Diazepinomicin
Identification
- Generic Name
- Diazepinomicin
- DrugBank Accession Number
- DB12420
- Background
Diazepinomicin has been used in trials studying the treatment of Glioblastoma Multiforme. It is a proprietary first-in-class small molecule with the potential to treat multiple solid tumours like the well known chemotherapeutics, doxorubicin and mitomycin C. Diazepinomicin is a natural product derived from a non-pathogenic micro-organism. Discovered using Thallion’s DECIPHER technology, diazepinomicin has completed preclinical studies conducted by the National Cancer Institute and Thallion to establish safety and efficacy in animal and in vitro models.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 462.59
Monoisotopic: 462.251857583 - Chemical Formula
- C28H34N2O4
- Synonyms
- 4,6,8-trihydroxy-10-(3,7,11-trimethyldodeca-2,6,10-trienyl)-5,10-dihydrodibenzo(b,e)(1,4)diazepin-11-one
- DIAZEPINOMICIN
- External IDs
- BU-4664L
- ECO-4601
- TLN-4601
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Diazepinomicin demonstrates broad in vitro cytotoxic activity across a diverse panel of tumour cell lines and in vivo efficacy in a number of xenograft tumour models. Preclinical data suggest that diazepinomicin is a targeted anti-cancer agent with dual activity: selective binding to the peripheral benzodiazepine receptor (PBR) and inhibition of the Ras-MAPK pathway.
- 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
- 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 dibenzodiazepines. These are compounds containing a dibenzodiazepine moiety, which consists of two benzene connected by diazepine ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzodiazepines
- Sub Class
- Dibenzodiazepines
- Direct Parent
- Dibenzodiazepines
- Alternative Parents
- Sesquiterpenoids / 1,4-benzodiazepines / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / 1,4-diazepines / Primary aromatic amines / Vinylogous amides / Tertiary carboxylic acid amides / Lactams / Amino acids and derivatives show 5 more
- Substituents
- 1,4-benzodiazepine / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxamide group / Carboxylic acid derivative show 17 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- YPH994Y0RF
- CAS number
- 733035-26-2
- InChI Key
- SALVHVNECODMJP-GNUCVDFRSA-N
- InChI
- InChI=1S/C28H34N2O4/c1-18(2)8-5-9-19(3)10-6-11-20(4)14-15-30-23-16-21(31)17-25(33)27(23)29-26-22(28(30)34)12-7-13-24(26)32/h7-8,10,12-14,16-17,29,31-33H,5-6,9,11,15H2,1-4H3/b19-10+,20-14+
- IUPAC Name
- 4,6,15-trihydroxy-9-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2,9-diazatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,12,14-hexaen-10-one
- SMILES
- CC(C)=CCC\C(C)=C\CC\C(C)=C\CN1C2=CC(O)=CC(O)=C2NC2=C(C=CC=C2O)C1=O
References
- General References
- Gourdeau H, McAlpine JB, Ranger M, Simard B, Berger F, Beaudry F, Farnet CM, Falardeau P: Identification, characterization and potent antitumor activity of ECO-4601, a novel peripheral benzodiazepine receptor ligand. Cancer Chemother Pharmacol. 2008 May;61(6):911-21. Epub 2007 Jul 11. [Article]
- External Links
- PubChem Compound
- 9868980
- PubChem Substance
- 347828664
- ChemSpider
- 8044671
- BindingDB
- 50481798
- ChEBI
- 156321
- ChEMBL
- CHEMBL550961
- ZINC
- ZINC000003938687
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Terminated Treatment Glioblastoma Multiforme (GBM) 1 1 Completed Treatment Breast Cancer / Colorectal Cancer / Glioma / Lung Cancer / Ovarian Cancer / Pancreatic Cancer / Prostate Cancer / Tumor 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.004 mg/mL ALOGPS logP 5.67 ALOGPS logP 7.47 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 8.88 Chemaxon pKa (Strongest Basic) 0.73 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 93.03 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 139.8 m3·mol-1 Chemaxon Polarizability 53.25 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-08fr-0102900000-268f56d875ffefc69525 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0000900000-8653cf7c6fa3c1c70286 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0011900000-1934ee718d8020bb95d1 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-059f-2309600000-4a1ea51d24cd88dc9e97 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05qj-0092300000-d66c4dfc66d55b3ede32 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01p9-2698300000-523dbbee5b72bd2bdd73 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]- 231.8199322 predictedDarkChem Lite v0.1.0 [M-H]- 219.9357322 predictedDarkChem Lite v0.1.0 [M-H]- 206.96837 predictedDeepCCS 1.0 (2019) [M+H]+ 227.3499322 predictedDarkChem Lite v0.1.0 [M+H]+ 215.5298322 predictedDarkChem Lite v0.1.0 [M+H]+ 209.36392 predictedDeepCCS 1.0 (2019) [M+Na]+ 226.9319322 predictedDarkChem Lite v0.1.0 [M+Na]+ 216.3877322 predictedDarkChem Lite v0.1.0 [M+Na]+ 215.93675 predictedDeepCCS 1.0 (2019)
Drug created at October 20, 2016 22:18 / Updated at December 01, 2022 11:27