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Becatecarin

Targets (2)

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

Identification

Name

Becatecarin

Accession Number

DB06362

Type

Small Molecule

Groups

Investigational

Description

Becatecarin is a derivative of rebeccamycin.

Structure

Similar Structures

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.

Target	Actions	Organism
UDNA topoisomerase 2-alpha	Not Available	Humans
UDNA topoisomerase 2-beta	Not Available	Humans

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

Not Available

External Links

ChemSpider: 91737
ChEMBL: CHEMBL2107313

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Completed	Treatment	Adult 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 Syndromes	1
1	Completed	Treatment	Malignant Lymphomas / Small Intestine Cancer / Unspecified Adult Solid Tumor, Protocol Specific	1
1	Terminated	Treatment	Unspecified Adult Solid Tumor, Protocol Specific	1
2	Completed	Treatment	Brain and Central Nervous System Tumors / Malignant Lymphomas / Neuroblastomas / Retinoblastoma / Sarcomas / Unspecified Childhood Solid Tumor, Protocol Specific	1
2	Completed	Treatment	Colorectal Cancers	1
2	Completed	Treatment	Lung Cancers	1
2	Completed	Treatment	Male Breast Cancer / Recurrent Breast Cancer / Stage IIIB Breast Cancer / Stage IV Breast Cancer	1
2	Completed	Treatment	Neuroblastomas	1
2	Completed	Treatment	Renal Cancers	1
2	Terminated	Treatment	Cancer of the Ovary	1
2	Terminated	Treatment	Extensive Stage Small Cell Lung Cancer / Limited Stage Small Cell Lung Cancer / Refractory Small cell lung cancer	1
2	Terminated	Treatment	Extrahepatic Bile Duct Cancer / Gallbladder Cancer / Liver Cancer	1
3	Terminated	Treatment	Biliary Tract Cancer	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

Property	Value	Source
Water Solubility	0.0132 mg/mL	ALOGPS
logP	4.14	ALOGPS
logP	3.55	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	11.86	ChemAxon
pKa (Strongest Basic)	9.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.49 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	173.48 m³·mol^-1	ChemAxon
Polarizability	69.43 Å³	ChemAxon
Number of Rings	7	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	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not 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

Details1. 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

Details2. DNA topoisomerase 2-beta

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 June 04, 2019 06:23

Becatecarin

Identification

Structure for Becatecarin (DB06362)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets