Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H18O3 |
| Molecular Weight | 246.3016 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=C(CO)C2=C(C)C3(CC3)[C@@](C)(O)C(=O)C2=C1
InChI
InChIKey=NICJCIQSJJKZAH-AWEZNQCLSA-N
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
| Molecular Formula | C15H18O3 |
| Molecular Weight | 246.3016 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
IROFULVEN is a semisynthetic derivative of a natural sesquiterpene toxin illudin S, isolated from the fungus Omphalotus illudens. It alkylates DNA and protein macromolecules, forms adducts, and arrests cells in the S-phase of the cell cycle. It requires NADPH-dependent metabolism by alkenal/one oxidoreductase for activity. IROFULVEN is more active in vitro against tumor cells of epithelial origin and is more resistant to deactivation by p53 loss and P-glycoprotein than other alkylating agents. IROFULVEN has been evaluated in 19 clinical trials, predominantly in refractory prostate and ovarian cancer patients. Results were positive, including a 10% response rate in patients with prostate cancer previously treated with docetaxel and 13% in ovarian cancer patients relapsing between 6 and 12 months after standard treatment with carboplatin and paclitaxel.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Sulfotransferase-independent genotoxicity of illudin S and its acylfulvene derivatives in bacterial and mammalian cells. | 2014-01 |
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| A phase 2 evaluation of irofulven as second-line treatment of recurrent or persistent intermediately platinum-sensitive ovarian or primary peritoneal cancer: a Gynecologic Oncology Group trial. | 2010-10 |
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| A ubiquitin-binding domain in Cockayne syndrome B required for transcription-coupled nucleotide excision repair. | 2010-06-11 |
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| Dissociation of CAK from core TFIIH reveals a functional link between XP-G/CS and the TFIIH disassembly state. | 2010-06-08 |
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| Structure-activity studies of urea, carbamate, and sulfonamide derivatives of acylfulvene. | 2010-02-11 |
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| The development of xenograft glioblastoma implants in nude mice brain. | 2010-01-30 |
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| Enantioselective total synthesis of (-)-acylfulvene and (-)-irofulven. | 2009-12-18 |
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| Profiling patterns of glutathione reductase inhibition by the natural product illudin S and its acylfulvene analogues. | 2009-09 |
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| Synergy of irofulven in combination with other DNA damaging agents: synergistic interaction with altretamine, alkylating, and platinum-derived agents in the MV522 lung tumor model. | 2008-12 |
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| Synergy of Irofulven in combination with various anti-metabolites, enzyme inhibitors, and miscellaneous agents in MV522 lung carcinoma cells: marked interaction with gemcitabine and 5-fluorouracil. | 2008-10 |
|
| Combination chemotherapy and photodynamic therapy with fab' fragment targeted HPMA copolymer conjugates in human ovarian carcinoma cells. | 2008-08-30 |
|
| Ovarian tumor growth regression using a combination of vascular targeting agents anginex or topomimetic 0118 and the chemotherapeutic irofulven. | 2008-07-08 |
|
| The postchemotherapy PSA surge syndrome. | 2008-07 |
|
| Influence of irofulven, a transcription-coupled repair-specific antitumor agent, on RNA polymerase activity, stability and dynamics in living mammalian cells. | 2008-04-15 |
|
| Systematic review of the clinical effect of glucocorticoids on nonhematologic malignancy. | 2008-03-28 |
|
| Synthesis and antitumor activity of amine analogs of irofulven. | 2007-12-15 |
|
| Gateways to clinical trials. | 2007-10-09 |
|
| A phase I and pharmacokinetic study of irofulven and capecitabine administered every 2 weeks in patients with advanced solid tumors. | 2007-10 |
|
| Gateways to clinical trials. | 2007-06 |
|
| BRCA1 contributes to cell cycle arrest and chemoresistance in response to the anticancer agent irofulven. | 2007-04 |
|
| Irofulven induces replication-dependent CHK2 activation related to p53 status. | 2007-02-15 |
|
| Comparison of antitumor activities in tumor xenograft treatment. | 2007-02 |
|
| Irofulven as first line therapy in recurrent or metastatic gastric cancer: a phase II multicenter study by the Cancer Therapeutics Research Group (CTRG). | 2007-02 |
|
| Fanconi anemia D2 protein confers chemoresistance in response to the anticancer agent, irofulven. | 2006-12 |
|
| Pharmacokinetics, metabolism, and routes of excretion of intravenous irofulven in patients with advanced solid tumors. | 2006-11 |
|
| Rescue of progeria in trichothiodystrophy by homozygous lethal Xpd alleles. | 2006-10 |
|
| Phase I trial of irofulven (MGI 114) in pediatric patients with solid tumors. | 2006-08 |
|
| A phase I and pharmacokinetic study of irofulven and cisplatin administered in a 30-min infusion every two weeks to patients with advanced solid tumors. | 2006-07 |
|
| Gateways to clinical trials. | 2006-06 |
|
| Non-hormonal systemic therapy in men with hormone-refractory prostate cancer and metastases: a systematic review from the Cancer Care Ontario Program in Evidence-based Care's Genitourinary Cancer Disease Site Group. | 2006-05-02 |
|
| A phase II study of irofulven in women with recurrent and heavily pretreated ovarian cancer. | 2006-04 |
|
| Characterizations of irofulven cytotoxicity in combination with cisplatin and oxaliplatin in human colon, breast, and ovarian cancer cells. | 2006-04 |
|
| Pharmacokinetic modelling of 5-FU production from capecitabine--a population study in 40 adult patients with metastatic cancer. | 2005-12 |
|
| Gateways to clinical trials. | 2005-09 |
|
| Enhanced antitumor activity of irofulven in combination with irinotecan in pediatric solid tumor xenograft models. | 2005-05 |
|
| Irofulven demonstrates clinical activity against metastatic hormone-refractory prostate cancer in a phase 2 single-agent trial. | 2005-02 |
|
| Cone damage in patients receiving high-dose irofulven treatment. | 2005-01 |
|
| Gateways to clinical trials. | 2004-12 |
|
| Characterization and multiparameter analysis of visual adverse events in irofulven single-agent phase I and II trials. | 2004-11-15 |
|
| Irofulven: resurgence for alkylating therapy in cancer? | 2004-11 |
|
| Gateways to clinical trials. | 2004-11 |
|
| Caspase-mediated apoptosis and caspase-independent cell death induced by irofulven in prostate cancer cells. | 2004-11 |
|
| Cell cycle effects and induction of premitotic apoptosis by irofulven in synchronized cancer cells. | 2004-11 |
|
| ATM-dependent CHK2 activation induced by anticancer agent, irofulven. | 2004-09-17 |
|
| Antitumor activity of irofulven against human ovarian cancer cell lines, human tumor colony-forming units, and xenografts. | 2004-09-14 |
|
| A phase II trial of 6-hydroxymethylacylfulvene (MGI-114, irofulven) in patients with relapsed or refractory non-small cell lung cancer. | 2004-09 |
|
| Irofulven cytotoxicity depends on transcription-coupled nucleotide excision repair and is correlated with XPG expression in solid tumor cells. | 2004-08-15 |
|
| Phase I and pharmacokinetic study of irofulven administered weekly or biweekly in advanced solid tumor patients. | 2004-05-15 |
|
| Acute retinal toxicity from the novel anti-tumor agent, Irofulven. | 2004-05 |
|
| Gateways to clinical trials. | 2004-05 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:14:43 GMT 2025
by
admin
on
Mon Mar 31 18:14:43 GMT 2025
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| Record UNII |
6B799IH05A
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| Record Status |
Validated (UNII)
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| Record Version |
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FDA ORPHAN DRUG |
125399
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FDA ORPHAN DRUG |
122198
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NCI_THESAURUS |
C1590
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FDA ORPHAN DRUG |
124399
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158440-71-2
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DTXSID50166423
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C1717
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148189
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m6406
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CHEMBL118218
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683863
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KK-16
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IROFULVEN
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100000086454
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SUB02773MIG
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6B799IH05A
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C102714
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1483
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DB05786
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7889
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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| Biological Half-life | PHARMACOKINETIC |
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