Human Metabolome Database Version 3.5

Showing metabocard for Pentamidine (HMDB14876)

Record Information
Version 3.5
Creation Date 2012-09-06 09:16:50 -0600
Update Date 2013-02-08 17:32:30 -0700
HMDB ID HMDB14876
Secondary Accession Numbers None
Metabolite Identification
Common Name Pentamidine
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.
Structure Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1,3-Bis(4-amidinophenoxy)pentane
  2. 4, 4'-Diamidinodiphenoxypentane
  3. Pentamide
  4. Pentamidine Isethionate
  5. PNT
Chemical Formula C19H24N4O2
Average Molecular Weight 340.4195
Monoisotopic Molecular Weight 340.189926032
IUPAC Name 4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide
Traditional IUPAC Name pentamidine
CAS Registry Number 100-33-4
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 Key XDRYMKDFEDOLFX-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Ethers
Sub Class Alkyl Aryl Ethers
Other Descriptors
  • Aromatic Homomonocyclic Compounds
  • Aromatic Homopolycyclic Compounds
  • carboxamidine(ChEBI)
Substituents
  • Carboxylic Acid Amidine
  • Imine
Direct Parent Alkyl Aryl Ethers
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction
  • Antifungal Agents
  • Antiprotozoal Agents
  • Trypanocidal Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 186.0 °C (decomposes) Not Available
Boiling Point Not Available Not Available
Water Solubility 2.36e-02 g/L Not Available
LogP 4 Not Available
Predicted Properties
Property Value Source
LogP 1.32 ALOGPS
LogP 2.32 ChemAxon
LogS -4.16 ALOGPS
pKa (strongest basic) 12.13 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 118.2 A2 ChemAxon
Rotatable Bond Count 10 ChemAxon
Refractivity 120.53 ChemAxon
Polarizability 38.85 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00738
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Taking drug identified by DrugBank entry DB00738
  • Not Applicable
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB00738 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID Not Available
KNApSAcK ID Not Available
Chemspider ID 4573 Link_out
KEGG Compound ID C07420 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Pentamidine Link_out
NuGOwiki Link HMDB14876 Link_out
Metagene Link HMDB14876 Link_out
METLIN ID Not Available
PubChem Compound 4735 Link_out
PDB ID PNT Link_out
ChEBI ID 45081 Link_out
References
Synthesis Reference Not 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 Link_out

Enzymes
Name: Cytochrome P450 4A11
Reactions: Not Available
Gene Name: CYP4A11
Uniprot ID: Q02928 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C19
Reactions: Not Available
Gene Name: CYP2C19
Uniprot ID: P33261 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 3A5
Reactions: Not Available
Gene Name: CYP3A5
Uniprot ID: P20815 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A1
Reactions: Not Available
Gene Name: CYP1A1
Uniprot ID: P04798 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2C8
Reactions: Not Available
Gene Name: CYP2C8
Uniprot ID: P10632 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: tRNA (cytosine(38)-C(5))-methyltransferase
Reactions: Not Available
Gene Name: TRDMT1
Uniprot ID: O14717 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA