Leflunomide (CHEM016754)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 03:42:43 UTC
Update Date2016-11-09 01:15:27 UTC
Accession NumberCHEM016754
Identification
Common NameLeflunomide
ClassSmall Molecule
DescriptionLeflunomide is a pyrimidine synthesis inhibitor belonging to the DMARD (disease-modifying antirheumatic drug) class of drugs, which are chemically and pharmacologically very heterogeneous. Leflunomide was approved by FDA and in many other countries (e.g., Canada, Europe) in 1999.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
5-Methyl-N-(4-(trifluoromethyl)phenyl)-4-isoxazolecarboxamideChEBI
5-Methylisoxazole-4-carboxylic acid (4-trifluoromethyl)anilideChEBI
alpha,alpha,alpha-Trifluoro-5-methyl-4-isoxazolecarboxy-p-toluidideChEBI
AravaChEBI
LeflunomidaChEBI
LeflunomidumChEBI
5-Methylisoxazole-4-carboxylate (4-trifluoromethyl)anilideGenerator
a,a,a-Trifluoro-5-methyl-4-isoxazolecarboxy-p-toluidideGenerator
Α,α,α-trifluoro-5-methyl-4-isoxazolecarboxy-p-toluidideGenerator
Aventis behring brand OF leflunomideHMDB
Aventis brand OF leflunomideHMDB
HWA 486HMDB
HWA-486HMDB
Aventis pharma brand OF leflunomideHMDB
Hoechst brand OF leflunomideHMDB
N-(4-Trifluoromethyphenyl)-5-methylisoxazole-4-carboxamideHMDB
Chemical FormulaC12H9F3N2O2
Average Molecular Mass270.207 g/mol
Monoisotopic Mass270.062 g/mol
CAS Registry Number75706-12-6
IUPAC Name5-methyl-N-[4-(trifluoromethyl)phenyl]-1,2-oxazole-4-carboxamide
Traditional Nameleflunomide
SMILESCC1=C(C=NO1)C(=O)NC1=CC=C(C=C1)C(F)(F)F
InChI IdentifierInChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)
InChI KeyVHOGYURTWQBHIL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAnilides
Direct ParentAromatic anilides
Alternative Parents
Substituents
  • Aromatic anilide
  • Trifluoromethylbenzene
  • Azole
  • Isoxazole
  • Heteroaromatic compound
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organopnictogen compound
  • Alkyl fluoride
  • Organic oxygen compound
  • Alkyl halide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.084 g/LALOGPS
logP2.52ALOGPS
logP2.51ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)10.41ChemAxon
pKa (Strongest Basic)-0.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.13 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity64.16 m³·mol⁻¹ChemAxon
Polarizability23.11 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-7970000000-03045269425a638f328cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-0390000000-1ac4065d1ef245442a16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-05gi-3920000000-db0dc9413f5ca5cb69e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00di-0390000000-1ac4065d1ef245442a16Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-03di-2920000000-819d0674f452a60be1a4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-00lr-9200000000-414a713461b4237c6e71Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-001i-9200000000-e21878adb74f0a5190bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-00lr-9050000000-6c169fcd04bf0a4c16a8Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-001i-9110000000-459c33159bb27094ea91Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-001i-9200000000-a48fe3379802d9cfce95Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-001i-9200000000-19d3236cea84dc0f5ff1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Positivesplash10-001i-9200000000-0ef7ffe353ea10020f8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0390000000-e07a793be0a4de994083Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1930000000-dbdbb3e67b067703099dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-7900000000-24b45cc5af1bf1c20902Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-3090000000-039b17df86bfcf213d45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9010000000-95fb3f6c8f86b32a3a33Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01q9-9100000000-0bee5f2dec9154ee9333Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-1190000000-320ce8ab21656bf61a98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2490000000-e7bd4a27fe1066098f17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-9320000000-01ed6f4bd00aeceec987Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-5090000000-2d9438c678553c6a4277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2920000000-70daf72ac22ca58c8b59Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0900000000-f53ae2f06f61c346c9e3Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01097
HMDB IDHMDB0015229
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkLeflunomide
Chemspider ID3762
ChEBI ID6402
PubChem Compound ID3899
Kegg Compound IDC07905
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Fox RI: Mechanism of action of leflunomide in rheumatoid arthritis. J Rheumatol Suppl. 1998 Jul;53:20-6.
2. Herrmann ML, Schleyerbach R, Kirschbaum BJ: Leflunomide: an immunomodulatory drug for the treatment of rheumatoid arthritis and other autoimmune diseases. Immunopharmacology. 2000 May;47(2-3):273-89.
3. Schattenkirchner M: The use of leflunomide in the treatment of rheumatoid arthritis: an experimental and clinical review. Immunopharmacology. 2000 May;47(2-3):291-8.
4. Goldenberg MM: Leflunomide, a novel immunomodulator for the treatment of active rheumatoid arthritis. Clin Ther. 1999 Nov;21(11):1837-52; discussion 1821.
5. Breedveld FC, Dayer JM: Leflunomide: mode of action in the treatment of rheumatoid arthritis. Ann Rheum Dis. 2000 Nov;59(11):841-9.
6. Sanders S, Harisdangkul V: Leflunomide for the treatment of rheumatoid arthritis and autoimmunity. Am J Med Sci. 2002 Apr;323(4):190-3.
7. Li EK, Tam LS, Tomlinson B: Leflunomide in the treatment of rheumatoid arthritis. Clin Ther. 2004 Apr;26(4):447-59.
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=10515382
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=10702725
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=10890256
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=11043056
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=11053058
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=11067959
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=11271257
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=11333342
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=11340750
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=11391470
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=11475244
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=11522581
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=11707749
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=11718154
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=11876141
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=11884931
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=11994686
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=12017890
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=12074690
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=12833393
28. https://www.ncbi.nlm.nih.gov/pubmed/?term=14622739
29. https://www.ncbi.nlm.nih.gov/pubmed/?term=15030575
30. https://www.ncbi.nlm.nih.gov/pubmed/?term=15127968
31. https://www.ncbi.nlm.nih.gov/pubmed/?term=15127974
32. https://www.ncbi.nlm.nih.gov/pubmed/?term=15188371
33. https://www.ncbi.nlm.nih.gov/pubmed/?term=15214907
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=15385935
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=15489872
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=15537652
37. https://www.ncbi.nlm.nih.gov/pubmed/?term=15652966
38. https://www.ncbi.nlm.nih.gov/pubmed/?term=15665760
39. https://www.ncbi.nlm.nih.gov/pubmed/?term=15789891
40. https://www.ncbi.nlm.nih.gov/pubmed/?term=15899055
41. https://www.ncbi.nlm.nih.gov/pubmed/?term=15934905
42. https://www.ncbi.nlm.nih.gov/pubmed/?term=16106593
43. https://www.ncbi.nlm.nih.gov/pubmed/?term=16142756
44. https://www.ncbi.nlm.nih.gov/pubmed/?term=16202258
45. https://www.ncbi.nlm.nih.gov/pubmed/?term=16284916
46. https://www.ncbi.nlm.nih.gov/pubmed/?term=16638062
47. https://www.ncbi.nlm.nih.gov/pubmed/?term=16638420
48. https://www.ncbi.nlm.nih.gov/pubmed/?term=16645972
49. https://www.ncbi.nlm.nih.gov/pubmed/?term=16688677
50. https://www.ncbi.nlm.nih.gov/pubmed/?term=16769661
51. https://www.ncbi.nlm.nih.gov/pubmed/?term=16778342
52. https://www.ncbi.nlm.nih.gov/pubmed/?term=17366662
53. https://www.ncbi.nlm.nih.gov/pubmed/?term=17604599
54. https://www.ncbi.nlm.nih.gov/pubmed/?term=17646975
55. https://www.ncbi.nlm.nih.gov/pubmed/?term=17854740
56. https://www.ncbi.nlm.nih.gov/pubmed/?term=18034546
57. https://www.ncbi.nlm.nih.gov/pubmed/?term=18173611
58. https://www.ncbi.nlm.nih.gov/pubmed/?term=18413415
59. https://www.ncbi.nlm.nih.gov/pubmed/?term=18496682
60. https://www.ncbi.nlm.nih.gov/pubmed/?term=18663553
61. https://www.ncbi.nlm.nih.gov/pubmed/?term=18688040
62. https://www.ncbi.nlm.nih.gov/pubmed/?term=19169882
63. https://www.ncbi.nlm.nih.gov/pubmed/?term=19190124
64. https://www.ncbi.nlm.nih.gov/pubmed/?term=19344337
65. https://www.ncbi.nlm.nih.gov/pubmed/?term=19581389
66. https://www.ncbi.nlm.nih.gov/pubmed/?term=19715969
67. https://www.ncbi.nlm.nih.gov/pubmed/?term=19751817
68. https://www.ncbi.nlm.nih.gov/pubmed/?term=19770782
69. https://www.ncbi.nlm.nih.gov/pubmed/?term=7496341
70. https://www.ncbi.nlm.nih.gov/pubmed/?term=7676489
71. https://www.ncbi.nlm.nih.gov/pubmed/?term=8610393
72. https://www.ncbi.nlm.nih.gov/pubmed/?term=9075844
73. https://www.ncbi.nlm.nih.gov/pubmed/?term=9123314
74. https://www.ncbi.nlm.nih.gov/pubmed/?term=9625011
75. https://www.ncbi.nlm.nih.gov/pubmed/?term=9777697