Details of the Drug

General Information of Drug (ID: DMSQLZJ)

Drug Name
Nifurtimox
Synonyms
NIFURTIMOX; Lampit; Bayer 2502; 23256-30-6; BAY 2502; Nifurtimox [INN:BAN]; Nifurtimoxum [INN-Latin]; CCRIS 2201; EINECS 245-531-0; CHEBI:7566; C10H13N3O5S; 4-Thiomorpholinamine, 3-methyl-N-((5-nitro-2-furanyl)methylene)-, 1,1-dioxide; 4-((5-Nitrofurfurylidene)amino)-3-methylthiomorpholine-1,1-dioxide; 3-Methyl-N-[(5-nitro-2-furanyl)methylene]-4-thiomorpholinamine 1,1-dioxide; 3-Methyl-4-(5'-nitrofurylidene-amino)-tetrahydro-4H-1,4-thiazine-1,1-dioxide
Indication
Disease Entry ICD 11 Status REF
Chagas disease IF53 Approved [1]
Trypanosomiasis 1D51-1F53 Phase 4 [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 287.29
Logarithm of the Partition Coefficient (xlogp) 1.3
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 7
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 5430 mcgh/L [3]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 425-568 mcg/L [3]
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 4 h [3]
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [4]
Clearance
The clearance of drug is 193.4 L/h [5]
Elimination
44% of the dose was mainly recovered in the urine as metabolites [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.4C3.6 hours [3]
Metabolism
The drug is metabolized via the nitroreductase enzymes [6]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 52.211 micromolar/kg/day [7]
Chemical Identifiers
Formula
C10H13N3O5S
IUPAC Name
(E)-N-(3-methyl-1,1-dioxo-1,4-thiazinan-4-yl)-1-(5-nitrofuran-2-yl)methanimine
Canonical SMILES
CC1CS(=O)(=O)CCN1/N=C/C2=CC=C(O2)[N+](=O)[O-]
InChI
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+
InChIKey
ARFHIAQFJWUCFH-IZZDOVSWSA-N
Cross-matching ID
PubChem CID
6842999
ChEBI ID
CHEBI:7566
CAS Number
23256-30-6
DrugBank ID
DB11820
TTD ID
D0FC1J
VARIDT ID
DR01396
ACDINA ID
D01282
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Brushite E00392 104805 Diluent
Magnesium stearate E00208 11177 lubricant
Hydrophobic colloidal silica E00285 24261 Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
Pregelatinized starch E00674 Not Available Binding agent; Diluent; Disintegrant
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Nifurtimox 30 mg tablet 30 mg Tablet Oral
Nifurtimox 120 mg tablet 120 mg Tablet Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health Human Services. 2020
2 ClinicalTrials.gov (NCT00906880) Clinical Study to Assess the Tolerability, Feasibility and Effectiveness of Nifurtimox and Eflornithine (NECT) for the Treatment of Trypanosoma Brucei Gambiense HumanAfrican Trypanosomiasis (HAT) in the Meningo-encephalitic Phase. U.S. National Institutes of Health.
3 FDA Approved Products: Lampit (nifurtimox) oral tablets
4 BDDCS applied to over 900 drugs
5 Gonzalez-Martin G, Thambo S, Paulos C, Vasquez I, Paredes J: The pharmacokinetics of nifurtimox in chronic renal failure. Eur J Clin Pharmacol. 1992;42(6):671-3. doi: 10.1007/BF00265935.
6 Hoffmann M, Kumar G, Schafer P, Cedzik D, Capone L, Fong KL, Gu Z, Heller D, Feng H, Surapaneni S, Laskin O, Wu A: Disposition, metabolism and mass balance of [(14)C]apremilast following oral administration. Xenobiotica. 2011 Dec;41(12):1063-75. doi: 10.3109/00498254.2011.604745. Epub 2011 Aug 23.
7 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
8 The transport of nifurtimox, an anti-trypanosomal drug, in an in vitro model of the human blood-brain barrier: evidence for involvement of breast cancer resistance protein. Brain Res. 2012 Feb 3;1436:111-21.