BAY 56-3722

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

MedKoo CAT#: 205949

CAS#: 215604-75-4 (BAY 56-3722 free base)

Description: BAY 56-3722 is a water-soluble camptothecin derivative conjugated to a carbohydrate moiety exhibiting antineoplastic activity. BAY 56-3722 stabilizes the topoisomerase I-DNA covalent complex and forms an enzyme-drug-DNA ternary complex. As a consequence of the formation of this complex, both the initial cleavage reaction and religation steps are inhibited and subsequent collision of the replication fork with the cleaved strand of DNA results in inhibition of DNA replication, double strand DNA breakage and triggering of apoptosis. The peptide carbohydrate moiety of this agent stabilizes the lactone form of camptothecin in blood.


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BAY 56-3722, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 205949
Name: BAY 56-3722
CAS#: 215604-75-4 (BAY 56-3722 free base)
Chemical Formula: C45H49N7O11S
Exact Mass: 895.32108
Molecular Weight: 895.98
Elemental Analysis: C, 60.32; H, 5.51; N, 10.94; O, 19.64; S, 3.58


Synonym: BAY 563722; BAY563722; BAY-563722; BAY 383441; BAY383441; BAY-383441.

IUPAC/Chemical Name: (S)-(S)-4-ethyl-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-4-yl 2-((S)-2-(3-(4-(((2R,3S,4R,5R,6S)-3,5-dihydroxy-4-methoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)phenyl)thioureido)-3-(1H-imidazol-4-yl)propanamido)-3-methylbutanoate

InChi Key: SLOJCSGNHWIKIG-JNYZSSQASA-N

InChi Code: InChI=1S/C45H49N7O11S/c1-6-45(30-17-33-35-25(15-24-9-7-8-10-31(24)49-35)19-52(33)40(56)29(30)20-60-43(45)58)63-41(57)34(22(2)3)51-39(55)32(16-27-18-46-21-47-27)50-44(64)48-26-11-13-28(14-12-26)62-42-37(54)38(59-5)36(53)23(4)61-42/h7-15,17-18,21-23,32,34,36-38,42,53-54H,6,16,19-20H2,1-5H3,(H,46,47)(H,51,55)(H2,48,50,64)/t23-,32-,34-,36+,37-,38+,42+,45-/m0/s1

SMILES Code: CC(C)[C@H](NC([C@@H](NC(NC1=CC=C(O[C@@H]2[C@@H](O)[C@H](OC)[C@H](O)[C@H](C)O2)C=C1)=S)CC3=CNC=N3)=O)C(O[C@](C4=C(CO5)C(N6CC7=CC8=CC=CC=C8N=C7C6=C4)=O)(CC)C5=O)=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

  Related:
 215604-75-4 (BAY 56-3722 free base)
215604-74-3 (BAY 56-3722 HCl salt).
 
 


References

1: Slingerland M, Gelderblom H. The fate of camptothecin glycoconjugate: report of a clinical hold during a phase II study of BAY 56-3722 (formerly BAY 38-3441), in patients with recurrent or metastatic colorectal cancer resistant/refractory to irinotecan. Invest New Drugs. 2012 Jun;30(3):1208-10. doi: 10.1007/s10637-011-9679-4. Epub 2011 May 6. PubMed PMID: 21547368; PubMed Central PMCID: PMC3348469.

2: Chen EX, Batist G, Siu LL, Bangash N, Maclean M, McIntosh L, Miller WH Jr, Oza AM, Lathia C, Petrenciuc O, Seymour L. Phase I and pharmacokinetic study of Bay 38-3441, a camptothecin glycoconjugate, administered as a 30-minute infusion daily for five days every 3 weeks in patients with advanced solid malignancies. Invest New Drugs. 2005 Oct;23(5):455-65. PubMed PMID: 16133797.

3: Mross K, Richly H, Schleucher N, Korfee S, Tewes M, Scheulen ME, Seeber S, Beinert T, Schweigert M, Sauer U, Unger C, Behringer D, Brendel E, Haase CG, Voliotis D, Strumberg D. A phase I clinical and pharmacokinetic study of the camptothecin glycoconjugate, BAY 38-3441, as a daily infusion in patients with advanced solid tumors. Ann Oncol. 2004 Aug;15(8):1284-94. PubMed PMID: 15277271.

4: Lerchen HG, Baumgarten J, von dem Bruch K, Lehmann TE, Sperzel M, Kempka G, Fiebig HH. Design and optimization of 20-O-linked camptothecin glycoconjugates as anticancer agents. J Med Chem. 2001 Nov 22;44(24):4186-95. PubMed PMID: 11708920.