Pafuramidine

Pafuramidine

Names
IUPAC name N′-Methoxy-4-[5-[4-[(Z)-N′-methoxycarbamimidoyl]phenyl]furan-2-yl] benzenecarboximidamide
Other names DB289
Identifiers
CAS Number	186953-56-0 837369-26-3 (maleate)
ChEMBL	ChEMBL319669
ChemSpider	4586633
Jmol interactive 3D	Image
PubChem	5480200
UNII	H1VG379J2X
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) 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
SMILES CO/N=C(\N)/C1=CC=C(C=C1)C2=CC=C(O2)C3=CC=C(C=C3)/C(=N/OC)/N
Properties
Chemical formula	C20H20N4O3
Molar mass	364.41 g·mol^−1
Pharmacology
Legal status	Investigational
Routes of administration	Oral
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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]

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.
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.