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Identification
NameFotemustine
Accession NumberDB04106  (EXPT03300)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
(+-)-Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate
Diethyl-1-(3-(2-chloroethyl)-3-nitrosoureido)ethylphosphonate
Fotemustina
Fotemustinum
External Identifiers
  • Servier-10036
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
UNIIGQ7JL9P5I2
CAS numberNot Available
WeightAverage: 315.691
Monoisotopic: 315.075084952
Chemical FormulaC9H19ClN3O5P
InChI KeyInChIKey=YAKWPXVTIGTRJH-QMMMGPOBSA-N
InChI
InChI=1S/C9H19ClN3O5P/c1-4-17-19(16,18-5-2)8(3)11-9(14)13(12-15)7-6-10/h8H,4-7H2,1-3H3,(H,11,14)/t8-/m0/s1
IUPAC Name
diethyl [(1S)-1-{[N-(2-chloroethyl)-N'-oxohydrazinecarbonyl]amino}ethyl]phosphonate
SMILES
CCOP(=O)(OCC)[C@@H](C)NC(=O)N(CCCl)N=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phosphonic acid diesters. These are organophosphorus compounds containing a diester derivative of phosphonic acid, with the general structure ROP(=O)OR' (R,R' = organyl group).
KingdomOrganic compounds
Super ClassOrganophosphorus compounds
ClassOrganic phosphonic acids and derivatives
Sub ClassPhosphonic acid diesters
Direct ParentPhosphonic acid diesters
Alternative Parents
Substituents
  • Phosphonic acid diester
  • Phosphonic acid ester
  • Nitrosourea
  • Nitrosamide
  • Semicarbazide
  • Organic nitrosamine
  • N-nitroso compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alkyl halide
  • Alkyl chloride
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9709
Blood Brain Barrier+0.7425
Caco-2 permeable-0.5823
P-glycoprotein substrateNon-substrate0.6191
P-glycoprotein inhibitor INon-inhibitor0.6195
P-glycoprotein inhibitor IINon-inhibitor0.755
Renal organic cation transporterNon-inhibitor0.8932
CYP450 2C9 substrateNon-substrate0.7887
CYP450 2D6 substrateNon-substrate0.8071
CYP450 3A4 substrateNon-substrate0.5117
CYP450 1A2 substrateNon-inhibitor0.7836
CYP450 2C9 inhibitorNon-inhibitor0.7355
CYP450 2D6 inhibitorNon-inhibitor0.8882
CYP450 2C19 inhibitorNon-inhibitor0.67
CYP450 3A4 inhibitorNon-inhibitor0.8724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8853
Ames testAMES toxic0.9107
CarcinogenicityCarcinogens 0.7102
BiodegradationNot ready biodegradable0.8846
Rat acute toxicity3.1868 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6413
hERG inhibition (predictor II)Non-inhibitor0.8627
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 Solubility4.11 mg/mLALOGPS
logP1.23ALOGPS
logP1.28ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.06ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area97.3 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity71.42 m3·mol-1ChemAxon
Polarizability29.12 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US4567169
General ReferencesNot Available
External Links
ATC CodesL01AD05
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Fotemustine.
BevacizumabBevacizumab may increase the cardiotoxic activities of Fotemustine.
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Fotemustine.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Fotemustine.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Fotemustine.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Fotemustine.
DigoxinDigoxin may decrease the cardiotoxic activities of Fotemustine.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Fotemustine.
OuabainOuabain may decrease the cardiotoxic activities of Fotemustine.
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Fotemustine.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Fotemustine.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Thioredoxin-disulfide reductase activity
Specific Function:
Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enhances the transcriptional activity of estrogen receptors alpha and beta while isoform 5 enhances the transcriptional activity of the beta receptor only. Isoform 5 also mediates cell death induced by a ...
Gene Name:
TXNRD1
Uniprot ID:
Q16881
Molecular Weight:
70905.58 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:24