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Lisofylline

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Synopsis

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Chemistry

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Also known as: (r)-lisofylline, 100324-81-0, Protec, Ct 1501r, Ct-1501r, Lisophylline

Molecular Formula

C₁₃H₂₀N₄O₃

Molecular Weight

280.32 g/mol

InChI Key

NSMXQKNUPPXBRG-SECBINFHSA-N

FDA UNII

L1F2Q2X956

Lisofylline has been investigated for the treatment of Type 1 Diabetes Mellitus.

1 2D Structure

Lisofylline

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(5R)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione

2.1.2 InChI

InChI=1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3/t9-/m1/s1

2.1.3 InChI Key

NSMXQKNUPPXBRG-SECBINFHSA-N

2.1.4 Canonical SMILES

CC(CCCCN1C(=O)C2=C(N=CN2C)N(C1=O)C)O

2.1.5 Isomeric SMILES

C[C@H](CCCCN1C(=O)C2=C(N=CN2C)N(C1=O)C)O

2.2 Other Identifiers

2.2.1 UNII

L1F2Q2X956

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(5'-hydroxyhexyl)-3,7-dimethylxanthine

2. 1-(5r-hydroxyhexyl)-3,7-dimethylxanthine

3. 3,7-dimethyl-1-(5-hydroxyhexyl)xanthine

4. A-802710

5. Bl 194

6. Ct-1501r

2.3.2 Depositor-Supplied Synonyms

1. (r)-lisofylline

2. 100324-81-0

3. Protec

4. Ct 1501r

5. Ct-1501r

6. Lisophylline

7. 1-[(5r)-5-hydroxyhexyl]-3,7-dimethylpurine-2,6-dione

8. Lisofylline, (r)-

9. (r)-lisophylline

10. 3,7-dihydro-1-[(5r)-5-hydroxyhexyl]-3,7-dimethyl-1h-purine-2,6-dione

11. 1-((r)-5-hydroxyhexyl)theobromine

12. 1-[(r)-5-hydroxyhexyl]theobromine

13. Lisofilina

14. Lisofyllinum

15. L1f2q2x956

16. (-)-lisofylline

17. 1-(5r-hydroxyhexyl)-3,7-dimethylxanthine

18. Protec (tn)

19. Lisofylline [mi]

20. Lisofylline [inn]

21. Lisofylline (usan/inn)

22. Lisofylline [usan]

23. Chembl1411

24. Schembl39131

25. (r)-lsf

26. Lisofylline [who-dd]

27. Gtpl9225

28. Dtxsid7058709

29. Ct1501r

30. 1h-purine-2,6-dione, 3,7-dihydro-1-(5-hydroxyhexyl)-3,7-dimethyl-, (r)-

31. Chebi:143527

32. Ex-a6722

33. Zinc1887263

34. Akos025394050

35. Db12406

36. Hy-109854a

37. Ncgc00186630-01

38. 1-(5-r-hydroxyhexyl)-3,7-dimethylxanthine

39. Cs-0034091

40. R-1-(5-hydroxyhexyl)-3,7-dimethylxanthine

41. (r)-1-(5-hydroxyhexyl)-3,7-dimethylxanthine

42. D04748

43. J-000102

44. Q15409404

45. 1-[(5r)-5-hydroxyhexyl]-3,7-dimethyl-purine-2,6-dione

46. (r)-1-(5-hydroxyhexyl)-3,7-dimethyl-1h-purine-2,6(3h,7h)-dione

47. 1-[(5r)-5-hydroxyhexyl]-3,7-dimethyl-3,7-dihydro-1h-purine-2,6-dione

48. 1-[(5r)-5-hydroxyhexyl]-3,7-dimethyl-2,3,6,7-tetrahydro-1h-purine-2,6-dione

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₂₀N₄O₃
Molecular Weight	280.32 g/mol
XLogP3	0.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	280.15354051 g/mol
Monoisotopic Mass	280.15354051 g/mol
Topological Polar Surface Area	78.7 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	390
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)

Radiation-Sensitizing Agents

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)

Anti-Inflammatory Agents, Non-Steroidal

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

4.2 Metabolism/Metabolites

Lisofylline has known human metabolites that include lisofylline 4,5-diol and pentoxifylline.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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