Triptorelin peptide , 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
See also: Gonadotropin-releasing hormone agonist § 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.
Triptorelin has been used as a chemical castration agent for reducing sexual urges in sex offenders.
Drug action decapeptyl triptorelin
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.
triptorelin 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 flushes 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). 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.
Antineoplastic drug
The active ingredient of triptorelin is a synthetic gonadotropin-releasing hormone (GnRH) analogue, which is also known as decapeptyl, diphereline, triptorelin acetate, gonadorelin. It is an antineoplastic drug, whose pharmacological effects are same with goserelin, buserelin, and its structure is modified by natural molecular structure of the sixth L-glycine that is replaced by D-tryptophan to promote efficiency and prolong the plasmic half-life time, as well as enhance drug efficacy. After intramuscular injection, it initially stimulates the pituitary gland to release luteinizing growth hormone (LH) and follicle-stimulating hormone (FSH). When the pituitary over a long period of stimulation will be into the refractory period, that reduced the release of gonadotropin, leading to sex hormones reduction to castrate levels. These effects are reversible. Subcutaneous administration is rapidly absorbed, and Tmax is 15min, and the effect is maximum at 1h.
Antineoplastic drug2
The intramuscular injection of sustained release formulations can maintain the efficacy reaching 28d or more. It Clinically uses for the treatment of endometriosis, hormone-dependent prostate cancer, breast cancer, precocious puberty, as well as it may also be used as assisted reproductive technology. The main side effects of triptorelin are as follows: In the early stage of treatment of male, it can cause urinary disorders, breast swelling and pain, bone pain, and it may also cause hot flashes, loss of libido and impotence. It rarely cause gynecomastia, testicular atrophy, and sleep disorders.
In the first week of treatment for children, girls will occur small amount of vaginal bleeding, which can be corrected by short-term additional therapy. During the treatment of women, hot flashes, bleeding or bleeding spots, vaginal dryness, headaches and weakness can occur. It can cause abdominal and (or) pelvic pain when it uses combination with gonadotropin. Since the concentration of estrogen reduces to the level of post-menopause, it can cause slight loss of trabecular bone matrix. Generally, after cessation of treatment six to nine months the adverse reations can return to normal. There may be irreversible amenorrhea after treatment in patients with endometriosis.
Description
Decapeptyl is a modified (D-Trp6) LH-RH. Like recently marketed buserelin and leuprolide (I). It is useful in achieving medical castration in the treatment of advanced prostate cancer.
Uses promoting ovulation
Triptorelin is a GnRH agaonist shown to inhibit estradiol-induced cancer cell proliferation.
[D-Trp6]-LH-RH (luteinizing hormone releasing hormone) has been used to study whether the (M. – X) region in electron capture dissociation provides information on amino acid composition of polypeptides. It is also used to study the effect of LH-RH on the production of progesterone (P). Estradiol (E2) or human chorionic gonadotropin (hCG) by JEG-3 choriocarcinoma cells.
Definition ChEBI: An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-tryptophyl, leucyl, arginyl, prolyl and glycinamide residues joined in sequence. It is an agonist analogue of gonadotropin-releasing hormone.
Triptorelin Chemical Properties
Melting point >180°C (dec.)
alpha D23 -58.8° (c = 0.33 in acetic acid)
density 1.52±0.1 g/cm3(Predicted)
storage temp. -20°C
solubility Aqueous Base (Slightly), Methanol (Very Slightly, Heated, Sonicated)
pka 9.82±0.15(Predicted)
form powder
color White to Off-White
Stability: Hygroscopic
InChIKey HPPONSCISKROOD-OYLNGHKZSA-N
CAS DataBase Reference 57773-63-4(CAS DataBase Reference)
More Introduction:https://en.wikipedia.org/wiki/Triptorelin
