nafarelin

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.

Chemical data

Formula: C66H83N17O13
Molecular weight: 1322.5 g/mol
IUPAC name: (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

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 1990
Admin. routes: topical
Indications: endometriosis, pain, infertility

via ChEMBL · EBI

Research

374 papers

Nafarelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical potential in sex hormone-related conditions.Drugs · 1990
Efficacy of nafarelin in assisted reproductive technology: a meta-analysis.Human reproduction update · 2001
Clinical use of nafarelin in the treatment of leiomyomas. A review of the literature.The Journal of reproductive medicine · 2000
Consensus statement on the use of gonadotropin-releasing hormone analogs in children.Pediatrics · 2009
Nafarelin in the management of endometriosis: quality of life assessment.American journal of obstetrics and gynecology · 1992

via PubMed

Wikidata facts

Mass: 1321.635626

Show 5 more facts

chemical formula: C₆₆H₈₃N₁₇O₁₃
canonical SMILES: CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)C(CC2=CC=CC3=CC=CC=C32)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8
isomeric SMILES: CC(C)C[C@H](NC(=O)[C@@H](CC1=CC2=C(C=CC=C2)C=C1)NC(=O)[C@H](CC3=CC=C(O)C=C3)NC(=O)[C@H](CO)NC(=O)[C@H](CC4=CNC5=C4C=CC=C5)NC(=O)[C@H](CC6=CNC=N6)NC(=O)[C@@H]7CCC(=O)N7)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N8CCC[C@H]8C(=O)NCC(N)=O
defined daily dose: 0.4
NCI Thesaurus ID: C61613

Sources (2)

via Wikidata · CC0

~9 min read

Article

16 sections

Contents

Medical uses
Dosages
Available forms
Side effects
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
History
Society and culture
Generic names
Brand names
Availability
See also
References
Further reading

{{Drugbox | Verifiedfields = verified | Watchedfields = verified | verifiedrevid = 462258124 | IUPAC_name = (2R)-N-[(2R)-5-carbamimidamido-1-[(2S)-2-[(carbamoylmethyl)carbamoyl]pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-2-[(2R)-2-[(2R)-3-hydroxy-2-[(2S)-2-[(2S)-3-(1H-imidazol-4-yl)-2-{[(2R)-5-oxopyrrolidin-2-yl]formamido}propanamido]-3-(1H-indol-3-yl)propanamido]propanamido]-3-(4-hydroxyphenyl)propanamido]-3-(naphthalen-2-yl)propanamido]-4-methylpentanamide | image = Nafarelin.svg | image_class = skin-invert-image | width = 250px