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MedKoo Cat#: 200520 | Name: BMS-275183

Description:

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

BMS-275183 is an oral C-4 methyl carbonate analogue of paclitaxel that has the same mechanism of action, stabilization of tubulin polymerization. BMS-275183 given p.o. was as effective as i.v. paclitaxel in five tumor models. BMS-275183 given p.o. was active in a human, hormone-dependent, prostate tumor model, CWR-22, and just as effective as anti-androgen chemotherapy. In a schedule dependency study, increasing the interval of time between oral administrations resulted in greater cumulative dose tolerance and improved therapeutic outcome. Recent clinical study showed that BMS-275185 is lack of evidence of clinical benefit with the occurrence of two fatal events of neutropenic sepsis.

Chemical Structure

BMS-275183
BMS-275183
CAS#355113-98-3

Theoretical Analysis

MedKoo Cat#: 200520

Name: BMS-275183

CAS#: 355113-98-3

Chemical Formula: C43H61NO15

Exact Mass: 831.4041

Molecular Weight: 831.94

Elemental Analysis: C, 62.08; H, 7.39; N, 1.68; O, 28.85

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
BMS 275183; BMS275183; BMS-275183.
IUPAC/Chemical Name
(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-4,4-dimethylpentanoyl)oxy)-11-hydroxy-4,6-dimethoxy-12b-((methoxycarbonyl)oxy)-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate
InChi Key
VWOQAHUNLAWCIE-GPWPDEGDSA-N
InChi Code
InChI=1S/C43H61NO15/c1-22-24(56-35(48)28(45)31(38(2,3)4)44-36(49)58-39(5,6)7)20-43(51)33(57-34(47)23-17-15-14-16-18-23)30-41(10,32(46)29(53-12)27(22)40(43,8)9)25(52-11)19-26-42(30,21-55-26)59-37(50)54-13/h14-18,24-26,28-31,33,45,51H,19-21H2,1-13H3,(H,44,49)/t24-,25-,26+,28+,29+,30-,31+,33-,41+,42-,43+/m0/s1
SMILES Code
O=C(O[C@@H]([C@@]1([H])[C@@]2(C)[C@@H](OC)C[C@@]3([H])OC[C@]31OC(OC)=O)[C@]4(O)C[C@H](OC([C@H](O)[C@@H](NC(OC(C)(C)C)=O)C(C)(C)C)=O)C(C)=C(C4(C)C)[C@@H](OC)C2=O)C5=CC=CC=C5
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
More Info
BMS-275183 is a taxane, the mechanism of action of which is like other known taxanes, and is the polymerization of tubulin. BMS-275183 given p.o. was as effective as i.v. paclitaxel in five tumor models [murine M109 lung and C3H mammary 16/C, and human A2780 ovarian (grown in mice and rats) and HCT/pk colon]. It was active in one other tumor model (human HCT-116 colon) but inferior to parenteral paclitaxel. BMS-275183 given p.o. was active in a human, hormone-dependent, prostate tumor model, CWR-22, and just as effective as anti-androgen chemotherapy. In a schedule dependency study, increasing the interval of time between oral administrations resulted in greater cumulative dose tolerance and improved therapeutic outcome. Oral BMS-275183 was evaluated as a combination therapy in conjunction with i.v. paclitaxel. Therapeutic advantages were evident for tumor-bearing mice that received the oral taxane either after induction chemotherapy or between courses of such treatment.  s ee: http://clincancerres.aacrjournals.org/content/7/7/2016.short .    

Preparing Stock Solutions

The following data is based on the product molecular weight 831.94 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.

Recalculate based on batch purity %
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
1: Heath EI, Lorusso P, Ramalingam SS, Awada A, Egorin MJ, Besse-Hamer T, Cardoso F, Valdivieso M, Has T, Alland L, Zhou X, Belani CP. A phase 1 study of BMS-275183, a novel oral analogue of paclitaxel given on a daily schedule to patients with advanced malignancies. Invest New Drugs. 2011 Dec;29(6):1426-31. doi: 10.1007/s10637-010-9498-z. Epub 2010 Aug 3. PubMed PMID: 20680660. 2: Ly VT, Caceres-Cortes J, Zhang D, Humphreys WG, Ekhato IV, Everett D, Cömezoğlu SN. Metabolism and excretion of an oral taxane analog, [14C]3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-deacetyl-3'-dephenyl-3'-N-debenzo yl-4-O-methoxy-paclitaxel (BMS-275183), in rats and dogs. Drug Metab Dispos. 2009 May;37(5):1115-28. doi: 10.1124/dmd.108.025809. Epub 2009 Feb 5. PubMed PMID: 19196843. 3: Zhang D, Ly VT, Lago M, Tian Y, Gan J, Humphreys WG, Cömezoglu SN. CYP3A4-mediated ester cleavage as the major metabolic pathway of the oral taxane 3'-tert-butyl-3'-N-tert-butyloxycarbonyl-4-deacetyl-3'-dephenyl-3'-N-debenzoyl-4- O-methoxycarbonyl-paclitaxel (BMS-275183). Drug Metab Dispos. 2009 Apr;37(4):710-8. doi: 10.1124/dmd.108.024398. Epub 2009 Jan 21. PubMed PMID: 19158314. 4: Bröker LE, Valdivieso M, Pilat MJ, Deluca P, Zhou X, Parker S, Giaccone G, Lorusso PM. Effect of food on the pharmacokinetic behavior of the potent oral taxane BMS-275183. Clin Cancer Res. 2008 Jul 1;14(13):4186-91. doi: 10.1158/1078-0432.CCR-07-4594. PubMed PMID: 18593998. 5: Bayés M, Rabasseda X. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2008 Jan-Feb;30(1):67-99. PubMed PMID: 18389098. 6: Yoo GH, Tran VR, Lemonnier LA, Ezzat WH, Subramanian G, Piechocki MP, Ensley JF, Lonardo F, Kim H, Lin HS. BMS-275183-induced gene expression patterns in head and neck carcinoma. Am J Otolaryngol. 2007 Sep-Oct;28(5):309-15. PubMed PMID: 17826531. 7: Bröker LE, Veltkamp SA, Heath EI, Kuenen BC, Gall H, Astier L, Parker S, Kayitalire L, Lorusso PM, Schellens JH, Giaccone G. A phase I safety and pharmacologic study of a twice weekly dosing regimen of the oral taxane BMS-275183. Clin Cancer Res. 2007 Jul 1;13(13):3906-12. PubMed PMID: 17606724. 8: Bröker LE, de Vos FY, van Groeningen CJ, Kuenen BC, Gall HE, Woo MH, Voi M, Gietema JA, de Vries EG, Giaccone G. Phase I trial with BMS-275183, a novel oral taxane with promising antitumor activity. Clin Cancer Res. 2006 Mar 15;12(6):1760-7. PubMed PMID: 16551860. 9: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Oct;26(8):639-63. PubMed PMID: 15605126. 10: Rose WC, Wild R. Therapeutic synergy of oral taxane BMS-275183 and cetuximab versus human tumor xenografts. Clin Cancer Res. 2004 Nov 1;10(21):7413-7. PubMed PMID: 15534118.