Irofulven

Irofulven
	IUPAC name (6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one
Identifiers
CAS number	158440-71-2
PubChem	148189
ChemSpider	130640
KEGG	D04614
ChEMBL	CHEMBL118218
Jmol-3D images	Image 1
	SMILES O=C1C/3=C/C(=C(C\3=C(/C2([C@]1(O)C)CC2)C)CO)C ;
	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 ; Key: NICJCIQSJJKZAH-AWEZNQCLSA-N InChI=1/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; Key: NICJCIQSJJKZAH-AWEZNQCLBL ;
Properties
Molecular formula	C15H18O3
Molar mass	246.302 g/mol
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

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Irofulven or 6-hydroxymethylacylfulvene (also known as HMAF of MGI-114) is an antitumor agent.^[1]^[2] It belongs to the family of drugs called alkylating agents.

It inhibits the replication of DNA.^[3]

Irofulven is an analogue of illudin S, a sesquiterpene toxin found in mushrooms of the genus Omphalotus. The compound was originally synthesized by Dr. Trevor McMorris (UCSD) and found to have anticancer properties by Dr. Michael J Kelner (UCSD).^[4]

[edit] Synthesis

McMorris, T. C.; Staake, M. D.; Kelner, M. J. (2004). "Synthesis and Biological Activity of Enantiomers of Antitumor Irofulven". The Journal of Organic Chemistry 69 (3): 619. doi:10.1021/jo035084j. PMID 14750783.

[edit] References

^ Escargueil, A. E.; Poindessous, V.; Soares, D. G.; Sarasin, A.; Cook, P. R.; Larsen, A. K. (April 2008). "Influence of Irofulven, a Transcription-Coupled Repair-Specific Antitumor Agent, on RNA Polymerase Activity, Stability and Dynamics in Living Mammalian Cells" (pdf). Journal of Cell Science 121 (Pt 8): 1275–1283. doi:10.1242/jcs.023259. PMID 18388315. http://jcs.biologists.org/content/121/8/1275.full.pdf.
^ Kelner, M. J.; McMorris, T. C.; Estes, L.; Wang, W.; Samson, K. M.; Taetle, R. (1996). "Efficacy of HMAF (MGI-114) in the MV522 Metastatic Lung Carcinoma Xenograft Model Nonresponsive to Traditional Anticancer Agents". Investigational New Drugs 14 (2): 161–167. doi:10.1007/BF00210787. PMID 8913837.
^ Wang, Y.; Wiltshire, T.; Senft, J.; Reed, E.; Wang, W. (February 2007). "Irofulven Induces Replication-Dependent CHK2 Activation Related to p53 Status" (pdf). Biochemical Pharmacology 73 (4): 469–480. doi:10.1016/j.bcp.2006.10.023. PMC 1800887. PMID 17118344. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1800887/pdf/nihms-16882.pdf.
^ MacDonald, J. R.; Muscoplat, C. C.; Dexter, D. L.; Mangold, G. L.; Chen, S. F.; Kelner, M. J.; McMorris, T. C.; Von Hoff, D. D. (1997). "Preclinical Antitumor Activity of 6-hydroxymethylacylfulvene, a Semisynthetic Derivative of the Mushroom Toxin Illudin S" (pdf). Cancer Research 57 (2): 279–283. PMID 9000568. http://cancerres.aacrjournals.org/content/57/2/279.full.pdf.

This antineoplastic or immunomodulatory drug article is a stub. You can help Wikipedia by expanding it.

[pmid18388315-0] Escargueil, A. E.; Poindessous, V.; Soares, D. G.; Sarasin, A.; Cook, P. R.; Larsen, A. K. (April 2008). "Influence of Irofulven, a Transcription-Coupled Repair-Specific Antitumor Agent, on RNA Polymerase Activity, Stability and Dynamics in Living Mammalian Cells" (pdf). Journal of Cell Science 121 (Pt 8): 1275–1283. doi:10.1242/jcs.023259. PMID 18388315. http://jcs.biologists.org/content/121/8/1275.full.pdf.

[pmid8913837-1] Kelner, M. J.; McMorris, T. C.; Estes, L.; Wang, W.; Samson, K. M.; Taetle, R. (1996). "Efficacy of HMAF (MGI-114) in the MV522 Metastatic Lung Carcinoma Xenograft Model Nonresponsive to Traditional Anticancer Agents". Investigational New Drugs 14 (2): 161–167. doi:10.1007/BF00210787. PMID 8913837.

[pmid17118344-2] Wang, Y.; Wiltshire, T.; Senft, J.; Reed, E.; Wang, W. (February 2007). "Irofulven Induces Replication-Dependent CHK2 Activation Related to p53 Status" (pdf). Biochemical Pharmacology 73 (4): 469–480. doi:10.1016/j.bcp.2006.10.023. PMC 1800887. PMID 17118344. http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1800887/pdf/nihms-16882.pdf.

[3] MacDonald, J. R.; Muscoplat, C. C.; Dexter, D. L.; Mangold, G. L.; Chen, S. F.; Kelner, M. J.; McMorris, T. C.; Von Hoff, D. D. (1997). "Preclinical Antitumor Activity of 6-hydroxymethylacylfulvene, a Semisynthetic Derivative of the Mushroom Toxin Illudin S" (pdf). Cancer Research 57 (2): 279–283. PMID 9000568. http://cancerres.aacrjournals.org/content/57/2/279.full.pdf.

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Irofulven

[edit] Synthesis

[edit] References

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