(D-2-Nal6)-LHRH acetate salt

Names

[ Name ]:
(D-2-Nal6)-LHRH acetate salt

[Synonym ]:
(2S)-N-(2-amino-2-oxoethyl)-1-{(2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-(2-methylpropyl)-8-(naphthalen-2-ylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-[(2S)-5-oxopyrrolidin-2-yl]-3,6,9,12,15,18,21-heptaazadocosan-1-oyl}pyrrolidine-2-carboxamide (non-preferred name)
Nacenyl
(2S)-N-(2-Amino-2-oxoethyl)-1-{(2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-isobutyl-8-(2-naphthylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-[(2S)-5-oxopyrrolidin-2-yl]-3,6,9,12,15,18,21-heptaazadocosan-1-oyl}pyrrolidine-2-carboxamide (non-preferred name)
Nafareline
UNII:1X0094V6JV
Synarel
(2S)-N-(2-Amino-2-oxoethyl)-1-{(2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-isobutyl-8-(2-naphthylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-[(2S)-5-oxo-2-pyrrolidinyl]-3,6,9,12,15,18,21-heptaazadocosan-1-oyl}-2-pyrrolidinecarboxamide
6-(3-(2-Naphthalenyl)-D-alanine)luteinizing Hormone-releasing Factor
glycinamide, 5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthalenyl)-D-alanyl-L-leucyl-L-arginyl-L-prolyl-
Synrelina
Nasanyl
Nafarelin Acetate

Biological Activity

[Description]:

Nafarelin is a gonadotropin-releasing hormone (GnRH) agonist that stimulates secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). Sequence: {Glp}-His-Trp-Ser-Tyr-{2-Naph-Ala}-Leu-Arg-Pro-Gly-NH2.

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> GNRH Receptor

Peptides

Research Areas >> Cancer

[Target]

GnRH[1].

[In Vitro]

Nafarelin is a gonadotropin-releasing hormone (GnRH) agonist that stimulates secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH)[1]. Nafarelin is used effectively in in vitro fertilisation programmes. Nafarelin is readily and rapidly absorbed following intranasal delivery, and is protected to some extent from enzymatic degradation GnRH[2].

[References]

[1]. Letassy NA et al. Nafarelin acetate: a gonadotropin-releasing hormone agonist for the treatment of endometriosis. DICP. 1990 Dec, 24(12):1204-9.

[2]. Chrisp P et al. Nafarelin. A review of its pharmacodynamic and pharmacokinetic properties, and clinical potential in sex hormone-related conditions.Drugs. 1990 Apr;39(4):523-51.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.5±0.1 g/cm3

[ Molecular Formula ]:
C₆₆H₈₃N₁₇O₁₃

[ Molecular Weight ]:
1322.471

[ Exact Mass ]:
1321.635620

[ PSA ]:
472.13000

[ LogP ]:
0.89

[ Index of Refraction ]:
1.711

[ Storage condition ]:
-20°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OK6371150

CHEMICAL NAME :: Luteinizing hormone-releasing factor (pig), 6-(3-(2-naphthalenyl)-D-alanine)-

CAS REGISTRY NUMBER :: 76932-56-4

LAST UPDATED :: 199703

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C66-H83-N17-O13

MOLECULAR WEIGHT :: 1322.66

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 448 ug/kg/8W-I

TOXIC EFFECTS :: Nutritional and Gross Metabolic - changes in potassium

REFERENCE :: LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 347,333,1996