Pentamidine (CHEM002528)

Record Information
Version1.0
Creation Date2009-07-30 17:59:04 UTC
Update Date2026-05-14 16:47:31 UTC
Accession NumberCHEM002528
Identification
Common NamePentamidine
ClassSmall Molecule
Description
Pentamidine is only found in individuals that have used or taken this drug. It is an 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. [PubChem] The mode of action of pentamidine is not fully understood. It is thought that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids, and proteins.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Antifungal Agent
  • Antiprotozoal Agent
  • Drug
  • Ether
  • Metabolite
  • Organic Compound
  • Synthetic Compound
  • Trypanocidal Agent
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,5-Bis(4-amidinophenoxy)pentaneChEBI
4,4'-(1,5-Pentanediylbis(oxy))bis-benzenecarboximidamideChEBI
4,4'-(Pentamethylenedioxy)dibenzamidineChEBI
4,4'-DiamidinodiphenoxypentaneChEBI
p,P'-(pentamethylenedioxy)dibenzamidineChEBI
PentamidinChEBI
LomidineKegg
1,3-Bis(4-amidinophenoxy)pentaneHMDB
4, 4'-DiamidinodiphenoxypentaneHMDB
PentamideHMDB
Pentamidine isethionateHMDB
PNTHMDB
JHC Brand OF pentamidine isethionateHMDB
PentacarinatHMDB
Rhône-poulenc rorer brand OF pentamidine isethionateHMDB
American pharmaceutical partners brand 1 OF pentamidine isethionateHMDB
American pharmaceutical partners brand 2 OF pentamidine isethionateHMDB
DiamidineHMDB
GlaxoSmithKline brand OF pentamidine isethionateHMDB
NebuPentHMDB
PentamHMDB
Sicor brand OF pentamidine isethionateHMDB
Aventis brand OF pentamidine isethionateHMDB
Pentamidine mesylateHMDB
Chemical FormulaC19H24N4O2
Average Molecular Mass340.420 g/mol
Monoisotopic Mass340.190 g/mol
CAS Registry Number100-33-4
IUPAC Name4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide
Traditional Namepentamidine
SMILESNC(=N)C1=CC=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1
InChI IdentifierInChI=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)
InChI KeyXDRYMKDFEDOLFX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Carboximidamide
  • Ether
  • Carboxylic acid amidine
  • Amidine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point186.0°C (decomposes)
Boiling PointNot Available
SolubilityComplete
Predicted Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP1.32ALOGPS
logP2.32ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)12.13ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.2 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity120.53 m³·mol⁻¹ChemAxon
Polarizability38.85 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureAbsorbed poorly through the gastrointestinal tract and is usually administered parenterally.
Mechanism of ToxicityThe mode of action of pentamidine is not fully understood. It is thought that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids, and proteins.
MetabolismHepatic. Half Life: 9.1-13.2 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of pneumonia due to Pneumocystis carinii.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include pain, nausea, anorexia, hypotension, fever, rash, bad taste in mouth, confusion/hallucinations, dizziness, and diarrhea.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00738
HMDB IDHMDB0014876
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDPNT
Wikipedia LinkPentamidine
Chemspider ID4573
ChEBI ID45081
PubChem Compound ID4735
Kegg Compound IDC07420
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Nguewa PA, Fuertes MA, Cepeda V, Iborra S, Carrion J, Valladares B, Alonso C, Perez JM: Pentamidine is an antiparasitic and apoptotic drug that selectively modifies ubiquitin. Chem Biodivers. 2005 Oct;2(10):1387-400.
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