Diazepinomicin

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Diazepinomicin
Accession Number
DB12420  (DB05923)
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
  • DIAZEPINOMICIN
External IDs
BU-4664L / ECO-4601 / TLN-4601
Categories
UNII
YPH994Y0RF
CAS number
733035-26-2
Weight
Average: 462.59
Monoisotopic: 462.251857583
Chemical Formula
C28H34N2O4
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:17622531]
External Links
PubChem Compound
9868980
PubChem Substance
347828664
ChemSpider
8044671
ChEMBL
CHEMBL550961

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCancer of the Ovary / Cancer, Breast / Colorectal Cancers / Gliomas / Lung Cancers / Malignant Neoplasm of Pancreas / Prostate Cancer / Tumors1
2TerminatedTreatmentGlioblastoma Multiforme (GBM)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
PropertyValueSource
Water Solubility0.004 mg/mLALOGPS
logP5.67ALOGPS
logP7.47ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)8.88ChemAxon
pKa (Strongest Basic)0.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area93.03 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity139.8 m3·mol-1ChemAxon
Polarizability53.25 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Dibenzodiazepine / Sesquiterpenoid / Farsesane sesquiterpenoid / 1,4-benzodiazepine / Para-diazepine / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Phenol / Benzenoid / Primary aromatic amine
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on October 20, 2016 16:18 / Updated on June 04, 2019 07:38