Leuprorelin

Leuprorelin
ATC Code H01CA04, L02AE02
Formula C59H84N16O12
Molar Mass (g·mol−1) 1209,40
Physical State solid
Melting Point (°C) 150-155
PKS Value 9.6
CAS Number 53714-56-0
PUB Number 657181
Drugbank ID DB00007

Basics

Leuprorelin, also known as leuprolide, is a synthetic derivative of the hormone GnRH (gonadotropin-releasing hormone) used to treat prostate cancer, breast cancer, endometriosis, uterine fibroids, pubertas praecox, and as part of transgender hormone therapy. It is administered by injection into a muscle or under the skin.

Leuprorelin was first approved as a daily subcutaneous injection in 1985 under the brand name Lupron™ by Abbvie Endocrine Inc. Delayed-action intramuscular and subcutaneous variants have since been developed, which only need to be given 2 times per year. Leuprorelin remains the first-line agent for all conditions for which it is approved.

Pharmacology

Pharmacodynamics

Gonadotropin-releasing hormone (GnRH) is a naturally occurring decapeptide that modulates the so-called hypothalamic-pituitary-gonadal (HPG) axis. GnRH binds to corresponding receptors on the anterior pituitary gland in the brain, which in turn release luteinizing hormone (LH) and follicle-stimulating hormone (FSH); these in turn influence the downstream synthesis and release of the sex hormones testosterone, dihydrotestosterone, estrone, and estradiol.

Despite the variety of conditions indicated for treatment with leuprolide, the underlying mechanism of action is the same in all cases. As a GnRHR agonist, leuprorelin binds to the GnRH receptor and initially stimulates downstream LH and FSH release. This initial increase in hormone levels is responsible for some of the adverse side effects associated with treatment. After 2-4 weeks of treatment, the continuous stimulation of GnRH receptors leads to what is known as negative feedback. In this process, due to the permanently elevated hormone levels, the release of hormones is throttled, ultimately leading to low hormone levels and therapeutic effect. These effects are reversible when treatment is discontinued.

Pharmacokinetics

Leuprolide is usually administered as a long-acting single-dose formulation using either microspheres or biodegradable solid depots. Regardless of the exact formulation and the strength of the initial dose, Cmax is usually reached 4-5 hours after injection. Leuprorelin has an apparent volume of distribution of 27 L after intravenous bolus administration. Plasma protein binding is 43% and 49%. Leuprolide has a terminal elimination half-life of approximately three hours.

Toxicity

Side effects

Leuprorelin is considered extremely safe, with low dose-related toxicity and comparatively few adverse effects.

Contraindications

Women being treated for endometriosis or uterine leiomyoma must be evaluated for pregnancy prior to use.

Toxicological data

LD50, mouse, i.v.: 137 mg/kg

Markus Falkenstätter

Markus Falkenstätter
Author

Markus Falkenstätter ist Autor zu pharmazeutischen Themen in der Medizin-Redaktion von Medikamio. Er befindet sich im letzten Semester seines Pharmaziestudiums an der Universität Wien und liebt das wissenschaftliche Arbeiten im Bereich der Naturwissenschaften.

Mag. pharm Stefanie Lehenauer

Mag. pharm Stefanie Lehenauer
Lector

Stefanie Lehenauer ist seit 2020 freie Autorin bei Medikamio und studierte Pharmazie an der Universität Wien. Sie arbeitet als Apothekerin in Wien und ihre Leidenschaft sind pflanzliche Arzneimittel und deren Wirkung.

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