MedKoo Cat#: 59802 | Name: Thymectacin

Description:

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

Thymectacin is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine with potential antineoplastic activity. Selectively active against tumor cells expressing high levels of thymidylate synthase (TS), brivudine phosphoramidate is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, deoxyuridine monophosphate, for binding to TS. Unlike TS inhibitors, this agent is a reversible substrate for TS catalysis. Thus, TS retains activity and converts BVdUMP into cytotoxic metabolites. As key enzyme in the de novo synthesis of dTMP, TS is an enzyme critical to DNA biosynthesis and is overexpressed in many solid tumors. (NCI Thesaurus)

Chemical Structure

Thymectacin
Thymectacin
CAS#232925-18-7

Theoretical Analysis

MedKoo Cat#: 59802

Name: Thymectacin

CAS#: 232925-18-7

Chemical Formula: C21H26BrN3O9P

Exact Mass: 574.0590

Molecular Weight: 575.32

Elemental Analysis: C, 43.84; H, 4.56; Br, 13.89; N, 7.30; O, 25.03; P, 5.38

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 #
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Synonym
Thymectacin; NB 1011; NB-1011; NB1011;
IUPAC/Chemical Name
L-Alanine, N-(5-((1E)-2-bromoethenyl)-2'-deoxy-P-phenyl-5'-uridylyl)-, methyl ester
InChi Key
QVZYEQMBGLYIOI-XGTZFBEQSA-N
InChi Code
InChI=1S/C21H26BrN3O9P/c1-13(20(28)32-2)24-35(30,31,15-6-4-3-5-7-15)33-12-17-16(26)10-18(34-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,23,27,29)(H2,24,30,31)/b9-8+/t13-,16-,17+,18+/m0/s1
SMILES Code
C[C@@H](C(OC)=O)NP(OC[C@@H]1[C@H](C[C@H](N2C(NC(C(/C=C/Br)=C2)=O)=O)O1)O)(O)(C3=CC=CC=C3)=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
Shelf Life
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 575.32 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: Miao X, Yang W, Feng T, Lin J, Huang P. Drug nanocrystals for cancer therapy. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2018 May;10(3):e1499. doi: 10.1002/wnan.1499. Epub 2017 Oct 17. Review. PubMed PMID: 29044971. 2: Congiatu C, Brancale A, Mason MD, Jiang WG, McGuigan C. Novel potential anticancer naphthyl phosphoramidates of BVdU: separation of diastereoisomers and assignment of the absolute configuration of the phosphorus center. J Med Chem. 2006 Jan 26;49(2):452-5. PubMed PMID: 16420029. 3: McGuigan C, Thiery JC, Daverio F, Jiang WG, Davies G, Mason M. Anti-cancer ProTides: tuning the activity of BVDU phosphoramidates related to thymectacin. Bioorg Med Chem. 2005 May 2;13(9):3219-27. PubMed PMID: 15809157.