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Revision as of 11:13, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,044 edits Saving copy of the {{drugbox}} taken from revid 477751446 of page Triptorelin for the Chem/Drugbox validation project (updated: 'ChemSpiderID', 'DrugBank', 'ChEMBL', 'ChEBI', 'StdInChI', 'StdInC...  Latest revision as of 08:15, 14 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,549 edits dark mode fix 
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{{Short description|GnRH-agonist}}
{{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
| verifiedrevid = 477556689
| Watchedfields = changed
| IUPAC_name = 5-oxo-<small>D</small>-prolyl-<small>L</small>-histidyl-<small>L</small>tryptophyl-<small>L</small>-seryl-<small>L</small>tyrosyl-3-(1''H''-indol-2-yl)-<small>L</small>-alanylleucyl-<small>L</small>-arginyl-<small>L</small>-prolylglycinamide
| verifiedrevid = 477865893
| image = Triptorelin.png
| drug_name = Triptorelin | image = Triptorelin.svg
| image_class = skin-invert-image
| width = 250
| alt =


<!--Clinical data--> <!--Clinical data-->
| tradename = | tradename = Decapeptyl, others
| Drugs.com = {{drugs.com|CONS|piperazine}} | Drugs.com = {{drugs.com|CONS|triptorelin}}
| MedlinePlus = a697045 | MedlinePlus =
| DailyMedID = Triptorelin
| pregnancy_category = D
| pregnancy_category =
| legal_status = ℞-only
| routes_of_administration = ] | routes_of_administration = ]
| class = ]; ]; ]
| ATC_prefix = L02
| ATC_suffix = AE04
| ATC_supplemental = {{ATCvet|H01|CA97}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment = <ref>{{cite web | title=Prescription medicines: registration of new chemical entities in Australia, 2015 | website=Therapeutic Goods Administration (TGA) | date=21 June 2022 | url=https://www.tga.gov.au/prescription-medicines-registration-new-chemical-entities-australia-2015 | access-date=10 April 2023}}</ref>
| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->
| legal_BR_comment =
| legal_CA = Rx-only
| 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_comment = <ref>{{cite web | title=Triptodur- triptorelin kit | work = DailyMed | publisher = U.S. National Library of Medicine | date=28 April 2022 | url= https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f41380e7-b830-432d-a5f5-a872932f107e | access-date=15 May 2022}}</ref>
| legal_EU =
| legal_EU_comment =
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = Rx-only


<!--Pharmacokinetic data--> <!--Pharmacokinetic data-->
| bioavailability =
| excretion = ]
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion = ]


<!--Identifiers--> <!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = <!-- blanked - oldvalue: 57773-63-4 --> | CAS_number = 57773-63-4
| PubChem = 25074470
| ATC_prefix = L02
| IUPHAR_ligand = 1177
| ATC_suffix = AE04
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| StdInChI = 1S/C4H10N2/c1-2-6-4-3-5-1/h5-6H,1-4H2
| DrugBank = DB06825
| StdInChIKey = GLUUGHFHXGJENI-UHFFFAOYSA-N
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| PubChem =
| ChemSpiderID = 17290424
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| UNII_Ref = {{fdacite|correct|FDA}}
| DrugBank = DB00592
| UNII = 9081Y98W2V
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| ChemSpiderID = 13835459
| KEGG = D06247
| UNII_Ref = {{fdacite|correct|FDA}}
| KEGG2 = D08649
| UNII = 9081Y98W2V
<!-- | KEGG3 = D06248 -->
| KEGG_Ref = {{keggcite|correct|kegg}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| KEGG =
| ChEBI = 63633
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEBI = 28568
| ChEMBL = 1201334
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| synonyms = <!--Chemical data-->
| ChEMBL = 1412
| IUPAC_name = 5-oxo-<small>D</small>-prolyl-<small>L</small>-histidyl-<small>L</small>tryptophyl-<small>L</small>-seryl-<small>L</small>tyrosyl-3-(1''H''-indol-2-yl)-<small>L</small>-alanylleucyl-<small>L</small>-arginyl-<small>L</small>-prolylglycinamide
| C=64 | H=82 | N=18 | O=13
| C = 64
| molecular_weight = 1311.5 g/mol
| H = 82
| N = 18
| O = 13
| SMILES = CC(C)C(C(=O)N(CCCNC(=N)N)C(=O)N1CCC1C(=O)NCC(=O)N)NC(=O)(Cc2cc3c2cccc3)NC(=O)(Cc4ccc(cc4)O)NC(=O)(CO)NC(=O)(Cc5cc6c5cccc6)NC(=O)(Cc7cnc7)NC(=O)8CCC(=O)N8
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C64H82N18O13/c1-34(2)23-46(56(88)75-45(13-7-21-69-64(66)67)63(95)82-22-8-14-52(82)62(94)72-31-53(65)85)76-58(90)48(25-36-28-70-42-11-5-3-9-40(36)42)78-57(89)47(24-35-15-17-39(84)18-16-35)77-61(93)51(32-83)81-59(91)49(26-37-29-71-43-12-6-4-10-41(37)43)79-60(92)50(27-38-30-68-33-73-38)80-55(87)44-19-20-54(86)74-44/h3-6,9-12,15-18,28-30,33-34,44-52,70-71,83-84H,7-8,13-14,19-27,31-32H2,1-2H3,(H2,65,85)(H,68,73)(H,72,94)(H,74,86)(H,75,88)(H,76,90)(H,77,93)(H,78,89)(H,79,92)(H,80,87)(H,81,91)(H4,66,67,69)/t44-,45-,46-,47-,48+,49-,50-,51-,52-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = VXKHXGOKWPXYNA-PGBVPBMZSA-N
}} }}

'''Triptorelin''', sold under the brand name '''Decapeptyl''' among others, is a ] that acts as an agonist analog of ], repressing expression of ] (LH) and ] (FSH).<ref name="encyclopedia.com">{{Cite web|url=https://www.encyclopedia.com/caregiving/dictionaries-thesauruses-pictures-and-press-releases/gonadorelin-analogue|title=gonadorelin analogue |website=Encyclopedia.com|access-date=2019-09-21}}</ref><ref name=":0">{{Cite book|title=British National Formulary (BNF) 70| author = Joint Formulary Committee|publisher=Pharmaceutical Press|year=2018|isbn=978-0-85711-173-9|location=London|pages=635}}</ref>

It is a ] (pGlu-His-Trp-Ser-Tyr-<small>D</small>-Trp-Leu-Arg-Pro-Gly-NH<sub>2</sub>) and a ] (GnRH agonist) used as the ] or ] ]s.

Primary indications include ],<ref>{{cite journal | vauthors = Leone Roberti Maggiore U, Scala C, Remorgida V, Venturini PL, Del Deo F, Torella M, Colacurci N, Salvatore S, Ferrari S, Papaleo E, Candiani M, Ferrero S | display-authors = 6 | title = Triptorelin for the treatment of endometriosis | journal = Expert Opinion on Pharmacotherapy | volume = 15 | issue = 8 | pages = 1153–1179 | date = June 2014 | pmid = 24832495 | doi = 10.1517/14656566.2014.916279 | publisher = Informa Healthcare | s2cid = 23843087 }}</ref> for the reduction of ], to treat ], and to treat male ] with severe sexual deviation.<ref name=":0" /> The drug has also been used off label to delay puberty in patients with gender dysphoria.<ref>{{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>

<!-- Society and culture -->
It was patented in 1975 and approved for medical use in 1986.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=514 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA514 }}</ref> It is on the ].<ref name="WHO22nd">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }}</ref>

==Medical uses==
{{See also|Gonadotropin-releasing hormone agonist#Medical uses}}Triptorelin is used to treat ] as part of androgen deprivation therapy.<ref name="DRUGS.COM">{{cite web|title=triptorelin (Intramuscular route)|url=https://www.drugs.com/cons/triptorelin-intramuscular-injection.html|website=Drugs.com|access-date=11 November 2016}}</ref>

Another common use in the United Kingdom is for hormone replacement therapy to suppress testosterone or estrogen levels in transgender people (in conjunction with ] for trans women or testosterone for trans men). ] and ] are other drugs used by trans people to suppress sex hormones, but these drugs have a completely different mechanism of action.<ref>{{cite journal | vauthors = Wylie KR, Fung Jr R, Boshier C, Rotchell M |title=Recommendations of endocrine treatment for patients with gender dysphoria|journal=Sexual and Relationship Therapy|volume=24|issue=2|pages=175–187|doi=10.1080/14681990903023306|year=2009 |s2cid=20471537}}</ref> It can also be used as a ]<ref>{{cite journal | vauthors = Shumer DE, Nokoff NJ, Spack NP | title = Advances in the Care of Transgender Children and Adolescents | journal = Advances in Pediatrics | volume = 63 | issue = 1 | pages = 79–102 | date = August 2016 | pmid = 27426896 | pmc = 4955762 | doi = 10.1016/j.yapd.2016.04.018 }}</ref> in the case of ].<ref name="DRUGS.COM"/>

Triptorelin has been used as a ] agent for reducing sexual urges in ]s.<ref>{{cite web | url = http://edition.cnn.com/HEALTH/9802/11/sex.offender.drug/ | title = Study: Drug effectively treats pedophilia | work = ] | date = 11 February 1998 }}</ref>

== Drug action ==
Triptorelin is a ], also known as ] (GnRH analogue, LHRH analogue).<ref name="encyclopedia.com"/> The drug binds to receptors in the pituitary gland and stimulates secretion of ]s (namely ] LH and ] FSH). This causes an initial phase of LH and FSH stimulation, prior to ] of the gonadotrophin-releasing hormone receptors, thereby reducing the release of gonadotropins in the long term, which in turn leads to the inhibition of ] and ] production.<ref name=":0" />

== Side-effects ==
General side effects can include:<ref name=":0" />

* Anaphylaxis
* Arthralgia
* Asthenia
* Asthma
* Breast tenderness (males and females)
* Changes in blood pressure
* Changes in breast size
* Depression
* Ovarian cysts
* Mood changes
* Skin rashes
* Hot flashes
* Weight changes

==Society and culture==

===Brand names===
Triptorelin is marketed under the brand names Decapeptyl (]) for treating prostate cancer, endometriosis, uterine myomas, and precocious puberty,<ref>{{Cite web |title=Decapeptyl SR 11.25mg (triptorelin pamoate) - Patient Information Leaflet (PIL) - (emc) |url=https://www.medicines.org.uk/emc/product/780/pil#gref |access-date=2022-11-14 |website=www.medicines.org.uk}}</ref> and Diphereline and Gonapeptyl (]).<ref>{{Cite web |title=Gonapeptyl Depot 3.75 mg - Summary of Product Characteristics (SmPC) - (emc) |url=https://www.medicines.org.uk/emc/product/2229/smpc#gref |access-date=2022-11-14 |website=www.medicines.org.uk}}</ref> In the United States, it is sold by ] as Trelstar <ref>{{Cite web |title=Trelstar intramuscular: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing | work = WebMD |url=https://www.webmd.com/drugs/2/drug-153984-8162/trelstar-intramuscular/triptorelin-3-month-11-25-mg-injection/details |access-date=2022-11-14 |language=en}}</ref> and by Arbor Pharmaceuticals as Triptodur (an extended-release 6-month depot injection).<ref>{{Cite web |title=Triptodur Intramuscular: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing | work = WebMD |url=https://www.webmd.com/drugs/2/drug-174078/triptodur-intramuscular/details |access-date=2022-11-14 |language=en}}</ref> In Iran, triptorelin is marketed under the brand name Variopeptyl. In the UK and Germany, it is sold as Salvacyl for the treatment of sexual deviations.<ref>{{Cite web |title=Salvacyl®, developed by Debiopharm, is launched in two European countries - a new therapeutic avenue for the treatment of sexual deviations |url=https://www.debiopharm.com/drug-development/press-releases/salvacyl-developed-by-debiopharm-is-launched-in-two-european-countries-a-new-therapeutic-avenue-for-the-treatment-of-sexual-deviations/ |access-date=2022-11-14 |website=Debiopharm |date=23 June 2009 |language=en-US}}</ref>

== History ==
Triptorelin was developed in ]'s lab at ].<ref>{{cite web|url=https://research.tulane.edu/oipm/about-us |accessdate=4 January 2024 |publisher=Tulane University |title=About Us – Technology Transfer at Tulane University}}</ref> ] licensed the drug from Tulane in 1982.<ref>{{cite web|url=https://www.fiercepharma.com/pharma/dr-reddy-s-launches-debiopharm-s-pamorelin%C2%AE-la-india-for-treatment-of-locally-advanced-or |accessdate=4 January 2024 |publisher=Fierce Pharma |date=7 December 2012 |title=Dr. Reddy's Launches Debiopharm's Pamorelin LA in India for the Treatment of Locally Advanced or Metastatic, Hormone-Dependent Prostate Cancer}}</ref>

==Research==
Triptorelin and other antiandrogens may be effective in the treatment of ].<ref name="pmid31814547">{{cite journal | vauthors = Nomani H, Mohammadpour AH, Moallem SM, YazdanAbad MJ, Barreto GE, Sahebkar A | title = Anti-Androgen Drugs in the Treatment of Obsessive-Compulsive Disorder: A Systematic Review | journal = Current Medicinal Chemistry | volume = 27 | issue = 40 | pages = 6825–6836 | date = December 2019 | pmid = 31814547 | doi = 10.2174/0929867326666191209142209 | s2cid = 208956450 }}</ref>

== References ==
{{Reflist}}

== Further reading ==
{{refbegin}}
* {{cite journal | vauthors = Lahlou N, Carel JC, Chaussain JL, Roger M | title = Pharmacokinetics and pharmacodynamics of GnRH agonists: clinical implications in pediatrics | journal = Journal of Pediatric Endocrinology & Metabolism | volume = 13 | issue = Suppl 1 | pages = 723–737 | date = July 2000 | pmid = 10969915 | doi = 10.1515/jpem.2000.13.s1.723 | s2cid = 3639804 }}
* {{cite journal | vauthors = Padula AM | title = GnRH analogues--agonists and antagonists | journal = Animal Reproduction Science | volume = 88 | issue = 1–2 | pages = 115–126 | date = August 2005 | pmid = 15955640 | doi = 10.1016/j.anireprosci.2005.05.005 }}
{{refend}}

== External links ==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/triptorelin | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Triptorelin }}

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

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Misplaced Pages:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Triptorelin: Difference between pages Add topic