METHOTREXATE

NSC - 740

SMILE String: n1cc(nc2c1nc(nc2N)N)CN(c1ccc(cc1)C(=O)N[CH](CCC(O)=O)C(O)=O)C


Ultraviolet Absorption:
(0.1 N NaOH)
X max                E
258 ± 2 nm     22,800 - 25,200   
303 ± 2 nm     23,200 - 25,200
372 ± 2 nm     7,350 - 8,200

CAS Registry Number: 59 -05 -2

Molecular Formula: C20H22N8O5.2H2O

Chemical Name: N-[4-[[(2,4-diamino-6-pteridinyl)-methyl]methylamino]benzoyl]glutamic acid,dihydrate

Other Names: MTX; Amethopterine; 4-amino-l0-methylfolic acid

M.W.:490.5


High Performance Liquid Chromatography:

Column: 300 mm x 4 mm i.d. Spherisorb ODS

Mobile Phase: 20% CH in 0.1 M KH at pH 6.7

Flow Rate: 2 mL /min

Detection: UV at 254 nm

Sample Preparation: 1 mg sample in 1.0 mL 0.02 N NaOH or internal standard solution

Internal Standard: 5 mg 4-deoxy-4-amino-N methylpteroic acid /5 mL 0.02 N NaOH

Retention Volume: 11.5 mL (NSC 740)
                  19.0 mL (I.S.)

Optical Rotation:
(c = 1, 0.05 M Na2CO3)   [a]20 D = +17.0 - 19.5°

Toxicity Data:

Man(iv): TD: 740 mg/kg
Archives of Internal Medicine,136,1321(1976)

Mouse(ip): LD50 mg/kg
Anatomical Record 178,465(1974)

Rat(po): LD50 135 mg/kg
Drugs in Japan. Ethical Drugs, 6th Ed.,(1982),p841

Rat(ip): LD50 6 mg/kg
Drugs in Japan. Ethical Drugs, 6th Ed.,(1982),p841