Afeletecan HCl

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MedKoo CAT#: 205949

CAS#: 215604-74-3 (HCl)

Description: Afeletecan, also known as 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.

Chemical Structure

Afeletecan HCl
CAS# 215604-74-3 (HCl)

Theoretical Analysis

MedKoo Cat#: 205949
Name: Afeletecan HCl
CAS#: 215604-74-3 (HCl)
Chemical Formula: C45H50ClN7O11S
Exact Mass: 895.32
Molecular Weight: 932.440
Elemental Analysis: C, 57.97; H, 5.41; Cl, 3.80; N, 10.52; O, 18.87; S, 3.44

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales or click below button.
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Related CAS #: 215604-75-4 (free base)   215604-74-3 (HCl),  

Synonym: Afeletecan HCl; Afeletecan hydrochloride; 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 hydrochloride


InChi Code: InChI=1S/C45H49N7O11S.ClH/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);1H/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.[H]Cl

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

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 932.44 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.