Elsamitrucin

Identification

Name
Elsamitrucin
Accession Number
DB05129
Type
Small Molecule
Groups
Investigational
Description

The cytostatic agent Elsamitrucin is a new fermentation product active in a variety of in vivo tumor models of murine and human origin. (PMID: 8150873)

Structure
Thumb
Synonyms
Not Available
External IDs
BBM-2478A / BMY-28090
Product Ingredients
Not Available
Approved Prescription Products
Not Available
Approved Generic Prescription Products
Not Available
Approved Over the Counter Products
Not Available
Unapproved/Other Products
Not Available
International/Other Brands
Not Available
Brand mixtures
Not Available
Categories
UNII
ZTV0FOB6NU
CAS number
97068-30-9
Weight
Average: 653.6299
Monoisotopic: 653.210840211
Chemical Formula
C33H35NO13
InChI Key
MGQRRMONVLMKJL-KWJIQSIXSA-N
InChI
InChI=1S/C33H35NO13/c1-11-9-10-16-19-17(11)29(38)46-25-18-14(24(36)21(20(19)25)30(39)44-16)7-6-8-15(18)45-32-28(33(4,40)27(37)13(3)43-32)47-31-22(34)26(41-5)23(35)12(2)42-31/h6-10,12-13,22-23,26-28,31-32,35-37,40H,34H2,1-5H3/t12-,13-,22-,23+,26-,27+,28+,31-,32+,33+/m1/s1
IUPAC Name
3-{[(2S,3R,4S,5S,6R)-3-{[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy}-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]icosa-1(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dione
SMILES

Pharmacology

Indication

Investigated for use/treatment in lymphoma (non-hodgkin's).

Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action

Elsamitrucin induces single strand breaks in DNA and inhibits topoisomerase I and II, enzymes that play an important role in DNA replication.

TargetActionsOrganism
UDNANot AvailableHuman
UDNA topoisomerase 1Not AvailableHuman
UDNA topoisomerase 2-alphaNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life

36–60 h

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Elsamitrucin.Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Elsamitrucin.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Elsamitrucin.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Elsamitrucin.Approved, Investigational
DeslanosideDeslanoside may decrease the cardiotoxic activities of Elsamitrucin.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Elsamitrucin.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Elsamitrucin.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Elsamitrucin.Approved, Investigational
OleandrinAnvirzel may decrease the cardiotoxic activities of Elsamitrucin.Experimental
OuabainOuabain may decrease the cardiotoxic activities of Elsamitrucin.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Elsamitrucin.Approved, Vet Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Elsamitrucin.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference
Not Available
General References
  1. Klein I, Welink J, van der Vijgh WJ: Determination of Elsamitrucin (BMY-28090) in plasma and urine by high-performance liquid chromatography with fluorescence detection. J Chromatogr. 1993 Dec 22;622(2):249-53. [PubMed:8150873 ]
External Links
PubChem Compound
5362259
PubChem Substance
175426950
ChemSpider
4514988
ChEMBL
CHEMBL2106409
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentChronic Lymphocytic Leukemia/Small Lymphocytic Lymphoma / Mantle Cell Lymphoma (MCL)1

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
PropertyValueSource
Water Solubility0.379 mg/mLALOGPS
logP1.95ALOGPS
logP2.35ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)9.1ChemAxon
pKa (Strongest Basic)7.98ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area205.69 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity160.65 m3·mol-1ChemAxon
Polarizability64.68 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7734
Blood Brain Barrier-0.9941
Caco-2 permeable-0.6837
P-glycoprotein substrateSubstrate0.5965
P-glycoprotein inhibitor INon-inhibitor0.799
P-glycoprotein inhibitor IINon-inhibitor0.8061
Renal organic cation transporterNon-inhibitor0.9595
CYP450 2C9 substrateNon-substrate0.8065
CYP450 2D6 substrateNon-substrate0.8871
CYP450 3A4 substrateNon-substrate0.5112
CYP450 1A2 substrateNon-inhibitor0.8134
CYP450 2C9 inhibitorNon-inhibitor0.9139
CYP450 2D6 inhibitorNon-inhibitor0.926
CYP450 2C19 inhibitorNon-inhibitor0.8572
CYP450 3A4 inhibitorNon-inhibitor0.7817
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8862
Ames testAMES toxic0.5534
CarcinogenicityNon-carcinogens0.9308
BiodegradationNot ready biodegradable0.9923
Rat acute toxicity2.2177 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9875
hERG inhibition (predictor II)Non-inhibitor0.9097
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )

Spectra

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

Taxonomy

Description
This compound belongs to the class of organic compounds known as naphthopyranone glycosides. These are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Naphthopyrans
Sub Class
Naphthopyranones
Direct Parent
Naphthopyranone glycosides
Alternative Parents
Aminoglycosides / Phenolic glycosides / O-glycosyl compounds / Naphthols and derivatives / Coumarins and derivatives / Isocoumarins and derivatives / Disaccharides / 1-benzopyrans / 2-benzopyrans / Pyranones and derivatives
show 13 more
Substituents
Naphthopyranone glycoside / Aminoglycoside core / Phenolic glycoside / 1-naphthol / O-glycosyl compound / Isocoumarin / Glycosyl compound / Coumarin / Disaccharide / 2-benzopyran
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

1. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
Unknown
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Releases the supercoiling and torsional tension of DNA introduced during the DNA replication and transcription by transiently cleaving and rejoining one strand of the DNA duplex. Introduces a singl...
Gene Name
TOP1
Uniprot ID
P11387
Uniprot Name
DNA topoisomerase 1
Molecular Weight
90725.19 Da
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Ubiquitin binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
Gene Name
TOP2A
Uniprot ID
P11388
Uniprot Name
DNA topoisomerase 2-alpha
Molecular Weight
174383.88 Da
Drug created on October 21, 2007 16:23 / Updated on September 01, 2017 11:24