Pentamidine

Base Information

• Chemical Name: Pentamidine
• CAS No.: 100-33-4
• Molecular Formula: C19H24N4O2
• Molecular Weight: 466.558
• Hs Code.: 2925290090
• European Community (EC) Number: 202-841-0,205-424-1
• NSC Number: 9921
• UNII: 673LC5J4LQ
• DSSTox Substance ID: DTXSID7023431
• Nikkaji Number: J5.512C
• Wikipedia: Pentamidine
• Wikidata: Q416206
• NCI Thesaurus Code: C731
• RXCUI: 7994
• Pharos Ligand ID: ZWTYU7KAJWPZ
• Metabolomics Workbench ID: 43042
• ChEMBL ID: CHEMBL55
• Mol file: 100-33-4.mol

Synonyms:Diamidine;Lomidine;NebuPent;Pentacarinat;Pentam;Pentamidin;Pentamidine;Pentamidine Isethionate;Pentamidine Mesylate

Chemical Property of Pentamidine

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 1.06E-11mmHg at 25°C
• Melting Point: 186 °C (dec.)
• Refractive Index: 1.6620 (estimate)
• Boiling Point: 539.4 °C at 760 mmHg
• PKA: pKa 11.4 (Uncertain)
• Flash Point: 280 °C
• PSA: 118.20000
• Density: 1.2 g/cm³
• LogP: 4.48290
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: DMSO, Methanol (Sparingly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 10
• Exact Mass: 340.18992602
• Heavy Atom Count: 25
• Complexity: 376

Purity/Quality:

97% ^*data from raw suppliers

Pentamidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antifungal/Anthelmintic Agents
• Canonical SMILES: C1=CC(=CC=C1C(=N)N)OCCCCCOC2=CC=C(C=C2)C(=N)N
• Recent ClinicalTrials: Pentamidine + Salvage Chemo for Relapsed/Refractory Classical Hodgkin Lymphoma
• Recent EU Clinical Trials: A Phase IIa Exploratory Study of OCZ103-OS in Combination with Platinum-Gemcitabine based Doublet First Line Therapy in Stage IV Non-Small Cell Lung Cancer (NSCLC) Patients
• Indications: Trypanosomiasis In the treatment of early-stage Trypanosoma brucei gambiense. Leishmaniasis In the treatment of patients with visceral, diffuse cutaneous, or mucocutaneous leishmaniasis due to L. aethiopica and L. guyanensis who are unresponsive or intolerant to antimony preparations. Pneumocystis carinii pneumonia Pentamidine is also used in the prophylaxis and treatment of Pneumocystis carinii pneumonia as a second choice. Pentamidine (Pentam 300) binds to DNA and may inhibit kinetoplast DNA replication and function. It also may act by inhibiting dihydrofolate reductase and interfering with polyamine metabolism. An effect on organism respiration, especially at high doses, also may play a role.
• Description: Pentamidine is an aromatic diamine that is effective against protozoal diseases, such as amoebic dysentery, malaria, trypanosomiasis, and leishmaniasis. In clinical studies, it has also been shown to be an effective prophylaxis against pneumocystis pneumonia.
• Uses: antiprotozoal, inhibits nucleic acid & protein synthesis 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) 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).
• Therapeutic Function: Antiprotozoal
• Clinical Use: Pentamidine is active against Pneumocystis carinii, trypanosomes, and leishmaniasis unresponsive to pentavalent antimonials. It is an alternative agent for the treatment of P. carinii pneumonia. Although it is more toxic than trimethoprim–sulfamethoxazole, it has been widely used in patients with acquired immunodeficiency syndrome (AIDS), in whom P. carinii infection is common. Pentamidine is an alternative drug for visceral leishmaniasis, especially when sodium stibogluconate has failed or is contraindicated. Pentamidine is also a reserve agent for the treatment of trypanosomiasis before the CNS is invaded. This characteristic largely restricts its use to Gambian trypanosomiasis. Human African trypanosomiasis (early stages before CNS involvement) Prophylaxis and therapy of Pn. jirovecii pneumonia Visceral leishmaniasis unresponsive to pentavalent antimonials and cutaneous leishmaniasis caused by L. guyanensis There is limited evidence for its use in the treatment of babesiosis.

Technology Process of Pentamidine

There total 11 articles about Pentamidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.6%

pentamidine isethionate salt → pentamidine (100-33-4)

Guidance literature:

With ammonium hydroxide; In water; Cooling with ice;

DOI:10.1021/acs.bioconjchem.1c00381

Reference yield:

4-[(5-{4-[ethoxy(imino)methyl]phenoxy}pentyl)oxy]-1-phenylimidic acid diethyl ester dihydrochloride → pentamidine (100-33-4)

Guidance literature:

With ammonia; at 50 ℃; for 6h;

DOI:10.1021/jm00166a026

Reference yield:

→ pentamidine (100-33-4)

Guidance literature:

With ammonia;

upstream raw materials:

1,5-dibromo-pentane

4,4′-(pentane-1,5-diylbis(oxy))dibenzonitrile

4-cyanophenol

Refernces

• 1、 Harel, Yifat,Israel, Liron Limor,Kannan, Sriram,Lellouche, Emmanuel,Lellouche, Jean-Paul,Michaeli, Shulamit,Tsubery, Merav Nadav,Varvak, Alexander. "Novel Nanocarrier Platform for Effective Treatment of Visceral Leishmaniasis". . p. 2327 - 2341. Retrieved 2021/11/13.
• 2、 Cavalier, Michael C.,Ansari, Mohd. Imran,Pierce, Adam D.,Wilder, Paul T.,McKnight, Laura E.,Raman, E. Prabhu,Neau, David B.,Bezawada, Padmavani,Alasady, Milad J.,Charpentier, Thomas H.,Varney, Kristen M.,Toth, Eric A.,MacKerell, Alexander D.,Coop, Andrew,Weber, David J.. "Small Molecule Inhibitors of Ca2+-S100B Reveal Two Protein Conformations". . p. 592 - 608. Retrieved 2016/02/09.