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{{drugbox
{{Drugbox
|IUPAC_name=(3''aR'')-2-[(3''S'')-1-azabicyclo[2.2.2]oct-3-yl]-2,3,3''a'',<br>4,5,6-hexahydro-1''H''-benz[''de'']isoquinolin-1-one
| Verifiedfields = changed
|image=Palonosetron.svg
| Watchedfields = changed
|image2 = Palenosetron_3D.png
| verifiedrevid = 464197120
|CAS_number=119904-90-4
| IUPAC_name = (3''aS'')-2-[(3''S'')-1-Azabicyclo[2.2.2]oct-3-yl]-2,3,3''a'',4,5,6-hexahydro-1''H''-benz[''de'']isoquinolin-1-one
|ATC_prefix=A04
| image = Palonosetron structure.svg
|ATC_suffix=AA05
| width = 200
|ATC_supplemental=
 
|PubChem=148211
<!--Clinical data-->
|DrugBank=APRD00351
| tradename =
|C=19|H=24|N=2|O=1
| Drugs.com = {{drugs.com|monograph|palonosetron-hydrochloride}}
|molecular_weight=296.407 g/mol
| MedlinePlus = a610002
|bioavailability=Low (oral)
| licence_US = Palonosetron
|protein_bound=62%
| pregnancy_AU = B1
|metabolism=[[Liver|Hepatic]], 50% (mostly [[CYP2D6]]-mediated, [[CYP3A4]] and [[CYP1A2]] also involved)
| pregnancy_US = B
|elimination_half-life=Approximately 40 hours
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 -->
|excretion=[[Kidney|Renal]], 80% (of which 49% unchanged)
| legal_UK = <!-- GSL / P / POM / CD -->
|pregnancy_AU=B1
| legal_US = Rx-only
|pregnancy_US=B
| routes_of_administration = [[Intravenous therapy|Intravenous]], oral
|pregnancy_category=
 
|legal_AU=<!-- Unscheduled / S2 / S4 / S8 -->
<!--Pharmacokinetic data-->
|legal_UK=<!-- GSL / P / POM / CD -->
| bioavailability = 97% (oral)
|legal_US=Rx-only
| protein_bound = 62%
|legal_status=
| metabolism = [[Liver|Hepatic]], 50% (mostly [[CYP2D6]]-mediated, [[CYP3A4]] and [[CYP1A2]] also involved)
|routes_of_administration=[[Intravenous therapy|Intravenous]]
| elimination_half-life = Approximately 40 hours
| excretion = [[Kidney|Renal]], 80% (of which 49% unchanged); fecal (5 to 8%)
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 135729-61-2
| ATC_prefix = A04
| ATC_suffix = AA05
| PubChem = 148211
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00377
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 85161
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4892289
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 5D06587D6R
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1189679
 
<!--Chemical data-->
| C=19 | H=24 | N=2 | O=1
| molecular_weight = 296.407 g/mol
| smiles = O=C5N([C@H]2C1CCN(CC1)C2)C[C@@H]4c3c5cccc3CCC4
| InChI = 1/C19H24N2O/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20/h2,4,6,13,15,17H,1,3,5,7-12H2/t15-,17-/m1/s1
| InChIKey = CPZBLNMUGSZIPR-NVXWUHKLBP
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C19H24N2O/c22-19-16-6-2-4-14-3-1-5-15(18(14)16)11-21(19)17-12-20-9-7-13(17)8-10-20/h2,4,6,13,15,17H,1,3,5,7-12H2/t15-,17-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CPZBLNMUGSZIPR-NVXWUHKLSA-N
}}
}}
'''Palonosetron''' ([[International Nonproprietary Name|INN]], trade name '''Aloxi''') is a [[5-HT3 antagonist|5-HT<sub>3</sub> antagonist]] used in the prevention and treatment of [[chemotherapy]]-induced [[nausea]] and [[vomiting]] (CINV). It is the most effective of the 5-HT<sub>3</sub> antagonists in controlling delayed CINV—nausea and vomiting that appear more than 24 hours after the first dose of a course of chemotherapy—and is the only drug of its class approved for this use by the U.S. [[Food and Drug Administration]].<ref name="pmid17106506">{{cite journal |author=De Leon A |title=Palonosetron (Aloxi): a second-generation 5-HT(3) receptor antagonist for chemotherapy-induced nausea and vomiting |journal=Proceedings (Baylor University. Medical Center) |volume=19 |issue=4 |pages=413–6 |year=2006 |pmid=17106506 |doi=}} {{PMC|1618755}}.</ref> [[As of 2007]], it is the most recent 5-HT<sub>3</sub> antagonist to enter clinical use.


Palonosetron is administered [[intravenous therapy|intravenously]], as a single dose, 30 minutes before chemotherapy.<ref name="pmid17106506"/> An oral formulation is in [[Clinical trial#Phase III|Phase III]] [[clinical trial]]s.<ref>{{cite web | url = http://www.mgipharma.com/wt/page/oral_aloxi | title = Aloxi<sup>&reg;</sup> Oral Capsule | year = 2007 | accessdate = 2007-05-16 | publisher = MGI Pharma}}</ref>
'''Palonosetron''' ([[International Nonproprietary Name|INN]], trade name '''Aloxi''') is a [[5-HT3 antagonist|5-HT<sub>3</sub> antagonist]] used in the prevention and treatment of [[chemotherapy-induced nausea and vomiting]] (CINV). It is used for the control of delayed CINV—nausea and vomiting and there are tentative data to suggest that it may be better than [[granisetron]].<ref>{{cite journal|last=Billio|first=A|author2=Morello, E |author3=Clarke, MJ |title=Serotonin receptor antagonists for highly emetogenic chemotherapy in adults.|journal=The Cochrane database of systematic reviews|date=Jan 20, 2010|issue=1|pages=CD006272|pmid=20091591|doi=10.1002/14651858.CD006272.pub2}}</ref>
 
Palonosetron is administered [[intravenous therapy|intravenously]], as a single dose, 30 minutes before chemotherapy,<ref name="pmid17106506">{{cite journal |author=De Leon A |title=Palonosetron (Aloxi): a second-generation 5-HT(3) receptor antagonist for chemotherapy-induced nausea and vomiting |journal=Proceedings (Baylor University. Medical Center) |volume=19 |issue=4 |pages=413–6 |year=2006 |pmid=17106506 |doi= |pmc=1618755}}</ref> or as a single oral capsule one hour before chemotherapy.<ref name=Medscape>{{cite web |url=http://www.medscape.com/viewarticle/580032 |title=FDA Approvals: Nplate, Aloxi, Vidaza |author=Waknine, Yael |date=September 4, 2008 |accessdate=2008-09-04 |publisher=[[Medscape]]}} Freely available with registration.</ref> The oral formulation was approved on August 22, 2008 for prevention of acute CINV alone, as a large clinical trial did not show oral administration to be as effective as intravenous use against delayed CINV.<ref name=Medscape/>
==See also==
* [[5-HT3 receptor antagonist:drug discovery and development|5-HT<sub>3</sub> receptor antagonist: Drug discovery and development]]


==References==
==References==
{{Reflist}}
{{Reflist}}


{{5-HT3 antagonists}}
{{5-HT3 antagonists}}
{{Serotonergics}}


{{pharma-stub}}
[[Category:5-HT3 antagonists]]
[[Category:Quinuclidines]]
[[Category:Isoquinolines]]
[[Category:Lactams]]


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Revision as of 13:51, 9 April 2015

Palonosetron
File:Palonosetron structure.svg
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa610002
[[Regulation of therapeutic goods |Template:Engvar data]]
Pregnancy
category
  • AU: B1
  • US: B (No risk in non-human studies)
Routes of
administration		Intravenous, oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability97% (oral)
Protein binding62%
MetabolismHepatic, 50% (mostly CYP2D6-mediated, CYP3A4 and CYP1A2 also involved)
Elimination half-lifeApproximately 40 hours
ExcretionRenal, 80% (of which 49% unchanged); fecal (5 to 8%)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEBI
ChEMBL
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
FormulaC19H24N2O
Molar mass296.407 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Palonosetron (INN, trade name Aloxi) is a 5-HT3 antagonist used in the prevention and treatment of chemotherapy-induced nausea and vomiting (CINV). It is used for the control of delayed CINV—nausea and vomiting and there are tentative data to suggest that it may be better than granisetron.[1]

Palonosetron is administered intravenously, as a single dose, 30 minutes before chemotherapy,[2] or as a single oral capsule one hour before chemotherapy.[3] The oral formulation was approved on August 22, 2008 for prevention of acute CINV alone, as a large clinical trial did not show oral administration to be as effective as intravenous use against delayed CINV.[3]

See also

References

  1. ↑ Billio, A; Morello, E; Clarke, MJ (Jan 20, 2010). "Serotonin receptor antagonists for highly emetogenic chemotherapy in adults". The Cochrane database of systematic reviews (1): CD006272. doi:10.1002/14651858.CD006272.pub2. PMID 20091591.
  2. ↑ De Leon A (2006). "Palonosetron (Aloxi): a second-generation 5-HT(3) receptor antagonist for chemotherapy-induced nausea and vomiting". Proceedings (Baylor University. Medical Center). 19 (4): 413–6. PMC 1618755. PMID 17106506.
  3. ↑ 3.0 3.1 Waknine, Yael (September 4, 2008). "FDA Approvals: Nplate, Aloxi, Vidaza". Medscape. Retrieved 2008-09-04. Freely available with registration.

Template:5-HT3 antagonists


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