Record Information |
---|
Version | 5.0 |
---|
Status | Detected but not Quantified |
---|
Creation Date | 2021-09-11 13:13:34 UTC |
---|
Update Date | 2021-09-26 23:07:51 UTC |
---|
HMDB ID | HMDB0254080 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | Licofelone |
---|
Description | Licofelone belongs to the class of organic compounds known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups. Licofelone is a drug which is used for the management of osteoarthritis. Licofelone is a weakly acidic compound (based on its pKa). It is currently under evaluation as a treatment for osteoarthritis (OA), the most common form of arthritis. Although phase III trials have been successfully completed in OA patients no dates for regulatory submission have yet been given. This group of drugs simultaneously inhibits the enzymes cyclooxygenase (COX) and 5-lipoxygenase (LO). Licofelone, through combined 5-LOX/COX-inhibition, reduces levels of inflammatory prostaglandins and leukotrienes. Licofelone belongs to a novel class of dual-acting anti-inflammatory drugs called COX/LO inhibitors. Developed by the German pharmaceutical company, Merckle GmbH, together with EuroAlliance partners Alfa Wassermann and Lacer, licofelone (ML3000) is a dual COX/LOX inhibitor and the first member of this new class of analgesic and anti-inflammatory drugs. This compound has been identified in human blood as reported by (PMID: 31557052 ). Licofelone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Licofelone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
---|
Structure | CC1(C)CN2C(CC(O)=O)=C(C(=C2C1)C1=CC=CC=C1)C1=CC=C(Cl)C=C1 InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27) |
---|
Synonyms | Value | Source |
---|
ML-3000Licofelone | ChEMBL | (2,2-Dimethyl-6-(4-chlorophenyl)-7-phenyl-2,3-dihydro-1H-pyrrolizine-5-yl)acetic acid | MeSH |
|
---|
Chemical Formula | C23H22ClNO2 |
---|
Average Molecular Weight | 379.879 |
---|
Monoisotopic Molecular Weight | 379.13390666 |
---|
IUPAC Name | 2-[6-(4-chlorophenyl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]acetic acid |
---|
Traditional Name | licofelone |
---|
CAS Registry Number | Not Available |
---|
SMILES | CC1(C)CN2C(CC(O)=O)=C(C(=C2C1)C1=CC=CC=C1)C1=CC=C(Cl)C=C1 |
---|
InChI Identifier | InChI=1S/C23H22ClNO2/c1-23(2)13-19-22(15-6-4-3-5-7-15)21(16-8-10-17(24)11-9-16)18(12-20(26)27)25(19)14-23/h3-11H,12-14H2,1-2H3,(H,26,27) |
---|
InChI Key | UAWXGRJVZSAUSZ-UHFFFAOYSA-N |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as diphenylpyrroles. These are aromatic heterocyclic compounds with a structure based on a pyrrole ring linked to exactly two phenyl groups. |
---|
Kingdom | Organic compounds |
---|
Super Class | Organoheterocyclic compounds |
---|
Class | Pyrroles |
---|
Sub Class | Substituted pyrroles |
---|
Direct Parent | Diphenylpyrroles |
---|
Alternative Parents | |
---|
Substituents | - 3,4-diphenylpyrrole
- Pyrrolizine
- Chlorobenzene
- Halobenzene
- Aryl chloride
- Aryl halide
- Monocyclic benzene moiety
- Benzenoid
- Heteroaromatic compound
- Carboxylic acid derivative
- Carboxylic acid
- Azacycle
- Monocarboxylic acid or derivatives
- Organopnictogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Organic nitrogen compound
- Carbonyl group
- Organohalogen compound
- Organochloride
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - Licofelone GC-MS (Non-derivatized) - 70eV, Positive | splash10-01qi-2319000000-343cbbea2e1a5e8c3ba2 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Licofelone GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Licofelone GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Licofelone GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-04 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 10V, Positive-QTOF | splash10-01q9-0009000000-c1edc68213358fc93429 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 20V, Positive-QTOF | splash10-01x0-0009000000-1b2272d4230ff5df65bc | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 40V, Positive-QTOF | splash10-0g59-2019000000-0b4c1cbc4c6846207e13 | 2017-07-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 10V, Negative-QTOF | splash10-004i-0009000000-77aa44a3ca13970ab586 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 20V, Negative-QTOF | splash10-003r-0009000000-1498932343eadedd74d9 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 40V, Negative-QTOF | splash10-03yj-1029000000-7fd8c56d74cd6c742f53 | 2017-07-26 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 10V, Positive-QTOF | splash10-001i-0009000000-3a7e62801604951e8a42 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 20V, Positive-QTOF | splash10-001i-0009000000-04f90cfe0fbd3eccbfb5 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 40V, Positive-QTOF | splash10-03k9-1097000000-fa7cad65e4c84223709a | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 10V, Negative-QTOF | splash10-001i-0009000000-fe5081000e9ed8a97647 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 20V, Negative-QTOF | splash10-001i-0009000000-c8a28569492b5af7f6f5 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Licofelone 40V, Negative-QTOF | splash10-001i-9023000000-cda563e3bfd319881d38 | 2021-10-12 | Wishart Lab | View Spectrum |
|
---|