Triptorelin

Last updated
Triptorelin
Triptorelin.svg
Clinical data
Trade names Decapeptyl, others
AHFS/Drugs.com Micromedex Detailed Consumer Information
License data
Routes of
administration 		Intramuscular
Drug class GnRH analogue; GnRH agonist; Antigonadotropin
ATC code
Legal status
Legal status
Pharmacokinetic data
Excretion Kidney
Identifiers
  • 5-oxo-D-prolyl-L-histidyl-Ltryptophyl-L-seryl-Ltyrosyl-3-(1H-indol-2-yl)-L-alanylleucyl-L-arginyl-L-prolylglycinamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.165.044 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C64H82N18O13
Molar mass 1311.473 g·mol−1
3D model (JSmol)
  • 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=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 X mark.svgN
  • Key:VXKHXGOKWPXYNA-PGBVPBMZSA-N X mark.svgN
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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). [3] [4]

Contents

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, [5] for the reduction of uterine fibroids, to treat prostate cancer, and to treat male hypersexuality with severe sexual deviation. [4] The drug has also been used off label to delay puberty in patients with gender dysphoria. [6]

It was patented in 1975 and approved for medical use in 1986. [7] It is on the World Health Organization's List of Essential Medicines. [8]

Medical uses

Triptorelin is used to treat prostate cancer as part of androgen deprivation therapy. [9]

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. [10] It can also be used as a puberty blocker [11] in the case of precocious puberty. [9]

Triptorelin has been used as a chemical castration agent for reducing sexual urges in sex offenders. [12]

Drug action

Triptorelin is a gonadorelin analogue, also known as luteinizing hormone releasing analogue (GnRH analogue, LHRH analogue). [3] 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. [4]

Side-effects

General side effects can include: [4]

Society and culture

Brand names

Triptorelin is marketed under the brand names Decapeptyl (Ipsen) for treating prostate cancer, endometriosis, uterine myomas, and precocious puberty, [13] and Diphereline and Gonapeptyl (Ferring Pharmaceuticals). [14] In the United States, it is sold by Watson Pharmaceuticals as Trelstar [15] and by Arbor Pharmaceuticals as Triptodur (an extended-release 6-month depot injection). [16] 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. [17]

History

Triptorelin was developed in Andrew V. Schally's lab at Tulane University. [18] Debiopharm licensed the drug from Tulane in 1982. [19]

Research

Triptorelin and other antiandrogens may be effective in the treatment of obsessive–compulsive disorder. [20]

Related Research Articles

<span class="mw-page-title-main">Gonadotropin-releasing hormone</span> Mammalian protein found in Homo sapiens

Gonadotropin-releasing hormone (GnRH) is a releasing hormone responsible for the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. GnRH is a tropic peptide hormone synthesized and released from GnRH neurons within the hypothalamus. The peptide belongs to gonadotropin-releasing hormone family. It constitutes the initial step in the hypothalamic–pituitary–gonadal axis.

<span class="mw-page-title-main">Goserelin</span> Chemical compound

Goserelin, sold under the brand name Zoladex among others, is a medication which is used to suppress production of the sex hormones, particularly in the treatment of breast and prostate cancer. It is an injectable gonadotropin releasing hormone agonist.

<span class="mw-page-title-main">Leuprorelin</span> Manufactured (artificial) injectable hormone

Leuprorelin, also known as leuprolide, is a manufactured version of a hormone used to treat prostate cancer, breast cancer, endometriosis, uterine fibroids, as part of transgender hormone therapy, for early puberty, or to perform chemical castration of violent sex offenders. It is given by injection into a muscle or under the skin.

<span class="mw-page-title-main">Gonadorelin</span> Chemical compound

Gonadorelin is a gonadotropin-releasing hormone agonist which is used in fertility medicine and to treat amenorrhea and hypogonadism. It is also used in veterinary medicine. The medication is a form of the endogenous GnRH and is identical to it in chemical structure. It is given by injection into a blood vessel or fat or as a nasal spray.

<span class="mw-page-title-main">Nafarelin</span> Pharmaceutical drug

Nafarelin, sold under the brand name Synarel among others, is a gonadotropin-releasing hormone agonist medication which is used in the treatment of endometriosis and early puberty. It is also used to treat uterine fibroids, to control ovarian stimulation in in vitro fertilization (IVF), and as part of transgender hormone therapy. The medication is used as a nasal spray two to three times per day.

<span class="mw-page-title-main">Buserelin</span> Chemical compound

Buserelin, sold under the brand name Suprefact among others, is a medication which is used primarily in the treatment of prostate cancer and endometriosis. It is also used for other indications such as the treatment of premenopausal breast cancer, uterine fibroids, and early puberty, in assisted reproduction for female infertility, and as a part of transgender hormone therapy. In addition, buserelin is used in veterinary medicine. The medication is typically used as a nasal spray three times per day, but is also available for use as a solution or implant for injection into fat.

<span class="mw-page-title-main">Gonadotropin-releasing hormone agonist</span> Drug class affecting sex hormones

A gonadotropin-releasing hormone agonist is a type of medication which affects gonadotropins and sex hormones. They are used for a variety of indications including in fertility medicine and to lower sex hormone levels in the treatment of hormone-sensitive cancers such as prostate cancer and breast cancer, certain gynecological disorders like heavy periods and endometriosis, high testosterone levels in women, early puberty in children, as a part of transgender hormone therapy, and to delay puberty in transgender youth among other uses. It is also used in the suppression of spontaneous ovulation as part of controlled ovarian hyperstimulation, an essential component in IVF. GnRH agonists are given by injections into fat, as implants placed into fat, and as nasal sprays.

<span class="mw-page-title-main">Gonadotropin-releasing hormone antagonist</span> Class of medications

Gonadotropin-releasing hormone antagonists are a class of medications that antagonize the gonadotropin-releasing hormone receptor and thus the action of gonadotropin-releasing hormone (GnRH). They are used in the treatment of prostate cancer, endometriosis, uterine fibroids, female infertility in assisted reproduction, and for other indications.

The gonadotropin-releasing hormone receptor (GnRHR), also known as the luteinizing hormone releasing hormone receptor (LHRHR), is a member of the seven-transmembrane, G-protein coupled receptor (GPCR) family. It is the receptor of gonadotropin-releasing hormone (GnRH). The GnRHR is expressed on the surface of pituitary gonadotrope cells as well as lymphocytes, breast, ovary, and prostate.

<span class="mw-page-title-main">Histrelin</span> Chemical compound

Histrelin acetate, sold under the brand names Vantas and Supprelin LA among others, is a nonapeptide analogue of gonadotropin-releasing hormone (GnRH) with added potency. When present in the bloodstream, it acts on particular cells of the pituitary gland called gonadotropes. Histrelin stimulates these cells to release luteinizing hormone and follicle-stimulating hormone. Thus it is considered a gonadotropin-releasing hormone agonist or GnRH agonist.

<span class="mw-page-title-main">Cetrorelix</span> Drug used in IVF procedures

Cetrorelix, or cetrorelix acetate, sold under the brand name Cetrotide, is an injectable gonadotropin-releasing hormone (GnRH) antagonist. A synthetic decapeptide, it is used in assisted reproduction to inhibit premature luteinizing hormone surges The drug works by blocking the action of GnRH upon the pituitary, thus rapidly suppressing the production and action of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). In addition, cetrorelix can be used to treat hormone-sensitive cancers of the prostate and breast and some benign gynaecological disorders. It is administered as either multiple 0.25 mg daily subcutaneous injections or as a single-dose 3 mg subcutaneous injection. The duration of the 3 mg single dose is four days; if human chorionic gonadotropin (hCG) is not administered within four days, a daily 0.25 mg dose is started and continued until hCG is administered.

<span class="mw-page-title-main">Degarelix</span> Chemical compound

Degarelix, sold under the brand name Firmagon among others, is a hormonal therapy used in the treatment of prostate cancer.

<span class="mw-page-title-main">Deslorelin</span> Chemical compound

Deslorelin, sold under the brand names Ovuplant, SucroMate, and Suprelorin among others, is an injectable gonadotropin releasing hormone superagonist which is used in veterinary medicine for various indications.

<span class="mw-page-title-main">Isolated 17,20-lyase deficiency</span> Medical condition

Isolated 17,20-lyase deficiency (ILD), also called isolated 17,20-desmolase deficiency, is a rare endocrine and autosomal recessive genetic disorder which is characterized by a complete or partial loss of 17,20-lyase activity and, in turn, impaired production of the androgen and estrogen sex steroids. The condition manifests itself as pseudohermaphroditism in males, in whom it is considered to be a form of intersex, and, in both sexes, as a reduced or absent puberty/lack of development of secondary sexual characteristics, resulting in a somewhat childlike appearance in adulthood.

An antigonadotropin is a drug which suppresses the activity and/or downstream effects of one or both of the gonadotropins, follicle-stimulating hormone (FSH) and luteinizing hormone (LH). This results in an inhibition of the hypothalamic-pituitary-gonadal (HPG) axis, and thus a decrease in the levels of the androgen, estrogen, and progestogen sex steroids in the body. Antigonadotropins also inhibit ovulation in women and spermatogenesis in men. They are used for a variety of purposes, including for the hormonal birth control, treatment of hormonally-sensitive cancers, to delay precocious puberty and puberty in transgender youth, as a form of chemical castration to reduce the sex drives of individuals with hypersexuality or pedophilia, and to treat estrogen-associated conditions in women such as menorrhagia and endometriosis, among others. High-dose antigonadotropin therapy has been referred to as medical castration.

<span class="mw-page-title-main">Relugolix</span> Chemical compound

Relugolix, sold under the brand names Orgovyx and Relumina among others, is a gonadotropin-releasing hormone antagonist medication which is used in the treatment of prostate cancer in men and uterine fibroids in women. It is taken by mouth.

<span class="mw-page-title-main">Progonadotropin</span> Drug class

A progonadotropin, or hypergonadotropin, also known as a gonad stimulant, is a type of drug which increases the secretion of one or both of the major gonadotropins, luteinizing hormone (LH) and follicle-stimulating hormone (FSH). This, in turn, results in increased function and maintenance of the gonads and increased gonadal steroidogenesis of sex hormones such as androgens, estrogens, and progestogens. Progonadotropins are the functional opposites of antigonadotropins. They have clinical applications in the treatment of hypogonadism and infertility. Conversely, hypergonadotropic effects can occur as a side effect of some drugs. Examples of progonadotropic drugs include gonadotropin-releasing hormone (GnRH) agonists when administered in a pulsatile manner, antiestrogens such as tamoxifen, clomifene, fulvestrant, and aromatase inhibitors like anastrozole, and, only in men, pure antiandrogens such as flutamide, bicalutamide, enzalutamide, and apalutamide.

<span class="mw-page-title-main">Gonadotropin-releasing hormone modulator</span> Type of medication which modulates the GnRH receptor

A GnRH modulator, or GnRH receptor modulator, also known as an LHRH modulator or LHRH receptor modulator, is a type of medication which modulates the GnRH receptor, the biological target of the hypothalamic hormone gonadotropin-releasing hormone. They include GnRH agonists and GnRH antagonists. These medications may be GnRH analogues like leuprorelin and cetrorelix – peptides that are structurally related to GnRH – or small-molecules like elagolix and relugolix, which are structurally distinct from and unrelated to GnRH analogues.

<span class="mw-page-title-main">Linzagolix</span> Chemical compound

Linzagolix, sold under the brand name Yselty, is a medication used in the treatment of uterine fibroids. Linzagolix is a small-molecule, non-peptide, orally active gonadotropin-releasing hormone antagonist developed by Kissei Pharmaceutical and ObsEva.

Drugs and sexual desire is about sexual desire being manipulated through drugs from various approaches. Sexual desire is generated under the effects from sex hormones and microcircuits from brain regions. Neurotransmitters play essential roles in stimulating and inhibiting the processes that lead to libido production in both men and women. For instance, a positive stimulation is modulated by dopamine from the medial preoptic area in the hypothalamus and norepinephrine. At the same time, inhibition occurs when prolactin and serotonin are released for action.

References

  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. 1 2 "gonadorelin analogue". Encyclopedia.com. Retrieved 2019-09-21.
  4. 1 2 3 4 Joint Formulary Committee (2018). British National Formulary (BNF) 70. London: Pharmaceutical Press. p. 635. ISBN   978-0-85711-173-9.
  5. ↑ 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.
  6. ↑ 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.
  7. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN   9783527607495.
  8. ↑ 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.
  9. 1 2 "triptorelin (Intramuscular route)". Drugs.com. Retrieved 11 November 2016.
  10. ↑ Wylie KR, Fung Jr R, Boshier C, Rotchell M (2009). "Recommendations of endocrine treatment for patients with gender dysphoria". Sexual and Relationship Therapy. 24 (2): 175–187. doi:10.1080/14681990903023306. S2CID   20471537.
  11. ↑ 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.
  12. ↑ "Study: Drug effectively treats pedophilia". CNN . 11 February 1998.
  13. ↑ "Decapeptyl SR 11.25mg (triptorelin pamoate) - Patient Information Leaflet (PIL) - (emc)". www.medicines.org.uk. Retrieved 2022-11-14.
  14. ↑ "Gonapeptyl Depot 3.75 mg - Summary of Product Characteristics (SmPC) - (emc)". www.medicines.org.uk. Retrieved 2022-11-14.
  15. ↑ "Trelstar intramuscular: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Retrieved 2022-11-14.
  16. ↑ "Triptodur Intramuscular: Uses, Side Effects, Interactions, Pictures, Warnings & Dosing". WebMD. Retrieved 2022-11-14.
  17. ↑ "Salvacyl®, developed by Debiopharm, is launched in two European countries - a new therapeutic avenue for the treatment of sexual deviations". Debiopharm. 23 June 2009. Retrieved 2022-11-14.
  18. ↑ "About Us – Technology Transfer at Tulane University". Tulane University. Retrieved 4 January 2024.
  19. ↑ "Dr. Reddy's Launches Debiopharm's Pamorelin LA in India for the Treatment of Locally Advanced or Metastatic, Hormone-Dependent Prostate Cancer". Fierce Pharma. 7 December 2012. Retrieved 4 January 2024.
  20. ↑ 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". Current Medicinal Chemistry. 27 (40): 6825–6836. doi:10.2174/0929867326666191209142209. PMID   31814547. S2CID   208956450.

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