Carmofur

Identification

Name
Carmofur
Accession Number
DB09010
Type
Small Molecule
Groups
Withdrawn
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
Synonyms
Not Available
International/Other Brands
Mifurol (Bayer)
Categories
UNII
HA82M3RAB2
CAS number
61422-45-5
Weight
Average: 257.2614
Monoisotopic: 257.117569598
Chemical Formula
C11H16FN3O3
InChI Key
AOCCBINRVIKJHY-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

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
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 Carmofur.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Carmofur.Experimental
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
CymarinCymarin may decrease the cardiotoxic activities of Carmofur.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Carmofur.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Carmofur.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Carmofur.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) 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
GitoformateGitoformate may decrease the cardiotoxic activities of Carmofur.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Carmofur.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Carmofur.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Carmofur.Experimental, Investigational
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
PeruvosidePeruvoside may decrease the cardiotoxic activities of Carmofur.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Carmofur.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Carmofur.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

U.S. Patent 4,071,519.

General References
Not Available
External Links
PubChem Compound
2577
PubChem Substance
310264969
ChemSpider
2479
BindingDB
50431275
ChEBI
31360
ChEMBL
CHEMBL460499
Drugs.com
Drugs.com Drug Page
Wikipedia
Carmofur
ATC Codes
L01BC04 — Carmofur

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Halopyrimidines
Alternative Parents
Pyrimidones / Hydropyrimidines / Aryl fluorides / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds
show 4 more
Substituents
Halopyrimidine / Pyrimidone / Aryl fluoride / Aryl halide / Hydropyrimidine / Heteroaromatic compound / Vinylogous amide / Lactam / Carbonic acid derivative / Urea
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on June 20, 2014 12:00 / Updated on November 09, 2017 04:44