Compound ID | 464

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Pafuramidine

Synonym(s): DB 289  |  DB-289  |  DB289  |  Pafuramidine maleate

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule;
Spectrum of activity: Antimycobacterial
Mechanism of action: DNA synthesis inhibitor. DNA minor groove binder
Target Pathogen: Active against Mycobacterium tuberculosis
Description: Prodrug of DB75/ Furamidine/ DB75; repurposed drug: potential treatment for Pneumocystis carinii pneumonia (PCP), tuberculosis, trypanosomiasis and malaria
Institute where first reported: George State University; CombinatoRx (Immtech Pharmaceuticals, USA)
Year first mentioned: 2001
Highest development stage: Phase 1 (NCT00619346)
Development status: Inactive
Reason dropped: Was in clinical trials but not for bacterial infections. Phase I trials demonstrated safety in humans; currently in FDA clinical hold due to safety concerns
Chemical structure(s):
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Molecular weight: 364.4
Iso. SMILES: CO/N=C(\N)/C1=CC=C(C=C1)C2=CC=C(O2)C3=CC=C(C=C3)/C(=N/OC)/N
InChI Key: UKOQVLAXCBRRGH-UHFFFAOYSA-N
Can. SMILES: CO/N=C(/C1=CC=C(C=C1)C2=CC=C(C3=CC=C(C=C3)/C(=N/OC)/N)O2)\N
InChI: InChI=1S/C20H20N4O3/c1-25-23-19(21)15-7-3-13(4-8-15)17-11-12-18(27-17)14-5-9-16(10-6-14)20(22)24-26-2/h3-12H,1-2H3,(H2,21,23)(H2,22,24)
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/5480200
Guide to Pharmacology: pafuramidine
Citation: https://pubmed.ncbi.nlm.nih.gov/14600842/

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