Synonym
DB-844; DB 844; DB844; CPD-594-12; CPD 594-12; CPD-594 12
IUPAC/Chemical Name
N-Methoxy-6-{5-[4-(N-methoxy-carbamimidoyl)-phenyl]-furan-2-yl}-nicotinamidine; N-Methoxy-6-{5-[4-(N-methoxyamidino)phenyl]-furan-2-yl}-nicotinamidine
InChi Key
WYHHQZBQOXLPPF-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H19N5O3/c1-25-23-18(20)13-5-3-12(4-6-13)16-9-10-17(27-16)15-8-7-14(11-22-15)19(21)24-26-2/h3-11H,1-2H3,(H2,20,23)(H2,21,24)
SMILES Code
N=C(NOC)C1=CN=C(C2=CC=C(C3=CC=C(C(NOC)=N)C=C3)O2)C=C1
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
>3 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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
365.39
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 |
1: Ansede JH, Voyksner RD, Ismail MA, Boykin DW, Tidwell RR, Hall JE. In vitro metabolism of an orally active O-methyl amidoxime prodrug for the treatment of CNS trypanosomiasis. Xenobiotica. 2005 Mar;35(3):211-26. PubMed PMID: 16019947.
2: Mathis AM, Holman JL, Sturk LM, Ismail MA, Boykin DW, Tidwell RR, Hall JE. Accumulation and intracellular distribution of antitrypanosomal diamidine compounds DB75 and DB820 in African trypanosomes. Antimicrob Agents Chemother. 2006 Jun;50(6):2185-91. PubMed PMID: 16723581; PubMed Central PMCID: PMC1479144.
3: Wenzler T, Boykin DW, Ismail MA, Hall JE, Tidwell RR, Brun R. New treatment option for second-stage African sleeping sickness: in vitro and in vivo efficacy of aza analogs of DB289. Antimicrob Agents Chemother. 2009 Oct;53(10):4185-92. doi: 10.1128/AAC.00225-09. Epub 2009 Jul 20. PubMed PMID: 19620327; PubMed Central PMCID: PMC2764217.
4: Thuita JK, Wang MZ, Kagira JM, Denton CL, Paine MF, Mdachi RE, Murilla GA, Ching S, Boykin DW, Tidwell RR, Hall JE, Brun R. Pharmacology of DB844, an orally active aza analogue of pafuramidine, in a monkey model of second stage human African trypanosomiasis. PLoS Negl Trop Dis. 2012;6(7):e1734. doi: 10.1371/journal.pntd.0001734. Epub 2012 Jul 24. PubMed PMID: 22848769; PubMed Central PMCID: PMC3404106.
5: Ju W, Yang S, Ansede JH, Stephens CE, Bridges AS, Voyksner RD, Ismail MA, Boykin DW, Tidwell RR, Hall JE, Wang MZ. CYP1A1 and CYP1B1-mediated biotransformation of the antitrypanosomal methamidoxime prodrug DB844 forms novel metabolites through intramolecular rearrangement. J Pharm Sci. 2014 Jan;103(1):337-49. doi: 10.1002/jps.23765. Epub 2013 Nov 1. PubMed PMID: 24186380; PubMed Central PMCID: PMC3865069.
