(-)-Irofulven

Modify Date: 2024-01-09 12:04:24

(-)-Irofulven Structure
(-)-Irofulven structure
 Common Name (-)-Irofulven
CAS Number 158440-71-2 Molecular Weight 246.30200
Density 1.28g/cm3 Boiling Point 501ºC at 760 mmHg
Molecular Formula C15H18O3 Melting Point N/A
MSDS N/A Flash Point 270.9ºC

 Use of (-)-Irofulven


(-)-Irofulven (MGI 114), an Illudin S analog, is a DNA alkylating agent. (-)-Irofulven inhibits the replication of DNA, induces tumor cells apoptosis, and has potent antitumor activity[1][2].

 Names

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

 (-)-Irofulven Biological Activity

Description (-)-Irofulven (MGI 114), an Illudin S analog, is a DNA alkylating agent. (-)-Irofulven inhibits the replication of DNA, induces tumor cells apoptosis, and has potent antitumor activity[1][2].
Related Catalog
In Vitro (-)-Irofulven (2.8 μM; 1 hour) induces p53-dependent cell cycle arrest[1]. (-)-Irofulven (0.8 μM, 0.9 μM and 2.8 μM; 1 hour) induces CHK2 activation is related to p53 status in cells[1]. (-)-Irofulven inhibits DNA replication and induces chromosome aberrations (breaks and radials)[1]. Cell Cycle Analysis[1] Cell Line: A2780, CAOV3 and HCT116 cells Concentration: 2.8 μM Incubation Time: 1 hour Result: p53 wild-type cells mainly arrested at G1/S phases, while p53-mutated or p53-null cells arrested at S and G2/M phases. Western Blot Analysis[1] Cell Line: A2780, CAOV3 and HCT116 cells Concentration: 0.8 μM, 0.9 μM and 2.8 μM Incubation Time: 1 hour Result: Induced the Thr 68 phosphorylation of CHK2 kinase in cells.
In Vivo (-)-Irofulven (7 mg/kg; i.p; on days 1-5 and 8-12) produces a statistically significant increase in the median survival of mice bearing tumor cells[2]. Animal Model: Male and female athymic BALB/c mice (nu/nu genotype, 6 weeks old or older) injected with human glioblastoma multiforme[2]. Dosage: 7 mg/kg Administration: i.p; on days 1-5 and 8-12 Result: Was active against all tumor lines.
References

[1]. Yutian Wang, et al. Irofulven induces replication-dependent CHK2 activation related to p53 status. Biochem Pharmacol. 2007 Feb 15;73(4):469-80.

[2]. H S Friedman, et al. Activity of irofulven (6-hydroxymethylacylfulvene) in the treatment of glioblastoma multiforme-derived xenografts in athymic mice. Cancer Chemother Pharmacol. 2001 Nov;48(5):413-6.

 Chemical & Physical Properties

Density 1.28g/cm3
Boiling Point 501ºC at 760 mmHg
Molecular Formula C15H18O3
Molecular Weight 246.30200
Flash Point 270.9ºC
Exact Mass 246.12600
PSA 57.53000
LogP 1.66560
Vapour Pressure 3.9E-12mmHg at 25°C
Index of Refraction 1.617
Storage condition -20°C

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
WH0204487
CHEMICAL NAME :
Spiro(cyclopropane-1,5'(5H)-inden)-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'- trimethyl-, (R)-
CAS REGISTRY NUMBER :
158440-71-2
LAST UPDATED :
199712
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C15-H18-O3
MOLECULAR WEIGHT :
246.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>6610 ug/kg
TOXIC EFFECTS :
Cardiac - other changes Blood - changes in bone marrow (not otherwise specified) Blood - changes in other cell count (unspecified)
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 36(1, Pt 2),180,1997
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
2 mg/kg
TOXIC EFFECTS :
Blood - thrombocytopenia Blood - changes in bone marrow (not otherwise specified) Blood - changes in other cell count (unspecified)
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 36(1, Pt 2),180,1997 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
20339 ug/kg/5D-I
TOXIC EFFECTS :
Cardiac - other changes Blood - changes in bone marrow (not otherwise specified) Blood - changes in other cell count (unspecified)
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 36(1, Pt 2),180,1997
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
3 mg/kg/5D-I
TOXIC EFFECTS :
Blood - thrombocytopenia Blood - changes in bone marrow (not otherwise specified) Blood - changes in other cell count (unspecified)
REFERENCE :
FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 36(1, Pt 2),180,1997

 Synonyms

HMAF
Spiro(cyclopropane-1,5'(5H)-inden)-7'(6'H)-one,6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-,(R)
[14C]-Irofulven
6-hydroxymethylacylfulvene
(-)-irofulven
Acylfulvene,6-(hydroxymethyl)
MGI 114
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