Goserelin

Goserelin, renowned for its synthetic nature, stands as a quintessential hormone deployed within the biomedicine industry, efficaciously combatting a myriad of hormone-responsive malignancies encompassing prostate and breast cancer. Its mechanism of action materializes through the tenacious inhibition of specific hormone synthesis, thus auspiciously subjugating the unbridled expansion of tumor cells while additionally alleviating consequential manifestations.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: R2019

CAS No:65807-02-5

Synonyms/Alias:goserelin;65807-02-5;Zoladex;Decapeptide I;Goserelina;Gosereline;Goserelinum;ICI 118630;ICI-118630;UNII-0F65R8P09N;Goserelinum [Latin];ICI 118,630;HSDB 7606;0F65R8P09N;D-Ser(t-Bu)(sup 6)aza-gly(sup 10)-GNRH;DTXSID7048297;Goserelinum (Latin);GOSERELIN (MART.);GOSERELIN [MART.];1-(5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-O-tert-butyl-D-seryl-L-leucyl-L-arginyl-L-prolyl)semicarbazide;1233494-97-7;GOSERELIN (EP MONOGRAPH);GOSERELIN [EP MONOGRAPH];(2S)-1-[(2S)-2-[(2S)-2-[(2R)-3-(TERT-BUTOXY)-2-[(2S)-2-[(2S)-3-HYDROXY-2-[(2S)-2-[(2S)-3-(1H-IMIDAZOL-4-YL)-2-{[(2S)-5-OXOPYRROLIDIN-2-YL]FORMAMIDO}PROPANAMIDO]-3-(1H-INDOL-3-YL)PROPANAMIDO]PROPANAMIDO]-3-(4-HYDROXYPHENYL)PROPANAMIDO]PROPANAMIDO]-4-METHYLPENTANAMIDO]-5-CARBAMIMIDAMIDOPENTANOYL]-N-(CARBAMOYLAMINO)PYRROLIDINE-2-CARBOXAMIDE;(S)-N-((6S,9S,12R,15S,18S,21S,24S)-21-((1H-indol-3-yl)methyl)-1-amino-12-(tert-butoxymethyl)-6-((S)-2-(2-carbamoylhydrazine-1-carbonyl)pyrrolidine-1-carbonyl)-15-(4-hydroxybenzyl)-18-(hydroxymethyl)-25-(1H-imidazol-4-yl)-1-imino-9-isobutyl-8,11,14,17,20,23-hexaoxo-2,7,10,13,16,19,22-heptaazapentacosan-24-yl)-5-oxopyrrolidine-2-carboxamide;Gosereline [French];Goserelina [Spanish];MFCD01747329;Goserelin [USAN:INN:BAN];goserelin-acetate;MFCD00867894;HS-2015;ZD-9393;GOSERELIN [INN];GOSERELIN [MI];Goserelin (USAN/INN);GOSERELIN [HSDB];GOSERELIN [USAN];GOSERELIN [WHO-DD];SCHEMBL8643;CHEBI:5523;GTPL3879;CHEMBL1201247;DTXCID2028272;SCHEMBL19712239;SCHEMBL20459194;L02AE03;HMS2089D16;AKOS015994653;AKOS030213245;DB00014;NCGC00390804-01;FS110042;HY-13673;[D-Ser(tBu)6,Azagly10]-LHRH acetate salt;NS00120430;(D-Ser(tBu)6,Azagly10)-LHRH (free base);D04405;AB01275466-01;EN300-7480905;Q1992653;BRD-K99504665-001-01-2;6-(O-(1,1-Dimethylethyl)-D-serine)-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig) 2-(aminocarbonyl)hydrazide;

Chemical Name:(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[(2S)-2-[(carbamoylamino)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide

Custom Peptide Synthesis
cGMP Peptide
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M.F/Formula
C59H84N18O14
M.W/Mr.
1269.4
Sequence
One Letter Code:XHWSYXLRP
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-D-Ser(tBu)-Leu-Arg-Pro-NHNHCONH2

Goserelin is a synthetic decapeptide analogue of luteinizing hormone-releasing hormone (LHRH), also known as gonadotropin-releasing hormone (GnRH). Structurally engineered to enhance metabolic stability and receptor affinity, it functions as a potent GnRH agonist, exerting precise regulatory effects on the hypothalamic-pituitary-gonadal axis. Its biochemical significance lies in its ability to modulate the secretion of gonadotropins—luteinizing hormone (LH) and follicle-stimulating hormone (FSH)—through sustained receptor activation and subsequent downregulation. Goserelin's unique properties make it a valuable tool in endocrine research, signal transduction studies, and the exploration of peptide-based regulatory mechanisms within reproductive biology.

Endocrine signaling research: Goserelin serves as an essential probe for dissecting the molecular mechanisms underlying GnRH receptor activation and downstream signaling pathways. By mimicking endogenous GnRH, it allows researchers to investigate receptor binding kinetics, desensitization processes, and the intricate feedback loops that govern gonadotropin release. Its use in in vitro and in vivo models provides critical insights into the regulation of reproductive hormones and the broader physiological roles of GnRH analogues in neuroendocrine systems.

Peptide-receptor interaction studies: The compound is widely employed in the characterization of ligand-receptor interactions, particularly within the context of GnRH receptor pharmacology. Its high affinity and resistance to enzymatic degradation enable reproducible experiments focusing on receptor binding specificity, conformational changes, and receptor internalization. These studies are pivotal for elucidating the structural determinants of peptide-receptor recognition and for guiding the rational design of next-generation peptide therapeutics and molecular probes.

Reproductive axis modulation: In preclinical models, goserelin is utilized to induce controlled suppression of the hypothalamic-pituitary-gonadal axis, facilitating investigations into the physiological consequences of altered gonadotropin levels. Such modulation is instrumental for exploring the roles of sex steroids in development, fertility, and metabolic regulation. Researchers leverage its predictable pharmacodynamics to create reversible states of hormonal suppression, supporting studies in endocrinology, developmental biology, and reproductive toxicology.

Peptide synthesis and analog development: As a well-characterized GnRH analogue, goserelin is frequently referenced in the synthesis and optimization of novel peptide-based ligands. Its sequence modifications, which confer enhanced stability and bioactivity, serve as a template for the development of new analogues with tailored properties. Synthetic chemists and peptide engineers use it as a benchmark to validate synthetic methodologies, assess structure-activity relationships, and advance the design of innovative peptide scaffolds for research applications.

Analytical method validation: The compound also plays a role in the calibration and validation of analytical techniques designed to quantify GnRH analogues and related peptides. Its defined structure and consistent bioactivity make it an ideal standard for high-performance liquid chromatography (HPLC), mass spectrometry, and immunoassay platforms. By providing a reliable reference, goserelin supports the development of robust analytical protocols that are critical for quality control, pharmacokinetic studies, and the precise quantification of peptide-based research compounds.

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
InChI Key
BLCLNMBMMGCOAS-URPVMXJPSA-N
Canonical SMILES
CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NNC(=O)N)NC(=O)C(COC(C)(C)C)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6
Isomeric SMILES
CC(C)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NNC(=O)N)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6

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