOYSA-N

Smiles

c1(ccc(OCCCCCOc2ccc(C(N)=N)cc2)cc1)C(N)=N

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 subcutaneous 100mg/kg (100mg/kg)   Bulletin de la Societe Chimique de France. Vol. -, Pg. 376, 1968.
man TDLo intramuscular 28mg/kg/1W-I (28mg/kg)   Archives of Internal Medicine. Vol. 145, Pg. 2247, 1985.
man TDLo intramuscular 28mg/kg/1W-I (28mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Archives of Internal Medicine. Vol. 145, Pg. 2247, 1985.
man TDLo parenteral 4mg/kg/3D (4mg/kg)   Lancet. Vol. 246, Pg. 338, 1944.
man TDLo parenteral 4mg/kg/3D (4mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Lancet. Vol. 246, Pg. 338, 1944.
mouse LD50 intraperitoneal 50mg/kg (50mg/kg)   Journal of Medicinal Chemistry. Vol. 18, Pg. 794, 1975.
women TDLo parenteral 4mg/kg (4mg/kg) ENDOCRINE: HYPOGLYCEMIA Annals of Internal Medicine. Vol. 99, Pg. 128, 1983.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 2.790 (none)   EST
Atmospheric OH Rate Constant 1.17E-10 cm3/molecule-sec 25 EST

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