NAV

Elsamitrucin

Identification

Generic Name
Elsamitrucin
DrugBank Accession Number
DB05129
Background

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)

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 653.6299
Monoisotopic: 653.210840211
Chemical Formula
C33H35NO13
Synonyms
  • Elsamitrucin
External IDs
  • BBM-2478A
  • BMY-28090
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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 AvailableHumans
UDNA topoisomerase 1Not AvailableHumans
UDNA topoisomerase 2-alphaNot AvailableHumans
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

Adverse Effects
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Elsamitrucin is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Elsamitrucin is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Elsamitrucin is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Elsamitrucin is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Elsamitrucin is combined with Bupivacaine.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1-benzopyran / 1-naphthol / 2-benzopyran / Acetal / Alcohol / Amine / Amino saccharide / Aminoglycoside core / Aromatic heteropolycyclic compound / Benzenoid
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
ZTV0FOB6NU
CAS number
97068-30-9
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[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dione
SMILES
CO[C@@H]1[C@@H](N)[C@@H](O[C@H]2[C@H](OC3=CC=CC4=C3C3=C5C(C(=O)OC6=C5C(=C(C)C=C6)C(=O)O3)=C4O)O[C@H](C)[C@H](O)[C@]2(C)O)O[C@H](C)[C@@H]1O

References

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. [Article]
PubChem Compound
5362259
PubChem Substance
175426950
ChemSpider
4514988
ChEMBL
CHEMBL2106409
ZINC
ZINC000004215770
Wikipedia
Elsamitrucin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentChronic Lymphocytic Leukemia (CLL)/Small Lymphocytic Lymphoma (SLL) / 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
Polarizability64.52 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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0003009000-79fc953308e535ca90c4
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0301019000-5fc44ce07e46ed7c16cb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-0204039000-639ce0fc2fb657124a8c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0pc0-0203419000-9349b2579ee7c9d560b6
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0wmi-0908042000-483323881b93e8e5cf4c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a59-0509328000-5c2d85c2ac345409b8d1
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-244.8119
predicted
DeepCCS 1.0 (2019)
[M+H]+246.8847
predicted
DeepCCS 1.0 (2019)
[M+Na]+253.05629
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. DNA
Kind
Nucleotide
Organism
Humans
Pharmacological action
Unknown
DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
Details2. DNA topoisomerase 1
Kind
Protein
Organism
Humans
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
Details3. DNA topoisomerase 2-alpha
Kind
Protein
Organism
Humans
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 at October 21, 2007 22:23 / Updated at February 21, 2021 18:51