Compound: methotrexate
SMILES: O=C(N[C@H](C(=O)O)CCC(=O)O)c1ccc(N(Cc2nc3c(nc(N)nc3N)nc2)C)cc1
InChIKey: FBOZXECLQNJBKD-ZDUSSCGKSA-N
Synonyms: methotrexate, 59-05-2, Amethopterin, Rheumatrex, Metatrexan, Hdmtx, Ledertrexate, Methylaminopterinum, Methotrexatum, Metotrexato, Antifolan, Rasuvo, Emtexate, L-Amethopterin, Amethopterine, NSC-740, Maxtrex, Farmitrexat, Medsatrexate, Methoblastin, Methotextrate, Methotrexat, Brimexate, Emthexat, Emthexate, Fauldexato, Lantarel, Lumexon, Metrotex, Novatrex, Otrexup, Tremetex, Trexeron, Trixilem, Texate, Metex, CL-14377, NCI-C04671, JYLAMVO, EMT 25,299, NSC 740, CL 14377, YL5FZ2Y5U1, R 9985, REDITREX, NSC740, DTXSID4020822, CHEBI:44185, ADX-2191, WR-19039, 4-amino-N(10)-methylpteroylglutamic acid, DTXCID80822, (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid, R-9985, N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid, Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-L-glutamova, Glutamic acid, N-(p-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, L-, L-Glutamic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-, 4-Amino-N10-methylpteroylglutamic acid, Ebetrex, Metoject, Zlatal, Emtexate pf, Emtexate high-pot, (2S)-2-((4-((2,4-diaminopteridin-6-yl)methyl-methylamino)benzoyl)amino)pentanedioic acid, N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutamic acid, Hydrate, Methotrexate, OTREXUP PFS, RefChem:6017, Metex 6013, Dicesium Salt Methotrexate, Methotrexate Methylaminopterin, L01BA01, L04AX03, GLUTAMIC ACID, N-(P-(((2,4-DIAMINO-6-PTERIDINYL)METHYL)METHYLAMINO)BENZOYL)-, L-(+)-, 4-Amino-4-deoxy-10-methylpteroyl-L-glutamic Acid, 4-AMINO-4-DEOXY-N(SUP 10)-METHYLPTEROYLGLUTAMATE, 4-AMINO-4-DEOXY-N(SUP 10)-METHYLPTEROYLGLUTAMIC ACID, N-(4-((2,4-Diaminopteridin-6-ylmethyl)(methyl)amino)benzoyl)-L-glutamic acid, 200-413-8, Methylaminopterin, (S)-2-(4-(((2,4-Diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioic acid, Mexate, MTX, 4-Amino-10-methylfolic acid, N-Bismethylpteroylglutamic acid, C20H22N8O5, Xatmep, Methotrexat-Ebewe, MFCD00064370, CHEMBL34259, TCMDC-125858, A-Methopterin, (2S)-2-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)formamido]pentanedioic acid, N-[(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}phenyl)carbonyl]-L-glutamic acid, NCGC00025060-04, A-Methpterin, Amethopterin L-, Folex-Pfs, Methotrexate, L-, Methotrexate (hydrate), X 133, Metotressato [DCIT], Metotressato, Metolate, MLS001401431, Methotrexatum [INN-Latin], Metotrexato [INN-Spanish], [3H]methotrexate, N-(4-{[(2,4-diaminopteridin-6-yl)methyl](methyl)amino}benzoyl)-L-glutamic acid, SMR000112001, [3H]-methotrexate, folic acid antagonist, CCRIS 1109, 4-Aminomethylpteroylglutamic acid, HSDB 3123, L-(+)-N-(p-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)glutamic acid, N-(p-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-(+)-glutamic acid, SR-01000075682, (+)-4-Amino-10-methylfolic acid, SMR000449324, EINECS 200-413-8, Methotrexate (1.0mg/mL in Methanol with 0.1N NaOH), UNII-YL5FZ2Y5U1, Nordimet, AI3-25299, Methotrexate RS, Extexate;, Maxtrex;, s1210, Intradose-MTX, Mexate;, 4-Amino-N(sup 10)-methylpteroylglutamic acid, Methotrexate CRS, Methylaminopterin;, 1dhi, 1dhj, 2drc, 4ocx, (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]pentanedioic acid, CAS-59-05-2, MPI-2505, Prestwick_322, Otrexup (TN), Xatmep (TN), CL14377, Kyselina 4-amino-N(sup 10)-methylpteroylglutamova [Czech], Methylaminopterin; MTX, Methotrexate [USAN:USP:INN:BAN:JAN], Spectrum_001836, Tocris-1230, 4kn0, Methotrexate (Standard), Prestwick0_000135, Prestwick1_000135, Prestwick2_000135, Spectrum2_001077, Spectrum3_000497, Spectrum4_000616, Spectrum5_000958, Abitrexate (Methotrexate), METHOTREXATE [MI], N-(p-(((2,4-Diamino-6-pteridyl)methyl)methylamino)benzoyl)glutamic acid, METHOTREXATE [INN], METHOTREXATE [JAN], Epitope ID:230085, METHOTREXATE [HSDB], METHOTREXATE [IARC], METHOTREXATE [USAN], N-(4-(((2,4-Diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutamicacid, NCIMech_000767, SCHEMBL3711, Kyselina N-(p-((2,4-diamino-6-pteridinylmethyl)methylamino)benzoyl)-L-glutamova [Czech], METHOTREXATE [VANDF], BIDD:PXR0175, Lopac0_000020, KBioGR_001172, KBioSS_002341, METHOTREXATE [MART.], Kyselina 4-amino-N(sup 10)-methylpteroylglutamova, MLS000049968, MLS002154208, DivK1c_000114, METHOTREXATE [USP-RS], METHOTREXATE [WHO-DD], METHOTREXATE [WHO-IP], SPBio_001094, SPBio_002149, Amethopterin (hydrate); CL14377 (hydrate); WR19039 (hydrate), cid_126941, cid_165528, GTPL4674, GTPL4815, orb1308506, orb3141220, SCHEMBL12421860, SCHEMBL23111732, SCHEMBL29349432, BDBM18050, BDBM66082, HMS500F16, KBio1_000114, KBio2_002338, KBio2_004906, KBio2_007474, KBio3_001493, Methotrexate (JP18/USP/INN), g301, NINDS_000114, Bio1_000486, Bio1_000975, Bio1_001464, GLXC-06696, HMS1568K12, HMS2095K12, HMS2233O18, HMS3260C21, HMS3414L09, HMS3678L07, HMS3712K12, METHOTREXATE [ORANGE BOOK], METHOTREXATE [EP MONOGRAPH], METHOTREXATE [USP IMPURITY], APC-2002, MPI-5004, MSK10330, METHOTREXATE [USP MONOGRAPH], Tox21_110944, Tox21_300269, Tox21_500020, CCG-35800, EBC-12158, EMT-25299, HY-14519R, METHOTREXATUM [WHO-IP LATIN], STL535338, AKOS016340329, Tox21_110944_1, CS-1732, DB00563, KS-5093, LP00020, SDCCGSBI-0050009.P003, IDI1_000114, Methotrexate for peak identification CRS, SMP2_000020, NCGC00025060-01, NCGC00025060-02, NCGC00025060-03, NCGC00025060-05, NCGC00025060-06, NCGC00025060-07, NCGC00025060-08, NCGC00025060-09, NCGC00025060-10, NCGC00025060-11, NCGC00025060-12, NCGC00025060-13, NCGC00025060-15, NCGC00025060-16, NCGC00254216-01, NCGC00260705-01, HY-14519, EU-0100020, G-301, NS00098764, SW198601-3, Methotrexate 1.0 mg/ml in Dimethyl Sulfoxide, C01937, D00142, EN300-119523, Q422232, SR-01000597411, W-60383, SR-01000075682-1, SR-01000075682-2, SR-01000075682-6, SR-01000597411-1, BRD-K59456551-001-09-3, BRD-K59456551-001-11-9, BRD-K59456551-001-19-2, BRD-K59456551-001-20-0, BRD-K59456551-001-22-6, Methotrexate (1 mg/mL in Methanol with 0.1N NaOH), WLN: T66 BN DN GN JNJ CZ EZ H1N1&R DVMYVQ2VQ, Z1521553982, Methotrexate, European Pharmacopoeia (EP) Reference Standard, Methotrexate, United States Pharmacopeia (USP) Reference Standard, Glutamic acid,4-diamino-6-pteridinyl)methyl] methylamino]benzoyl]-, L-(+)-, L-Glutamic acid,4-diamino-6-pteridinyl)methyl]- methylamino]benzoyl]-, L-Glutamic acid,N-[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-,hydrate(9ci), Methotrexate for peak identification, European Pharmacopoeia (EP) Reference Standard, Methotrexate for system suitability, European Pharmacopoeia (EP) Reference Standard, Methotrexate, Pharmaceutical Secondary Standard; Certified Reference Material, N-[4-[[(2,4-Diamino-6-pteridinyl)methyl] methylamino]benzoyl]-L-glutamic acid, (2S)-2-((4-(((2,4-DIAMINOPTERIDIN-6-YL)METHYL)(METHYL)AMINO)BENZOYL)AMINO)PENTANEDIOIC ACID, (2S)-2-[[[4-[(2,4-diamino-6-pteridinyl)methyl-methylamino]phenyl]-oxomethyl]amino]pentanedioic acid;hydrate, (2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methyl-amino]benzoyl]amino]glutaric acid;hydrate, (2S)-2-[[4-[[2,4-bis(azanyl)pteridin-6-yl]methyl-methyl-amino]phenyl]carbonylamino]pentanedioic acid;hydrate, 102613-64-9
Theoretical properties:
molecular_formula: C20H22N8O5
molecular_weight: 454.4 g/mol
exact_mass: 454.17131583 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 5
hydrogen_bond_acceptor_count: 12
rotatable_bond_count: 9
heavy_atom_count: 33
topological_polar_surface_area: 211 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Orange-brown, crystalline powder
color: Orange-brown, crystalline powder
melting_point: 365 to 399 °F (decomposes) (NTP, 1992)
solubility: less than 1 mg/mL at 66 °F (NTP, 1992)
vapor_pressure: 2.1X10-19 mm Hg at 25 °C /Estimated/
Descriptions:
pubchem: Methotrexate can cause developmental toxicity according to an independent committee of scientific and health experts.
chembl: METHOTREXATE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Methotrexate, formerly known as amethopterin, is a chemotherapy agent and immune-system suppressant. It is used to treat cancer, autoimmune diseases, and ectopic pregnancies. Types of cancers it is used for include breast cancer, leukemia, lung cancer, lymphoma, gestational trophoblastic disease, and osteosarcoma. Types of autoimmune diseases it is used for include psoriasis, rheumatoid arthritis, and Crohn's disease. It can be given by mouth or by injection.
Common side effects include nausea, feeling tired, fever, increased risk of infection, low white blood cell counts, and breakdown of the skin inside the mouth. Other side effects may include liver disease, lung disease, lymphoma, and severe skin rashes. People on long-term treatment should be regularly checked for side effects. It is not safe during breastfeeding. In those with kidney problems, lower doses may be needed. It acts by blocking the body's use of folic acid.
Methotrexate was first made in 1947 and initially was used to treat cancer, as it was less toxic than the then-current treatments. In 1956 it provided the first cures of a metastatic cancer. It is on the World Health Organization's List of Essential Medicines. Methotrexate is available as a generic medication. In 2023, it was the 130th most commonly prescribed medication in the United States, with more than 4 million prescriptions.