Identification
NameCarmofur
Accession NumberDB09010
TypeSmall Molecule
GroupsWithdrawn
Description

Carmofur is a derivative of fluorouracil, and is an antineoplastic agent that has been used in the treatment of breast and colorectal cancer. Carmofur has been known to induce leukoencephalopathy.

Structure
Thumb
SynonymsNot Available
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MifurolBayer
Brand mixturesNot Available
Categories
UNIIHA82M3RAB2
CAS number61422-45-5
WeightAverage: 257.2614
Monoisotopic: 257.117569598
Chemical FormulaC11H16FN3O3
InChI KeyAOCCBINRVIKJHY-UHFFFAOYSA-N
InChI
InChI=1S/C11H16FN3O3/c1-2-3-4-5-6-13-10(17)15-7-8(12)9(16)14-11(15)18/h7H,2-6H2,1H3,(H,13,17)(H,14,16,18)
IUPAC Name
5-fluoro-N-hexyl-4-hydroxy-2-oxo-1,2-dihydropyrimidine-1-carboximidic acid
SMILES
CCCCCCN=C(O)N1C=C(F)C(O)=NC1=O
Pharmacology
IndicationNot Available
Structured Indications Not 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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Carmofur.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Carmofur.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Carmofur.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Carmofur.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Carmofur.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Carmofur.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Carmofur.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Carmofur.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Carmofur.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Carmofur.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Carmofur.Approved, Vet Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Carmofur.Approved, Investigational
Food InteractionsNot Available
References
Synthesis Reference

U.S. Patent 4,071,519.

General ReferencesNot Available
External Links
ATC CodesL01BC04 — Carmofur
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)283U.S. Patent 4,071,519.
Predicted Properties
PropertyValueSource
Water Solubility0.0273 mg/mLALOGPS
logP1.74ALOGPS
logP2.62ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)5.55ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area85.49 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.23 m3·mol-1ChemAxon
Polarizability25.84 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassDiazines
Direct ParentHalopyrimidines
Alternative ParentsPyrimidones / Hydropyrimidines / Aryl fluorides / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
SubstituentsHalopyrimidine / Pyrimidone / Aryl fluoride / Aryl halide / Hydropyrimidine / Heteroaromatic compound / Vinylogous amide / Lactam / Carbonic acid derivative / Urea
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Drug created on June 20, 2014 12:00 / Updated on September 01, 2017 12:01