Home > Compound List > Compound details
100-33-4 molecular structure
click picture or here to close

4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide

ChemBase ID: 618
Molecular Formular: C19H24N4O2
Molecular Mass: 340.41946
Monoisotopic Mass: 340.18992603
SMILES and InChIs

SMILES:
O(CCCCCOc1ccc(cc1)C(=N)N)c1ccc(cc1)C(=N)N
Canonical SMILES:
NC(=N)c1ccc(cc1)OCCCCCOc1ccc(cc1)C(=N)N
InChI:
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

Cite this record

CBID:618 http://www.chembase.cn/molecule-618.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-{[5-(4-carbamimidoylphenoxy)pentyl]oxy}benzene-1-carboximidamide
IUPAC Traditional name
pentamidine
Brand Name
NebuPent
Pentacarinat
Pentam
Pentam 300
Pneumopent
Synonyms
Pentamidine Isethionate
Pentamide
4, 4'-Diamidinodiphenoxypentane
PNT
1,3-bis(4-amidinophenoxy)pentane
Pentamidine
4,4'-[1,5-Pentanediylbis(oxy)]bis-benzenecarboximidamide
4,4'-Diamidino-.alpha.,.omega.-diphenoxypentane
MP 601205
NSC 9921
p,p'-(Pentamethylenedioxy)dibenzamidine
4,4'-(Pentane-1,5-diylbis(oxy))dibenzimidamide
CAS Number
100-33-4
PubChem SID
160964081
46508562
PubChem CID
4735

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -2.5083592  LogD (pH = 7.4) -2.500071 
Log P 2.322452  Molar Refractivity 120.5294 cm3
Polarizability 37.864697 Å3 Polar Surface Area 118.2 Å2
Rotatable Bonds 10  Lipinski's Rule of Five true 
Log P 1.32  LOG S -4.16 
Solubility (Water) 2.36e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Complete expand Show data source
DMSO expand Show data source
Methanol (Sparingly) expand Show data source
Apperance
Off-White Solid expand Show data source
Melting Point
198-200°C (dec.) expand Show data source
Hydrophobicity(logP)
4 expand Show data source
Storage Condition
-20°C Freezer, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Purity
95+% expand Show data source
97% expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00738 external link
Item Information
Drug Groups approved
Description 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]
Indication For the treatment of pneumonia due to Pneumocystis carinii.
Pharmacology Pentamidine is an antiprotozoal agent. It is an aromatic diamidine, and is known to have activity against Pneumocystis carinii. The exact nature of its antiprotozoal action is unknown. in vitro studies with mammalian tissues and the protozoan Crithidia oncopelti indicate that the drug interferes with nuclear metabolism producing inhibition of the synthesis of DNA, RNA, phospholipids and proteins. Little is known about the drug's pharmacokinetics. The medication is also useful in Leishmaniasis and in prophylaxis against sleeping sickness caused by Trypanosoma brucei gambiense. Hydration before treatment lessens the incidence and severity of side effects, which include liver or kidney dysfunction, hypertension, hypotension, hypoglycemia, hypocalemia, leukopenia, thrombcytopenia, anemia, and allergic reaction. It is generally well-tolerated.
Toxicity Symptoms of overdose include pain, nausea, anorexia, hypotension, fever, rash, bad taste in mouth, confusion/hallucinations, dizziness, and diarrhea.
Affected Organisms
Pneumocystis carinii
Biotransformation Hepatic.
Absorption Absorbed poorly through the gastrointestinal tract and is usually administered parenterally.
Half Life 9.1-13.2 hours
Protein Binding 69%
References
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]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals - P272500 external link
Has been widely used as a drug to treat protozoal diseases, such as malaria, amoebic dysentery and trypanosomiasis. It has also been shown to be effective for both prophylaxis of pneumocystic carinii pneumonia (PCC).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • Goa, K.L., et al.: Drugs, 33, 242 (1987)
  • • Debs, R.J., et al.: Antimicrob. Agents Chemother., 31, 37 (1987)
  • • Walzer, P.D., et al.: Antimicrob. Agents Chemother., 32, 896 (1987)
  • • Hesk, D., et al.: J. Lab. Comp. Radiopharm., 28, 11, 1309 (1990)
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle