Goserelin

Goserelin
Clinical data
Trade names	Zoladex, others
Other names	D-Ser(But)6Azgly10-GnRH
AHFS/Drugs.com	Monograph
MedlinePlus	a601002
Routes of; administration	Implant
Drug class	GnRH analogue; GnRH agonist; Antigonadotropin
ATC code	L02AE03 (WHO) ;
Legal status
Legal status	CA: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	27.3%
Elimination half-life	4–5 hours
Identifiers
	IUPAC name N-(21-((1H-indol-3-yl)methyl)-1,1-diamino-12-(tert-butoxymethyl)-6-(2-(2-carbamoylhydrazinecarbonyl)cyclopentanecarbonyl)-15-(4-hydroxybenzyl)-18-(hydroxymethyl)-25-(1H-imidazol-5-yl)-9-isobutyl-8,11,14,17,20,23-hexaoxo-2,7,10,13,16,19,22-heptaazapentacos-1-en-24-yl)-5-oxopyrrolidine-2-carboxamide;
CAS Number	65807-02-5 ;
PubChem CID	5311128;
IUPHAR/BPS	3879;
DrugBank	DB00014 ;
ChemSpider	4470656 ;
UNII	0F65R8P09N;
KEGG	D04405 ;
ChEBI	CHEBI:5523 ;
ChEMBL	ChEMBL1201247 ;
CompTox Dashboard (EPA)	DTXSID7048297 ;
ECHA InfoCard	100.212.024
Chemical and physical data
Formula	C59H84N18O14
Molar mass	1269.433 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)C[C@H](NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NNC(N)=O;
	InChI InChI=1S/C59H84N18O14/c1-31(2)22-40(49(82)68-39(12-8-20-64-57(60)61)56(89)77-21-9-13-46(77)55(88)75-76-58(62)90)69-54(87)45(29-91-59(3,4)5)74-50(83)41(23-32-14-16-35(79)17-15-32)70-53(86)44(28-78)73-51(84)42(24-33-26-65-37-11-7-6-10-36(33)37)71-52(85)43(25-34-27-63-30-66-34)72-48(81)38-18-19-47(80)67-38/h6-7,10-11,14-17,26-27,30-31,38-46,65,78-79H,8-9,12-13,18-25,28-29H2,1-5H3,(H,63,66)(H,67,80)(H,68,82)(H,69,87)(H,70,86)(H,71,85)(H,72,81)(H,73,84)(H,74,83)(H,75,88)(H4,60,61,64)(H3,62,76,90)/t38-,39-,40-,41-,42-,43-,44-,45+,46-/m0/s1 ; Key:BLCLNMBMMGCOAS-URPVMXJPSA-N ;
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Goserelin, sold under the brand name Zoladex among others, is a medication which is used to suppress production of the sex hormones (testosterone and estrogen), particularly in the treatment of breast cancer and prostate cancer.^[2]^[3] It is an injectable gonadotropin releasing hormone agonist (GnRH agonist).

Structurally, it is a decapeptide. It is the natural GnRH decapeptide with two substitutions to inhibit rapid degradation.

Goserelin stimulates the production of the sex hormones testosterone and estrogen in a non-pulsatile (non-physiological) manner. This causes the disruption of the endogenous hormonal feedback systems, resulting in the down-regulation of testosterone and estrogen production.

It was patented in 1976 and approved for medical use in 1987.^[4] It is on the World Health Organization's List of Essential Medicines.^[5]

^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
^ Dictionary of Organic Compounds. CRC Press. 1996. pp. 3372–. ISBN 978-0-412-54090-5.
^ Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 136–. ISBN 978-94-011-4439-1.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 9783527607495.
^ 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.

[1] "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.

[CRCPress-2] Dictionary of Organic Compounds. CRC Press. 1996. pp. 3372–. ISBN 978-0-412-54090-5.

[MortonHall2012-3] Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 136–. ISBN 978-94-011-4439-1.

[Fis2006-4] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 514. ISBN 9783527607495.

[WHO22nd-5] 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.

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