Trimetrexate Glucuronate

Synopsis, Chemistry

DOSSIERs // Finished Dosage Formulations

2 Dossiers, 2 FDA Orange Book

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Also known as: Ci 898 dihydrochloride, Trimetrexate d-glucuronate, 82952-64-5, Trimetrexate glucuronate [usan], L137u4a79k, Nsc-352122

Molecular Formula

C₂₅H₃₃N₅O₁₀

Molecular Weight

563.6 g/mol

InChI Key

ZCJXQWYMBJYJNB-LRDBBFHQSA-N

FDA UNII

L137U4A79K

Trimetrexate Glucuronate is a lipid soluble methotrexate derivative with potential antineoplastic activity. Trimetrexate glucuronate inhibits the enzyme dihydrofolate reductase, thereby preventing the synthesis of purine nucleotides and thymidylate, with subsequent inhibition of DNA and RNA synthesis. Trimetrexate glucuronate also exhibits antiviral activity. (NCI04)

1 2D Structure

Trimetrexate Glucuronate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline-2,4-diamine;(2S,3S,4S,5R)-2,3,4,5-tetrahydroxy-6-oxohexanoic acid

2.1.2 InChI

InChI=1S/C19H23N5O3.C6H10O7/c1-10-11(5-6-13-16(10)18(20)24-19(21)23-13)9-22-12-7-14(25-2)17(27-4)15(8-12)26-3;7-1-2(8)3(9)4(10)5(11)6(12)13/h5-8,22H,9H2,1-4H3,(H4,20,21,23,24);1-5,8-11H,(H,12,13)/t;2-,3+,4-,5-/m.0/s1

2.1.3 InChI Key

ZCJXQWYMBJYJNB-LRDBBFHQSA-N

2.1.4 Canonical SMILES

CC1=C(C=CC2=C1C(=NC(=N2)N)N)CNC3=CC(=C(C(=C3)OC)OC)OC.C(=O)C(C(C(C(C(=O)O)O)O)O)O

2.1.5 Isomeric SMILES

CC1=C(C=CC2=C1C(=NC(=N2)N)N)CNC3=CC(=C(C(=C3)OC)OC)OC.C(=O)[C@@H]([C@H]([C@@H]([C@@H](C(=O)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

L137U4A79K

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Neutrexin

2. Nsc 352122

3. Nsc-352122

4. Trimetrexate Glucuronic Acid Combination

2.3.2 Depositor-Supplied Synonyms

1. Ci 898 Dihydrochloride

2. Trimetrexate D-glucuronate

3. 82952-64-5

4. Trimetrexate Glucuronate [usan]

5. L137u4a79k

6. Nsc-352122

7. 2,4-diamino-5-methyl-6-((3,4,5-trimethoxyanilino)methyl)quinazoline Mono-d-glucuronate

8. 2,4-quinazolinediamine, 5-methyl-6-(((3,4,5-trimethoxyphenyl)amino)methyl)-, Mono-d-glucuronate

9. D-glucuronic Acid, Compd. With 5-methyl-6-(((3,4,5-trimethoxyphenyl)amino)methyl)-2,4-quinazolinediamine (1:1)

10. Trimetrexate Glucuronate (usan)

11. Neutrexin (tn)

12. Drg-0183

13. Nsc 352122

14. Schembl3635

15. Unii-l137u4a79k

16. Dtxsid90273968

17. Trimetrexate D-glucuronate [mi]

18. 6-(((3,4,5-trimethoxyphenyl)amino)methyl)-5-methyl-2,4-quinazolinediamine Glucuronate

19. Trimetrexate Glucuronate [mart.]

20. Trimetrexate Glucuronate [vandf]

21. Trimetrexate Glucuronate [who-dd]

22. Hy-103396

23. Cs-0027819

24. Trimetrexate Glucuronate [orange Book]

25. D06239

26. Q27282570

27. 5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline-2,4-diamine;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxy-6-oxohexanoic Acid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₅H₃₃N₅O₁₀
Molecular Weight	563.6 g/mol
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	11
Exact Mass	563.22274227 g/mol
Monoisotopic Mass	563.22274227 g/mol
Topological Polar Surface Area	253 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	648
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2