Triptorelin: Difference between revisions

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			{{Short description\|GnRH-agonist}}
	{{Drugbox		{{Drugbox
	\| Verifiedfields = changed		\| Verifiedfields = changed
	\| Watchedfields = changed		\| Watchedfields = changed
	\| verifiedrevid = 477865893		\| verifiedrevid = 477865893
			\| image = Triptorelin.svg
	\| 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
			\| width = 250
	\| image = Triptorelin.png
			\| alt =
	\| width = 250px

	<!--Clinical data-->		<!--Clinical data-->
	\| tradename = Decapeptyl~~, Gonapeptyl, Triptodur~~, others		\| tradename = Decapeptyl, others
	\| Drugs.com = {{drugs.com\|CONS\|triptorelin}}		\| Drugs.com = {{drugs.com\|CONS\|triptorelin}}
	\| MedlinePlus =		\| MedlinePlus =
			\| DailyMedID = Triptorelin
	\| pregnancy_category = X
			\| pregnancy_category =
	\| legal_status = ℞-only
	\| routes_of_administration =		\| routes_of_administration = ]
	\| class = ]; ]; ]		\| 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 =		\| bioavailability =
	\| protein_bound =		\| protein_bound =
	\| metabolism =		\| metabolism =
	\| elimination_half-life =		\| elimination_half-life =
	\| excretion = ]		\| excretion = ]

	<!--Identifiers-->		<!--Identifiers-->
			\| CAS_number_Ref = {{cascite\|changed\|??}}
	\| IUPHAR_ligand = 1177
			\| CAS_number = 57773-63-4
	\| CAS_number_Ref = {{cascite\|changed\|??}}
			\| PubChem = 25074470
	\| CAS_number = 57773-63-4
			\| IUPHAR_ligand = 1177
	\| ATC_prefix = L02
			\| DrugBank_Ref = {{drugbankcite\|changed\|drugbank}}
	\| ATC_suffix = AE04
			\| DrugBank = DB06825
	\| ATC_supplemental = {{ATCvet\|H01\|CA97}}
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
	\| PubChem = 25074470
			\| ChemSpiderID = 17290424
	\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
	\| ChemSpiderID = 17290424
			\| UNII = 9081Y98W2V
	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| KEGG_Ref = {{keggcite\|changed\|kegg}}
	\| UNII = 9081Y98W2V
			\| KEGG = D06247
	\| KEGG_Ref = {{keggcite\|changed\|kegg}}
			\| KEGG2 = D08649
	\| KEGG = D06247
			<!-- \| KEGG3 = D06248 -->
	\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
	\| ChEBI = 63633
			\| ChEBI = 63633
	\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
	\| ChEMBL = 1201334
			\| ChEMBL = 1201334
	\| DrugBank_Ref = {{drugbankcite\|changed\|drugbank}}
			\| synonyms = <!--Chemical data-->
	\| DrugBank = DB06825
			\| 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
	\| synonyms =
			\| C = 64

			\| H = 82
	<!--Chemical data-->
	\| ~~C=64~~ \| ~~H=82~~ \| ~~N=18~~ \| O=13		\| 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
			\| 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_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
			\| 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_Ref = {{stdinchicite\|changed\|chemspider}}
	\| StdInChIKey = VXKHXGOKWPXYNA-PGBVPBMZSA-N
			\| StdInChIKey = VXKHXGOKWPXYNA-PGBVPBMZSA-N
	}}		}}

	'''Triptorelin''', sold under the brand ~~names~~ '''Decapeptyl~~''' and '''Gonapeptyl~~''' among others, is a medication that acts as an agonist analog of ], ~~thus~~ ~~reversibly repressing~~ of ] (LH) and ] (FSH)<ref>{{Cite web\|url=https://www.encyclopedia.com/caregiving/dictionaries-thesauruses-pictures-and-press-releases/gonadorelin-analogue\|title=gonadorelin analogue ~~{{!}} Encyclopedia.com~~\|website=~~www.encyclopedia~~.com\|access-date=2019-09-21}}</ref><ref name=":0">{{Cite book\|title=British National Formulary (BNF) 70\|~~last~~=Joint ~~Forumlary~~ Committee\|publisher=Pharmaceutical Press\|year=2018\|isbn=978-0-85711-173-9\|location=London\|pages=635~~\|url-status=live~~}}</ref>.		'''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 decapeptide (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.		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 endometriosis, for the reduction of fibroids, ~~for~~ ~~prostatic~~ cancer, and to treat male hypersexuality 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\|~~last1~~=Barnes\|~~first1=Hannah\|last2=Cohen\|first2=Deborah\|date=2019-09-20\|~~title=Gender dysphoria in children: puberty blockers study draws further criticism\|~~url=https://www.bmj.com/content/366/bmj.l5647\|~~journal=BMJ\|~~language=en\|~~volume=366\|pages=l5647\|doi=10.1136/bmj.l5647\|~~pmid=31540909\|~~s2cid=202711942~~\|issn=0959-8138~~}}</ref>		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 -->		<!-- Society and culture -->
	It was patented in 1975 and approved for medical use in 1986.<ref name=Fis2006>{{cite book \|~~last1~~=Fischer ~~\|first1=Jnos~~ ~~\|last2=~~Ganellin ~~\|first2=C. Robin~~ \|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 \|~~language~~=en}}</ref>		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==		==Medical uses==
	Triptorelin is used to treat ] ~~(PCa)~~ as part of androgen deprivation therapy ~~(ADT)~~. ~~Another ADT injectable medicine commonly used to treat PCa includes Lupron which also targets the pituitary~~.~~<ref~~>{{cite web\|title=triptorelin (Intramuscular route)\|url=https://www.drugs.com/cons/triptorelin-intramuscular-injection.html\|website=~~drugs~~.com\|~~accessdate~~=11 November 2016}}</ref>		{{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 ] 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\|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\|~~last1~~=~~Wylie~~\|~~first1~~=~~Kevan~~ ~~Richard~~\|~~last2~~=~~Fung~~\|~~first2~~=~~Robert~~\|~~last3~~=~~Boshier~~\|~~first3~~=~~Claudia~~\|~~last4~~=~~Rotchell~~\|~~first4~~=~~Margaret~~\|~~s2cid~~=~~20471537~~}}</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>, ], ~~February~~ 11, 1998.</ref>		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 ==		== Drug action ==
	Triptorelin is a ], also known as ] (GnRH analogue, LHRH analogue).<ref~~>{{Cite~~ ~~web\|url~~=~~https://www.~~encyclopedia.com/~~caregiving/dictionaries-thesauruses-pictures-and-press-releases/gonadorelin-analogue\|title=gonadorelin analogue {{!}} Encyclopedia.com\|website=www.encyclopedia.com\|access-date=2019-09-21}}</ref~~> The drug binds to receptors in the pituitary gland and stimulates secretion of ~~gonadotrophins~~ (namely ] and ]). This causes an initial phase of LH and FSH stimulation, prior to ] of the gonadotrophin-releasing hormone receptors, thereby reducing the release of ~~gonadotrophins~~ in the long term, which in turn leads to the inhibition of ] and ] production.<ref name=":0" />		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 ==		== Side-effects ==
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	* Asthma		* Asthma
	* Breast tenderness (males and females)		* Breast tenderness (males and females)
	* Changes in ~~Blood~~ pressure		* Changes in blood pressure
	* Changes in breast size		* Changes in breast size
	* Depression		* Depression
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	* Mood changes		* Mood changes
	* Skin rashes		* Skin rashes
	* Hot ~~flushes~~		* Hot flashes
	* Weight changes		* Weight changes

	== Contra-indications and precautions ==
	Triptorelin should not be used for more than 6 months for endometriosis<ref name=":0" />, and should be used with care in patients with metabolic bone disease and osteoporosis due to the risk of ].<ref name=":0" />

	==Society and culture==		==Society and culture==

	===Brand names===		===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>
	Triptorelin is marketed under the brand names Decapeptyl (]) and Diphereline and Gonapeptyl (]). In the ], it is sold by ] as Trelstar and by ] as Triptodur (an extended-release 6-month depot injection). In ], triptorelin is marketed under the brand name Variopeptyl.

			== 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==		==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 = ~~Curr~~ ~~Med~~ ~~Chem~~ \| date = December 2019 \| pmid = 31814547 \| doi = 10.2174/0929867326666191209142209}}</ref>		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>

	==~~See~~ ~~also~~==		== References ==
	* ]

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

	==Further reading==		== 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=J Pediatr Endocrinol Metab \|volume=13 Suppl 1 \|issue= \|pages=723–37 \|date=July 2000 \|pmid=10969915 \|doi=10.1515/jpem.2000.13.s1.723\|s2cid=3639804 }}
	* {{cite journal \|~~author~~=~~Padula~~ AM \|title=~~GnRH~~ ~~analogues—agonists~~ and ~~antagonists~~ \|journal=] \|volume=88 \|issue=~~1–2~~ \|pages=~~115–26~~ \|date=~~August~~ ~~2005~~ \|pmid=~~15955640~~ \|doi=10.~~1016~~/j.~~anireprosci~~.~~2005~~.05.~~005~~}}		* {{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 gonadotropins}}
	{{GnRH and gonadotropin receptor modulators}}		{{GnRH and gonadotropin receptor modulators}}
			{{Portal bar \| Medicine}}

	]		]
	]		]
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Latest revision as of 14:33, 25 November 2024

GnRH-agonist Pharmaceutical compound

Triptorelin
Clinical data

Trade names	Decapeptyl, others
AHFS/Drugs.com	Micromedex Detailed Consumer Information
License data	US DailyMed: Triptorelin
Routes of administration	Intramuscular
Drug class	GnRH analogue; GnRH agonist; Antigonadotropin
ATC code	L02AE04 (WHO) QH01CA97 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: ℞-only US: ℞-only In general: ℞ (Prescription only)
Pharmacokinetic data
Excretion	Kidney
Identifiers
IUPAC name 5-oxo-D-prolyl-L-histidyl-Ltryptophyl-L-seryl-Ltyrosyl-3-(1H-indol-2-yl)-L-alanylleucyl-L-arginyl-L-prolylglycinamide
CAS Number	57773-63-4
PubChem CID	25074470
IUPHAR/BPS	1177
DrugBank	DB06825
ChemSpider	17290424
UNII	9081Y98W2V
KEGG	D06247 D08649
ChEBI	CHEBI:63633
ChEMBL	ChEMBL1201334
CompTox Dashboard (EPA)	DTXSID2048375
ECHA InfoCard	100.165.044
Chemical and physical data
Formula	C₆₄H₈₂N₁₈O₁₃
Molar mass	1311.473 g·mol
3D model (JSmol)	Interactive image
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
InChI InChI=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 Key:VXKHXGOKWPXYNA-PGBVPBMZSA-N
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Triptorelin, sold under the brand name Decapeptyl among others, is a medication that acts as an agonist analog of gonadotropin-releasing hormone, repressing expression of luteinizing hormone (LH) and follicle-stimulating hormone (FSH).

It is a decapeptide (pGlu-His-Trp-Ser-Tyr-D-Trp-Leu-Arg-Pro-Gly-NH₂) and a gonadotropin-releasing hormone agonist (GnRH agonist) used as the acetate or pamoate salts.

Primary indications include endometriosis, for the reduction of uterine fibroids, to treat prostate cancer, and to treat male hypersexuality with severe sexual deviation. The drug has also been used off label to delay puberty in patients with gender dysphoria.

It was patented in 1975 and approved for medical use in 1986. It is on the World Health Organization's List of Essential Medicines.

Medical uses

Triptorelin is used to treat prostate cancer as part of androgen deprivation therapy.

Another common use in the United Kingdom is for hormone replacement therapy to suppress testosterone or estrogen levels in transgender people (in conjunction with estradiol valerate for trans women or testosterone for trans men). Spironolactone and cyproterone acetate are other drugs used by trans people to suppress sex hormones, but these drugs have a completely different mechanism of action. It can also be used as a puberty blocker in the case of precocious puberty.

Triptorelin has been used as a chemical castration agent for reducing sexual urges in sex offenders.

Drug action

Triptorelin is a gonadorelin analogue, also known as luteinizing hormone releasing analogue (GnRH analogue, LHRH analogue). The drug binds to receptors in the pituitary gland and stimulates secretion of gonadotropins (namely luteinizing hormone LH and follicle-stimulating hormone FSH). This causes an initial phase of LH and FSH stimulation, prior to down-regulation of the gonadotrophin-releasing hormone receptors, thereby reducing the release of gonadotropins in the long term, which in turn leads to the inhibition of androgen and estrogen production.

Side-effects

General side effects can include:

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 (Ipsen) for treating prostate cancer, endometriosis, uterine myomas, and precocious puberty, and Diphereline and Gonapeptyl (Ferring Pharmaceuticals). In the United States, it is sold by Watson Pharmaceuticals as Trelstar and by Arbor Pharmaceuticals as Triptodur (an extended-release 6-month depot injection). 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.