Triptorelin

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
Elimination half-life	The elimination half-life for patients with hepatic impairment was similar to that of patients with renal impairment (geometric mean t(1/2, z): 6.6 h, 7.7 h and 7.6 h for Groups II, III and IV, respectively), but significantly longer than in healthy volunteers (2.8 h for Group I) Triptorelin is a gonadotropin-releasing hormone (GnRH) analogue with enhanced affinity for GnRH receptors and a prolonged half-life due to its resistance to enzymatic degradation.
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−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C[C@@H](C(=O)N[C@@H](CCCNC(=N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)[C@@H](Cc2c[nH]c3c2cccc3)NC(=O)[C@H](Cc4ccc(cc4)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc5c[nH]c6c5cccc6)NC(=O)[C@H](Cc7cnc[nH]7)NC(=O)[C@@H]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).^[4]^[5]

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,^[6] for the reduction of uterine fibroids, to treat prostate cancer, and to treat male hypersexuality with severe sexual deviation.^[5] The drug has also been used off label to delay puberty in patients with gender dysphoria.^[7]

It was patented in 1975 and approved for medical use in 1986.^[8] It is on the World Health Organization's List of Essential Medicines.^[9]

^ "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
^ "Triptodur- triptorelin kit". DailyMed. U.S. National Library of Medicine. 28 April 2022. Retrieved 15 May 2022.
^ Müller FO, Terblanchè J, Schall R, van Zyl Smit R, Tucker T, Marais K, et al. (October 1997). "Pharmacokinetics of triptorelin after intravenous bolus administration in healthy males and in males with renal or hepatic insufficiency". British Journal of Clinical Pharmacology. 44 (4): 335–341. doi:10.1046/j.1365-2125.1997.t01-1-00592.x. PMC 2042859. PMID 9354307.
^ "gonadorelin analogue". Encyclopedia.com. Retrieved 2019-09-21.
^ ^a ^b Joint Formulary Committee (2018). British National Formulary (BNF) 70. London: Pharmaceutical Press. p. 635. ISBN 978-0-85711-173-9.
^ Leone Roberti Maggiore U, Scala C, Remorgida V, Venturini PL, Del Deo F, Torella M, et al. (June 2014). "Triptorelin for the treatment of endometriosis". Expert Opinion on Pharmacotherapy. 15 (8). Informa Healthcare: 1153–1179. doi:10.1517/14656566.2014.916279. PMID 24832495. S2CID 23843087.
^ Cohen D, Barnes H (September 2019). "Gender dysphoria in children: puberty blockers study draws further criticism". BMJ. 366: l5647. doi:10.1136/bmj.l5647. PMID 31540909. S2CID 202711942.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 9783527607495.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[1] "Prescription medicines: registration of new chemical entities in Australia, 2015". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.

[2] "Triptodur- triptorelin kit". DailyMed. U.S. National Library of Medicine. 28 April 2022. Retrieved 15 May 2022.

[3] Müller FO, Terblanchè J, Schall R, van Zyl Smit R, Tucker T, Marais K, et al. (October 1997). "Pharmacokinetics of triptorelin after intravenous bolus administration in healthy males and in males with renal or hepatic insufficiency". British Journal of Clinical Pharmacology. 44 (4): 335–341. doi:10.1046/j.1365-2125.1997.t01-1-00592.x. PMC 2042859. PMID 9354307.

[encyclopedia.com-4] "gonadorelin analogue". Encyclopedia.com. Retrieved 2019-09-21.

[:0-5] Joint Formulary Committee (2018). British National Formulary (BNF) 70. London: Pharmaceutical Press. p. 635. ISBN 978-0-85711-173-9.

[6] Leone Roberti Maggiore U, Scala C, Remorgida V, Venturini PL, Del Deo F, Torella M, et al. (June 2014). "Triptorelin for the treatment of endometriosis". Expert Opinion on Pharmacotherapy. 15 (8). Informa Healthcare: 1153–1179. doi:10.1517/14656566.2014.916279. PMID 24832495. S2CID 23843087.

[7] Cohen D, Barnes H (September 2019). "Gender dysphoria in children: puberty blockers study draws further criticism". BMJ. 366: l5647. doi:10.1136/bmj.l5647. PMID 31540909. S2CID 202711942.

[Fis2006-8] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 9783527607495.

[WHO22nd-9] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

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