Fotemustine

Identification

Name
Fotemustine
Accession Number
DB04106  (EXPT03300)
Type
Small Molecule
Groups
Experimental, Investigational
Description
Not Available
Structure
Thumb
Synonyms
  • (+-)-Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate
  • Diethyl-1-(3-(2-chloroethyl)-3-nitrosoureido)ethylphosphonate
  • Fotemustina
  • Fotemustinum
External IDs
Servier-10036
Categories
UNII
GQ7JL9P5I2
CAS number
Not Available
Weight
Average: 315.691
Monoisotopic: 315.075084952
Chemical Formula
C9H19ClN3O5P
InChI Key
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)[[email protected]@H](C)NC(=O)N(CCCl)N=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UThioredoxin reductase 1, cytoplasmicNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Fotemustine.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Fotemustine.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of Fotemustine.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Fotemustine.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Fotemustine.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Fotemustine.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Fotemustine.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Fotemustine.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Fotemustine.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Fotemustine.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Fotemustine.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Fotemustine.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Fotemustine.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Fotemustine.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Fotemustine.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Fotemustine.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Fotemustine.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Fotemustine.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Fotemustine.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference
US4567169
General References
Not Available
External Links
PubChem Compound
46936889
PubChem Substance
46505097
ChemSpider
26330202
ChEBI
131854
ATC Codes
L01AD05 — Fotemustine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentGlioblastoma Multiforme1
2CompletedTreatmentMalignant Melanoma1
2CompletedTreatmentMalignant Melanoma Stage IV1
2CompletedTreatmentMelanoma (Skin)1
2CompletedTreatmentMetastatic Malignant Melanoma1
3CompletedTreatmentMalignant Melanoma / Recurrent Melanoma1
3RecruitingTreatmentMetastatic Brain Tumors1
3TerminatedTreatmentIntraocular Melanoma / Metastatic Cancers1

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 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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as dialkyl alkylphosphonates. These are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphonic acids and derivatives
Sub Class
Phosphonic acid diesters
Direct Parent
Dialkyl alkylphosphonates
Alternative Parents
Phosphonic acid esters / Nitrosoureas / Semicarbazides / Nitrosamides / Organopnictogen compounds / Organophosphorus compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
show 1 more
Substituents
Dialkyl alkylphosphonate / Nitrosourea / Phosphonic acid ester / Semicarbazide / Nitrosamide / Carbonic acid derivative / Organic n-nitroso compound / Organic nitroso compound / Organic oxygen compound / Hydrocarbon derivative
show 12 more
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not 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 enha...
Gene Name
TXNRD1
Uniprot ID
Q16881
Uniprot Name
Thioredoxin reductase 1, cytoplasmic
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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:37