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Chemistry

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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
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 Weight 563.6 g/mol
Molecular Formula C25H33N5O10
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count15
Rotatable Bond Count11
Exact Mass563.22274227 g/mol
Monoisotopic Mass563.22274227 g/mol
Topological Polar Surface Area253 Ų
Heavy Atom Count40
Formal Charge0
Complexity648
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2

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