BECATECARIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C33H34Cl2N4O7
Molecular Weight	669.552
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCN1C(=O)C2=C(C1=O)C3=C(N([C@@H]4O[C@H](CO)[C@@H](OC)[C@H](O)[C@H]4O)C5=C3C=CC=C5Cl)C6=C2C7=C(N6)C(Cl)=CC=C7

InChI

InChIKey=JSKFWUPVIZYJMR-UDOAKELVSA-N

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

HIDE SMILES / InChI

Molecular Formula	C33H34Cl2N4O7
Molecular Weight	669.552
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2009/10/WC500005857.pdf
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/11387367 http://www.ncbi.nlm.nih.gov/pubmed/12678746

Rebeccamycin analog (RA, Becatecarin/ BMS 181176, rebeccamycin derivative, NSC 655649) is an antitumor antibiotic with inhibitory activity against both topoisomerase I and II, and DNA-intercalating properties. The mechanism of action of becatecarin is not exactly known, but it is thought that by inhibiting (blocking) the function of topoisomerase enzymes, it will destroy cancer cells and slow down the growth of the tumour. On 25 July 2006, orphan designation (EU/3/06/388) was granted by the European Commission to Helsinn Birex Pharmaceuticals Ltd, Ireland, for becatecarin for the treatment of cancers of the biliary tree.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA 278 Target ID: DNA Sources: http://www.ncbi.nlm.nih.gov/pubmed/7727062	Binding Agent 1064

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancers of the biliary tree 1 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2009/10/WC500005857.pdf	Primary		Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
5.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11387367	744 mg/m² single, intravenous dose: 744 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BECATECARIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
14.5 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12114420	572 mg/m² single, intravenous dose: 572 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BECATECARIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
83.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11387367	744 mg/m² single, intravenous dose: 744 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BECATECARIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5262 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12114420	572 mg/m² single, intravenous dose: 572 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BECATECARIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
73.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11387367	744 mg/m² single, intravenous dose: 744 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BECATECARIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
28.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12114420	572 mg/m² single, intravenous dose: 572 mg/m² route of administration: Intravenous experiment type: SINGLE co-administered:		BECATECARIN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P008S42	https://www.1pchem.com/search?query=1P008S42
AK Scientific	X2117	https://aksci.com/item_detail.php?cat=X2117
BOC Sciences	119673-08-4	http://www.bocsci.com/description.asp?cas=119673-08-4
Cayman Chemical	15576	http://www.caymanchem.com/app/template/Product.vm/catalog/15576
Compound Cloud	101524
MolPort	MolPort-027-720-812	https://www.molport.com/shop/molecule-link/MolPort-027-720-812
eMolecules	44696661	https://orderbb.emolecules.com/search/#?query=44696661
mcule	MCULE-8636163203	https://mcule.com/MCULE-8636163203/

PubMed

Title	Date	PubMed
Becatecarin (Helsinn Healthcare).	2005 Oct	16254805
Becatecarin (rebeccamycin analog, NSC 655649) is a transport substrate and induces expression of the ATP-binding cassette transporter, ABCG2, in lung carcinoma cells.	2009 Aug	19132374
A phase I study of rebeccamycin analog in combination with oxaliplatin in patients with refractory solid tumors.	2011 Feb	19774342

Patents

Sample Use Guides

In Vivo Use Guide

Recommended phase II doses are 500 mg/m(2) and 572 mg/m(2) IV once every 3 weeks for heavily pretreated (HP) patients and minimally pretreated (MP) respectively

Route of Administration: Intravenous

In Vitro Use Guide

Tumor cells from 14 established cell lines and 20 patient specimens were exposed in vitro for 1 hour to NSC# 655649 (rebeccamycin tartrate salt ) at concentrations ranging from 0.015 to 15.0 uM. The cytotoxicity (IC50) of this agent against established cell lines was determined using both the MTT (cytotoxic) and clonogenic/soft agar cloning (cytostatic) assays. Tumor specimens from children undergoing biopsy or surgical resection were also evaluated in vitro against NSC# 655649 using the clonogenic assay. For studies using patient specimens, antitumor activity was measured by comparing the number of tumor colonies from NSC# 655649-treated cells with those from solvent-treated controls.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:44:33 UTC 2023` Edited by `admin` on `Fri Dec 15 15:44:33 UTC 2023`
Record UNII	A60X6MBU6G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BECATECARIN

Official Name

English

BMS-181176

Code

English

NSC-655649

Code

English

6-(2-(DIETHYLAMINO)ETHYL)-REBECCAMYCIN

Common Name

English

Becatecarin [WHO-DD]

Common Name

English

XL119

Code

English

5H-INDOLO(2,3-A)PYRROLO(3,4-C)CARBAZOLE-5,7(6H)-DIONE, 1,11-DICHLORO-6-(2-(DIETHYLAMINO)ETHYL)-12,13-DIHYDRO-12-(4-O-METHYL-.BETA.-D-GLUCOPYRANOSYL)-

Common Name

English

DEAE-REBECCAMYCIN

Common Name

English

BMY-27557

Code

English

XL-119

Code

English

BECATECARIN [MART.]

Common Name

English

BECATECARIN [USAN]

Common Name

English

becatecarin [INN]

Common Name

English

1,11-DICHLORO-6-(2-(DIETHYLAMINO)ETHYL)-12,13-DIHYDRO-12-(4-O-METHYL-.BETA.-D-GLUCOPYRANOSYL)-5H-INDOLO(2,3-A)PYRROLO(3,4-C)CARBAZOLE-5,7(6H)-DIONE

Systematic Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/06/388