Becatecarin

    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.


Chemical Structure

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Becatecarin
CAS# 119673-08-4

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

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Pricing updated 2021-03-01. Prices are subject to change without notice.

Becatecarin is currnetly out of stock.

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

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).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 669.55166 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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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



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