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Also known as: Arfolitixorin, 31690-11-6, Modufolin, 6r-mthf, Methylenetetrahydrofolic acid, l-(+)-, Arfolitixorin [usan]

Molecular Formula

C₂₀H₂₃N₇O₆

Molecular Weight

457.4 g/mol

InChI Key

QYNUQALWYRSVHF-OLZOCXBDSA-N

FDA UNII

Z8R4A37V9Q

Arfolitixorin is the R-isomer of folitixorin, a reduced folate-based biomodulator and active metabolite of folate drugs leucovorin (LV) and levoleucovorin (l-LV) that can be used to increase the efficacy of certain antimetabolites, such as the cytotoxic agent 5-fluorouracil (5-FU), and reduce as well as protect against certain antimetabolite-associated adverse effects, such as those seen with high-dose (HD) methotrexate. Upon administration of arfolitixorin, 5,10-methylenetetrahydrofolate (MTHF) is a reduced folate substrate for the enzyme thymidylate synthase (TS) and stabilizes, upon co-administration of 5-FU, the covalent binding of the 5-FU metabolite 5-fluoro-2'-deoxyuridine-5'-monophosphate (FdUMP), instead of deoxyuridine monophosphate (dUMP), to its target enzyme TS, which results in an inhibition of TS. This inhibits the synthesis of deoxythymidine monophosphate (dTMP) and leads to the depletion of thymidine triphosphate (TTP), which is a necessary constituent of DNA. This inhibits DNA synthesis, which leads to an inhibition of cellular proliferation and induces tumor cell death. As MTHF is able to stabilize and strengthen the ternary complex, co-administration of arfolitixorin enhances the inhibition of DNA synthesis and increases the cytotoxic effect of 5-FU. As MTHF is the active form of folate and the active metabolite of LV and l-LV, arfolitixorin does not need to be converted to an active metabolite to become activated. In DNA synthesis, a ternary complex is formed between the reduced folate substrate MTHF, the TS enzyme and dUMP in order to convert dUMP to the DNA building block dTMP, which is necessary for DNA synthesis.

1 2D Structure

Arfolitixorin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[[4-[(6aR)-3-amino-1-oxo-2,5,6,6a,7,9-hexahydroimidazo[1,5-f]pteridin-8-yl]benzoyl]amino]pentanedioic acid

2.1.2 InChI

InChI=1S/C20H23N7O6/c21-20-24-16-15(18(31)25-20)27-9-26(8-12(27)7-22-16)11-3-1-10(2-4-11)17(30)23-13(19(32)33)5-6-14(28)29/h1-4,12-13H,5-9H2,(H,23,30)(H,28,29)(H,32,33)(H4,21,22,24,25,31)/t12-,13+/m1/s1

2.1.3 InChI Key

QYNUQALWYRSVHF-OLZOCXBDSA-N

2.1.4 Canonical SMILES

C1C2CN(CN2C3=C(N1)N=C(NC3=O)N)C4=CC=C(C=C4)C(=O)NC(CCC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

C1[C@@H]2CN(CN2C3=C(N1)N=C(NC3=O)N)C4=CC=C(C=C4)C(=O)N[C@@H](CCC(=O)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

Z8R4A37V9Q

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5,10-methylene-5,6,7,8-tetrahydrofolate

2. 5,10-methylenetetrahydrofolate

3. 5,10-methylenetetrahydrofolate Monohydrochloride, (l-glu)-isomer

4. 5,10-methylenetetrahydrofolate, (d-glu)-isomer

5. 5,10-methylenetetrahydrofolate, (l-glu)-(s)-isomer

6. 5,10-methylenetetrahydrofolic Acid

7. Ch2h4fol

8. Ch2h4folate

9. N5,n10-methylene-5,6,7,8-tetrahydrofolic Acid

10. Tetrahydromethylenefolate

2.3.2 Depositor-Supplied Synonyms

1. Arfolitixorin

2. 31690-11-6

3. Modufolin

4. 6r-mthf

5. Methylenetetrahydrofolic Acid, L-(+)-

6. Arfolitixorin [usan]

7. (6r)-5,10-methylenetetrahydrofolic Acid

8. Chebi:1989

9. Z8r4a37v9q

10. Iso-901

11. L-(+)-methylenetetrahydrofolic Acid

12. 5,10-methylene-thf

13. 5,10-methylene-(6r)-tetrahydrofolic Acid

14. (2s)-2-[[4-[(6ar)-3-amino-1-oxo-4,5,6,6a,7,9-hexahydroimidazo[1,5-f]pteridin-8-yl]benzoyl]amino]pentanedioic Acid

15. 3432-99-3

16. 5,10-methylenetetrahydrofolate

17. N-({4-[(6ar)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9h)-yl]phenyl}carbonyl)-l-glutamic Acid

18. N-{4-[(6ar)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9h)-yl]benzoyl}-l-glutamic Acid

19. Unii-z8r4a37v9q

20. Arfolitixorin [inn]

21. Arfolitixorin (usan/inn)

22. Schembl186747

23. Arfolitixorin [who-dd]

24. Chembl1234270

25. Dtxsid60185584

26. Bcp09003

27. Zinc4228243

28. (6r)-5,10-mthf

29. Who 10689

30. Db12676

31. 5,10-methylene,5,6,7,8-tetrahydrofolate

32. D11447

33. D-n5,n10-methylene-l-tetrahydrofolic Acid

34. Q26995704

35. (6r,s)-5,10-methylene-5,6,7,8-tetrahydrofolic Acid

36. [6r]-5,10-methylenetetrahydrofolate ([6r]-5,10- Mthf)

37. (6r)-5,10-methylene-5,6,7,8-tetrahydrofolic Acid

38. (2s)-2-[[4-[(6ar)-3-amino-1-oxo-2,5,6,6a,7,9-hexahydroimidazo[1,5-f]pteridin-8-yl]benzoyl]amino]pentanedioic Acid

39. (s)-2-(4-((r)-3-amino-1-oxo-5,6,6a,7-tetrahydroimidazo[1,5-f]pteridin-8(1h,4h,9h)-yl)benzamido)pentanedioic Acid

40. (s)-2-(4-((r)-3-amino-1-oxo-5,6,6a,7-tetrahydroimidazo[1,5-f]pteridin-8(1h,4h,9h)-yl)benzamido)pentanedioicacid

41. L-glutamic Acid, N-(4-((6ar)-3-amino-1,2,5,6,6a,7-hexahydro-1-oxoimidazo(1,5-f)pteridin-8(9h)-yl)benzoyl)-

42. N-({4-[(6ar)-3-amino-1-oxo-1,4,5,6,6a,7-hexahydroimidazo[1,5-f]pteridin-8(9h)-yl]phenyl}carbonyl)-l-glutamic Acid

43. N-(4-((6ar)-3-amino-1-oxo-1,2,5,6,6a,7-hexahydroimidazo(1,5-f)pteridin-8(9h)- Yl)benzoyl)-l-glutamic Acid

2.4 Create Date

2019-01-15

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₃N₇O₆
Molecular Weight	457.4 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	6
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	7
Exact Mass	457.17098148 g/mol
Monoisotopic Mass	457.17098148 g/mol
Topological Polar Surface Area	190 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	911
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Treatment of colorectal cancer

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