Ximelagatran

Ximelagatran
Clinical data
Trade names	Exanta
Pregnancy; category	Uncategorized;
Routes of; administration	Oral (tablets)
ATC code	B01AE05 (WHO) ;
Legal status
Legal status	Withdrawn from market;
Pharmacokinetic data
Bioavailability	20%
Metabolism	to melagatran
Elimination half-life	3–5 hours
Excretion	Renal (80%)
Identifiers
	IUPAC name ethyl 2-[[(1R)-1-cyclohexyl-2-; [(2S)-2-[[4-(N'-hydroxycarbamimidoyl); phenyl]methylcarbamoyl]azetidin-1-yl]-; 2-oxo-ethyl]amino]acetate;
CAS Number	192939-46-1 ;
PubChem CID	9574101;
IUPHAR/BPS	6381;
DrugBank	DB04898 ;
ChemSpider	7848559 ;
UNII	49HFB70472;
KEGG	D01981 ;
ChEMBL	ChEMBL522038 ;
CompTox Dashboard (EPA)	DTXSID5049075 ;
Chemical and physical data
Formula	C24H35N5O5
Molar mass	473.574 g·mol−1 (429 g/mol after conversion)
3D model (JSmol)	Interactive image;
	SMILES O=C(NCc1ccc(C(=N\O)\N)cc1)[C@H]3N(C(=O)[C@H](NCC(=O)OCC)C2CCCCC2)CC3;
	InChI InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1 ; Key:ZXIBCJHYVWYIKI-PZJWPPBQSA-N ;
	(what is this?) (verify)

Ximelagatran (Exanta or Exarta, H 376/95) is an anticoagulant that has been investigated extensively as a replacement for warfarin^[1] that would overcome the problematic dietary, drug interaction, and monitoring issues associated with warfarin therapy. In 2006, its manufacturer AstraZeneca announced that it would withdraw pending applications for marketing approval after reports of hepatotoxicity (liver damage) during trials, and discontinue its distribution in countries where the drug had been approved (Germany, Portugal, Sweden, Finland, Norway, Iceland, Austria, Denmark, France, Switzerland, Argentina and Brazil).^[2]

^ Hirsh J, O'Donnell M, Eikelboom JW (July 2007). "Beyond unfractionated heparin and warfarin: current and future advances". Circulation. 116 (5): 552–560. doi:10.1161/CIRCULATIONAHA.106.685974. PMID 17664384.
^ "AstraZeneca Decides to Withdraw Exanta" (Press release). AstraZeneca. February 14, 2006. Retrieved 2012-07-16.

[1] Hirsh J, O'Donnell M, Eikelboom JW (July 2007). "Beyond unfractionated heparin and warfarin: current and future advances". Circulation. 116 (5): 552–560. doi:10.1161/CIRCULATIONAHA.106.685974. PMID 17664384.

[az-2] "AstraZeneca Decides to Withdraw Exanta" (Press release). AstraZeneca. February 14, 2006. Retrieved 2012-07-16.

[1]

[2]

Clinical data

Trade names	Exanta
Pregnancy category	Uncategorized
Routes of administration	Oral (tablets)
ATC code	B01AE05 (WHO)
Legal status
Legal status	Withdrawn from market
Pharmacokinetic data
Bioavailability	20%
Metabolism	to melagatran
Elimination half-life	3–5 hours
Excretion	Renal (80%)
Identifiers
IUPAC name ethyl 2-[[(1R)-1-cyclohexyl-2- [(2S)-2-[[4-(N'-hydroxycarbamimidoyl) phenyl]methylcarbamoyl]azetidin-1-yl]- 2-oxo-ethyl]amino]acetate
CAS Number	192939-46-1^N
PubChem CID	9574101
IUPHAR/BPS	6381
DrugBank	DB04898^Y
ChemSpider	7848559^Y
UNII	49HFB70472
KEGG	D01981^Y
ChEMBL	ChEMBL522038^Y
CompTox Dashboard (EPA)	DTXSID5049075
Chemical and physical data
Formula	C₂₄H₃₅N₅O₅
Molar mass	473.574 g·mol⁻¹ (429 g/mol after conversion)
3D model (JSmol)	Interactive image
SMILES O=C(NCc1ccc(C(=N\O)\N)cc1)[C@H]3N(C(=O)[C@H](NCC(=O)OCC)C2CCCCC2)CC3
InChI InChI=1S/C24H35N5O5/c1-2-34-20(30)15-26-21(17-6-4-3-5-7-17)24(32)29-13-12-19(29)23(31)27-14-16-8-10-18(11-9-16)22(25)28-33/h8-11,17,19,21,26,33H,2-7,12-15H2,1H3,(H2,25,28)(H,27,31)/t19-,21+/m0/s1^Y Key:ZXIBCJHYVWYIKI-PZJWPPBQSA-N^Y
^NY (what is this?) (verify)