Details
Stereochemistry | RACEMIC |
Molecular Formula | C9H19ClN3O5P |
Molecular Weight | 315.691 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOP(=O)(OCC)C(C)NC(=O)N(CCCl)N=O
InChI
InChIKey=YAKWPXVTIGTRJH-UHFFFAOYSA-N
InChI=1S/C9H19ClN3O5P/c1-4-17-19(16,18-5-2)8(3)11-9(14)13(12-15)7-6-10/h8H,4-7H2,1-3H3,(H,11,14)
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15020614Curator's Comment: The description was created based on several sources, including
https://www.drugs.com/international/fotemustine.html | https://www.ncbi.nlm.nih.gov/pubmed/24213227 | https://clinicaltrials.gov/ct2/show/NCT01960192 | https://www.ncbi.nlm.nih.gov/pubmed/26951379 | https://www.ncbi.nlm.nih.gov/pubmed/25702193
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15020614
Curator's Comment: The description was created based on several sources, including
https://www.drugs.com/international/fotemustine.html | https://www.ncbi.nlm.nih.gov/pubmed/24213227 | https://clinicaltrials.gov/ct2/show/NCT01960192 | https://www.ncbi.nlm.nih.gov/pubmed/26951379 | https://www.ncbi.nlm.nih.gov/pubmed/25702193
Fotemustine is a novel chloroethylnitrosourea alkylating agent approved for use in the treatment of metastasizing melanoma and Recurrent Malignant Gliomas. The antitumor activity of fotemustine is related to its ability to alkylate DNA. It's in vitro or in vivo pharmacological activity is similar or greater than that of other nitrosoureas. Significant activity has been found in mice xenograft models of human primary cerebral tumors after fotemustine intraperitoneal administration. Fotemustine has been registered for use in two indications: disseminated malignant melanoma, including cerebral metastases, and primary brain tumors. Fotemustine is currently used in Europe, particularly in France and Italy, as a salvage therapy for recurrent malignant gliomas. Myelosuppression, leucopenia, and thrombocytopenia are the most frequent side effects of treatment with fotemustine. The objective response to this treatment is between 26% and 70%, and the reported median survival time is 10 months. New drug combinations containing fotemustine and angiogenesis inhibitors, such as bevacizumab, are currently under development.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24213227 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Muphoran Approved UseUnknown |
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Primary | Muphoran Approved UseUnknown |
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Primary | Muphoran Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15020614
Fotemustine was administered weekly for 3 consecutive weeks (days 1, 8, and 15) at 100 mg/m2 as a 60-minute infusion, followed by a 5-week rest period
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25557167
The BRAFV600E A375, Malme-3M, A2058 and RPMI7951 and wild-type SK-Mel537, SK-Mel505, RPMI18332 and SK-Mel187 melanoma cell lines were used for activity evaluation. Cells were treated with the chemotherapeutic (Fotemustine, FM) and the number of cell divisions following 120h incubation was determined using flow cytometry of CFSE stained cells. The cellular division rate was determined using carboxyfluorescein diacetate succinimidyl ester (CFSE) stained cells [39]. One day after labeling the control sample (0h) was harvested and analyzed by flow cytometry (FACS Canto II). On this day cells were treated or not with vemurafenib, TMZ, FM or combinations of the drugs, and 120h later samples were harvested and subjected to flow cytometry analysis. Using the mean 0h fluorescence signal, a standard curve was plotted to determine the number of cell divisions after 120h incubation in treated and untreated cells.
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WHO-ATC |
L01AD05
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NCI_THESAURUS |
C699
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WHO-VATC |
QL01AD05
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C054368
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1249
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100000080464
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92118-27-9
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SUB07809MIG
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m5559
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5982
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GQ7JL9P5I2
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104799
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DTXSID80869091
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C1106
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FOTEMUSTINE
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CHEMBL549386
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DB04106
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7762
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ACTIVE MOIETY