Thymectacin: Difference between revisions

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	\| PubChem = 6440764\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}		\| PubChem = 6440764\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| ChemSpiderID = 4945015		\| ChemSpiderID = 4945015
			\| synonyms = NB-1011; NB-101; ''N''--2'-deoxyuridin-5'-O-yl]](phenoxy)phosphoryl]-<small>L</small>-alanine methyl ester

	<!--Chemical data-->		<!--Chemical data-->
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	\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}		\| StdInChIKey_Ref = {{stdinchicite\|changed\|chemspider}}
	\| StdInChIKey = CFBLUORPOFELCE-BACVZHSASA-N		\| StdInChIKey = CFBLUORPOFELCE-BACVZHSASA-N

	}}		}}

	'''Thymectacin''' (NB-1011, NB-101~~, N--2~~'~~-deoxyuridin-5~~'~~-O-yl]](phenoxy)phosphoryl]-L-alanine methyl ester~~) is an anticancer ] of ] monophosphate. It developed by ] and it ~~has~~ entered in phase I clinical trials for colon cancer.<ref>{{cite journal \| vauthors = Wilson RH \| title = Novel therapeutic developments other than EGFR and VEGF inhibition in colorectal cancer \| journal = The Oncologist \| volume = 11 \| issue = 9 \| pages = 1018–24 \| date = October 2006 \| pmid = 17030644 \| doi = 10.1634/theoncologist.11-9-1018 \| url = http://theoncologist.alphamedpress.org/cgi/content/full/11/9/1018 }}</ref>		'''Thymectacin''' ('''NB-1011''', '''NB-101''') is an experimental anticancer ] of ] monophosphate. It is being ] by ] and it entered in phase I clinical trials for colon cancer in 2006.<ref>{{cite journal \| vauthors = Wilson RH \| title = Novel therapeutic developments other than EGFR and VEGF inhibition in colorectal cancer \| journal = The Oncologist \| volume = 11 \| issue = 9 \| pages = 1018–24 \| date = October 2006 \| pmid = 17030644 \| doi = 10.1634/theoncologist.11-9-1018 \| url = http://theoncologist.alphamedpress.org/cgi/content/full/11/9/1018 }}</ref>

	~~Description of~~ Thymectacin~~: Thymectacin, also known as NB-1011,~~ 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), ~~BVdU pronucleotide analogue NB1011~~ 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.		Thymectacin is a small molecule phosphoramidate derivative of (''E'')-5-(2-bromovinyl)-2'-deoxyuridine (BVdU) with potential antineoplastic activity.<ref>{{cite web \| url = https://www.cancer.gov/publications/dictionaries/cancer-drug/def/brivudine-phosphoramidate \| title = Brivudine phosphoramidate \| work = NCI Drug Dictionary \| publisher = ] }}</ref> It is selectively active against tumor cells expressing high levels of ] (TS). Thymectacin is converted intracellularly by TS to bromovinyldeoxyuridine monophosphate (BVdUMP) which competes with the natural substrate, ], 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.

	== References ==		== References ==

Revision as of 02:27, 9 July 2021

Pharmaceutical compound

Thymectacin
Clinical data


Other names	NB-1011; NB-101; N--2'-deoxyuridin-5'-O-yl]](phenoxy)phosphoryl]-L-alanine methyl ester
Identifiers
IUPAC name (2S)-methyl 2-((((2R,3S,5R)-5-(5-((E)-2-bromovinyl)-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-hydroxytetrahydrofuran-2-yl)methoxy)(phenoxy)phosphorylamino)propanoate
CAS Number	232925-18-7
PubChem CID	6440764
ChemSpider	4945015
UNII	2ZRZ4TSW3F
CompTox Dashboard (EPA)	DTXSID00177862
Chemical and physical data
Formula	C₂₁H₂₅BrN₃O₉P
Molar mass	574.321 g·mol
3D model (JSmol)	Interactive image
SMILES C(C(=O)OC)NP(=O)(OC1(C(O1)n2cc(c(=O)c2=O)/C=C/Br)O)Oc3ccccc3
InChI InChI=1S/C21H25BrN3O9P/c1-13(20(28)31-2)24-35(30,34-15-6-4-3-5-7-15)32-12-17-16(26)10-18(33-17)25-11-14(8-9-22)19(27)23-21(25)29/h3-9,11,13,16-18,26H,10,12H2,1-2H3,(H,24,30)(H,23,27,29)/b9-8+/t13-,16-,17+,18+,35?/m0/s1 Key:CFBLUORPOFELCE-BACVZHSASA-N
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Thymectacin (NB-1011, NB-101) is an experimental anticancer prodrug of brivudine monophosphate. It is being developed by New Biotics and it entered in phase I clinical trials for colon cancer in 2006.

Thymectacin is a small molecule phosphoramidate derivative of (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVdU) with potential antineoplastic activity. It is selectively active against tumor cells expressing high levels of thymidylate synthase (TS). Thymectacin 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.

References

Wilson RH (October 2006). "Novel therapeutic developments other than EGFR and VEGF inhibition in colorectal cancer". The Oncologist. 11 (9): 1018–24. doi:10.1634/theoncologist.11-9-1018. PMID 17030644.
"Brivudine phosphoramidate". NCI Drug Dictionary. National Institutes of Health.

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