Pafuramidine

Last updated
Pafuramidine
Pafuramidine.svg
Names
IUPAC name
N′-Methoxy-4-[5-[4-[(Z)-N′-methoxycarbamimidoyl]phenyl]furan-2-yl] benzenecarboximidamide
Other names
DB289
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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)
    Key: UKOQVLAXCBRRGH-UHFFFAOYSA-N
  • InChI=1/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)
    Key: UKOQVLAXCBRRGH-UHFFFAOYAE
  • CO/N=C(\N)/C1=CC=C(C=C1)C2=CC=C(O2)C3=CC=C(C=C3)/C(=N/OC)/N
Properties
C20H20N4O3
Molar mass 364.405 g·mol−1
Pharmacology
Oral
Legal status
  • Investigational
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pafuramidine (formulated as the maleic acid salt pafuramidine maleate) is an experimental drug for the treatment of pneumocystis pneumonia (PCP). In 2006, pafuramidine was given orphan drug status by the US Food and Drug Administration for PCP in patients with HIV/AIDS. [1] Preliminary clinical trials indicated that pafuramide was effective against pneumocystis pneumonia and had the potential for fewer side effects than the standard treatment with trimethoprim/sulfamethoxazole (TMP-SMX). [2]

Pafuramidine also reached Phase III clinical trials for the treatment of first stage African sleeping sickness, but development was halted in 2008 over concerns about kidney toxicity. [3] [4]

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<span class="mw-page-title-main">Trimethoprim</span> Antibiotic

Trimethoprim (TMP) is an antibiotic used mainly in the treatment of bladder infections. Other uses include for middle ear infections and travelers' diarrhea. With sulfamethoxazole or dapsone it may be used for Pneumocystis pneumonia in people with HIV/AIDS. It is taken by mouth.

<span class="mw-page-title-main">Pentamidine</span> Medical antimicrobial drug

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References

  1. "US FDA Grants Immtech's Oral Drug Candidate Pafuramidine (DB289) Orphan Drug Status for Treatment of PCP". Drugs.com. November 21, 2006.
  2. Chen D, Marsh R, Aberg JA (2007). "Pafuramidine for Pneumocystis jiroveci pneumonia in HIV-infected individuals". Expert Review of Anti-infective Therapy. 5 (6): 921–8. doi:10.1586/14787210.5.6.921. PMID   18039076. S2CID   22249374.
  3. "Pafuramidine maleate (DB289)". Swiss Tropical and Public Health Initiative.
  4. Harrill AH, Desmet KD, Wolf KK, Bridges AS, Eaddy JS, Kurtz CL, Hall JE, Paine MF, Tidwell RR, Watkins PB (2012). "A mouse diversity panel approach reveals the potential for clinical kidney injury due to DB289 not predicted by classical rodent models". Toxicol. Sci. 130 (2): 416–26. doi:10.1093/toxsci/kfs238. PMC   3498743 . PMID   22940726.