WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H326798
CAS#: 186953-56-0
Description: Pafuramidine, also known as DB289, is an orally bioavailable prodrug of furamidine (DB75) which was developed for the treatment of human African trypanosomiasis. Pafuramidine is less toxic than previous diamidines such as pentamidine. To date, human trials suggest that pafuramidine is well tolerated overall and has clinical activity against Pneumocystis pneumonia. DB289 is a promising new antimalarial compound that could become an important component of new antimalarial combinations.
Hodoodo Cat#: H326798
Name: Pafuramidine
CAS#: 186953-56-0
Chemical Formula: C20H20N4O3
Exact Mass: 364.15
Molecular Weight: 364.405
Elemental Analysis: C, 65.92; H, 5.53; N, 15.38; O, 13.17
Related CAS #: 186953-56-0 837369-26-3 (maleate)
Synonym: DB289; DB-289; DB 289; Pafuramidine
IUPAC/Chemical Name: N'-methoxy-4-[5-[4-[(Z)-N'-methoxycarbamimidoyl]phenyl]furan-2-yl]benzenecarboximidamide
InChi Key: UKOQVLAXCBRRGH-UHFFFAOYSA-N
InChi Code: 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)
SMILES Code: N/C(C1=CC=C(C2=CC=C(C3=CC=C(/C(N)=N/OC)C=C3)O2)C=C1)=N\OC
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info: Related CAS# 186953-56-0 (Pafuramidine) 837369-26-3 (Pafuramidine maleate)
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 364.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
21: Ismail MA, Arafa RK, Brun R, Wenzler T, Miao Y, Wilson WD, Generaux C, Bridges A, Hall JE, Boykin DW. Synthesis, DNA affinity, and antiprotozoal activity of linear dications: Terphenyl diamidines and analogues. J Med Chem. 2006 Aug 24;49(17):5324-32. PubMed PMID: 16913722.
22: Werbovetz K. Diamidines as antitrypanosomal, antileishmanial and antimalarial agents. Curr Opin Investig Drugs. 2006 Feb;7(2):147-57. Review. PubMed PMID: 16499285.
23: Saulter JY, Kurian JR, Trepanier LA, Tidwell RR, Bridges AS, Boykin DW, Stephens CE, Anbazhagan M, Hall JE. Unusual dehydroxylation of antimicrobial amidoxime prodrugs by cytochrome b5 and NADH cytochrome b5 reductase. Drug Metab Dispos. 2005 Dec;33(12):1886-93. Epub 2005 Aug 30. PubMed PMID: 16131524.
24: Yeramian P, Meshnick SR, Krudsood S, Chalermrut K, Silachamroon U, Tangpukdee N, Allen J, Brun R, Kwiek JJ, Tidwell R, Looareesuwan S. Efficacy of DB289 in Thai patients with Plasmodium vivax or acute, uncomplicated Plasmodium falciparum infections. J Infect Dis. 2005 Jul 15;192(2):319-22. Epub 2005 Jun 7. PubMed PMID: 15962227.
25: Jannin J, Cattand P. Treatment and control of human African trypanosomiasis. Curr Opin Infect Dis. 2004 Dec;17(6):565-71. Review. PubMed PMID: 15640711.
26: Sturk LM, Brock JL, Bagnell CR, Hall JE, Tidwell RR. Distribution and quantitation of the anti-trypanosomal diamidine 2,5-bis(4-amidinophenyl)furan (DB75) and its N-methoxy prodrug DB289 in murine brain tissue. Acta Trop. 2004 Jul;91(2):131-43. PubMed PMID: 15234662.
27: Zhou L, Thakker DR, Voyksner RD, Anbazhagan M, Boykin DW, Hall JE, Tidwell RR. Metabolites of an orally active antimicrobial prodrug, 2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime, identified by liquid chromatography/tandem mass spectrometry. J Mass Spectrom. 2004 Apr;39(4):351-60. PubMed PMID: 15103648.
28: New oral drug for PCP. AIDS Patient Care STDS. 2003 Nov;17(11):609-10. PubMed PMID: 14748360.
29: Yeates C. DB-289 Immtech International. IDrugs. 2003 Nov;6(11):1086-93. Review. PubMed PMID: 14600842.
30: Givens MD, Dykstra CC, Brock KV, Stringfellow DA, Kumar A, Stephens CE, Goker H, Boykin DW. Detection of inhibition of bovine viral diarrhea virus by aromatic cationic molecules. Antimicrob Agents Chemother. 2003 Jul;47(7):2223-30. PubMed PMID: 12821472; PubMed Central PMCID: PMC161853.
31: Zhou L, Lee K, Thakker DR, Boykin DW, Tidwell RR, Hall JE. Enhanced permeability of the antimicrobial agent 2,5-bis(4-amidinophenyl)furan across Caco-2 cell monolayers via its methylamidoidme prodrug. Pharm Res. 2002 Nov;19(11):1689-95. PubMed PMID: 12458675.
32: Legros D, Ollivier G, Gastellu-Etchegorry M, Paquet C, Burri C, Jannin J, Büscher P. Treatment of human African trypanosomiasis--present situation and needs for research and development. Lancet Infect Dis. 2002 Jul;2(7):437-40. Review. PubMed PMID: 12127356.
33: Zhou L, Voyksner RD, Thakker DR, Stephens CE, Anbazhagan M, Boykin DW, Hall JE, Tidwell RR. Characterizing the fragmentation of 2,5-bis (4-amidinophenyl)furan-bis-O-methylamidoxime and selected metabolites using ion trap mass spectrometry. Rapid Commun Mass Spectrom. 2002;16(11):1078-85. PubMed PMID: 11992511.
