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Revision as of 14:27, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456785472 of page Histrelin for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CAS_number').  Latest revision as of 01:28, 1 October 2024 edit Citation bot (talk | contribs)Bots5,417,120 edits Added doi. | Use this bot. Report bugs. | Suggested by Abductive | Category:Articles needing additional medical references from September 2024 | #UCB_Category 6/8 
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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.}}
{{Use dmy dates|date=September 2024}}
{{Drugbox
{{cs1 config |name-list-style=vanc |display-authors=6}}
{{More medical citations needed|date=September 2024}}
{{Infobox drug
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 400110408
| verifiedrevid = 461769932
| IUPAC_name = 5-oxo-<small>L</small>-prolyl-<small>L</small>-histidyl-<small>L</small>-tryptophyl-<small>L</small>-seryl-<small>L</small>-tyrosyl-1-benzyl-<small>D</small>-histidyl-<small>L</small>-leucyl-''N''<sup>5</sup>-(diaminomethylene)-<small>L</small>-ornithyl-''N''-ethyl-<small>L</small>-prolinamide
| image = Histrelin.svg | image = Histrelin.svg
| width = 225
| alt =


<!--Clinical data--> <!-- Clinical data -->
| tradename = | pronounce =
| tradename = Vantas, Supprelin LA, others
| Drugs.com = {{drugs.com|monograph|histrelin}} | Drugs.com = {{drugs.com|monograph|histrelin}}
| MedlinePlus = a601146 | MedlinePlus = a601146
| DailyMedID = Histrelin
| pregnancy_US = X
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_AU_comment =
| pregnancy_category =
| routes_of_administration = ]
| class = ]; ]; ]
| ATC_prefix = L02
| ATC_suffix = AE05
| ATC_supplemental =

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| legal_AU_comment =
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled -->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = Rx-only | legal_US = Rx-only
| legal_US_comment = <ref>{{cite web | title=Supprelin LA- histrelin acetate implant | website=DailyMed | date=30 April 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=d8fb000e-3cc9-4803-b71d-2cc597661977 | access-date=25 September 2024}}</ref>
| routes_of_administration = Subcutaneous ]
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = <!-- For countries not listed above -->


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = 92% | bioavailability = 92%
| protein_bound = 70% | protein_bound = 70%
| metabolism = ] | metabolism = ]
| metabolites =
| elimination_half-life = 4 hours
| onset =
| excretion = Undetermined
| elimination_half-life = 4.0 hours
| duration_of_action =
| excretion =


<!--Identifiers--> <!-- Identifiers -->
| index2_label = as salt
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 76712-82-8 -->
| CAS_number = 76712-82-8
| ATC_prefix = H01
| CAS_number2 = 220810-26-4
| ATC_suffix = CA03
| PubChem = 25077993 | PubChem = 25077993
| PubChem2 = 56927879
| IUPHAR_ligand = 3884
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank = DB06788
| DrugBank2 = DBSALT001172
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10482012 | ChemSpiderID = 10482012
| ChemSpiderID2 = 26606349
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H50H3S3W74 | UNII = H50H3S3W74
| UNII2 = QMG7HLD1ZE
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02369 | KEGG = D02369
| ChEBI = 5739
| ChEBI2 = 63530
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = <!-- blanked - oldvalue: 1201255 --> | ChEMBL = 1201255
| ChEMBL2 = 1200509
| C=66 | H=86 | N=18 | O=12
| NIAID_ChemDB =
| molecular_weight = 1323.5 g/mol
| PDB_ligand =
| InChI = 1/C66H86N18O12/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71)/t47-,48-,49-,50-,51-,52-,53+,54-,55-/m0/s1
| synonyms = ORF-17070, RWJ-17070
| InChIKey = HHXHVIJIIXKSOE-QILQGKCVBR

<!-- Chemical and physical data -->
| IUPAC_name = 5-oxo-<small>L</small>-prolyl-<small>L</small>-histidyl-<small>L</small>-tryptophyl-<small>L</small>-seryl-<small>L</small>-tyrosyl-1-benzyl-<small>D</small>-histidyl-<small>L</small>-leucyl-''N''<sup>5</sup>-(diaminomethylene)-<small>L</small>-ornithyl-''N''-ethyl-<small>L</small>-prolinamide
| C=66 | H=86 | N=18 | O=12
| SMILES = CCNC(=O)1CCCN1C(=O)(CCCNC(=N)N)NC(=O)(CC(C)C)NC(=O)(Cc2cn(Cc3ccccc3)cn2)NC(=O)(Cc4ccc(cc4)O)NC(=O)(CO)NC(=O)(Cc5cc6ccccc56)NC(=O)(Cc7ccn7)NC(=O)8CCC(=O)N8
| SMILES2 = CCNC(=O)1CCCN1C(=O)(CCCNC(=N)N)NC(=O)(CC(C)C)NC(=O)(Cc2cn(Cc3ccccc3)cn2)NC(=O)(Cc4ccc(cc4)O)NC(=O)(CO)NC(=O)(Cc5cc6ccccc56)NC(=O)(Cc7ccn7)NC(=O)8CCC(=O)N8.CC(=O)O.CC(=O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C66H86N18O12/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71)/t47-,48-,49-,50-,51-,52-,53+,54-,55-/m0/s1 | StdInChI = 1S/C66H86N18O12/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71)/t47-,48-,49-,50-,51-,52-,53+,54-,55-/m0/s1
| StdInChI2 = 1S/C66H86N18O12.2C2H4O2/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47;2*1-2(3)4/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71);2*1H3,(H,3,4)/t47-,48-,49-,50-,51-,52-,53+,54-,55-;;/m0../s1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = HHXHVIJIIXKSOE-QILQGKCVSA-N | StdInChIKey = HHXHVIJIIXKSOE-QILQGKCVSA-N
| StdInChIKey2 = BKEMVGVBBDMHKL-VYFXDUNUSA-N
| density =
| density_notes =
| melting_point =
| melting_high =
| melting_notes =
| boiling_point =
| boiling_notes =
| solubility =
| sol_units =
| specific_rotation =
}} }}

'''Histrelin''' acetate, sold under the brand name '''Supprelin''' among others, is a nonapeptide analogue of ] (GnRH) with added potency.<ref name="def">{{cite web | vauthors = Davis M | veditors = Chandramouli J | url = http://uuhsc.utah.edu/pharmacy/bulletins/histrelin.html | archive-url = https://web.archive.org/web/20060510173906/https://uuhsc.utah.edu/pharmacy/bulletins/histrelin.html | archive-date = 10 May 2006 | title = Histrelin acetate (Vantas) | date = 25 February 2005 | work = New Drug Bulletins | publisher = University of Utah Hospitals & Clinics }}</ref> When present in the bloodstream, it acts on particular cells of the ] called ]s. Histrelin stimulates these cells to release ] and ]. Thus it is considered a ] or GnRH ].

==Medical uses==
Histrelin is used to treat hormone-sensitive cancers of the ] in men and ] in women. In addition, histrelin has been proven to be highly effective in treating central ] in children.<ref>{{cite web | url = https://www.drugs.com/cons/Histrelin.html | title = Histrelin consumer information | work = Drugs.com }}</ref><ref>{{cite journal | vauthors = Eugster EA, Clarke W, Kletter GB, Lee PA, Neely EK, Reiter EO, Saenger P, Shulman D, Silverman L, Flood L, Gray W, Tierney D | display-authors = 6 | title = Efficacy and safety of histrelin subdermal implant in children with central precocious puberty: a multicenter trial | journal = The Journal of Clinical Endocrinology and Metabolism | volume = 92 | issue = 5 | pages = 1697–1704 | date = May 2007 | pmid = 17327379 | doi = 10.1210/jc.2006-2479 | doi-access = }}</ref>

It is available as a daily intramuscular injection.

Histrelin is also available in a 12-month subcutaneous implant (Vantas) for the palliative treatment of advanced prostate cancer, since 2005 in the US, and since January 2010 in the UK.

A 12-month subcutaneous implant (Supprelin LA) for central precocious puberty (CPP) was approved in May 2007, by the US ].

Histrelin can be part of the primary care protocol in transgender children/youth, which is an ] in the USA<ref>{{Cite web|title = Primary Care Protocol for Transgender Patient Care: Hormone Administration | work = Center of Excellence for Transgender Health | publisher = University of California, San Francisco, Department of Family and Community Medicine | date = April 2011|url = http://transhealth.ucsf.edu/trans?page=protocol-hormones |access-date = 29 September 2015|archive-url = https://web.archive.org/web/20120117030324/http://www.transhealth.ucsf.edu/trans?page=protocol-hormones|archive-date = 17 January 2012|url-status= dead }}</ref> and the UK,<ref name="BMJsept2017">{{cite journal | vauthors = Cohen D, Barnes H | title = Gender dysphoria in children: puberty blockers study draws further criticism | journal = BMJ | volume = 366 | pages = l5647 | date = September 2019 | pmid = 31540909 | doi = 10.1136/bmj.l5647 | s2cid = 202711942 }}</ref> and is used in suppressing cis-sex puberty, until the patient is ready to begin cross-sex hormonal therapy. It is also sometimes prescribed to transgender adults who benefit from having their sex hormone production halted.
In this application, patients often keep the implant for two years before replacing, with regular blood tests to monitor the hormone levels. Implants left too long are more difficult to replace.<ref>{{cite book | vauthors = Marinkovic M, Carswell J, Roberts SA | chapter = Emerging Developments in Pubertal Suppression for Gender Incongruent/Gender Dysphoric Youth | veditors = Finlayson C | title = Pubertal Suppression in Transgender Youth |date=2019 |pages=95–100 | isbn = 978-0-323-56963-7 |doi=10.1016/B978-0-323-56963-7.00012-0| s2cid = 186736821 }}</ref>

==Side effects==
Common side effects include headache, ], ], reduced ], ], ], renal impairment, weight loss, testicular atrophy, and ].<ref>]: Histrelin {{drugs.com|monograph|histrelin}}</ref>

==Pharmacology==
In a process known as ], daily stimulation of pituitary gonadotropes causes them to become ] to the effects of histrelin. As a consequence, levels of ] (LH) and ] (FSH) fall after a short period of time. From that point forward, as long as histrelin is administered, the levels of LH and FSH in the blood remain low.<ref name="Mutschler">{{Cite book | vauthors = Mutschler E, Schäfer-Korting M |title= Arzneimittelwirkungen |language=German |location=Stuttgart|publisher=Wissenschaftliche Verlagsgesellschaft |year=2001 |edition=8th |pages=372–3 |isbn=3-8047-1763-2 }}</ref><ref>{{cite journal | vauthors = Wuttke W, Jarry H, Feleder C, Moguilevsky J, Leonhardt S, Seong JY, Kim K | title = The neurochemistry of the GnRH pulse generator | journal = Acta Neurobiologiae Experimentalis | volume = 56 | issue = 3 | pages = 707–713 | year = 1996 | doi = 10.55782/ane-1996-1176 | pmid = 8917899 | url = http://www.ane.pl/linkout.php?vol=56&no=3&fpp=707 | access-date = 27 November 2015 | archive-date = 8 December 2015 | archive-url = https://web.archive.org/web/20151208053059/http://www.ane.pl/linkout.php?vol=56&no=3&fpp=707 | url-status = dead }}</ref>

This prolonged lowering of LH and FSH levels is the rationale for therapy using GnRH agonists. Since LH and FSH stimulate the ]s to produce ]s and ]s in females and males respectively, histrelin can effectively be used to decrease the ]s in the blood of patients.

== Society and culture ==
Since 2020, Vantas is not available anymore. Endo, its manufacturer said batches of the medication were not coming out right. They added that although Supprelin and Vantas were manufactured in the same facility, they were not identical product (though both contain 50 mg of histrelin acetate.) As of 2023, Vantas is still not available and the only available implant is Supprelin LA.<ref>{{Cite web | vauthors = Lupkin S | date = 6 November 2021 | work = National Public Radio (NPR) |title = Drugmaker drops cheaper version of drug, leaving patients stuck with pricier one|url = https://www.npr.org/sections/health-shots/2021/11/06/1051878026/drugmaker-drops-cheaper-version-of-drug-leaving-patients-stuck-with-pricier-one}}</ref>

=== Economics ===
Vantas was priced around $4400 in 2004 while Supprelin LA was priced at $37,000 in 2007.<ref>{{Cite web | vauthors = Lupkin S | date = 24 February 2020 | work = National Public Radio (NPR) |title = Hormone Blocker Sticker Shock: Kids Drug Costs 8 Times More Than One For Adults|url = https://www.npr.org/sections/health-shots/2020/02/24/808049526/hormone-blocker-sticker-shock-kids-drug-costs-8-times-more-than-one-for-adults}}</ref>

== References ==
{{Reflist}}

{{GnRH and gonadotropins}}
{{GnRH and gonadotropin receptor modulators}}
{{Portal bar | Medicine}}
{{Authority control}}

]
]
]