Record Information
Version3.6
Creation Date2012-09-06 15:16:50 UTC
Update Date2013-02-09 00:32:30 UTC
HMDB IDHMDB14876
Secondary Accession NumbersNone
Metabolite Identification
Common NamePentamidine
DescriptionPentamidine 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.
Structure
Thumb
Synonyms
  1. 1,3-Bis(4-amidinophenoxy)pentane
  2. 4, 4'-Diamidinodiphenoxypentane
  3. Pentamide
  4. Pentamidine Isethionate
  5. PNT
Chemical FormulaC19H24N4O2
Average Molecular Weight340.4195
Monoisotopic Molecular Weight340.189926032
IUPAC Name4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide
Traditional IUPAC Namepentamidine
CAS Registry Number100-33-4
SMILES
NC(=N)C1=CC=C(OCCCCCOC2=CC=C(C=C2)C(N)=N)C=C1
InChI Identifier
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)
InChI KeyXDRYMKDFEDOLFX-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassEthers
Sub ClassAlkyl Aryl Ethers
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • carboxamidine(ChEBI)
Substituents
  • Carboxylic Acid Amidine
  • Imine
Direct ParentAlkyl Aryl Ethers
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
Biofunction
  • Antifungal Agents
  • Antiprotozoal Agents
  • Trypanocidal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point186.0 °C (decomposes)Not Available
Boiling PointNot AvailableNot Available
Water Solubility2.36e-02 g/LNot Available
LogP4Not Available
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 area118.2ChemAxon
rotatable bond count10ChemAxon
refractivity120.53ChemAxon
polarizability38.85ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00738
  • Not Applicable
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00738
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00738
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4573
KEGG Compound IDC07420
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPentamidine
NuGOwiki LinkHMDB14876
Metagene LinkHMDB14876
METLIN IDNot Available
PubChem Compound4735
PDB IDPNT
ChEBI ID45081
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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. Pubmed: 17191940

Enzymes

Gene Name:
CYP4A11
Uniprot ID:
Q02928
Gene Name:
CYP3A4
Uniprot ID:
P08684
Gene Name:
CYP2C19
Uniprot ID:
P33261
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP3A5
Uniprot ID:
P20815
Gene Name:
CYP1A1
Uniprot ID:
P04798
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
CYP2C8
Uniprot ID:
P10632