Alarelin
[CAS# 79561-22-1]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other protected amino acids
• Name: Alarelin
• Synonyms: acetic acid;(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]-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
• Molecular Formula: C₆₀H₈₆N₁₆O₁₆
• Molecular Weight: 1287.42
• Protein Sequence: XHWSYALRP
• CAS Registry Number: 79561-22-1
• EC Number: 635-974-1
• SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6.CC(=O)O.CC(=O)O

Properties

• Solubility: 10mM (DMSO)

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H360
• Safety Statements: P203-P280-P318-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	1B	H360

Discovery and Applications

Alarelin, a synthetic analog of gonadotropin-releasing hormone (GnRH), was developed to mimic the natural hormone's effects but with increased potency and stability. First synthesized in the late 20th century, Alarelin was designed to control and manipulate the reproductive system more effectively. This discovery was part of broader research into peptide hormones and their analogs, driven by the need to manage reproductive health issues in both humans and animals. The synthesis of Alarelin provided researchers and clinicians with a powerful tool for regulating the secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH), essential for fertility and reproductive function.

Alarelin is used in the treatment of reproductive health disorders. It can induce ovulation in women undergoing fertility treatments, making it a valuable drug in assisted reproductive technologies such as in vitro fertilization (IVF). By stimulating the release of LH and FSH, Alarelin helps in the maturation and release of eggs, improving the chances of successful conception.

In women with endometriosis, Alarelin helps manage symptoms by reducing the levels of estrogen in the body. This hormonal regulation can shrink endometrial tissue and alleviate pain, providing relief to patients who suffer from this chronic condition. Alarelin's ability to modulate hormone levels makes it an effective treatment option for managing endometriosis.

Alarelin is widely used in veterinary medicine to manage the reproductive cycles of livestock and other animals. It is used to synchronize estrus in female animals, improving breeding programs and increasing reproductive efficiency. This application is particularly important in the dairy and meat industries, where controlled breeding is essential for productivity and economic efficiency.

In scientific research, Alarelin serves as a valuable tool for studying the endocrine system and reproductive physiology. Researchers use it to investigate the mechanisms of hormone release, the effects of GnRH analogs on different tissues, and the regulation of reproductive cycles. Alarelin's precise and potent effects make it ideal for experimental studies aimed at understanding hormonal control and developing new therapeutic strategies.

Alarelin is also being explored for its potential in treating hormone-dependent cancers, such as prostate and breast cancer. By downregulating the production of sex hormones, Alarelin can inhibit the growth of hormone-sensitive tumors. This application is still under research but shows promise as part of hormone therapy for certain cancers.

References

2019. A Second Dose of GnRHa in Combination with Luteal GnRH Antagonist May Eliminate Ovarian Hyperstimulation Syndrome in Women with ≥30 Follicles Measuring ≥11 mm in Diameter on Trigger Day and/or Pre-trigger Peak Estradiol Exceeding 10 000 pg/mL. Current Medical Science, 39(2).
DOI: 10.1007/s11596-019-2031-5

2017. Pre-treatment with GnRHa or ulipristal acetate prior to laparoscopic and laparotomic myomectomy: A systematic review and meta-analysis. PLOS ONE, 12(10).
DOI: 10.1371/journal.pone.0186158

2016. Gonadotropin-Releasing Hormone Analogue Treatment in Females with Moderately Early Puberty: No Effect on Final Height. Journal of Clinical Research in Pediatric Endocrinology, 8(2).
DOI: 10.4274/jcrpe.2356