129311-55-3

Basic information

• Product Name: Ganirelix
• Synonyms: GANIRELIX;N-Acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N6-[bis(ethylaMino)Methylene]-D-lysyl-L-leucyl-N6-[bis(ethylaMino)Methylene]-L-lysyl-L-prolyl-;Ganirelix acetate salt;N-Acetyl-3-(2-naphthalenyl)-D-alanyl-4-chloro-D-phenylalanyl-3-(3-pyridinyl)-D-alanyl-L-seryl-L-tyrosyl-N6-[bis(ethylamino)methylene]-D-lysyl-L-leucyl-N6-[bis(ethylamino)methylene]-L-lysyl-L-prolyl-D-alaninamide diacetate
• CAS NO: 129311-55-3
• Molecular Formula: C80H113ClN18O13
• Molecular Weight: 1570.31902
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 129311-55-3.mol
• Article Data: 0

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: white/
• Density: 1.31g/cm³
• Storage Temp.: ?20°C
• PKA: 4.2 (3-pyridinylalanine); 9.8 (tyrosine)
• CAS DataBase Reference: Ganirelix(CAS DataBase Reference)
• NIST Chemistry Reference: Ganirelix(129311-55-3)
• EPA Substance Registry System: Ganirelix(129311-55-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• WGK Germany: 3
• Hazardous Substances Data: 129311-55-3(Hazardous Substances Data)

Usage

Description

Ganirelix, also known as Ganirelix Acetate, is a decapeptide LH-RH antagonist that functions as a highly bioavailable compound. It is a third-generation LH-RH antagonist, introduced as prefilled syringes for subcutaneous injections. Ganirelix is designed to inhibit premature luteinizing hormone (LH) surges in women undergoing controlled ovarian hyperstimulation. As an analog of luteinizing hormone-releasing hormone (LH-RH), it effectively blocks the endogenous release of LH and follicle-stimulating hormone (FSH), which are crucial for ovulation induction. Due to its short half-life, pituitary-gonadal function is rapidly recovered after treatment discontinuation. Ganirelix is known for its minimal histamine-releasing effects, avoiding side effects such as facial and extremities edema. It is also highly resistant to hydrolysis and has good water solubility, distinguishing it from other LH-RH antagonists.

Uses

Used in Infertility Treatment:
Ganirelix is used as a therapeutic agent for the treatment of infertility. It is particularly effective in preventing premature LH surges during controlled ovarian hyperstimulation with recombinant FSH before in vitro fertilization or similar reproductive techniques. This helps in achieving better outcomes in assisted reproductive technology by ensuring optimal timing for ovulation.
Used in Reproductive Medicine:
In the field of reproductive medicine, Ganirelix is used as a decapeptide LH-RH antagonist to manage and control the hormonal environment during fertility treatments. Its ability to block the release of LH and FSH allows for better control over the process of ovulation, leading to improved success rates in fertility treatments.
Brand Name:
Orgalutran

Originator

Roche Bioscience (US)

Biochem/physiol Actions

Ganirelix is a decapeptide GnRH antagonist. Ganirelix acts by blocking the action of GnRH upon the pituitary, thus rapidly suppressing the production and action of LH and FSH.

InChI:InChI=1/C80H113ClN18O13.2C2H4O2/c1-9-84-79(85-10-2)88-39-17-15-27-60(70(104)94-62(42-49(5)6)71(105)93-61(28-16-18-40-89-80(86-11-3)87-12-4)78(112)99-41-21-29-68(99)77(111)90-50(7)69(82)103)92-72(106)63(44-53-32-36-58(102)37-33-53)97-76(110)67(48-100)98-74(108)65(45-54-22-20-38-83-47-54)96-73(107)64(43-52-30-34-57(81)35-31-52)95-75(109)66(91-51(8)101)46-56-25-19-24-55-23-13-14-26-59(55)56;2*1-2(3)4/h13-14,19-20,22-26,30-38,47,49-50,60-68,100,102H,9-12,15-18,21,27-29,39-46,48H2,1-8H3,(H2,82,103)(H,90,111)(H,91,101)(H,92,106)(H,93,105)(H,94,104)(H,95,109)(H,96,107)(H,97,110)(H,98,108)(H2,84,85,88)(H2,86,87,89);2*1H3,(H,3,4)/t50-,60-,61+,62+,63+,64-,65-,66-,67+,68+;;/m1../s1