Fotemustine
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Identification
- Summary
Fotemustine is an alkylating agent used in the treatment of metastatic melanoma.
- Generic Name
- Fotemustine
- DrugBank Accession Number
- DB04106
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 315.691
Monoisotopic: 315.075084952 - Chemical Formula
- C9H19ClN3O5P
- Synonyms
- (+-)-Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate
- Diethyl-1-(3-(2-chloroethyl)-3-nitrosoureido)ethylphosphonate
- Fotemustina
- Fotemustine
- Fotemustinum
- Mustoforan
- External IDs
- S 10036
- S-10036
- Servier-10036
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Metastatic melanoma •••••••••••• ••••••• ••• ••••••••• •••••••• - Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UThioredoxin reductase 1, cytoplasmic Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Fotemustine is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Fotemustine is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Fotemustine is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Fotemustine is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Fotemustine is combined with Bupivacaine. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
Categories
- ATC Codes
- L01AD05 — Fotemustine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as dialkyl alkylphosphonates. These are compounds containing a phosphonic acid that is diesterified with alkyl groups, and the phosphorus atom is also directly attached to an alkyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Organic phosphonic acids and derivatives
- Sub Class
- Phosphonic acid diesters
- Direct Parent
- Dialkyl alkylphosphonates
- Alternative Parents
- Phosphonic acid esters / Nitrosoureas / Semicarbazides / Nitrosamides / Organopnictogen compounds / Organophosphorus compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds show 1 more
- Substituents
- Aliphatic acyclic compound / Alkyl chloride / Alkyl halide / Carbonic acid derivative / Carbonyl group / Dialkyl alkylphosphonate / Hydrocarbon derivative / Nitrosamide / Nitrosourea / Organic n-nitroso compound show 12 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- GQ7JL9P5I2
- CAS number
- 92118-27-9
- InChI Key
- YAKWPXVTIGTRJH-QMMMGPOBSA-N
- InChI
- 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)/t8-/m0/s1
- IUPAC Name
- diethyl [(1S)-1-{[N-(2-chloroethyl)-N'-oxohydrazinecarbonyl]amino}ethyl]phosphonate
- SMILES
- CCOP(=O)(OCC)[C@@H](C)NC(=O)N(CCCl)N=O
References
- Synthesis Reference
- US4567169
- General References
- Not Available
- External Links
- PubChem Compound
- 46936889
- PubChem Substance
- 46505097
- ChemSpider
- 26330202
- ChEBI
- 131854
- ZINC
- ZINC000005859934
- Wikipedia
- Fotemustine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Malignant Melanoma / Recurrent Melanoma 1 3 Terminated Treatment Intraocular Melanoma / Metastatic Cancer 1 3 Unknown Status Treatment Brain Metastases 1 2 Completed Treatment Glioblastoma Multiforme (GBM) 1 2 Completed Treatment Malignant Melanoma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Powder, for solution Intravenous 208 MG Injection, powder, for solution Intravenous 200 mg/4ml Solution Intravenous 208 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.11 mg/mL ALOGPS logP 1.23 ALOGPS logP 1.28 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 11.81 Chemaxon pKa (Strongest Basic) -5.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 97.3 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 71.42 m3·mol-1 Chemaxon Polarizability 29 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9709 Blood Brain Barrier + 0.7425 Caco-2 permeable - 0.5823 P-glycoprotein substrate Non-substrate 0.6191 P-glycoprotein inhibitor I Non-inhibitor 0.6195 P-glycoprotein inhibitor II Non-inhibitor 0.755 Renal organic cation transporter Non-inhibitor 0.8932 CYP450 2C9 substrate Non-substrate 0.7887 CYP450 2D6 substrate Non-substrate 0.8071 CYP450 3A4 substrate Non-substrate 0.5117 CYP450 1A2 substrate Non-inhibitor 0.7836 CYP450 2C9 inhibitor Non-inhibitor 0.7355 CYP450 2D6 inhibitor Non-inhibitor 0.8882 CYP450 2C19 inhibitor Non-inhibitor 0.67 CYP450 3A4 inhibitor Non-inhibitor 0.8724 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8853 Ames test AMES toxic 0.9107 Carcinogenicity Carcinogens 0.7102 Biodegradation Not ready biodegradable 0.8846 Rat acute toxicity 3.1868 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6413 hERG inhibition (predictor II) Non-inhibitor 0.8627
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0pb9-5590000000-18944c7128f74192be3f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000i-0390000000-e45f8846e5ec1adb7ec9 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00dr-1091000000-758bca253eca5b1c624f Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0490000000-f9e7fa2a2d150f7ba2ba Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-7910000000-f581d34c916677cf0e0d Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0900-4910000000-65f7481584631d703448 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-7930000000-3ea904693334ffa3b7b0 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 164.25882 predictedDeepCCS 1.0 (2019) [M+H]+ 166.61682 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.70995 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
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1. DetailsThioredoxin reductase 1, cytoplasmic
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Thioredoxin-disulfide reductase activity
- Specific Function
- Isoform 1 may possess glutaredoxin activity as well as thioredoxin reductase activity and induces actin and tubulin polymerization, leading to formation of cell membrane protrusions. Isoform 4 enha...
- Gene Name
- TXNRD1
- Uniprot ID
- Q16881
- Uniprot Name
- Thioredoxin reductase 1, cytoplasmic
- Molecular Weight
- 70905.58 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 09, 2021 08:40