{{Chembox | ImageFile = Pafuramidine.svg | ImageClass = skin-invert-image | ImageAlt = | IUPACName = ''N′''-Methoxy-4-[5-[4-[(''Z'')-''N′''-methoxycarbamimidoyl]phenyl]furan-2-yl] benzenecarboximidamide | OtherNames = DB289 |Section1={{Chembox Identifiers | CASNo = 186953-56-0 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo1 = 837369-26-3 | CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1_Comment = (maleate) | PubChem = 5480200 | ChEMBL = 319669 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = H1VG379J2X | UNII1_Ref = {{fdacite|correct|FDA}} | UNII1 = K27F04K3A9 | UNII1_Comment = (maleate)
| SMILES = CO/N=C(\N)/C1=CC=C(C=C1)C2=CC=C(O2)C3=CC=C(C=C3)/C(=N/OC)/N | ChemSpiderID = 4586633 | 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) | InChIKey = UKOQVLAXCBRRGH-UHFFFAOYAE | StdInChI = 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) | StdInChIKey = UKOQVLAXCBRRGH-UHFFFAOYSA-N}} |Section2={{Chembox Properties | C=20 | H=20 | N=4 | O=3 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} |Section5={{Chembox Pharmacology | AdminRoutes = Oral | Bioavail = | Metabolism = | HalfLife = | ProteinBound = | Excretion = | Legal_status = Investigational | Legal_US = | Legal_UK = | Legal_AU = | Legal_CA = | Pregnancy_category = | Pregnancy_AU = }}
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'''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.<ref>{{cite web| url = https://www.drugs.com/nda/db289_061121.html | title = US FDA Grants Immtech's Oral Drug Candidate Pafuramidine (DB289) Orphan Drug Status for Treatment of PCP | publisher = Drugs.com | date = November 21, 2006}}</ref> 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).<ref>{{cite journal | vauthors = Chen D, Marsh R, Aberg JA | title = Pafuramidine for Pneumocystis jiroveci pneumonia in HIV-infected individuals | journal = Expert Review of Anti-Infective Therapy | volume = 5 | issue = 6 | pages = 921–928 | date = December 2007 | pmid = 18039076 | doi = 10.1586/14787210.5.6.921 | s2cid = 22249374 }}</ref>
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.<ref>{{cite web | url =http://www.swisstph.ch/about-us/departments/medicines-research/pharmaceutical-medicine/experience/pafuramidine-maleate-db289.html | title = Pafuramidine maleate (DB289) | publisher = Swiss Tropical and Public Health Initiative}}</ref><ref name="pmid22940726">{{cite journal | vauthors = Harrill AH, Desmet KD, Wolf KK, Bridges AS, Eaddy JS, Kurtz CL, Hall JE, Paine MF, Tidwell RR, Watkins PB | display-authors = 6 | title = A mouse diversity panel approach reveals the potential for clinical kidney injury due to DB289 not predicted by classical rodent models | journal = Toxicological Sciences | volume = 130 | issue = 2 | pages = 416–426 | date = December 2012 | pmid = 22940726 | pmc = 3498743 | doi = 10.1093/toxsci/kfs238 }}</ref>
== References == {{reflist}}
Category:Furans Category:Antiparasitic agents Category:Amidines