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Methotrexate

Catalog Number: EVT-252981

CAS Number: 59-05-2

Molecular Formula: C20H22N8O5

Molecular Weight: 454.4 g/mol

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Product Introduction

Description

Methotrexate is a widely used drug in the treatment of various diseases, including cancer, autoimmune disorders, and ectopic pregnancy. It is a folate antagonist that inhibits the synthesis of DNA, RNA, and proteins, leading to the death of rapidly dividing cells. Methotrexate has been in use for over 60 years and has proven to be effective in treating a range of diseases. This paper will discuss the method of synthesis or extraction, chemical structure and biological activity, biological effects, applications, future perspectives, and challenges of methotrexate.

Properties

CAS Number

59-05-2

Product Name

Methotrexate

IUPAC Name

(2S)-2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]pentanedioic acid

Molecular Formula

C20H22N8O5

Molecular Weight

454.4 g/mol

InChI

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

InChI Key

FBOZXECLQNJBKD-ZDUSSCGKSA-N

SMILES

CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O

Solubility

less than 1 mg/mL at 66° F (NTP, 1992)
Insoluble in water , alcohol, chloroform, ether; slightly soluble in dilute hydrochloric acid; soluble in dil solns of alkali hydroxides and carbonates.
Practically insoluble in water and in alcohol.
In water, 2.6X10+3 mg/L at 25 °C /Estimated/
1.71e-01 g/L

Synonyms

Amethopterin
Dicesium Salt Methotrexate
Hydrate, Methotrexate
Methotrexate
Methotrexate Hydrate
Methotrexate Sodium
Methotrexate, (D)-Isomer
Methotrexate, (DL)-Isomer
Methotrexate, Dicesium Salt
Methotrexate, Disodium Salt
Methotrexate, Sodium Salt
Mexate
Sodium, Methotrexate

Canonical SMILES

CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)NC(CCC(=O)O)C(=O)O

Isomeric SMILES

CN(CC1=CN=C2C(=N1)C(=NC(=N2)N)N)C3=CC=C(C=C3)C(=O)N[C@@H](CCC(=O)O)C(=O)O

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