Goserelin

Goserelin

Clinical data
Trade names	Zoladex
AHFS/Drugs.com	Monograph
MedlinePlus	a601002
Pregnancy category	D (3.6mg) / X (10.8mg) (USA)
Routes of administration	implant
ATC code	L02AE03 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	27.3%
Biological half-life	4-5 hours
Excretion	hepatic
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
Synonyms	D-Ser(But)6Azgly10LHRH
CAS Number	65807-02-5 Y
PubChem CID	5311128
IUPHAR/BPS	3879
DrugBank	DB00014 Y
ChemSpider	4470656 Y
UNII	0F65R8P09N
KEGG	D04405 Y
ChEBI	CHEBI:5523 N
ChEMBL	CHEMBL1201247 N
ECHA InfoCard	100.212.024
Chemical and physical data
Formula	C59H84N18O14
Molar mass	1269.410 g/mol
3D model (Jmol)	Interactive image
SMILES CC(C)C[C@H](NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)[C@H](CC1=CN=CN1)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 Y Key:BLCLNMBMMGCOAS-URPVMXJPSA-N Y
NY (what is this?)

Goserelin (INN, USAN, BAN) (brand name Zoladex, by AstraZeneca), or goserelin acetate, is a drug used to suppress production of the sex hormones (testosterone and estrogen), particularly in the treatment of breast and prostate cancer. It is an injectable gonadotropin releasing hormone superagonist (GnRH agonist), also known as a luteinizing hormone releasing hormone (LHRH) agonist.

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

Goserelin acetate 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.

Zoladex was approved by the U.S. Food and Drug Administration in 1989 for treatment of prostate cancer.

Goserelin is a synthetic analogue of a naturally occurring luteinizing-hormone releasing hormone (LHRH). Bioavailability is almost complete. Goserelin is poorly protein bound and has a serum elimination half-life of two to four hours in patients with normal renal function. The half-life increases with patients with impaired renal function. There is no significant change in pharmacokinetics in subjects with liver failure. After administration, peak serum concentrations are reached in about two hours. It rapidly binds to the LHRH receptor cells in the pituitary gland thus leading to an initial increase in production of luteinizing hormone and thus leading to an initial increase in the production of corresponding sex hormones. This initial flare may be treated by co-prescribing/co-administering an androgen receptor antagonist such as bicalutamide (Casodex). Eventually, after a period of about 14–21 days, production of LH is greatly reduced due to receptor downregulation, and sex hormones are generally reduced to castrate levels.