Ligand id: 4815

Name: methotrexate

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Structure and Physico-chemical Properties

2D Structure
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Calculated Physico-chemical Properties
Hydrogen bond acceptors 13
Hydrogen bond donors 5
Rotatable bonds 10
Topological polar surface area 210.54
Molecular weight 454.17
XLogP -2.67
No. Lipinski's rules broken 1

Molecular properties generated using the CDK

Immunopharmacology Comments
Methotrexate is a DMARD prescribed for rheumatoid arthritis, psoriatic arthritis and vasculitis. In inflammation its mode of action relates to its ability to inhibit folate pathway enzymes, including aminoimidazole carboxamide adenosine ribonucleotide transformylase (ATIC; P31939). In vivo conversion of methotrexate to methotrexate-polyglutamates is required for ATIC inhibition [2]. ATIC inhibition leads to intracellular accumulation of its substrate aminoimidazole carboxamide adenosine ribonucleotide (AICAR), increased adenosine release and modulation of immune cell (neutrophils, natural killer cells, monocytes/macrophages and T cells) function, effects which ultimately produce a potent anti-inflammatory effect [1,3]. Key inflammatory mediators such as IL-17, IL-22, IL-23 and CCL20 are downregulated by methotrexate.
Immunopharmacology Disease
Disease X-Refs Comment References
Vasculitis Disease Ontology: DOID:865
Approved drug for vasculitis.
Rheumatoid arthritis Disease Ontology: DOID:7148
OMIM: 180300
Approved drug for RA.
Psoriatic arthritis Disease Ontology: DOID:9008
Approved drug for PsA.
Juvenile idiopathic arthritis Oral solution of methotrexate approved for JIA in pediatric pateints.
Immunopaedia Case Studies Links
My eyes cross at twilight
14 year old with severe hip pain
A 7 year old with severe muscle weakness and difficulty walking
A case of scaly annular plaques
Case of eye injury and decreased vision