Becatecarin
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200450

CAS#: 119673-08-4

Description: Becatecarin, also known as BMY-27557, XL119 and BMS-181176, is a synthetic diethylaminoethyl analogue of the indolocarbazole glycoside antineoplastic antibiotic rebeccamycin. 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.


Price and Availability

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Price

1mg
USD 777
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Price

Size
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Becatecarin purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200450
Name: Becatecarin
CAS#: 119673-08-4
Chemical Formula: C33H34Cl2N4O7
Exact Mass: 668.18045
Molecular Weight: 669.55166
Elemental Analysis: C, 59.20; H, 5.12; Cl, 10.59; N, 8.37; O, 16.73


Synonym: BMS-181176; BMS 181176; BMS181176; BMY-27557; BMY27557; BMY 27557; XL119; XL 119; XL-119; Becatecarin.

IUPAC/Chemical Name: 1,11-dichloro-6-(2-(diethylamino)ethyl)-12-((2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxytetrahydro-2H-pyran-2-yl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione

InChi Key: JSKFWUPVIZYJMR-UDOAKELVSA-N

InChi Code: 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

SMILES Code: O=C1N(CCN(CC)CC)C(C2=C1C3=C(C4=C2C5=C(N4[C@H]6[C@H](O)[C@@H](O)[C@H](OC)[C@@H](CO)O6)C(Cl)=CC=C5)NC7=C3C=CC=C7Cl)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

 
 
 
 


References

1. Mann, David Marshall. Gene expression profiling in the pulmonary artery in the selection of therapies for vascular-related diseases. PCT Int. Appl. (2009), 115pp. CODEN: PIXXD2 WO 2009121031 A1 20091001 CAN 151:418165 AN 2009:1194632

2. Robey, Robert W.; Obrzut, Tomasz; Shukla, Suneet; Polgar, Orsolya; Macalou, Sira; Bahr, Julian C.; Pietro, Attilio; Ambudkar, Suresh V.; Bates, Susan E. Becatecarin (rebeccamycin analog, NSC 655649) is a transport substrate and induces expression of the ATP-binding cassette transporter, ABCG2, in lung carcinoma cells. Cancer Chemotherapy and Pharmacology (2009), 64(3), 575-583. CODEN: CCPHDZ ISSN:0344-5704. CAN 152:254419 AN 2009:689908

3. Li, Chiang Jia; Mikule, Keith; Li, Youzhi. Compositions and methods using Stat3 pathway inhibitors or cancer stem cell inhibitors for combination cancer treatment. PCT Int. Appl. (2009), 81pp. CODEN: PIXXD2 WO 2009036101 A1 20090319 CAN 150:345478 AN 2009:332545

4. Burstein, Harold J.; Overmoyer, Beth; Gelman, Rebecca; Silverman, Paula; Savoie, Jennifer; Clarke, Kathryn; Dumadag, Leda; Younger, Jerry; Ivy, Percy; Winer, Eric P. Rebeccamycin analog for refractory breast cancer: a randomized phase II trial of dosing schedules. Investigational New Drugs (2007), 25(2), 161-164. CODEN: INNDDK ISSN:0167-6997. CAN 146:287832 AN 2006:1347363

5. Dowlati, Afshin; Chapman, Robert; Subbiah, Shanmuga; Fu, Pingfu; Ness, Anne; Cortas, Tania; Patrick, Lauren; Reynolds, Sherrie; Xu, Natalie; Levitan, Nathan; Ivy, Percy; Remick, Scot C. Randomized phase II trial of different schedules of administration of rebeccamycin analogue as second line therapy in non-small cell lung cancer. Investigational New Drugs (2005), 23(6), 563-567. CODEN: INNDDK ISSN:0167-6997. CAN 144:480540 AN 2006:65782

6. Ricart, Alejandro D.; Hammond, Lisa A.; Kuhn, John G.; Takimoto, Chris H.; Goetz, Andrew; Forouzesh, Bahram; Forero, Leonardo; Ochoa-Bayona, Jose L.; Berg, Kristin; Tolcher, Anthony W.; Rowinsky, Eric K. Phase I and Pharmacokinetic Study of Sequences of the Rebeccamycin Analogue NSC 655649 and Cisplatin in Patients with Advanced Solid Tumors. Clinical Cancer Research (2005), 11(24, Pt. 1), 8728-8736. CODEN: CCREF4 ISSN:1078-0432. CAN 144:460400 AN 2005:1318349

7. Rewcastle, Gordon W. Becatecarin(Helsinn Healthcare). IDrugs (2005), 8(10), 838-847. CODEN: IDRUFN ISSN:1369-7056. CAN 144:183759 AN 2005:1173150

8. Moreau, Pascale; Holbeck, Susan; Prudhomme, Michelle; Sausville, Edward A. Cytotoxicities of three rebeccamycin derivatives in the National Cancer Institute screening of 60 human tumor cell lines. Anti-Cancer Drugs (2005), 16(2), 145-150. CODEN: ANTDEV ISSN:0959-4973. CAN 142:348304 AN 2005:40758

9. Masferrer, Jaime L. Method using a cyclooxygenase 2 (COX-2) inhibitor and a topoisomerase II inhibitor as a combination therapy in the treatment of neoplasia. U.S. Pat. Appl. Publ. (2003), 85 pp., Cont.-in-part of U.S. Ser. No. 865,177. CODEN: USXXCO US 2003225150 A1 20031204 CAN 140:726 AN 2003:950066

10. Hussain, Maha; Vaishampayan, Ulka; Heilbrun, Lance K.; Jain, Vikash; LoRusso, Patricia M.; Ivy, Percy; Flaherty, Lawrence. A phase II study of rebeccamycin analog (NSC-655649) in metastatic renal cell cancer. Investigational New Drugs (2003), 21(4), 465-471. CODEN: INNDDK ISSN:0167-6997. CAN 141:16967 AN 2003:833153