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Revision as of 19:41, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456664060 of page Abarelix for the Chem/Drugbox validation project (updated: 'DrugBank', 'CAS_number').  Latest revision as of 21:04, 8 February 2024 edit VastV0idInSpace0 (talk | contribs)Extended confirmed users2,345 edits →References: Fixed spacing between stub template and category templates.Tag: 2017 wikitext editor 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = changed
| verifiedrevid = 456663059 | verifiedrevid = 477237014
| IUPAC_name = acetyl-D-β-naphthylalanyl- D-4-chlorophenylalanyl-D-3-pyridylalanyl-L-seryl-L- N-methyl- tyrosyl-D-asparagyl-L-leucyl-L-N(e )-isopropyl-lysyl-L-prolyl-D-alanyl-amide<!--not validated by ]--> | IUPAC_name = N-acetyl-3-(2-naphthyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridyl)-D-alanyl-L-seryl-N-methyl-L-tyrosyl-D-asparagyl-L-leucyl-N6-isopropyl-L-lysyl-L-prolyl-D-alaninamide<ref>{{cite web| title=Abarelix| website=PubChem| date=2017-07-29| url=https://pubchem.ncbi.nlm.nih.gov/compound/Abarelix}}</ref><!--not validated by ]-->
| image = Abarelix.svg | image = Abarelix.svg
| width = 250px


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Plenaxis
| Drugs.com = {{drugs.com|monograph|abarelix}} | Drugs.com = {{drugs.com|monograph|abarelix}}
| pregnancy_category = | pregnancy_US = X
| legal_status = | legal_status =
| routes_of_administration = | routes_of_administration = ]
| class = ]; ]; ]


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability = | bioavailability =
| protein_bound = 96–99% | protein_bound = 96–99%
| metabolism = | metabolism =
| elimination_half-life = | elimination_half-life =
| excretion =


<!--Identifiers--> <!--Identifiers-->
| CASNo_Ref = {{cascite|??|??}}
| CAS_number_Ref = {{cascite|changed|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 183552-38-7 --> | CAS_number = 183552-38-7
| CAS_supplemental = <!--not validated by ]--> | CAS_supplemental =
| ATC_prefix = L02 | ATC_prefix = L02
| ATC_suffix = BX01 | ATC_suffix = BX01
| ATC_supplemental = | ATC_supplemental =
| PubChem = 16131215 | PubChem = 16131215
| IUPHAR_ligand = 1188 | IUPHAR_ligand = 1188
| DrugBank_Ref = {{drugbankcite|changed|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00106 | DrugBank = DB00106
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1252 | ChEMBL = 1252
| synonyms =


<!--Chemical data--> <!--Chemical data-->
| C=72 | H=95 | Cl=1 | N=14 | O=14 | C=72 | H=95 | Cl=1 | N=14 | O=14
⚫ | SMILES = CC(C)C(NC(=O)(CC(N)=O)NC(=O)(Cc1ccc(O)cc1)N(C)C(=O)(CO)NC(=O)(Cc2cccnc2)NC(=O)(Cc3ccc(Cl)cc3)NC(=O)(NCc5ccc4ccccc4c5)NC(C)=O)C(=O)N(CCCCNC(C)C)C(=O)N6CCC6C(=O)N(C)C(N)=O
| molecular_weight = 1416.06 g/mol
⚫ | smiles = O=C(N(C)C(N)=O)6CCCN6C(=O)(CCCCNC(C)C)NC(=O)(CC(C)C)NC(=O)(CC(N)=O)NC(=O)(Cc1ccc(O)cc1)N(C)C(=O)(CO)NC(=O)(Cc2cccnc2)NC(=O)(Cc3ccc(Cl)cc3)NC(=O)(\nCc4ccc5ccccc5c4)NC(=O)C
| InChI = 1/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+/m1/s1
| InChIKey = AIWRTTMUVOZGPW-HSPKUQOVBF
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+/m1/s1 | StdInChI = 1S/C72H95ClN14O14/c1-41(2)32-54(64(93)80-53(17-10-11-30-77-42(3)4)72(101)87-31-13-18-60(87)69(98)78-43(5)63(75)92)81-68(97)58(38-62(74)91)84-70(99)61(37-46-22-27-52(90)28-23-46)86(7)71(100)59(40-88)85-67(96)57(36-48-14-12-29-76-39-48)83-66(95)56(34-45-20-25-51(73)26-21-45)82-65(94)55(79-44(6)89)35-47-19-24-49-15-8-9-16-50(49)33-47/h8-9,12,14-16,19-29,33,39,41-43,53-61,77,88,90H,10-11,13,17-18,30-32,34-38,40H2,1-7H3,(H2,74,91)(H2,75,92)(H,78,98)(H,79,89)(H,80,93)(H,81,97)(H,82,94)(H,83,95)(H,84,99)(H,85,96)/t43-,53+,54+,55-,56-,57-,58-,59+,60+,61+/m1/s1
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| StdInChIKey = AIWRTTMUVOZGPW-HSPKUQOVSA-N | StdInChIKey = AIWRTTMUVOZGPW-HSPKUQOVSA-N
}} }}

'''Abarelix''', sold under the brand name '''Plenaxis''', is an injectable ] antagonist (]) which is marketed in ] and the ]. It is primarily used in ] to reduce the amount of ] made in patients with advanced symptomatic ] for which no other treatment options are available.<ref name="Drugs.com-2">{{cite web | work = Drugs.com | url = https://www.drugs.com/mtm/abarelix.html | title = Abarelix | access-date = 2018-01-23 | archive-date = 2018-02-10 | archive-url = https://web.archive.org/web/20180210163254/https://www.drugs.com/mtm/abarelix.html | url-status = dead }}</ref><ref>{{cite journal | vauthors = Boccon-Gibod L, van der Meulen E, Persson BE | title = An update on the use of gonadotropin-releasing hormone antagonists in prostate cancer | journal = Therapeutic Advances in Urology | volume = 3 | issue = 3 | pages = 127–40 | date = June 2011 | pmid = 21904569 | pmc = 3159401 | doi = 10.1177/1756287211414457 }}</ref>

It was originally marketed by Praecis Pharmaceuticals as ''Plenaxis'',<ref name="Drugs.com-2" /> and is now marketed by Speciality European Pharma in Germany<ref>Pharmazeutische Zeitung online: {{in lang|de}}</ref> after receiving a marketing authorization in 2005. The drug was introduced in the ] in 2003, but was discontinued in this country in May 2005 due to poor sales and a higher-than-expected incidence of severe ]s.<ref name="Minev2011">{{cite book| first = Boris | last = Minev | name-list-style = vanc |title=Cancer Management in Man: Chemotherapy, Biological Therapy, Hyperthermia and Supporting Measures|url=https://books.google.com/books?id=mOdKDLAAd0AC&pg=PA182|date=13 January 2011|publisher=Springer Science & Business Media|isbn=978-90-481-9704-0|pages=182–}}</ref> It remains marketed in ] and the ] however.<ref name="Drugs.com">{{cite web | title = Abarelix | url = https://www.drugs.com/international/abarelix.html | work = Drugs.com | access-date = 2018-08-27 | archive-date = 2019-08-29 | archive-url = https://web.archive.org/web/20190829113846/https://www.drugs.com/international/abarelix.html | url-status = dead }}</ref>

== See also ==
* ]

== References ==
{{Reflist}}

{{GnRH and gonadotropins}}
{{GnRH and gonadotropin receptor modulators}}

]
]


{{pharma-stub}}