Compound: BUSERELIN
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)NCC)CCC2)CCCNC(=N)N)CC(C)C)COC(C)(C)C)Cc3ccc(O)cc3)CO)Cc4c5c(cccc5)[nH]c4)Cc6[nH]cnc6)CC1
InChIKey: CUWODFFVMXJOKD-UVLQAERKSA-N
Synonyms: BUSERELIN, 57982-77-1, Etilamide, Buserelina, Busereline, Buserelinum, Tiloryth, PXW8U3YXDV, HOE 766, ICI 123215, DTXSID301024155, NSC725176, RefChem:54577, L02AE01, DTXCID601508411, S74-6766, 261-061-9, 6-(O-(1,1-Dimethylethyl)-D-serine)-9-(N-ethyl-L-prolinamide)-10-deglycinamide Luteinizing Hormone-Releasing Factor (Pig), 6-(O-(1,1-Dimethylethyl)-D-serine)-9-(N-ethyl-L-prolinamide)-10-deglycinamide-luteinizing Hormone-releasing Factor (Pig), (2S)-N-((2S)-1-(((2S)-1-(((2S)-1-(((2S)-1-(((2R)-1-(((2S)-1-(((2S)-5-(diaminomethylideneamino)-1-((2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl)-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, (Des-Gly10,D-Ser(tBu)6,Pro-NHEt9)-LHRH, Buserelin (INN), BUSERELIN [INN], Buserelin [INN:BAN], UNII-PXW8U3YXDV, Busereline [INN-French], Buserelinum [INN-Latin], C60H86N16O13, Buserelina [INN-Spanish], Metrelef, CCRIS 2657, HOE 766A, Tiloryth (TN), EINECS 261-061-9, D-Ser-(TBu)(sup 6)-LHRH-ethylamide, BUSERELIN [MI], (D-Ser(tbu)(sup 6)-EA(sup 10))-LHRH, BUSERELIN [MART.], BUSERELIN [WHO-DD], SCHEMBL13354, S 746766, GTPL3860, pE-HWSY(dS)(tBu)LRP-NHEt, BUSERELIN [EP MONOGRAPH], Buserelin for NMR identification, CHEMBL2110824, D-Ser(tbu(sup 6))-LH-RH-(1-9)-nonapeptide ethylamide, SCHEMBL19409318, SCHEMBL19459955, SCHEMBL29371677, SCHEMBL29598917, SCHEMBL29833854, Buserelin for peak identification, CHEBI:135907, CUWODFFVMXJOKD-UVLQAERKSA-N, (D-Ser(Bu(sup t)(sup 6)))-LH-RH(1-9)nonapeptide-ethylamide, Buserelin for NMR identification CRS, MFCD00941414, AKOS015994645, AKOS030213242, HS-2005, NCGC00181295-01, 1-9-Luteinizing hormone-releasing factor (swine),6-[O-(1,1-dimethylethyl)-D-serine]-9-(N-ethyl-L-prolinamide)-, FD109219, D07259, H37445, Q414745, Pyr-His-Trp-Ser-Tyr-D-Ser(tBu)-Leu-Arg-Pro-NHEt, (Des-Gly10,D-Ser(tBu)6,Pro-NHEt 9)-LHRH acetate salt, (S)-1-((3S,6S,9S,12S,15R,18S,21S)-3-((1H-imidazol-5-yl)methyl)-6-((1H-indol-3-yl)methyl)-15-(tert-butoxymethyl)-21-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-18-isobutyl-1,4,7,10,13,16,19-heptaoxo-1-((S)-5-oxopyrrolidin-2-yl)-2,5,8,11,14,1, 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-O-(2-methyl-2-propanyl)-D-seryl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide, 5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosyl-o-tert-butyl-d-seryl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide
Theoretical properties:
molecular_formula: C60H86N16O13
molecular_weight: 1239.4 g/mol
exact_mass: 1238.65602686 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 15
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 33
heavy_atom_count: 89
topological_polar_surface_area: 441 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Buserelin is an oligopeptide.
chembl: BUSERELIN is a protein listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Buserelin, sold under the brand name Suprefact among others, is a medication which is used primarily in the treatment of prostate cancer and endometriosis. It is also used for other indications such as the treatment of premenopausal breast cancer, uterine fibroids, and early puberty, in assisted reproduction for female infertility, and as a part of transgender hormone therapy. In addition, buserelin is used in veterinary medicine. The medication is typically used as a nasal spray three times per day, but is also available for use as a solution or implant for injection into fat.
Side effects of buserelin are related to sex hormone deprivation and include symptoms of low testosterone levels and low estrogen levels such as hot flashes, sexual dysfunction, vaginal atrophy, and osteoporosis. Buserelin is a gonadotropin-releasing hormone agonist (GnRH agonist) and works by preventing the production of sex hormones by the gonads. It can lower sex hormone levels by about 95% in both sexes. Buserelin is a peptide and an analogue of GnRHTooltip gonadotropin-releasing hormone.
Buserelin was first patented in 1974 and approved for medical use in 1985. It is not available in the United States, but is marketed widely elsewhere in the world, including in the United Kingdom, Canada, and many other countries. The medication is one of only two medically used GnRH analogues that are available as nasal sprays, the other being nafarelin. Buserelin is available as a generic medication.