Rx00154 - Methotrexate


Name:
Methotrexate
Rx ID:
Rx00154
Validation Level:
Phenomic Similarity:
0.432
Reference ID:
DB00563
Primary Indications:
Cancer
Orphan Indications:
No annotated orphan indications.
Rare Indications:
No annotated rare indications.
Common Indications:
Psoriasis; Rheumatoid Arthritis
Pathways:
Antimetabolite Pathway - Folate Cycle, Pharmacodynamics; Thiopurine Pathway, Pharmacokinetics/Pharmacodynamics; Methotrexate Pathway (Cancer Cell), Pharmacodynamics
Drug Interactions:
Acetylsalicylic acid; Acitretin; Amoxicillin; Ampicillin; Bacampicillin; Benzylpenicillin; Bismuth Subsalicylate; Carbenicillin; Cholestyramine; Ciprofloxacin; ...
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Food Interactions:
Milk appears to reduce its absorption. Take without regard to meals. Limit caffeine intake.

Interactive 3D Model

Interactive Drug Target Network

Interactive Bipartite Drug Repurposing Graph

Rx00154
Primary Indication
Secondary Indication

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Chemical, Pharmacological and Biological Annotations


ATC Code:
L01BA01 L04AX03;
Brands:
Abitrexate (Teva); Alltrex (Naprod); Artrait (TRB); Atrexel (Schering-Plough); Bendatrexat (Bendalis); Carditrex (Cadila); Dermotrex (East West); Ebetrex (Ebewe); Emtexate; Ledertrexate (Biodim); Maxtrex (Pfizer); Meisusheng (Hospira); Mexate (Cadila HC); Rheumatrex (Wyeth KK); Trexan (Atafarm); Zexate (Dabur Pharma)
Categories:
Antirheumatic Agents; Dermatologic Agents; Immunosuppressive Agents; Enzyme Inhibitors; Folic Acid Antagonists; Nucleic Acid Synthesis Inhibitors; Antimetabolites, Antineoplastic; Abortifacient Agents, Nonsteroidal; Abortifacient Agents
ChEBI ID:
6837
PubChem ID:
126941
KEGG Drug ID:
D00142
SMILE:
CN(CC1=CN=C2N=C(N)N=C(N)C2=N1)C1=CC=C(C=C1)C(=O)N[C@@H](CCC(O)=O)C(O)=O
InChI:
1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m0/s1
Classification:
Kingdom:
Organic Compounds
Superclass:
Benzenoids
Class:
Benzene and Substituted Derivatives
Subclass:
Benzamides
Indication:
Methotrexate is indicated in the treatment of gestational choriocarcinoma, chorioadenoma destruens and hydatidiform mole. In acute lymphocytic leukemia, methotrexate is indicated in the prophylaxis of meningeal leukemia and is used in maint...
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Pharmacodynamics:
Methotrexate is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cel...
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Description:
An antineoplastic antimetabolite with immunosuppressant properties. It is an inhibitor of tetrahydrofolate dehydrogenase and prevents the formation of tetrahydrofolate, necessary for synthesis of thymidylate, an essential component of DNA. ...
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Mechanism:
Methotrexate anti-tumor activity is a result of the inhibition of folic acid reductase, leading to inhibition of DNA synthesis and inhibition of cellular replication. The mechanism involved in its activity against rheumatoid arthritis is no...
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Adsorption, Distribution, Metabolism, Excretion and Toxicity


Human Intestinal Absorption:
+
Blood Brain Barrier:
-
Caco-2 permeable:
-
P-glycoprotein substrate:
Substrate
P-glycoprotein inhibitor I:
Non-inhibitor
P-glycoprotein inhibitor II:
Non-inhibitor
Renal organic cation transporter:
Non-inhibitor
CYP450 2C9 substrate:
Non-inhibitor
CYP450 2D6 substrate:
Non-inhibitor
CYP450 2C19 substrate:
Non-inhibitor
CYP450 inhibitory promiscuity:
Low CYP Inhibitory Promiscuity
Ames test:
Non AMES toxic
Carcinogenicity:
Non-carcinogens
Biodegradation:
Not ready biodegradable
Rat acute toxicity:
3.4955 LD50, mol/kg
hERG inhibition (predictor I):
Weak inhibitor
hERG inhibition (predictor II):
Non-inhibitor

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Please contact us if you have questions or comments about RepurposeDB. You can also contact us if you need help in submitting your drug repositioning investigation to RepurposeDB.


Dudley Laboratory
Department of Genetics and Genomic Sciences
Icahn Institute for Genomics and Multiscale Biology
Icahn School of Medicine at Mount Sinai
One Gustave L. Levy Place, Box 1498
Manhattan, New York City, NY
repurposedb@dudleylab.org