NAV

Tretazicar

Identification

Generic Name
Tretazicar
DrugBank Accession Number
DB04253
Background

Tretazicar is under investigation in clinical trial NCT00746590 (Study of Anti-tumour Effects and Safety of Prolarix™ in Hepatocellular Carcinoma).

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 252.1836
Monoisotopic: 252.049469386
Chemical Formula
C9H8N4O5
Synonyms
  • Tretazicar
External IDs
  • CB-1954
  • CB1954
  • NSC-115829
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
URibosyldihydronicotinamide dehydrogenase [quinone]Not AvailableHumans
UOxygen-insensitive NAD(P)H nitroreductaseNot AvailableEscherichia coli (strain K12)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AmbroxolThe risk or severity of methemoglobinemia can be increased when Tretazicar is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Tretazicar is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Tretazicar is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Tretazicar is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Tretazicar is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dinitroanilines. These are organic compounds containing an aniline moiety, which is substituted at 2 positions by a nitro group.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Aniline and substituted anilines
Direct Parent
Dinitroanilines
Alternative Parents
Aminobenzamides / Benzamides / Phenylaziridines / Indoles / Nitrobenzenes / Benzoyl derivatives / Dialkylarylamines / Nitroaromatic compounds / Amino acids and derivatives / Primary carboxylic acid amides
show 8 more
Substituents
Allyl-type 1,3-dipolar organic compound / Amine / Amino acid or derivatives / Aminobenzamide / Aminobenzoic acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Aziridine / Benzamide / Benzoic acid or derivatives
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
7865D5D01M
CAS number
21919-05-1
InChI Key
WOCXQMCIOTUMJV-UHFFFAOYSA-N
InChI
InChI=1S/C9H8N4O5/c10-9(14)5-3-7(11-1-2-11)8(13(17)18)4-6(5)12(15)16/h3-4H,1-2H2,(H2,10,14)
IUPAC Name
5-(aziridin-1-yl)-2,4-dinitrobenzamide
SMILES
NC(=O)C1=CC(N2CC2)=C(C=C1[N+]([O-])=O)[N+]([O-])=O

References

General References
Not Available
PubChem Compound
89105
PubChem Substance
46509068
ChemSpider
80403
BindingDB
50004681
ChEMBL
CHEMBL23330
ZINC
ZINC000004475105
PDBe Ligand
CB1
PDB Entries
1idt / 1xi2 / 1zx1 / 2bzs / 7ak4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2TerminatedTreatmentHepatocellular Carcinoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.904 mg/mLALOGPS
logP0.04ALOGPS
logP0.64Chemaxon
logS-2.4ALOGPS
pKa (Strongest Acidic)10.98Chemaxon
pKa (Strongest Basic)-2.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area132.38 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity60.24 m3·mol-1Chemaxon
Polarizability21.62 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9849
Blood Brain Barrier+0.9518
Caco-2 permeable-0.5201
P-glycoprotein substrateNon-substrate0.6154
P-glycoprotein inhibitor INon-inhibitor0.938
P-glycoprotein inhibitor IINon-inhibitor0.9581
Renal organic cation transporterNon-inhibitor0.9005
CYP450 2C9 substrateNon-substrate0.8779
CYP450 2D6 substrateNon-substrate0.8267
CYP450 3A4 substrateNon-substrate0.527
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.6828
BiodegradationNot ready biodegradable0.6136
Rat acute toxicity2.4518 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9656
hERG inhibition (predictor II)Non-inhibitor0.8456
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-07w9-9560000000-441bfb4f7430881cfcfb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-163.8235185
predicted
DarkChem Lite v0.1.0
[M-H]-153.14604
predicted
DeepCCS 1.0 (2019)
[M+H]+164.2643185
predicted
DarkChem Lite v0.1.0
[M+H]+156.40611
predicted
DeepCCS 1.0 (2019)
[M+Na]+164.0399185
predicted
DarkChem Lite v0.1.0
[M+Na]+164.3042
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Ribosyldihydronicotinamide dehydrogenase [quinone]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadph dehydrogenase (quinone) activity
Specific Function
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinones involved in detoxification pathways as well as in biosynthetic processes such as the vi...
Gene Name
NQO2
Uniprot ID
P16083
Uniprot Name
Ribosyldihydronicotinamide dehydrogenase [quinone]
Molecular Weight
25918.4 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Oxygen-insensitive NAD(P)H nitroreductase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nad(p)h nitroreductase activity
Specific Function
Reduction of a variety of nitroaromatic compounds using NADH (and to lesser extent NADPH) as source of reducing equivalents; two electrons are transferred. Capable of reducing nitrofurazone, quinon...
Gene Name
nfsB
Uniprot ID
P38489
Uniprot Name
Oxygen-insensitive NAD(P)H nitroreductase
Molecular Weight
23904.99 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51