Compound: goserelin
SMILES: O=C1N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2[C@H](C(=O)NNC(=O)N)CCC2)CCCN=C(N)N)CC(C)C)COC(C)(C)C)Cc3ccc(O)cc3)CO)Cc4c5c(cccc5)[nH]c4)Cc6[nH]cnc6)CC1
InChIKey: BLCLNMBMMGCOAS-URPVMXJPSA-N
Synonyms: goserelin, 65807-02-5, Decapeptide I, Goserelina, Gosereline, Goserelinum, ICI-118630, ICI 118630, ICI 118,630, 0F65R8P09N, DTXSID7048297, ICI118630, Acetate, Goserelin, RefChem:57538, DTXCID2028272, L02AE03, 6-(O-(1,1-Dimethylethyl)-D-serine)-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig) 2-(aminocarbonyl)hydrazide, (2S)-1-((2S)-2-((2S)-2-((2R)-3-(tert-butoxy)-2-((2S)-2-((2S)-3-hydroxy-2-((2S)-2-((2S)-3-(1H-imidazol-5-yl)-2-(((2S)-5-oxopyrrolidin-2-yl)formamido)propanamido)-3-(1H-indol-3-yl)propanamido)propanamido)-3-(4-hydroxyphenyl)propanamido)propanamido)-4-methylpentanamido)-5-((diaminomethylidene)amino)pentanoyl)-N-(carbamoylamino)pyrrolidine-2-carboxamide, (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-(3H-imidazol-4-yl)-1-oxopropan-2-yl)-5-oxopyrrolidine-2-carboxamide, Zoladex, 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, Gosereline [French], Goserelinum [Latin], Goserelina [Spanish], Goserelin [USAN:INN:BAN], UNII-0F65R8P09N, goserelin-acetate, Goserelin CRS, HSDB 7606, C59H84N18O14, MFCD00867894, HS-2015, ZD-9393, GOSERELIN [INN], GOSERELIN [MI], Goserelin (USAN/INN), GOSERELIN [HSDB], GOSERELIN [USAN], D-Ser(t-Bu)(sup 6)aza-gly(sup 10)-GNRH, GOSERELIN [MART.], GOSERELIN [WHO-DD], SCHEMBL8643, (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, CHEBI:5523, GTPL3879, orb1179810, CHEMBL1201247, GOSERELIN [EP MONOGRAPH], SCHEMBL19712239, SCHEMBL20459194, SCHEMBL29381733, SCHEMBL29405686, SCHEMBL29551046, SCHEMBL29833872, HMS2089D16, BDBM50247974, EBC-27545, EX-A15488, Goserelin for NMR identification CRS, AKOS015994653, AKOS030213245, DB00014, NCGC00390804-01, (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, FS110042, HY-13673, NS00120430, (D-Ser(tBu)6,Azagly10)-LHRH (free base), D04405, AB01275466-01, EN300-7480905, Q1992653, BRD-K99504665-001-01-2, (S)-N-((6S,9S,12R,15S,18S,21S,24S)-21-((1H-indol-3-yl)methyl)-1,1-diamino-12-(tert-butoxymethyl)-6-((S)-2-(2-carbamoylhydrazine-1-carbonyl)pyrrolidine-1-carbonyl)-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
Theoretical properties:
molecular_formula: C59H84N18O14
molecular_weight: 1269.4 g/mol
exact_mass: 1268.64143943 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 17
hydrogen_bond_acceptor_count: 16
rotatable_bond_count: 32
heavy_atom_count: 91
topological_polar_surface_area: 496 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: Soluble
Descriptions:
pubchem: Goserelin is an organic molecular entity.
chembl: GOSERELIN is a protein listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: 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. 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. Goserelin is a therapeutic alternative on the World Health Organization's List of Essential Medicines.