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
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
DescriptionSources: http://www.ema.europa.eu/docs/en_GB/document_library/Orphan_designation/2009/10/WC500005857.pdfCurator'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
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
Sources: http://adisinsight.springer.com/drugs/800016411
Curator's Comment: # Bristol-Myers Squibb
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: DNA Sources: http://www.ncbi.nlm.nih.gov/pubmed/7727062 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
Cmax
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 |
T1/2
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 |
Sample Use Guides
In Vivo Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11387367
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9544164
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.
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Classification Tree | Code System | Code | ||
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EU-Orphan Drug |
EU/3/06/388
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FDA ORPHAN DRUG |
179903
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NCI_THESAURUS |
C582
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NCI_THESAURUS |
C1904
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119673-08-4
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C1620
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655649
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101524
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QQ-56
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DTXSID60869635
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CHEMBL2107313
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8564
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DB06362
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100000089433
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A60X6MBU6G
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C093269
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SUB25405
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ACTIVE MOIETY