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Details

Stereochemistry RACEMIC
Molecular Formula C10H13N3O5S
Molecular Weight 287.2938
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NIFURTIMOX

SMILES

CC1CS(=O)(=O)CCN1/N=C(\[H])/c2ccc(N(=O)=O)o2

InChI

InChIKey=ARFHIAQFJWUCFH-IZZDOVSWSA-N
InChI=1S/C10H13N3O5S/c1-8-7-19(16,17)5-4-12(8)11-6-9-2-3-10(18-9)13(14)15/h2-3,6,8H,4-5,7H2,1H3/b11-6+

HIDE SMILES / InChI

Molecular Formula C10H13N3O5S
Molecular Weight 287.2938
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 1
Optical Activity ( + / - )

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/27282514 | https://www.drugs.com/international/nifurtimox.html | https://www.ncbi.nlm.nih.gov/pubmed/23518280

Nifurtimox is a nitrofuran derivative used as a primary agent in the treatment of American trypanosomiasis (Chagas' disease) caused by Trypanosoma cruzi, especially in the acute, early stage of the disease. The efficacy of nifurtimox in the treatment of chronic Chagas' disease varies from one country to another, possibly due to variation in the sensitivity of different strains of the organism. Nifurtimox has also been used to treat African trypanosomiasis (sleeping sickness) and is active in the second stage of the disease (central nervous system involvement). When nifurtimox is given on its own, about half of all patients will relapse, but the combination of melarsoprol with nifurtimox appears to be efficacious. Nifurtimox forms a nitro-anion radical metabolite that reacts with nucleic acids of the parasite causing significant break down of DNA. Nifurtimox undergoes reduction and creates oxygen radicals such as superoxide. These radicals are toxic to T. cruzi. Mammalian cells are protected by the presence of catalase, glutathione, peroxidases, and superoxide dismutase. Accumulation of hydrogen peroxide to cytotoxic levels results in parasite death. Side effects occur following chronic administration, particularly in elderly people. Major toxicities include immediate hypersensitivities such as anaphylaxis and delayed hypersensitivity reaction involving icterus and dermatitis. Central nervous system disturbances and peripheral neuropathy may also occur.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.80000000000000004 µM [IC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Treatment of experimental pneumocystosis: review of 7 years of experience and development of a new system for classifying antimicrobial drugs.
1992 Sep
Nifurtimox plus pyrimethamine for treatment of murine toxoplasmosis.
1998 Oct
Nitroreductive metabolic activation of some carcinogenic nitro heterocyclic food contaminants in rat mammary tissue cellular fractions.
2009 Jan
Patents

Sample Use Guides

In Vivo Use Guide
For acute and chronic infections: Oral, 8 to 10 mg per kg of body weight per day in three or four divided doses after meals, for ninety to one hundred twenty days.
Route of Administration: Oral
Neural tumor cell lines (U-87, U373, CHLA-02-ATRT and PFSK-1), medulloblastoma cell lines (Daoy and D283) and TC-71, 143B, MG-63, MMH-ES, RD-ES, SK-ES-1 and SK-N-MC cell lines were used for activity evaluation. The viability of cells exposed to nifurtimox and BSO was determined using a modified methyl tetrazolium (MTT; Sigma) assay. 0.5–1.0 × 10^4 cells/well of exponentially growing cells were plated in 96-well plates. 24 hours later, nifurtimox or BSO was added to each well at concentrations up to 200mkM. After 72, 96, or 120 hours of continuous drug exposure, 15 μL of 5 mg/ml MTT was added to each well and the plates were incubated for 4 hours at 37 °C. Medium was replaced with 150 μL of DMSO and the optical density (OD) was measured at 550 nm using a microplate spectrophotometer (Anthos Analytical, Durham, NC). Cell numbers were estimated from OD measurements in individual wells. Relative cell viability was calculated by subtracting the background OD of media alone and then dividing by the OD of control wells.
Substance Class Chemical
Created
by admin
on Sat Jun 26 16:12:23 UTC 2021
Edited
by admin
on Sat Jun 26 16:12:23 UTC 2021
Record UNII
M84I3K7C2O
Record Status Validated (UNII)
Record Version
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Name Type Language
NIFURTIMOX
INN   MART.   MI   USAN   WHO-DD   WHO-IP  
INN   USAN  
Official Name English
NIFURTIMOX [WHO-DD]
Common Name English
BAYER-2502
Code English
4-((5-NITROFURFURYLIDENE)AMINO)-3-METHYLTHIOMORPHOLINE 1,1-DIOXIDE
Systematic Name English
NIFURTIMOX [USAN]
Common Name English
NIFURTIMOX [MART.]
Common Name English
NIFURTIMOX [WHO-IP]
Common Name English
BAYER 2502
Code English
THIOMORPHOLINE, 3-METHYL-4-((5-NITROFURFURYLIDENE)AMINO)-, 1,1-DIOXIDE
Systematic Name English
4-THIOMORPHOLINAMINE, 3-METHYL-N-((5-NITRO-2-FURANYL)METHYLENE)-, 1,1-DIOXIDE
Systematic Name English
DNDI1613515
Code English
(RS)-3-METHYL-N-((1E)-(5-NITRO-2-FURYL)METHYLENE)THIOMORPHOLIN-4-AMINE 1,1-DIOXIDE
Systematic Name English
BAY-2502
Code English
NIFURTIMOX [MI]
Common Name English
NIFURTIMOX [INN]
Common Name English
BAY-A2502
Code English
TETRAHYDRO-3-METHYL-4-((5-NITROFURFURYLIDENE)AMINO)-4H-1,4-THIAZINE 1,1-DIOXIDE
Systematic Name English
LAMPIT
Brand Name English
(+/-)-NIFURTIMOX
Common Name English
NIFURTIMOXUM [WHO-IP LATIN]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 6.5.5.1
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
FDA ORPHAN DRUG 310110
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WHO-VATC QP51AC01
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WHO-ESSENTIAL MEDICINES LIST 6.5.5.2
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
NCI_THESAURUS C277
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FDA ORPHAN DRUG 419213
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WHO-ATC P01CC01
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Code System Code Type Description
MERCK INDEX
M7892
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PRIMARY Merck Index
DRUG BANK
DB11820
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PRIMARY
LACTMED
Nifurtimox
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PRIMARY
ECHA (EC/EINECS)
245-531-0
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PRIMARY
ChEMBL
CHEMBL290960
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PRIMARY
RXCUI
7421
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PRIMARY RxNorm
EPA CompTox
23256-30-6
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PRIMARY
MESH
D009547
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PRIMARY
CAS
23256-30-6
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PRIMARY
WIKIPEDIA
Nifurtimox
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
PRIMARY
EVMPD
SUB09280MIG
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
PRIMARY
INN
2615
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PRIMARY
DRUG CENTRAL
1929
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PRIMARY
FDA UNII
M84I3K7C2O
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NIFURTIMOX
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
PRIMARY Description: A yellow to orange-yellow, crystalline powder; odourless. Solubility: Practically insoluble in water and ether R; freely soluble in dimethylformamide R; sparingly soluble in dioxan R. Category: Antitrypanosomal drug. Storage: Nifurtimox should be kept in a well-closed container. Definition: Nifurtimox contains not less than 98.0% and not more than 102.0% of C10H13N3O5S, calculated with reference to thedried substance.
PUBCHEM
6842999
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
PRIMARY
NCI_THESAURUS
C71734
Created by admin on Sat Jun 26 16:12:24 UTC 2021 , Edited by admin on Sat Jun 26 16:12:24 UTC 2021
PRIMARY
Related Record Type Details
BINDER->LIGAND
BINDING
Related Record Type Details
METABOLITE INACTIVE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
IN FASTED STATE
URINE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC FED CONDITION

Biological Half-life PHARMACOKINETIC