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Irofulven

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Chemistry

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Also known as: Hmaf, Mgi 114, 158440-71-2, 6-hydroxymethylacylfulvene, (-)-irofulven, Mgi-114

Molecular Formula

C₁₅H₁₈O₃

Molecular Weight

246.30 g/mol

InChI Key

NICJCIQSJJKZAH-AWEZNQCLSA-N

FDA UNII

6B799IH05A

A novel anti-cancer compound synthesized by scientists at the University of California, San Diego more than a decade ago from toxins of the poisonous jack-o-lantern mushroom, has been granted fast track status by the U.S. Food and Drug Administration (FDA) after demonstrating promise against one of the most deadly cancers. MGI-114 (Irofulven) is currently being developed by MGI PHARMA, Inc., an emerging oncology-focused pharmaceutical company based in Minneapolis. Phase III clinical trials involving the drug have been underway since early 2001 at sites in the U.S. and Europe.

1 2D Structure

Irofulven

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one

2.1.2 InChI

InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1

2.1.3 InChI Key

NICJCIQSJJKZAH-AWEZNQCLSA-N

2.1.4 Canonical SMILES

CC1=C(C2=C(C3(CC3)C(C(=O)C2=C1)(C)O)C)CO

2.1.5 Isomeric SMILES

CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO

2.2 Other Identifiers

2.2.1 UNII

6B799IH05A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 6-(hydroxymethyl)acylfulvene

2. 6-hydroxymethylacylfulvene

3. Hmaf Cpd

4. Mgi 114

5. Mgi-114

6. Mgi.114

2.3.2 Depositor-Supplied Synonyms

1. Hmaf

2. Mgi 114

3. 158440-71-2

4. 6-hydroxymethylacylfulvene

5. (-)-irofulven

6. Mgi-114

7. Nsc 683863

8. (hydroxymethyl)acylfulvene

9. Nsc-683863

10. (5'r)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one

11. 6b799ih05a

12. Lp-100

13. (r)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5h)inden)-7'(6'h)-one

14. 6-(hydroxymethyl)acylfulvene

15. Acylfulvene, 6-(hydroxymethyl)-

16. Irofulven [usan:inn]

17. Unii-6b799ih05a

18. Mgi.114

19. Irofulven [inn]

20. Irofulven [mi]

21. Irofulven (usan/inn)

22. Irofulven [usan]

23. Irofulven [who-dd]

24. Schembl8800

25. Chembl118218

26. Dtxsid50166423

27. Chebi:135002

28. Zinc3916310

29. Bdbm50410835

30. Nsc683863

31. Akos027256650

32. Db05786

33. (r)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'h)-one

34. Hy-14429

35. Nci60_030149

36. Spiro(cyclopropane-1,5'(5h)-inden)-7'(6'h)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (r)-

37. Cs-0003353

38. D04614

39. Q6072197

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₈O₃
Molecular Weight	246.30 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	246.125594432 g/mol
Monoisotopic Mass	246.125594432 g/mol
Topological Polar Surface Area	57.5 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	558
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 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in brain cancer, breast cancer, endometrial cancer, liver cancer, lung cancer, ovarian cancer, pancreatic cancer, pediatric indications, prostate cancer, and sarcoma.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents, Alkylating

A class of drugs that differs from other alkylating agents used clinically in that they are monofunctional and thus unable to cross-link cellular macromolecules. Among their common properties are a requirement for metabolic activation to intermediates with antitumor efficacy and the presence in their chemical structures of N-methyl groups, that after metabolism, can covalently modify cellular DNA. The precise mechanisms by which each of these drugs acts to kill tumor cells are not completely understood. (From AMA, Drug Evaluations Annual, 1994, p2026) (See all compounds classified as Antineoplastic Agents, Alkylating.)

Radiation-Sensitizing Agents

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

5.2 Mechanism of Action

MGI-114(Irofulven) has unique mechanism of action as an anti-tumor agent is due to its ability to be rapidly absorbed by tumor cells. Once inside the cells, the compound binds to DNA and protein targets. This binding interferes with DNA replication and cell division of tumor cells, leading to tumor-specific apoptotic cell death, or cell suicide. During this process, tumor cells tend to automatically shut themselves down when they sense their function is compromised.

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