Compound: NAFARELIN
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(=O)N)CCC2)CCCNC(=N)N)CC(C)C)Cc3cc4c(cccc4)cc3)Cc5ccc(O)cc5)CO)Cc6c7c(cccc7)[nH]c6)Cc8nc[nH]c8)CC1
InChIKey: RWHUEXWOYVBUCI-ITQXDASVSA-N
Synonyms: NAFARELIN, 76932-56-4, Nafareline, Nafarelina, Nafarelinum, 1X0094V6JV, Lhrh, 6(d-nal(2)), DTXSID001031284, CHEBI:7445, RefChem:57060, 6-D-(2-naphthyl)alanyl-GnRH, H01CA02, DTXCID501516287, N-(5-carbamimidamido-1-(2-((carbamoylmethyl)carbamoyl)pyrrolidin-1-yl)-1-oxopentan-2-yl)-2-(2-(2-(3-hydroxy-2-(2-(3-(1H-imidazol-4-yl)-2-((5-oxopyrrolidin-2-yl)formamido)propanamido)-3-(1H-indol-3-yl)propanamido)propanamido)-3-(4-hydroxyphenyl)propanamido)-3-(naphthalen-2-yl)propanamido)-4-methylpentanamide, (2S)-N-((2S)-1-(((2S)-1-(((2S)-1-(((2S)-1-(((2R)-1-(((2S)-1-(((2S)-1-((2S)-2-((2-amino-2-oxoethyl)carbamoyl)pyrrolidin-1-yl)-5-(diaminomethylideneamino)-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-3-naphthalen-2-yl-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, MFCD00871253, Nafareline [French], Nafarelinum [Latin], Nafarelina [Spanish], Nafarelin [INN:BAN], (S)-1-(((R)-2-((S)-2-((S)-2-((S)-2-((S)-3-(1H-Imidazol-5-yl)-2-((S)-5-oxopyrrolidine-2-carboxamido)propanamido)-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido)-3-(naphthalen-2-yl)propanoyl)-L-leucyl-L-arginyl)-N-(2-amino-2-oxoethyl)pyrrolidine-2-carboxamide, NAFARELIN [INN], C66H83N17O13, UNII-1X0094V6JV, Nafarelin?, LHRH, Ala(2-naphthyl)(6)-, HS-2018, NAFARELIN [MI], NAFARELIN [VANDF], NAFARELIN [WHO-DD], SCHEMBL22518, BIDD:GT0760, GTPL3902, orb1181779, SCHEMBL29390346, SCHEMBL30198542, BDBM84707, EBC-27552, AKOS015895038, CCG-270673, DB00666, FN65097, (S)-1-(((R)-2-((S)-2-((S)-2-((S)-2-((S)-3-(1H-imidazol-4-yl)-2-((S)-5-oxopyrrolidine-2-carboxamido)propanamido)-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido)-3-(naphthalen-2-yl)propanoyl)-L-leucyl-L-arginyl)-N-(2-amino-2-oxoethyl)pyrrolidine-2-carboxamide, NS00078790, C76463, EN300-7480908, Q3869873, 5-OXOPRO-HIS-TRP-SER-TYR-D-NAL(2)-LEU-ARG-PRO-GLY-NH2, (S)-1-((3S,6S,9S,12S,15R,18S,21S)-3-((1H-imidazol-5-yl)methyl)-6-((1H-indol-3-yl)methyl)-21-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-18-isobutyl-15-(naphthalen-2-ylmethyl)-1,4,7,10,13,16,19-heptaoxo-1-((S)-5-oxopyrrolidin-2-yl)-2,5,8,11,14,17,20-heptaazadocosan-22-oyl)-N-(2-amino-2-oxoethyl)pyrrolidine-2-carboxamide
Theoretical properties:
molecular_formula: C66H83N17O13
molecular_weight: 1322.5 g/mol
exact_mass: 1321.63562577 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 16
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 33
heavy_atom_count: 96
topological_polar_surface_area: 475 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Nafarelin Acetate can cause developmental toxicity according to state or federal government labeling requirements.
chebi: An oligopeptide comprising of 5-oxo-<small>L</small>-proline, <small>L</small>-histidine, <small>L</small>-tryptophan, <small>L</small>-serine, <small>L</small>-tyrosine, 3-(2-naphthyl)-<small>D</small>-alanine, <small>L</small>-leucine, <small>L</small>-arginine and <small>L</small>-prolylglycinamide residues joined sequence by peptide linkages. It is a gonadotropin releasing hormone agonist that is used to treat central precocious puberty in children and endometriosis in women.
wikipedia: Nafarelin, sold under the brand name Synarel among others, is a gonadotropin-releasing hormone agonist (GnRH agonist) medication which is used in the treatment of endometriosis and early puberty. It is also used to treat uterine fibroids, to control ovarian stimulation in in vitro fertilization (IVF), and as part of transgender hormone therapy. The medication is used as a nasal spray two to three times per day.
Side effects of nafarelin 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. Nafarelin 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 95% in both sexes. Nafarelin is a peptide and an analogue of GnRHTooltip gonadotropin-releasing hormone.
Nafarelin was introduced for medical use in 1990. It is available widely throughout the world, including in North America, Europe, and elsewhere throughout the world. The medication is one of only two medically used GnRH analogues that are available as nasal sprays, the other being buserelin.