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| 化学名: | ナファレリン | | 英語化学名: | Nafarelin | | 别名: | (D-2-NAL6)-LHRH;NAFARELIN 98.0+%;Nafareline;C07613;Pyr-His-Trp-Ser-Tyr-D-2-Nal-Leu-Arg-Pro-Gly-NH2 acetate salt;Nacenyl;Nasanyl;RS-94991-298 | | CAS番号: | 76932-56-4 | | 分子式: | C66H83N17O13 | | 分子量: | 1322.47 | | EINECS: | 686-425-8 | | カテゴリ情報: | hormones | | Mol File: | 76932-56-4.mol |  |
| 比重(密度) | 1.49±0.1 g/cm3(Predicted) | | 溶解性 | DMSO (Slightly), Methanol (Slightly), Water (Slightly, Sonicated) | | 酸解離定数(Pka) | 9.82±0.15(Predicted) | | 外見 | Solid | | 色 | White to Off-White | | InChIKey | RWHUEXWOYVBUCI-ITQXDASVSA-N |
| | ナファレリン Usage And Synthesis |
| 効能 | 子宮内膜症治療薬, 性腺刺激ホルモン放出ホルモン受容体作動薬 | | 説明 | Nafarelin is a gonadorelin analogue. It produces an initial phase of stimulation followed by down-regulation of gonadotrophin-releasing hormone receptors, thus reducing the release of FSH and LH, leading to inhibition of androgen and oestrogen production. | | 化学的特性 | Nafarelin is a synthetic analogue of gonadotrophin-releasing hormone (GnRH), which is about 200 times more potent than the native hormone and is more resistant to proteolysis Chrisp and Goa (1990), Parker and Schimmer (2001). Like GnRH, it binds with high affinity to the GnRH receptor on anterior pituitary cells, where it acts as an agonist. | | Originator | Nafarelin Acetate,Bachem AG | | 使用 | LHRH agonist. | | brand name | Synarel (Searle). | | Therapeutic Function | Gonadotropic | | 生物学の機能 | Acutely, Nafarelin stimulates the secretion of LH and FSH from the anterior pituitary, but prolonged, continuous exposure leads to inhibition of secretion by desensitization of the pituitary gonadotropes Vickery (1985). The initial stimulation of gonadotrophin secretion results in an increase in serum concentrations of estradiol in females and testosterone in males. These then decrease to very low concentrations equivalent to those found in menopausal women and castrated men respectively. | | 臨床応用 | Nafarelin has potential wide therapeutic applications in the treatment of endometriosis, uterine leiomyoma (fibroids), malignant neoplasms, and in assisted reproduction protocols. However, its use is currently restricted to the treatment of endometriosis and in assisted reproduction protocols. | | 副作用 | Nafarelin does not have the same androgenic adverse effects as danazol, but it can cause menopausal symptoms. The most commonly reported symptoms are hot flushes, vaginal dryness, altered libido and headaches. Treatment for 6 months results in a loss of bone density. The vertebral trabecular bone density falls by nearly 9% and may not return to normal after treatment. Nafarelin also has a similar effect to oestrogen deficiency on blood lipids e.g. concentrations of total cholesterol and triglycerides may increase. | | 合成 | i. 1 mmol from preparation A was placed in the reaction vessel of a 5 L Vega 296 automatic solid phase peptide synthesizer.
ii. Following amino acids were added to the Preparation A resin:
Nα-Boc-Pro 2 equiv.
Nα-Boc-Arg 2 equiv.
Nα-Boc-Leu 2 equiv.
Nα-Boc-D-NaI 1.5 equiv.
Nα-Boc-Tyr 1.5 quiv
Nα-Boc-Ser(tBu) 2 equiv.
Nα-Boc-Trp 1.75 equiv.
Nα-Boc-His(tos) 1.75 equiv.
(pyro)Glu 2.5 equiv.
iii. Crude peptide was dissolved in 2M acetic acid and converted to acetate salt by passage through a column of AG3-X4A resin.
iv. Acetate was dissolved in minimal amount of methanol.
v. It was then reprecipitated using acetone.
vi. It was then purified using HPLC to get the Nafarelin. |
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