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Identification
NameCB1954
Accession NumberDB04253  (EXPT00837)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII7865D5D01M
CAS numberNot Available
WeightAverage: 252.1836
Monoisotopic: 252.049469386
Chemical FormulaC9H8N4O5
InChI KeyWOCXQMCIOTUMJV-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
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Oxygen-insensitive NAD(P)H nitroreductaseProteinunknownNot AvailableEscherichia coli (strain K12)P38489 details
Ribosyldihydronicotinamide dehydrogenase [quinone]ProteinunknownNot AvailableHumanP16083 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of CB1954.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of CB1954.Investigational
BevacizumabBevacizumab may increase the cardiotoxic activities of CB1954.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with CB1954.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of CB1954.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of CB1954.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of CB1954.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of CB1954.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with CB1954.Approved, Investigational
OuabainOuabain may decrease the cardiotoxic activities of CB1954.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with CB1954.Approved, Vet Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of CB1954.Approved, Investigational
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.904 mg/mLALOGPS
logP0.04ALOGPS
logP0.64ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)11.29ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area137.74 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity62.25 m3·mol-1ChemAxon
Polarizability21.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilines
Direct ParentDinitroanilines
Alternative Parents
Substituents
  • Dinitroaniline
  • Aminobenzoic acid or derivatives
  • Phenylaziridine
  • Nitrobenzene
  • Indole
  • Benzoic acid or derivatives
  • Benzamide
  • Aminobenzamide
  • Dialkylarylamine
  • Benzoyl
  • Organic nitro compound
  • Tertiary amine
  • Primary carboxylic acid amide
  • Organic nitrite
  • C-nitro compound
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Allyl-type 1,3-dipolar organic compound
  • Organic oxoazanium
  • Carboxylic acid derivative
  • Aziridine
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available

Targets

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, quinones and the anti-tumor agent CB1954 (5-(aziridin-1-yl)-2,4-dinitrobenzamide). The reduction of CB1954 results in the generation of cytotoxic species.
Gene Name:
nfsB
Uniprot ID:
P38489
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  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. [PubMed:10592235 ]
Kind
Protein
Organism
Human
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 vitamin K-dependent gamma-carboxylation of glutamate residues in prothrombin synthesis.
Gene Name:
NQO2
Uniprot ID:
P16083
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. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24