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Pafuramidine

CAS No.:
186953-56-0
Catalog Number:
AG00ABL7
Molecular Formula:
C20H20N4O3
Molecular Weight:
364.3978
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
98%
1 week
United States
$473
- +
10mg
98%
1 week
United States
$690
- +
50mg
98%
1 week
United States
$1557
- +
100mg
98%
1 week
United States
$2390
- +
Product Description
Catalog Number:
AG00ABL7
Chemical Name:
Pafuramidine
CAS Number:
186953-56-0
Molecular Formula:
C20H20N4O3
Molecular Weight:
364.3978
MDL Number:
MFCD09954138
IUPAC Name:
N'-methoxy-4-[5-[4-[(Z)-N'-methoxycarbamimidoyl]phenyl]furan-2-yl]benzenecarboximidamide
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)
InChI Key:
UKOQVLAXCBRRGH-UHFFFAOYSA-N
SMILES:
CON=C(c1ccc(cc1)c1ccc(o1)c1ccc(cc1)C(=NOC)N)N
UNII:
H1VG379J2X
Properties
Complexity:
477  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
2  
Exact Mass:
364.154g/mol
Formal Charge:
0
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
364.405g/mol
Monoisotopic Mass:
364.154g/mol
Rotatable Bond Count:
6  
Topological Polar Surface Area:
108A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.2  
Literature
Title Journal
Synthesis and antiprotozoal activity of dicationic 2,6-diphenylpyrazines and aza-analogues. Bioorganic & medicinal chemistry 20131101
A mouse diversity panel approach reveals the potential for clinical kidney injury due to DB289 not predicted by classical rodent models. Toxicological sciences : an official journal of the Society of Toxicology 20121201
Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps). PLoS computational biology 20111201
Mechanisms underlying differences in systemic exposure of structurally similar active metabolites: comparison of two preclinical hepatic models. The Journal of pharmacology and experimental therapeutics 20110501
Combined treatment of heterocyclic analogues and benznidazole upon Trypanosoma cruzi in vivo. PloS one 20110101
Diamidines for human African trypanosomiasis. Current opinion in investigational drugs (London, England : 2000) 20100801
Synthesis and antiprotozoal activity of 2,5-bis[amidinoaryl]thiazoles. Bioorganic & medicinal chemistry 20100515
Synthesis and antiprotozoal activity of cationic 1,4-diphenyl-1H-1,2,3-triazoles. Journal of medicinal chemistry 20100114
Application of monoclonal antibodies to measure metabolism of an anti-trypanosomal compound in vitro and in vivo. Journal of clinical laboratory analysis 20100101
Phase I/II evaluation of the prophylactic antimalarial activity of pafuramidine in healthy volunteers challenged with Plasmodium falciparum sporozoites. The American journal of tropical medicine and hygiene 20090401
Efficacy of the diamidine DB75 and its prodrug DB289, against murine models of human African trypanosomiasis. Acta tropica 20081001
Synthesis and antiprotozoal activity of novel bis-benzamidino imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines. Bioorganic & medicinal chemistry 20080115
Carbamate prodrugs of N-alkylfuramidines. European journal of medicinal chemistry 20080101
Pafuramidine for Pneumocystis jiroveci pneumonia in HIV-infected individuals. Expert review of anti-infective therapy 20071201
Human enteric microsomal CYP4F enzymes O-demethylate the antiparasitic prodrug pafuramidine. Drug metabolism and disposition: the biological fate of chemicals 20071101
Pharmacokinetics and metabolism of the prodrug DB289 (2,5-bis[4-(N-methoxyamidino)phenyl]furan monomaleate) in rat and monkey and its conversion to the antiprotozoal/antifungal drug DB75 (2,5-bis(4-guanylphenyl)furan dihydrochloride). Drug metabolism and disposition: the biological fate of chemicals 20070601
CYP4F enzymes are the major enzymes in human liver microsomes that catalyze the O-demethylation of the antiparasitic prodrug DB289 [2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime]. Drug metabolism and disposition: the biological fate of chemicals 20061201
Synthesis, DNA affinity, and antiprotozoal activity of linear dications: Terphenyl diamidines and analogues. Journal of medicinal chemistry 20060824
Diamidines as antitrypanosomal, antileishmanial and antimalarial agents. Current opinion in investigational drugs (London, England : 2000) 20060201
Unusual dehydroxylation of antimicrobial amidoxime prodrugs by cytochrome b5 and NADH cytochrome b5 reductase. Drug metabolism and disposition: the biological fate of chemicals 20051201
Efficacy of DB289 in Thai patients with Plasmodium vivax or acute, uncomplicated Plasmodium falciparum infections. The Journal of infectious diseases 20050715
Treatment and control of human African trypanosomiasis. Current opinion in infectious diseases 20041201
O-alkoxyamidine prodrugs of furamidine: in vitro transport and microsomal metabolism as indicators of in vivo efficacy in a mouse model of Trypanosoma brucei rhodesiense infection. Journal of medicinal chemistry 20040812
Novel dicationic imidazo[1,2-a]pyridines and 5,6,7,8-tetrahydro-imidazo[1,2-a]pyridines as antiprotozoal agents. Journal of medicinal chemistry 20040701
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 tropica 20040701
Metabolites of an orally active antimicrobial prodrug, 2,5-bis(4-amidinophenyl)furan-bis-O-methylamidoxime, identified by liquid chromatography/tandem mass spectrometry. Journal of mass spectrometry : JMS 20040401
DB-289 Immtech International. IDrugs : the investigational drugs journal 20031101
New oral drug for PCP. AIDS patient care and STDs 20031101
Synthesis and antiprotozoal activity of aza-analogues of furamidine. Journal of medicinal chemistry 20031023
Detection of inhibition of bovine viral diarrhea virus by aromatic cationic molecules. Antimicrobial agents and chemotherapy 20030701
Enhanced permeability of the antimicrobial agent 2,5-bis(4-amidinophenyl)furan across Caco-2 cell monolayers via its methylamidoidme prodrug. Pharmaceutical research 20021101
Treatment of human African trypanosomiasis--present situation and needs for research and development. The Lancet. Infectious diseases 20020701
Characterizing the fragmentation of 2,5-bis (4-amidinophenyl)furan-bis-O-methylamidoxime and selected metabolites using ion trap mass spectrometry. Rapid communications in mass spectrometry : RCM 20020101
Properties