Leuprorelin

Leuprorelin
Clinical data
Trade names	Lupron, Eligard, Lucrin, Lupaneta, others
Other names	leuprolide, leuprolidine, A-43818, Abbott-43818, DC-2-269, TAP-144
AHFS/Drugs.com	Monograph
MedlinePlus	a685040
License data	US DailyMed: Leuprolide;
Pregnancy; category	AU: D;
Routes of; administration	implant, subcutaneous, intramuscular
Drug class	GnRH analogue; GnRH agonist; Antigonadotropin
ATC code	L02AE02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Elimination half-life	3 hours
Excretion	Kidney
Identifiers
	IUPAC name N-[1-[[1-[[1-[[1-[[1-[[1-[[5-(diaminomethylideneamino)-1-; [2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxo-pentan-2-; yl]carbamoyl]-3-methyl-butyl]carbamoyl]-3-methyl-; butyl]carbamoyl]-2-(4-hydroxyphenyl)ethyl]; carbamoyl]-2-hydroxy-ethyl]carbamoyl]-2-(1H-indol-3-; yl)ethyl]carbamoyl]-2-(3H-imidazol-4-yl)ethyl]-5-oxo-; pyrrolidine-2-carboxamide;
CAS Number	53714-56-0 ; 74381-53-6 (acetate);
PubChem CID	657181;
IUPHAR/BPS	1175;
DrugBank	DB00007 ;
ChemSpider	571356 ;
UNII	EFY6W0M8TG;
KEGG	D08113 ;
ChEMBL	ChEMBL1201199 ;
CompTox Dashboard (EPA)	DTXSID50872411 ;
ECHA InfoCard	100.161.466
Chemical and physical data
Formula	C59H84N16O12
Molar mass	1209.421 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](CO)NC(=O)[C@H](Cc3c[nH]c4c3cccc4)NC(=O)[C@H](Cc5c[nH]cn5)NC(=O)[C@@H]6CCC(=O)N6;
	InChI InChI=1S/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1 ; Key:GFIJNRVAKGFPGQ-LIJARHBVSA-N ;
	(what is this?) (verify)

Leuprorelin, also known as leuprolide, is a manufactured version of a hormone used to treat prostate cancer, breast cancer, endometriosis, uterine fibroids, for early puberty, as part of transgender hormone therapy, or to perform chemical castration of violent sex offenders.^[10]^[11]^[12] It is given by injection into a muscle or under the skin.^[10]

Leuprorelin is in the gonadotropin-releasing hormone (GnRH) analogue family of medications.^[10] It works by decreasing gonadotropins and therefore decreasing testosterone and estradiol.^[10] Common side effects include hot flashes, unstable mood, trouble sleeping, headaches, and pain at the site of injection.^[10] Other side effects may include high blood sugar, allergic reactions, and problems with the pituitary gland.^[10] Use during pregnancy may harm foetal development.^[10]

Leuprorelin was patented in 1973 and approved for medical use in the United States in 1985.^[10]^[13] It is on the World Health Organization's List of Essential Medicines.^[11] It is sold under the brand name Lupron, among others.^[10]

^ ELIGARD (Mundipharma Pty Ltd) Department of Health and Aged Care. Retrieved 30 March 2023
^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
^ "Regulatory Decision Summary for Eligard". Drug and Health Products Portal. 21 September 2023. Retrieved 2 April 2024.
^ Cite error: The named reference Lupron FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Eligard FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Fensolvi FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Viadur FDA label was invoked but never defined (see the help page).
^ Cite error: The named reference Lupron Depot FDA label was invoked but never defined (see the help page).
^ "Camcevi EPAR". European Medicines Agency (EMA). 22 March 2022. Retrieved 21 June 2022.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Leuprolide Acetate". The American Society of Health-System Pharmacists. Archived from the original on 23 December 2016. Retrieved 8 December 2016.
^ ^a ^b World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ Silvani M, Mondaini N, Zucchi A (September 2015). "Androgen deprivation therapy (castration therapy) and pedophilia: What's new". Archivio Italiano di Urologia, Andrologia. 87 (3): 222–226. doi:10.4081/aiua.2015.3.222. hdl:11568/1073189. PMID 26428645. S2CID 5181746.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 978-3-527-60749-5. Archived from the original on 20 June 2021. Retrieved 19 September 2020.

[1] ELIGARD (Mundipharma Pty Ltd) Department of Health and Aged Care. Retrieved 30 March 2023

[2] "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.

[3] "Regulatory Decision Summary for Eligard". Drug and Health Products Portal. 21 September 2023. Retrieved 2 April 2024.

[Lupron_FDA_label-4] Cite error: The named reference Lupron FDA label was invoked but never defined (see the help page).

[Eligard_FDA_label-5] Cite error: The named reference Eligard FDA label was invoked but never defined (see the help page).

[Fensolvi_FDA_label-6] Cite error: The named reference Fensolvi FDA label was invoked but never defined (see the help page).

[Viadur_FDA_label-7] Cite error: The named reference Viadur FDA label was invoked but never defined (see the help page).

[Lupron_Depot_FDA_label-8] Cite error: The named reference Lupron Depot FDA label was invoked but never defined (see the help page).

[Camcevi_EPAR-9] "Camcevi EPAR". European Medicines Agency (EMA). 22 March 2022. Retrieved 21 June 2022.

[AHFS2016-10] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Leuprolide Acetate". The American Society of Health-System Pharmacists. Archived from the original on 23 December 2016. Retrieved 8 December 2016.

[WHO21st-11] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[12] Silvani M, Mondaini N, Zucchi A (September 2015). "Androgen deprivation therapy (castration therapy) and pedophilia: What's new". Archivio Italiano di Urologia, Andrologia. 87 (3): 222–226. doi:10.4081/aiua.2015.3.222. hdl:11568/1073189. PMID 26428645. S2CID 5181746.

[Fis2006-13] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 978-3-527-60749-5. Archived from the original on 20 June 2021. Retrieved 19 September 2020.

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