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Details

Stereochemistry ACHIRAL
Molecular Formula C20H20N4O3.C4H4O4
Molecular Weight 480.47
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PAFURAMIDINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CONC(=N)C1=CC=C(C=C1)C2=CC=C(O2)C3=CC=C(C=C3)C(=N)NOC

InChI

InChIKey=SWMNGXODFOCPKQ-BTJKTKAUSA-N
InChI=1S/C20H20N4O3.C4H4O4/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;5-3(6)1-2-4(7)8/h3-12H,1-2H3,(H2,21,23)(H2,22,24);1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C20H20N4O3
Molecular Weight 364.3978
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Pafuramidine or DB289, [2,5-bis-(4-amidinophenyl)furan bis-O-methylamidoxime] is a pro-drug of DB75, [2,5-bis(4-amidinophenyl)furan] also known as furamidine. The biotransformation process of DB289 to DB75 in the human liver consists of three O-demethylation reactions catalyzed by the Cyp4F enzyme subfamily and three N-dehydroxylation reactions catalyzed by cytrochrome b5 and NADH-cytochrome b5 reductase. DB289 was studied for therapeutic treatment against human African trypanosomiasis, Pneumocystis pneumonia and malaria. In November 2006, Immtech Pharmaceuticals, Inc. announced that the U.S. Food and Drug Administration (FDA) had granted orphan drug designation for pafuramidine (DB289) to treat Pneumocystis jiroveci pneumonia (PCP), a common life-threatening opportunistic infection in HIV/AIDS and other immunosuppressed patients. Despite the high efficacy of DB289 in patients, the mechanism of action of DB75 is unknown. The mechanism of antimicrobial activity of diamidine compounds is incompletely understood. They undergo active uptake by purine transporter systems in trypanosomes and their mechanism of action may involve interference with DNA-associated enzymes inhibition of heme crystallization11 or/and collapse of the transmitochondrial membrane potential.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
A mouse diversity panel approach reveals the potential for clinical kidney injury due to DB289 not predicted by classical rodent models.
2012 Dec
Patents

Sample Use Guides

In Vivo Use Guide
Sleeping sickness (human African trypanosomiasis [HAT]) patients were treated 100 mg of pafuramidine orally twice a day for 10 days (Phase 3 Clinical Trial)
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Tue Oct 22 01:50:21 UTC 2019
Edited
by admin
on Tue Oct 22 01:50:21 UTC 2019
Record UNII
K27F04K3A9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PAFURAMIDINE MALEATE
USAN  
USAN  
Official Name English
BENZENECARBOXIMIDAMIDE, 4,4'-(2,5-FURANDIYL)BIS(N-METHOXY-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
4,4'-(FURAN-2,5-DIYL)BIS(N-METHOXYBENZENECARBOXIMIDAMIDE)(2Z)-2-BUTENEDIOATE (1:1)
Common Name English
DB-289
Code English
DB289
Code English
4,4'-(2,5-FURANDIYL)BIS(N-METHOXY-BENZENECARBOXIMIDAMIDE) MALEATE
Systematic Name English
PAFURAMIDINE MALEATE [USAN]
Common Name English
2,5-BIS(4-(N-METHOXYAMIDINO)PHENYL)FURAN MONOMALEATE SALT
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 244507
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
FDA ORPHAN DRUG 241207
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
FDA ORPHAN DRUG 220706
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
NCI_THESAURUS C271
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
Code System Code Type Description
CAS
837369-26-3
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
PRIMARY
NCI_THESAURUS
C81703
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
PRIMARY
ChEMBL
CHEMBL319669
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
PRIMARY
WIKIPEDIA
Pafuramidine maleate
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
PRIMARY
PUBCHEM
11691495
Created by admin on Tue Oct 22 01:50:21 UTC 2019 , Edited by admin on Tue Oct 22 01:50:21 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY