Becatecarin

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
Becatecarin
Accession Number
DB06362
Type
Small Molecule
Groups
Investigational
Description

Becatecarin is a derivative of rebeccamycin.

Structure
Thumb
Synonyms
Not Available
External IDs
BMS-181176 / BMY-27557 / NSC-655649 / XL 119 / XL-119 / XL119
Categories
UNII
A60X6MBU6G
CAS number
119673-08-4
Weight
Average: 669.56
Monoisotopic: 668.1804549
Chemical Formula
C33H34Cl2N4O7
InChI Key
JSKFWUPVIZYJMR-UDOAKELVSA-N
InChI
InChI=1S/C33H34Cl2N4O7/c1-4-37(5-2)12-13-38-31(43)22-20-15-8-6-10-17(34)24(15)36-25(20)27-21(23(22)32(38)44)16-9-7-11-18(35)26(16)39(27)33-29(42)28(41)30(45-3)19(14-40)46-33/h6-11,19,28-30,33,36,40-42H,4-5,12-14H2,1-3H3/t19-,28-,29-,30-,33-/m1/s1
IUPAC Name
5,21-dichloro-13-[2-(diethylamino)ethyl]-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-3,13,23-triazahexacyclo[14.7.0.0^{2,10}.0^{4,9}.0^{11,15}.0^{17,22}]tricosa-1(16),2(10),4,6,8,11(15),17(22),18,20-nonaene-12,14-dione
SMILES
CCN(CC)CCN1C(=O)C2=C(C1=O)C1=C(N([C@@H]3O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]3O)C3=C(Cl)C=CC=C13)C1=C2C2=C(N1)C(Cl)=CC=C2

Pharmacology

Indication

Investigated for use/treatment in cancer/tumors (unspecified), liver cancer, gastric cancer, and leukemia (unspecified).

Pharmacodynamics
Not Available
Mechanism of action

Becatecarin is a small molecule, anticancer compound for the treatment of hepatobiliary duct tumors, a rare and aggressive form of cancer with a high medical need and very limited survival. Becatecarin intercalates into DNA and stabilizes the DNA-topoisomerase I complex, thereby interfering with the topoisomerase I-catalyzed DNA breakage-reunion reaction and initiating DNA cleavage and apoptosis.

TargetActionsOrganism
UDNA topoisomerase 2-alphaNot AvailableHumans
UDNA topoisomerase 2-betaNot AvailableHumans
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
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

References

General References
Not Available
External Links
ChemSpider
91737
ChEMBL
CHEMBL2107313

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentAdult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With T(15;17)(q22;q12) / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Blastic Phase Chronic Myelogenous Leukemia / Chronic Myelomonocytic Leukemia / De Novo Myelodysplastic Syndromes / Previously Treated Myelodysplastic Syndromes / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Adult Acute Myeloid Leukemia / Refractory Anemia With Excess Blasts / Refractory Anemia With Excess Blasts in Transformation / Relapsing Chronic Myelogenous Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Secondary Myelodysplastic Syndromes1
1CompletedTreatmentMalignant Lymphomas / Small Intestine Cancer / Unspecified Adult Solid Tumor, Protocol Specific1
1TerminatedTreatmentUnspecified Adult Solid Tumor, Protocol Specific1
2CompletedTreatmentBrain and Central Nervous System Tumors / Malignant Lymphomas / Neuroblastomas / Retinoblastoma / Sarcomas / Unspecified Childhood Solid Tumor, Protocol Specific1
2CompletedTreatmentColorectal Cancers1
2CompletedTreatmentLung Cancers1
2CompletedTreatmentMale Breast Cancer / Recurrent Breast Cancer / Stage IIIB Breast Cancer / Stage IV Breast Cancer1
2CompletedTreatmentNeuroblastomas1
2CompletedTreatmentRenal Cancers1
2TerminatedTreatmentExtensive Stage Small Cell Lung Cancer / Limited Stage Small Cell Lung Cancer / Refractory Small cell lung cancer1
2TerminatedTreatmentExtrahepatic Bile Duct Cancer / Gallbladder Cancer / Liver Cancer1
2TerminatedTreatmentOvarian Cancer1
3TerminatedTreatmentBiliary Tract Cancer1

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 Solubility0.0132 mg/mLALOGPS
logP4.14ALOGPS
logP3.55ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)11.86ChemAxon
pKa (Strongest Basic)9.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area140.49 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity173.48 m3·mol-1ChemAxon
Polarizability69.43 Å3ChemAxon
Number of Rings7ChemAxon
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 indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Carbazoles
Direct Parent
Indolocarbazoles
Alternative Parents
Pyrrolo[2,3-a]carbazoles / Pyrroloindoles / Glycosylamines / Isoindolones / N-alkylindoles / Indoles / Isoindoles / Substituted pyrroles / Aryl chlorides / Monosaccharides
show 14 more
Substituents
Indolocarbazole / Pyrrolo[2,3-a]carbazole / Pyrroloindole / Glycosyl compound / N-glycosyl compound / N-alkylindole / Isoindolone / Indole / Isoindole / Isoindole or derivatives
show 29 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

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
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase c binding
Specific Function
Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks.
Gene Name
TOP2B
Uniprot ID
Q02880
Uniprot Name
DNA topoisomerase 2-beta
Molecular Weight
183265.825 Da

Drug created on March 19, 2008 10:27 / Updated on December 02, 2019 07:21