Methotrexate

Description: Methotrexate (MTX; alphamethopterin; amethopterin; methylaminopterin; CL-14377; NCIC04671; WR19039; NCI-C04671) is an FDA approved antineoplastic and immunosuppressant drug that belongs to the antimetabolite and antifolate class of drugs. It acts by inhibiting the metabolism of folic acid in activated peripheral T cells. Specifically, methotrexate binds to and inhibits the enzyme dihydrofolate reductase, resulting in inhibition of purine nucleotide and thymidylate synthesis and, subsequently, inhibition of DNA and RNA syntheses. Methotrexate (Amethopterin) is the disease-modifying antirheumatic drug(DMARD) of first choice for the treatment of RA in most countriesworldwide. Methotrexate is an antineoplastic agent used to fight anumber of different cancers, such as acute lymphoblastic leukemia andsolid cancers.

References: J Clin Invest. 1998 Jul 15; 102(2):322-8; J Clin Invest. 1993 Dec; 92(6):2675-82.

Related CAS #: 7413-34-5 (disodium) 59-05-2 (free acid) 7532-09-4 (monosodium) 6745-93-3 (hydrate) 15475-56-6 (sodium)

Chemical Name: (S)-2-(4-(((2, 4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioic acid.

InChi Key: FBOZXECLQNJBKD-ZDUSSCGKSA-N

InChi Code: 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

SMILES Code: O=C(O)[CH](NC(C1=CC=C(N(CC2=NC3=C(N)N=C(N)N=C3N=C2)C)C=C1)=O)CCC(O)=O