NAV

Carmofur

Identification

Generic Name
Carmofur
DrugBank Accession Number
DB09010
Background

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.

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 257.2614
Monoisotopic: 257.117569598
Chemical Formula
C11H16FN3O3
Synonyms
  • Carmofur
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
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

Adverse Effects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Carmofur is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Carmofur is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Carmofur is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Carmofur is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Carmofur is combined with Bupivacaine.
Food Interactions
Not Available

Products

Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
International/Other Brands
Mifurol (Bayer) / Yamaful

Categories

ATC Codes
L01BC04 — Carmofur
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Carbonic acid derivative / Halopyrimidine / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
HA82M3RAB2
CAS number
61422-45-5
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-2,4-dioxo-1,2,3,4-tetrahydropyrimidine-1-carboxamide
SMILES
CCCCCCNC(=O)N1C=C(F)C(=O)NC1=O

References

Synthesis Reference

U.S. Patent 4,071,519.

General References
Not Available
KEGG Drug
D01784
PubChem Compound
2577
PubChem Substance
310264969
ChemSpider
2479
BindingDB
50431275
ChEBI
31360
ChEMBL
CHEMBL460499
ZINC
ZINC000001542916
Drugs.com
Drugs.com Drug Page
Wikipedia
Carmofur

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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 Solubility0.0491 mg/mLALOGPS
logP2.57ALOGPS
logP1.44Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.88Chemaxon
pKa (Strongest Basic)-8.3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area78.51 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity62.39 m3·mol-1Chemaxon
Polarizability25.66 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/MSsplash10-0a4i-1290000000-4891e18640d1f04bb002
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0890000000-b2d86d3d6d64390c258d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-053r-9600000000-fd958b70213f5d0c0810
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-5900000000-13889de7e775c81fcac8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9400000000-8d34a32c5ab82cb0b6db
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-053u-8900000000-3f9fec08626b68e5a464
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-156.6568
predicted
DeepCCS 1.0 (2019)
[M+H]+159.30777
predicted
DeepCCS 1.0 (2019)
[M+Na]+167.44633
predicted
DeepCCS 1.0 (2019)

Drug created at June 20, 2014 18:00 / Updated at February 21, 2021 18:52