Sapacitabine information

Sapacitabine
Clinical data
Other names	N-[1-[(2R,3S,4S,5R)-3-Cyano-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]hexadecanamide
ATC code	none;
Identifiers
	IUPAC name 1-(2-cyano-2-deoxy-β-D-arabinofuranosyl)-4-(palmitoylamino)pyrimidin-2(1H)-one;
CAS Number	151823-14-2 ;
PubChem CID	153970;
ChemSpider	135703 ;
UNII	W335P73C3L;
KEGG	D09722;
ChEBI	CHEBI:145429;
CompTox Dashboard (EPA)	DTXSID90164887 ;
Chemical and physical data
Formula	C26H42N4O5
Molar mass	490.645 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCCCCCCCCCCCC(=O)NC1=NC(=O)N(C=C1)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)C#N;
	InChI InChI=1S/C26H42N4O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-23(32)28-22-16-17-30(26(34)29-22)25-20(18-27)24(33)21(19-31)35-25/h16-17,20-21,24-25,31,33H,2-15,19H2,1H3,(H,28,29,32,34)/t20-,21+,24-,25+/m0/s1 ; Key:LBGFKUUHOPIEMA-PEARBKPGSA-N ;
	(what is this?) (verify)

Sapacitabine is a chemotherapeutic drug developed by US biotechnology firm Cyclacel currently undergoing clinical trials against leukemia.^[1]^[2]

Sapacitabine is an orally available nucleoside analog prodrug of 2′-C-cyano-2′-deoxy-1-β-D-arabino-pentofuranosyl-cytosine (CNDAC) that acts through a dual mechanism. CNDAC lasts longer in the bloodstream by being metabolized from sapacitibine than it would do so by being directly administered.^[3]

The compound interferes with DNA synthesis by causing single-strand DNA breaks due to CNDAC being incorporated into DNA during replication or repair,^[3] then inducing arrest of the cell division cycle at G2 phase.

Both sapacitabine and its major metabolite, CNDAC, have demonstrated potent anti-tumor activity in both blood and solid tumors in preclinical studies. In a liver metastatic mouse model, sapacitabine was shown to be superior to gemcitabine or 5-FU, two widely used nucleoside analogs, in delaying the onset and growth of liver metastasis.

^ Faderl S, Gandhi V, Kantarjian HM (March 2008). "Potential role of novel nucleoside analogs in the treatment of acute myeloid leukemia". Current Opinion in Hematology. 15 (2): 101–107. doi:10.1097/MOH.0b013e3282f46e94. PMID 18300755. S2CID 10744649.
^ Serova M, Galmarini CM, Ghoul A, Benhadji K, Green SR, Chiao J, et al. (September 2007). "Antiproliferative effects of sapacitabine (CYC682), a novel 2'-deoxycytidine-derivative, in human cancer cells". British Journal of Cancer. 97 (5): 628–636. doi:10.1038/sj.bjc.6603896. PMC 2360357. PMID 17637678.
^ ^a ^b Cite error: The named reference :1 was invoked but never defined (see the help page).

[pmid18300755-1] Faderl S, Gandhi V, Kantarjian HM (March 2008). "Potential role of novel nucleoside analogs in the treatment of acute myeloid leukemia". Current Opinion in Hematology. 15 (2): 101–107. doi:10.1097/MOH.0b013e3282f46e94. PMID 18300755. S2CID 10744649.

[pmid17637678-2] Serova M, Galmarini CM, Ghoul A, Benhadji K, Green SR, Chiao J, et al. (September 2007). "Antiproliferative effects of sapacitabine (CYC682), a novel 2'-deoxycytidine-derivative, in human cancer cells". British Journal of Cancer. 97 (5): 628–636. doi:10.1038/sj.bjc.6603896. PMC 2360357. PMID 17637678.

[:1-3] Cite error: The named reference :1 was invoked but never defined (see the help page).