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Identification
- Generic Name
- Chlorotoxin I-131
- DrugBank Accession Number
- DB05462
- Background
Chlorotoxin I-131 is investigated in clinical trials for treating brain cancer. Chlorotoxin I-131 binds to and reduces the activity of a matrix metalloproteinase (MMP) that regulates functioning of the chloride channels on cell membranes. Chlorotoxin is a small 36-amino-acid peptide that selectively binds to glioma cells but not normal brain parenchyma. It is a synthetic version of a neurotoxin isolated from the venom of the Giant Yellow Israeli scorpion Leiurus quinquestriatus. The synthetic version of this peptide has been manufactured and covalently linked to iodine 131 as a means of targeting radiation to tumor cells in the treatment of brain cancer. The selective effects of Chlorotoxin I-131 are regulated by its action on MMP2 receptors.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Chlorotoxin I-131 (DB05462)
- Weight
- Average: 373.5304
Monoisotopic: 373.240564619 - Chemical Formula
- C26H31NO
- Synonyms
- I(131)-TM-601 (chlorotoxin)
- External IDs
- I(131)-TM-601
- TM-601 I-131
Pharmacology
- Indication
Investigated for use/treatment in various forms of brain cancer; Malignant Glioma, Glioblastoma Multiforme, GBM, Anaplastic Astrocytoma, Oligo-Astrocytoma, Gliosarcoma
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As a synthetic version of a neurotoxin isolated from the venom of the Giant Yellow Israeli scorpion Leiurus Quinquestriatus, TM-601 is a small 36 amino acid peptide that has been manufactured and covalently linked to iodine 131 ((131)I-TM-601). Its unique binding to gliomal cells makes it a unique means of targeting radiation to tumor cells in the treatment of brain cancer.
- Mechanism of action
TX binds to and reduces the activity of a matrix metalloproteinase (MMP) that is regulates functioning of the chloride channels on cell membranes. CTX reduced the migration ability of glioma cells through tight extracellular spaces in the brain tissue by inhibition of the MMP2, because this prevented the cells from shrinking and releasing from the extracellular matrix.
- 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
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Found safe in clinical trials.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Stilbenes
- Sub Class
- Not Available
- Direct Parent
- Stilbenes
- Alternative Parents
- Diphenylmethanes / Phenylpropanes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Alkyl aryl ether / Amine / Aromatic homomonocyclic compound / Benzenoid / Diphenylmethane / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organic oxygen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 544WOQ7W6W
- CAS number
- Not Available
- InChI Key
- YUFAHBUWIVNVNJ-UHFFFAOYSA-N
- InChI
- InChI=1S/C26H31NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18,25-26H,4,19-20H2,1-3H3
- IUPAC Name
- {2-[4-(1,2-diphenylbutyl)phenoxy]ethyl}dimethylamine
- SMILES
- CCC(C(C1=CC=CC=C1)C1=CC=C(OCCN(C)C)C=C1)C1=CC=CC=C1
References
- General References
- Mamelak AN, Jacoby DB: Targeted delivery of antitumoral therapy to glioma and other malignancies with synthetic chlorotoxin (TM-601). Expert Opin Drug Deliv. 2007 Mar;4(2):175-86. [Article]
- Mamelak AN, Rosenfeld S, Bucholz R, Raubitschek A, Nabors LB, Fiveash JB, Shen S, Khazaeli MB, Colcher D, Liu A, Osman M, Guthrie B, Schade-Bijur S, Hablitz DM, Alvarez VL, Gonda MA: Phase I single-dose study of intracavitary-administered iodine-131-TM-601 in adults with recurrent high-grade glioma. J Clin Oncol. 2006 Aug 1;24(22):3644-50. [Article]
- Soroceanu L, Gillespie Y, Khazaeli MB, Sontheimer H: Use of chlorotoxin for targeting of primary brain tumors. Cancer Res. 1998 Nov 1;58(21):4871-9. [Article]
- Authors unspecified: TransMolecular receives FDA approval for 131-I-TM-601 IND application. Expert Rev Anticancer Ther. 2002 Apr;2(2):139. [Article]
- External Links
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 6.91e-05 mg/mL ALOGPS logP 5.85 ALOGPS logP 6.52 Chemaxon logS -6.7 ALOGPS pKa (Strongest Basic) 8.78 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 12.47 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 118.67 m3·mol-1 Chemaxon Polarizability 44.5 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9955 Blood Brain Barrier + 0.8495 Caco-2 permeable + 0.884 P-glycoprotein substrate Substrate 0.6851 P-glycoprotein inhibitor I Inhibitor 0.5267 P-glycoprotein inhibitor II Non-inhibitor 0.8262 Renal organic cation transporter Inhibitor 0.6724 CYP450 2C9 substrate Non-substrate 0.7787 CYP450 2D6 substrate Substrate 0.8889 CYP450 3A4 substrate Substrate 0.6919 CYP450 1A2 substrate Inhibitor 0.9082 CYP450 2C9 inhibitor Non-inhibitor 0.8418 CYP450 2D6 inhibitor Inhibitor 0.9214 CYP450 2C19 inhibitor Non-inhibitor 0.8823 CYP450 3A4 inhibitor Non-inhibitor 0.9393 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6783 Ames test Non AMES toxic 0.8804 Carcinogenicity Non-carcinogens 0.5742 Biodegradation Not ready biodegradable 0.9741 Rat acute toxicity 2.1637 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.5748 hERG inhibition (predictor II) Inhibitor 0.6865
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00xu-9736000000-a9b1edd6b1e6e42283be Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00xu-9713000000-7803ffb2bba602eac1f4 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0fk9-0129000000-0f00b15543e0abfaacfc Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-9300000000-6b51e3cbd1046976f3e1 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0fk9-1669000000-66b14675e54af3f2fd53 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00di-1291000000-752eef4a87107ccd2a95 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]- 190.40257 predictedDeepCCS 1.0 (2019) [M+H]+ 192.96303 predictedDeepCCS 1.0 (2019) [M+Na]+ 200.38853 predictedDeepCCS 1.0 (2019)
Drug created at November 18, 2007 18:25 / Updated at July 18, 2023 22:56