Triptorelin

Triptorelin
Names
Trade namesDecapeptyl, Gonapeptyl, Triptodur, others
IUPAC name
  • 5-oxo-D-prolyl-L-histidyl-Ltryptophyl-L-seryl-Ltyrosyl-3-(1H-indol-2-yl)-L-alanylleucyl-L-arginyl-L-prolylglycinamide
Clinical data
Drug classGnRH analogue; GnRH agonist; antigonadotropin
Main usesEndometriosis, fibroids, prostatic cancer, precocious puberty, male hypersexuality with sexual deviation[1][2]
Side effectsFlushing, sexual dysfunction, pain at the site of injection, high blood sugar[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • X
Routes of
use		IM
External links
AHFS/Drugs.comMonograph
Legal
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetics
ExcretionKidney
Chemical and physical data
FormulaC64H82N18O13
Molar mass1311.473 g·mol−1
3D model (JSmol)
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 ☒N
  • Key:VXKHXGOKWPXYNA-PGBVPBMZSA-N ☒N

Triptorelin, sold under the brand names Decapeptyl among others, is a medication used for endometriosis, fibroids, prostatic cancer, precocious puberty, and to male hypersexuality with severe sexual deviation.[1][2] It has also been used to delay puberty in people with gender dysphoria.[3] It is given by injection into a muscle.[1]

Common side effects include flushing, sexual dysfunction, pain at the site of injection, and high blood sugar.[1] Other side effects may include pituitary apoplexy, irritability, blood clots, and anaphylaxis.[1] Use during pregnancy may harm the baby.[1] It is a gonadotropin-releasing hormone which decreases the production of androgens and estrogen.[2]

Triptorelin was patented in 1975 and approved for medical use in 1986.[4] It is on the World Health Organization's List of Essential Medicines as an alternative to leuprorelin.[5] In the United Kingdom a 3.75 mg dose costs the NHS about £82 as of 2021.[2] This amount in the United States costs about 860 USD.[6]

Medical uses

See also: Gonadotropin-releasing hormone agonist § Medical uses

Triptorelin is used to treat prostate cancer as part of androgen deprivation therapy.[7]

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.[8] It can also be used as a puberty blocker[9]

Triptorelin has been used as a chemical castration agent for reducing sexual urges in sex offenders.[10]

Dosage

The typical dose is 3 to 22.5 mg.[2] It is give every 4 weeks to 6 months depending on the condition being treated.[2]

Side effects

Side effects can include:[11]

  • 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 flushes
  • Weight changes

Triptorelin should not be used for more than 6 months for endometriosis,[11] and should be used with care in people with metabolic bone disease and osteoporosis due to the risk of osteopenia.[11]

Mechanism of action

Triptorelin is a Gonadorelin analogue, also known as Luteinizing hormone releasing analogue (GnRH analogue, LHRH analogue).[12] The drug binds to receptors in the pituitary gland and stimulates secretion of gonadotropins (namely luteinzing hormone and Follicle-stimulating hormone). 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 oestrogen production.[11]

Society and culture

Brand names

Triptorelin is marketed under the brand names Decapeptyl (Ipsen) 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.

Research

Triptorelin and other antiandrogens may be effective in the treatment of obsessive–compulsive disorder.[13]

See also

  • Gonadotropin-releasing hormone receptor § Agonists

References

  1. 1 2 3 4 5 6 7 "Triptorelin Monograph for Professionals". Drugs.com. Archived from the original on 27 January 2021. Retrieved 20 September 2021.
  2. 1 2 3 4 5 6 BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 781. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)
  3. ↑ Barnes, Hannah; Cohen, Deborah (2019-09-20). "Gender dysphoria in children: puberty blockers study draws further criticism". BMJ. 366: l5647. doi:10.1136/bmj.l5647. ISSN 0959-8138. PMID 31540909. S2CID 202711942. Archived from the original on 2021-06-16. Retrieved 2021-07-14.
  4. ↑ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 9783527607495. Archived from the original on 2021-06-20. Retrieved 2021-07-14.
  5. ↑ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  6. ↑ "Trelstar Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 19 April 2021. Retrieved 20 September 2021.
  7. ↑ "triptorelin (Intramuscular route)". drugs.com. Archived from the original on 12 November 2016. Retrieved 11 November 2016.
  8. ↑ Wylie, Kevan Richard; Fung, Robert; Boshier, Claudia; Rotchell, Margaret (2009). "Recommendations of endocrine treatment for patients with gender dysphoria". Sexual and Relationship Therapy. 24 (2): 175–187. doi:10.1080/14681990903023306. S2CID 20471537.
  9. ↑ Shumer, DE; Nokoff, NJ; Spack, NP (August 2016). "Advances in the Care of Transgender Children and Adolescents". Advances in Pediatrics. 63 (1): 79–102. doi:10.1016/j.yapd.2016.04.018. PMC 4955762. PMID 27426896.
  10. ↑ Study: Drug effectively treats pedophilia Archived 2021-07-11 at the Wayback Machine, CNN, February 11, 1998.
  11. 1 2 3 4 Joint Formulary Committee (2018). British National Formulary (BNF) 70. London: Pharmaceutical Press. p. 635. ISBN 978-0-85711-173-9.
  12. ↑ "gonadorelin analogue | Encyclopedia.com". www.encyclopedia.com. Archived from the original on 2019-09-21. Retrieved 2019-09-21.
  13. ↑ Nomani H, Mohammadpour AH, Moallem SM, YazdanAbad MJ, Barreto GE, Sahebkar A (December 2019). "Anti-androgen drugs in the treatment of obsessive-compulsive disorder: a systematic review". Curr Med Chem. 27 (40): 6825–6836. doi:10.2174/0929867326666191209142209. PMID 31814547.
Identifiers:
  • Lahlou N, Carel JC, Chaussain JL, Roger M (July 2000). "Pharmacokinetics and pharmacodynamics of GnRH agonists: clinical implications in pediatrics". J Pediatr Endocrinol Metab. 13 Suppl 1: 723–37. doi:10.1515/jpem.2000.13.s1.723. PMID 10969915. S2CID 3639804.
  • Padula AM (August 2005). "GnRH analogues—agonists and antagonists". Anim Reprod Sci. 88 (1–2): 115–26. doi:10.1016/j.anireprosci.2005.05.005. PMID 15955640.
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