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{{drugbox
{{Drugbox
| IUPAC_name       = ''N'''-(5-chloropyridin-2-yl)-''N''-[(1''S'',2''R'',4''S'')-4-(dimethylcarbamoyl)-2-[(5-methyl-6,7-dihydro-4''H''-[1,3]thiazolo[5,4-c]pyridine-2-carbonyl)amino]cyclohexyl]oxamide
| Verifiedfields = changed
| image             = Edoxaban_skeletal.svg
| verifiedrevid = 415900881
| width             = 200
| IUPAC_name = ''N'''-(5-chloropyridin-2-yl)-''N''-[(1''S'',2''R'',4''S'')-4-(dimethylcarbamoyl)-2-[(5-methyl-6,7-dihydro-4''H''-[1,3]thiazolo[5,4-c]pyridine-2-carbonyl)amino]cyclohexyl]oxamide
| CAS_number        = 912273-65-5
| image = Edoxaban.png
| ATC_prefix        = none
| width = 200
| ATC_suffix        =
 
| PubChem          = 25022378
<!--Clinical data-->
| DrugBank          =
| tradename = Lixiana
| C = 24 | H = 30 | Cl = 1 | N = 7 | O = 4 | S = 1
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| molecular_weight  = 548.056 g/mol
| pregnancy_US = <!-- A / B            / C / D / X -->
| smiles            =
| pregnancy_category =   
| bioavailability  =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| protein_bound    =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| metabolism        =
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| elimination_half-life =
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| excretion        =  
| legal_status =
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| routes_of_administration =
| pregnancy_US     = <!-- A / B            / C / D / X -->
 
| pregnancy_category=   
<!--Pharmacokinetic data-->
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| bioavailability = 
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| protein_bound = 
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| metabolism = 
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| elimination_half-life = 
| legal_status     =  
| excretion = 
| routes_of_administration =  
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 912273-65-5
| ATC_prefix = none
| PubChem = 25022378
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = NDU3J18APO
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = D09710
 
<!--Chemical data-->
| C=24 | H=30 | Cl=1 | N=7 | O=4 | S=1
| molecular_weight = 548.056 g/mol
| smiles = 
}}
}}
__NOTOC__
{{SI}}
{{CMG}}


{{SI}}
==Overview==
 
'''Edoxaban''' ([[International Nonproprietary Name|INN]], codenamed '''DU-176b''', trade name '''Lixiana''') is an [[anticoagulant]] drug which acts as a [[direct factor Xa inhibitor]]. It is being developed by [[Daiichi Sankyo]]. It was approved in July 2011 in Japan for prevention of venous thromboembolisms (VTE) following lower-limb orthopedic surgery.<ref name="url_Daiichi_Sankyo_Europe_GmbH">{{cite web | url = http://www.daiichi-sankyo.eu/media/press-news-in-english/news-detail/article/first-market-approval-in-japan-for-lixianaR-edoxaban.html | title = First market approval in Japan for LIXIANA (Edoxaban)  | date =  2011-04-22 | work = Press Release | publisher = Daiichi Sankyo Europe GmbH }}</ref>
 
== Preclinical Research ==
 
In animal studies, edoxaban is potent, selective for factor Xa and has good oral bioavailability.<ref name="pmid18624979">{{cite journal | author = Furugohri T, Isobe K, Honda Y, Kamisato-Matsumoto C, Sugiyama N, Nagahara T, Morishima Y, Shibano T | title = DU-176b, a potent and orally active factor Xa inhibitor: in vitro and in vivo pharmacological profiles | journal = J. Thromb. Haemost. | volume = 6 | issue = 9 | pages = 1542–9 |date=September 2008  | pmid = 18624979 | doi = 10.1111/j.1538-7836.2008.03064.x }}</ref>
 
== Clinical Trials ==


'''Edoxaban''' ([[International Nonproprietary Name|INN]], codenamed '''DU-176b''') is an [[anticoagulant]] drug which acts as a [[direct factor Xa inhibitor]]. It is being developed by [[Daiichi Sankyo]]. In animal studies, edoxaban is potent, selective for factor Xa and has good oral bioavailability,<ref name="pmid18624979">{{cite journal |author=Furugohri T, Isobe K, Honda Y, Kamisato-Matsumoto C, Sugiyama N, Nagahara T, Morishima Y, Shibano T |title=DU-176b, a potent and orally active factor Xa inhibitor: in vitro and in vivo pharmacological profiles |journal=Journal of Thrombosis and Haemostasis : JTH |volume=6 |issue=9 |pages=1542–9 |year=2008 |month=September |pmid=18624979 |doi=10.1111/j.1538-7836.2008.03064.x |url=}}</ref> but it has not been approved for use in humans.<ref name="pmid19739042">{{cite journal |author=Sobieraj-Teague M, O'Donnell M, Eikelboom J |title=New anticoagulants for atrial fibrillation |journal=Seminars in Thrombosis and Hemostasis |volume=35 |issue=5 |pages=515–24 |year=2009 |month=July |pmid=19739042 |doi=10.1055/s-0029-1234147 |url=}}</ref>
Several Phase II [[clinical trial]]s have been conducted, for example for [[thromboprophylaxis]] after [[total hip replacement]]<ref>{{pmid|20589317}}</ref> (phase III early results compare well to [[enoxaparin]]<ref name=Dec2010>{{cite web |url=http://www.genengnews.com/gen-news-highlights/phase-iii-trial-finds-edoxaban-outclasses-enoxaparin-in-preventing-venous-thromboembolic-events/81244351/ |title=Phase III Trial Finds Edoxaban Outclasses Enoxaparin in Preventing Venous Thromboembolic Events |date=8 Dec 2010 }}</ref>), and for [[stroke]] prevention in patients with [[atrial fibrillation]]<ref name="pmid">{{cite journal | author = Weitz JI, Connolly SJ, Patel I, Salazar D, Rohatagi S, Mendell J, Kastrissios H, Jin J, Kunitada S | title = Randomised, parallel-group, multicentre, multinational phase 2 study comparing edoxaban, an oral factor Xa inhibitor, with warfarin for stroke prevention in patients with atrial fibrillation | journal = Thromb. Haemost. | volume = 104 | issue = 3 | pages = 633–41 |date=September 2010  | pmid = | doi = 10.1160/TH10-01-0066 }}</ref> (phase III has completed enrollment<ref name=Dec2010/>).


Several Phase II [[clinical trial]]s have been conducted, for example for [[thromboprophylaxis]] after [[total hip replacement]]<ref>{{pmid|20589317}}</ref> and for [[stroke]] prevention in patients with [[atrial fibrillation]]<ref>{{pmid|20694273}}</ref>.
A large phase III trial showed that edoxaban was non inferior to [[warfarin]] in preventing recurrent venous thromboembolic events with fewer episodes of major bleeding.<ref name="pmid23991658">{{cite journal | author = | title = Edoxaban versus Warfarin for the Treatment of Symptomatic Venous Thromboembolism | journal = N. Engl. J. Med. | volume = | issue = | pages = |date=August 2013  | pmid = 23991658 | doi = 10.1056/NEJMoa1306638 }}</ref> This paper follows similar recent major trials showing similar results for the other new [[factor Xa inhibitor]]s, [[rivaroxaban]] and [[apixaban]].<ref name="pmid">{{cite journal | author = Tahir F, Riaz H, Riaz T, Badshah MB, Riaz IB, Hamza A, Mohiuddin H | title = The new oral anti-coagulants and the phase 3 clinical trials - a systematic review of the literature | journal = Thromb J | volume = 11 | issue = 1 | pages = 18 |date=September 2013  | pmid = | doi = 10.1186/1477-9560-11-18 }}</ref>


==References==
==References==
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{{Antithrombotics}}
{{Antithrombotics}}


[[Category:Drug]]
[[Category:Cardiovascular Drugs]]
[[Category:Anticoagulants]]
[[Category:Anticoagulants]]
[[Category:Thiazolopyridines]]
[[Category:Organochlorides]]
[[Category:Cardiology]]
{{WH}}
{{WS}}

Revision as of 19:44, 27 July 2014

Edoxaban
Clinical data
Trade namesLixiana
ATC code
  • none
Identifiers
CAS Number
PubChem CID
UNII
KEGG
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC24H30ClN7O4S
Molar mass548.056 g/mol
 ☒N☑Y (what is this?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Edoxaban (INN, codenamed DU-176b, trade name Lixiana) is an anticoagulant drug which acts as a direct factor Xa inhibitor. It is being developed by Daiichi Sankyo. It was approved in July 2011 in Japan for prevention of venous thromboembolisms (VTE) following lower-limb orthopedic surgery.[1]

Preclinical Research

In animal studies, edoxaban is potent, selective for factor Xa and has good oral bioavailability.[2]

Clinical Trials

Several Phase II clinical trials have been conducted, for example for thromboprophylaxis after total hip replacement[3] (phase III early results compare well to enoxaparin[4]), and for stroke prevention in patients with atrial fibrillation[5] (phase III has completed enrollment[4]).

A large phase III trial showed that edoxaban was non inferior to warfarin in preventing recurrent venous thromboembolic events with fewer episodes of major bleeding.[6] This paper follows similar recent major trials showing similar results for the other new factor Xa inhibitors, rivaroxaban and apixaban.[5]

References

  1. ↑ "First market approval in Japan for LIXIANA (Edoxaban)". Press Release. Daiichi Sankyo Europe GmbH. 2011-04-22.
  2. ↑ Furugohri T, Isobe K, Honda Y, Kamisato-Matsumoto C, Sugiyama N, Nagahara T, Morishima Y, Shibano T (September 2008). "DU-176b, a potent and orally active factor Xa inhibitor: in vitro and in vivo pharmacological profiles". J. Thromb. Haemost. 6 (9): 1542–9. doi:10.1111/j.1538-7836.2008.03064.x. PMID 18624979.
  3. ↑ PMID 20589317
  4. ↑ 4.0 4.1 "Phase III Trial Finds Edoxaban Outclasses Enoxaparin in Preventing Venous Thromboembolic Events". 8 Dec 2010.
  5. ↑ 5.0 5.1 Weitz JI, Connolly SJ, Patel I, Salazar D, Rohatagi S, Mendell J, Kastrissios H, Jin J, Kunitada S (September 2010). "Randomised, parallel-group, multicentre, multinational phase 2 study comparing edoxaban, an oral factor Xa inhibitor, with warfarin for stroke prevention in patients with atrial fibrillation". Thromb. Haemost. 104 (3): 633–41. doi:10.1160/TH10-01-0066.
  6. ↑ "Edoxaban versus Warfarin for the Treatment of Symptomatic Venous Thromboembolism". N. Engl. J. Med. August 2013. doi:10.1056/NEJMoa1306638. PMID 23991658.
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