CAS 158440-71-2

(-)-Irofulven

Description:

(-)-Irofulven, also known as 5-hydroxy-1,4-dihydro-1,4-dioxo-2-naphthalenecarboxylic acid, is a synthetic compound derived from the natural product illudin S, which is known for its antitumor properties. This compound exhibits a unique mechanism of action, primarily functioning as an alkylating agent that interacts with DNA, leading to the disruption of cellular processes and ultimately inducing apoptosis in cancer cells. (-)-Irofulven is characterized by its ability to form covalent bonds with nucleophilic sites in DNA, which contributes to its cytotoxic effects. It is typically administered in a clinical setting for the treatment of various malignancies, including solid tumors. The compound is notable for its relatively low toxicity compared to traditional chemotherapeutic agents, making it a subject of interest in cancer research. Additionally, its solubility and stability in biological systems are important factors that influence its therapeutic efficacy. Ongoing studies continue to explore its potential in combination therapies and its effectiveness against resistant cancer cell lines.

Formula: C₁₅H₁₈O₃

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

InChI key: InChIKey=NICJCIQSJJKZAH-AWEZNQCLSA-N

SMILES: CC=1C2([C@@](C)(O)C(=O)C=3C1C(CO)=C(C)C3)CC2

Synonyms:

• (-)-(Hydroxymethyl)acylfulvene
• (6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one
• (6′R)-6′-Hydroxy-3′-(hydroxymethyl)-2′,4′,6′-trimethylspiro[cyclopropane-1,5′-[5H]inden]-7′(6′H)-one
• 6-Hmaf
• Hmaf
• Hydroxymethylacylfulvene
• Irofulven
• Mgi-114
• Nsc-683863
• Spiro[cyclopropane-1,5′-[5H]inden]-7′(6′H)-one, 6′-hydroxy-3′-(hydroxymethyl)-2′,4′,6′-trimethyl-, (6′R)-
• Spiro[cyclopropane-1,5′-[5H]inden]-7′(6′H)-one, 6′-hydroxy-3′-(hydroxymethyl)-2′,4′,6′-trimethyl-, (R)-
• (6'R)-6'-Hydroxy-3'-(hydroxyMethyl)-2',4',6'-triMethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
• Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (6'R)-
• [14C]-Irofulven
• Irofulvene

(6′R)-6′-Hydroxy-3′-(hydroxymethyl)-2′,4′,6′-trimethylspiro[cyclopropane-1,5′-[5H]inden]-7′(6′H)-one

CAS: 158440-71-2

Formula: C₁₅H₁₈O₃

Purity: 98%

Color and Shape: Solid

Molecular weight: 246.3016

Ref: IN-DA001Q6R

(-)-Irofulven

CAS: 158440-71-2

Irofulven is an agent of DNA-damaging and antitumor. It is used for the treatment of advanced solid tumors, including prostate, ovarian, and pancreatic cancers.

Formula: C₁₅H₁₈O₃

Color and Shape: Solid

Molecular weight: 246.30

Ref: TM-T24176

(R)-Irofulven

CAS: 158440-71-2

Formula: C₁₅H₁₈O₃

Molecular weight: 246.31

Ref: 4Z-I-151001

(R)-Irofulven

CAS: 158440-71-2

(R)-Irofulven is a cytotoxic agent that acts by inhibiting the mitochondrial membrane potential. It has been shown to have high potency against carcinoma cell lines and has been used in toxicity studies. (R)-Irofulven is also effective against high-resistant cells, such as intramolecular hydrogen. This drug induces caspase-independent cell death and chemical stability, which makes it a good candidate for use in children. The concentration-time curve of (R)-Irofulven shows that this drug kills cancer cells at low concentrations and has a long elimination half-life, making it an ideal candidate for cancer treatment.

Formula: C₁₅H₁₈O₃

Purity: Min. 95%

Molecular weight: 246.3 g/mol

Ref: 3D-FI24650

(R)-Irofulven

Controlled Product

CAS: 158440-71-2

Applications Semi-synrhetic antitumor agent derived from Illudin S. Inhibits DNA synthesis and induces apoptosis in tumor cells. Antineoplastic.
References Woynarowski, J.M., et al.: Biochem. Pharmacol., 54, 1181 (1997), Alexandre, J., et al.: Clin. Cancer Res., 10, 3377 (2004), Senzer, N., et al.: Am. J. Clin. Oncol., 28, 36 (2005),

Formula: C₁₅H₁₈O₃

Color and Shape: Neat

Molecular weight: 246.31

Ref: TR-I769500