Ganirelix acetate
new
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 333111

CAS#: 123246-29-7 (acetate)

Description: Ganirelix is is an antagonist of GnRH that competitively antagonizes the gonadotropic GnRH receptor, thereby mutating the pathway and causing rapid and reversible inhibition of gonadotropin (luteinizing hormone LH and follicle stimulating hormone FSH) secretion. Ganirelix Acetate acts by competitively blocking the GnRH receptors on the pituitary gonadotroph and subsequent transduction pathway. It induces a rapid, reversible suppression of gonadotropin secretion. The suppression of pituitary LH secretion by Ganirelix Acetate is more pronounced than that of FSH.


Chemical Structure

img
Ganirelix acetate
CAS# 123246-29-7 (acetate)

Theoretical Analysis

MedKoo Cat#: 333111
Name: Ganirelix acetate
CAS#: 123246-29-7 (acetate)
Chemical Formula: C84H121ClN18O17
Exact Mass: 0.00
Molecular Weight: 1,690.451
Elemental Analysis: C, 59.68; H, 7.22; Cl, 2.10; N, 14.91; O, 16.09

Price and Availability

Size Price Availability Quantity
25mg USD 450 2 Weeks
50mg USD 750 2 Weeks
100mg USD 1350 2 Weeks
200mg USD 2050 2 Weeks
500mg USD 3250 2 Weeks
1g USD 4850 2 Weeks
2g USD 7450 2 Weeks
Bulk inquiry

Related CAS #: 124904-93-4 (free base)   123246-29-7 (acetate)    

Synonym: D 24598; D-24598; D24598; Ganirelix; Orgalutran; RS 26306; RS26306; RS-26306;

IUPAC/Chemical Name: (S)-1-(N2-N2-((R)-2-((R)-2-((R)-2-acetamido-3-(naphthalen-2-yl)propanamido)-3-(4-chlorophenyl)propanamido)-3-(pyridin-3-yl)propanoyl)-L-seryl-L-tyrosyl-N6-(bis(ethylamino)methylene)-D-lysyl-L-leucyl-N6-(bis(ethylamino)methylene)-L-lysyl)-N-((R)-1-amino-1-oxopropan-2-yl)pyrrolidine-2-carboxamide diacetate

InChi Key: OVBICQMTCPFEBS-SATRDZAXSA-N

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

SMILES Code: C[C@H](C(N)=O)NC([C@H]1N(C([C@H](CCCC/N=C(NCC)/NCC)NC([C@H](CC(C)C)NC([C@@H](CCCC/N=C(NCC)/NCC)NC([C@H](CC2=CC=C(O)C=C2)NC([C@H](CO)NC([C@@H](CC3=CC=CN=C3)NC([C@@H](CC4=CC=C(Cl)C=C4)NC([C@@H](CC5=CC=C6C=CC=CC6=C5)NC(C)=O)=O)=O)=O)=O)=O)=O)=O)=O)CCC1)=O.CC(O)=O.CC(O)=O

Appearance: To be determined

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Ganirelix is a synthetic decapeptide and a competitive gonadotropin-releasing hormone (GnRH) antagonist. Derived from endogenous GnRH, ganirelix has amino acid substitutions. Ganirelix is indicated for controlled ovarian hyperstimulation in assisted reproduction techniques.5 The first case of pregnancy achieved after the use of ganirelix in an assisted reproduction program was reported in 1998.2 Ganirelix was first approved by the FDA on July 29, 1999.

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 1,690.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: Sönmez Ünal G, Albak Y, Yurtcu N, Yıldız Ç, Çetin M, Durna Daştan S, Gümüş E, Çetin A. Effects of metformin and ganirelix on subcutaneous endometriosis in a mouse model of autophagy-related cell death. Turk J Obstet Gynecol. 2023 Sep 4;20(3):219-226. doi: 10.4274/tjod.galenos.2023.85616. PMID: 37667560; PMCID: PMC10478719.


2: Mannaerts B. Ganirelix and the prevention of premature luteinizing hormone surges. F S Rep. 2023 Feb 24;4(2 Suppl):56-61. doi: 10.1016/j.xfre.2023.02.009. PMID: 37223764; PMCID: PMC10201301.


3: Chatterjee S, Bandyopadhyay A. Synthesis and characterization of two potential impurities (des-ethyl-Ganirelix) generated in the Ganirelix manufacturing process. J Pept Sci. 2023 Sep;29(9):e3489. doi: 10.1002/psc.3489. Epub 2023 Apr 13. PMID: 36967632.


4: Ummiti K, Kumar JVS, Prasad MM, Subbappa PK. Evaluation of effects of temperature and humidity on the secondary structure of Ganirelix in an injectable formulation and comparison with Orgalutran® using circular dichroism spectroscopy. Chirality. 2023 Jul;35(7):427-434. doi: 10.1002/chir.23552. Epub 2023 Feb 26. PMID: 36843151.


5: Salas A, García-García P, Díaz-Rodríguez P, Évora C, Almeida TA, Delgado A. New local ganirelix sustained release therapy for uterine leiomyoma. Evaluation in a preclinical organ model. Biomed Pharmacother. 2022 Dec;156:113909. doi: 10.1016/j.biopha.2022.113909. Epub 2022 Oct 21. PMID: 36279721.


6: Li R, Gong F, Chen H, Wang Q, Qiao J. Correlation of LH level and steroid concentrations in GnRH antagonist protocol: A sub-analysis of Ganirelix phase III study of China. J Gynecol Obstet Hum Reprod. 2022 May;51(5):102363. doi: 10.1016/j.jogoh.2022.102363. Epub 2022 Mar 19. PMID: 35318120.


7: Han EJ, Lyu SW, Kwak IP, Kwon H, Choi DH, Kim JY, Park HM, Kim JW, Chang EM, Lee HJ, Kim MK, Lee HN, Kim JY, Park S, Lee WS. Efficacy and safety of newly developed ganirelix acetate in infertile women for assisted reproductive technology: a prospective, randomised, controlled study. J Obstet Gynaecol. 2022 Aug;42(6):2197-2202. doi: 10.1080/01443615.2022.2036955. Epub 2022 Mar 7. PMID: 35254199.


8: Choudhary RA, Vora PH, Darade KK, Pandey S, Ganla KN. A Prospective Randomised Comparative Clinical Trial Study of Luteal PhaseLetrozole versus Ganirelix Acetate Administration to Prevent Severity of Early Onset OHSS in ARTs. Int J Fertil Steril. 2021 Oct;15(4):263-268. doi: 10.22074/IJFS.2021.139562.1042. Epub 2021 Oct 16. PMID: 34913294; PMCID: PMC8530210.


9: Ummiti K, Shanmukha Kumar JV. Establishment of validated stability indicating purity method based on the stress degradation behavior of gonadotropin-releasing hormone antagonist (ganirelix) in an injectable formulation using HPLC and LC- MS-QTOF. Eur J Mass Spectrom (Chichester). 2021 Apr;27(2-4):126-140. doi: 10.1177/14690667211005335. Epub 2021 Apr 7. PMID: 33823624.


10: Ummiti K, Kumar JVS. Evaluation of temperature, excipients impact on the primary structure of Ganirelix in an injectable formulation, and comparison with Orgalutran® using MALDI-TOF/TOF-MS. J Mass Spectrom. 2020 Oct;55(10):e4610. doi: 10.1002/jms.4610. PMID: 32786175.


11: Ummiti K, Kumar JVS. Determination of Amino Acid Composition of Ganirelix Acetate in an Injectable Formulation by Pre-column Derivatization with 6-Aminoquinolyl-N-hydroxysuccinimidyl Carbamate. J Chromatogr Sci. 2020 Aug 21;58(8):687-694. doi: 10.1093/chromsci/bmaa030. PMID: 32676669.


12: Zhang J, Zhou X, Chen Y, Zhang Q, Li Y, Zhe J, Chen X, Chen S. [Effects of cetrorelix versus ganirelix in gonadotropin-releasing hormone antagonist cycles for preventing premature luteinizing hormone surges and on clinical outcomes of IVF-ET cycles]. Nan Fang Yi Ke Da Xue Xue Bao. 2019 Oct 30;39(10):1207-1212. Chinese. doi: 10.12122/j.issn.1673-4254.2019.10.12. PMID: 31801718; PMCID: PMC6867944.


13: Beguería R, García D, Vassena R, Rodríguez A. Medroxyprogesterone acetate versus ganirelix in oocyte donation: a randomized controlled trial. Hum Reprod. 2019 May 1;34(5):872-880. doi: 10.1093/humrep/dez034. PMID: 30927417.


14: Bhardwaj A, Nayan V, Sharma P, Kumar S, Pal Y, Singh J. Molecular characterization, modeling, in silico analysis of equine pituitary gonadotropin alpha subunit and docking interaction studies with ganirelix. In Silico Pharmacol. 2016 Dec;5(1):5. doi: 10.1007/s40203-017-0025-1. Epub 2017 Jul 18. PMID: 28721542; PMCID: PMC5515723.


15: Frattarelli JL, Hillensjö T, Broekmans FJ, Witjes H, Elbers J, Gordon K, Mannaerts B. Clinical impact of LH rises prior to and during ganirelix treatment started on day 5 or on day 6 of ovarian stimulation. Reprod Biol Endocrinol. 2013 Sep 12;11:90. doi: 10.1186/1477-7827-11-90. PMID: 24028076; PMCID: PMC3847921.


16: Qiao J, Lu G, Zhang HW, Chen H, Ma C, Olofsson JI, Witjes H, Heijnen E, Mannaerts B. A randomized controlled trial of the GnRH antagonist ganirelix in Chinese normal responders: high efficacy and pregnancy rates. Gynecol Endocrinol. 2012 Oct;28(10):800-4. doi: 10.3109/09513590.2012.665103. Epub 2012 Mar 20. PMID: 22429192.


17: Check JH, Cohen R, Amui J, Choe JK, Brasile D. Evidence that the main adverse effect of ganirelix on pregnancy and implantation rates is on the embryo rather than the endometrium. Clin Exp Obstet Gynecol. 2011;38(4):326-7. PMID: 22268265.


18: DiLuigi AJ, Engmann L, Schmidt DW, Benadiva CA, Nulsen JC. A randomized trial of microdose leuprolide acetate protocol versus luteal phase ganirelix protocol in predicted poor responders. Fertil Steril. 2011 Jun 30;95(8):2531-3. doi: 10.1016/j.fertnstert.2011.01.134. Epub 2011 Feb 16. PMID: 21324455.


19: Russo A, Castiglione F, Salonia A, Benigni F, Rigatti P, Montorsi F, Andersson KE, Hedlund P. Effects of the gonadotropin-releasing hormone antagonist ganirelix on normal micturition and prostaglandin E(2)-induced detrusor overactivity in conscious female rats. Eur Urol. 2011 May;59(5):868-74. doi: 10.1016/j.eururo.2010.12.007. Epub 2010 Dec 21. PMID: 21196074.


20: Check JH, Wilson C, Choe JK, Amui J, Katsoff B. A comparison of pregnancy rates following fresh and frozen embryo transfer according to the use of leuprolide acetate vs ganirelix vs cetrorelix. Clin Exp Obstet Gynecol. 2010;37(2):105-7. PMID: 21077496.