Methotrexate
Structural Formula Vector Image
Title: Methotrexate
CAS Registry Number: 59-05-2
CAS Name: N-[4-[[(2,4-Diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-glutamic acid
Additional Names: 4-amino-N10-methylpteroylglutamic acid; 4-amino-10-methylfolic acid; methylaminopterin; amethopterin; MTX
Manufacturers' Codes: CL-14377
Trademarks: Ledertrexate (Wyeth); Maxtrex (Pharmacia)
Molecular Formula: C20H22N8O5
Molecular Weight: 454.44
Percent Composition: C 52.86%, H 4.88%, N 24.66%, O 17.60%
Literature References: Folic acid antagonist. Prepn: D. R. Seeger et al., J. Am. Chem. Soc. 71, 1753 (1949); J. M. Smith, D. B. Cosulich, US 2512572 (1950 to American Cyanamid). Metabolism: M. V. Freeman, J. Pharmacol. Exp. Ther. 122, 154 (1958); E. S. Henderson et al., Cancer Res. 25, 1008, 1018 (1965). Toxicity data: H. R. Scherf et al., Arzneim.-Forsch. 20, 1467 (1970). Comprehensive description: A. R. Chamberlin et al., Anal. Profiles Drug Subs. 5, 283-306 (1976). Review of metabolism and pharmacokinetics: W. E. Evans, Appl. Pharmacokinet. 1980, 518-548; of clinical pharmacology and toxicity: J. R. Bertino, Cancer Chemother. 3, 359-375 (1981); J. Jolivet et al., N. Engl. J. Med. 309, 1094-1104 (1983). Symposium on clinical experience in rheumatoid arthritis: J. Rheumatol. 12, Suppl. 12, 1-44 (1985). Review of use in leukemia: O. G. Jonsson, B. A. Kamen, Cancer Invest. 9, 53-60 (1991). Clinical trials in Crohn's disease: B. G. Feagan et al., N. Engl. J. Med. 332, 292 (1995); idem et al., ibid. 342, 1627 (2000). CE determn in blood: C.-Y. Kuo et al., J. Chromatogr. A 1014, 93 (2003). Review of pulmonary toxicity: O. Lateef et al., Expert Opin. Drug Saf. 4, 723-730 (2005).
 
Derivative Type: Monohydrate
CAS Registry Number: 6745-93-3
Properties: Yellow crystals from dil HCl, dec 185-204° (bath preheated to 160°). uv max (0.1N HCl): 244, 307 nm; (0.1N NaOH): 257, 302, 370 nm. Soluble in alkaline solns with decompn. LD50 i.v. in rats: 14 mg/kg (Scherf).
Absorption maximum: uv max (0.1N HCl): 244, 307 nm; (0.1N NaOH): 257, 302, 370 nm
Toxicity data: LD50 i.v. in rats: 14 mg/kg (Scherf)
 
Derivative Type: Disodium salt
CAS Registry Number: 7413-34-5
Trademarks: Folex (Pfizer); Mexate (BMS); Rheumatrex (Stada)
Molecular Formula: C20H20N8Na2O5
Molecular Weight: 498.40
Percent Composition: C 48.20%, H 4.04%, N 22.48%, Na 9.23%, O 16.05%
 
Therap-Cat: Antineoplastic; antirheumatic.
Keywords: Antiarthritic/Antirheumatic; Antineoplastic; Antimetabolites; Folic Acid Analogs/Antagonists.

Other Monographs:
TrisilaneLead Antimonate(V)Behenic AcidCottonseed Oil
Fluanisone2,2,3,3,4,4,5,5-Octafluoro-1-pentanolWoollins' ReagentBenzo[a]pyrene
Indocyanine GreenDipipanoneHeparamineZolpidem
ActinobolinHalobetasol PropionateRiboflavin MonophosphateVitamin E
©2006-2023 DrugFuture->Chemical Index Database