Ganirelix

Ganirelix

Ganirelix acetate (or diacetate) is an injectable competitive gonadotropin-releasing hormone antagonist (GnRH antagonist). It works by blocking the action of GnRH upon the pituitary, thus rapidly suppressing the production and action of LH and FSH.

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CAT No: 10-101-61

CAS No: 123246-29-7

Synonyms/Alias: Ganirelix;124904-93-4;Orgalutran;Antagon;Ganirelixum;123246-29-7;UNII-IX503L9WN0;IX503L9WN0;Ganirelixum [INN-Latin];CHEMBL1251;Ganirelix (INN);CID 16134406;GANIRELIX [INN];Ganirelixum (INN-Latin);D-Alaninamide, N-acetyl-3-(1-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, 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 [INN:BAN];Orgalutran (TN);D 24598;D-24598;GANIRELIX [MI];GANIRELIX [VANDF];GANIRELIX [WHO-DD];GANIRELIX [EMA EPAR];SCHEMBL19712192;H01CC01;CHEBI:135910;GJNXBNATEDXMAK-PFLSVRRQSA-N;DTXSID401027283;GLXC-26188;BDBM50102454;LHRH,N-Ac-2-Nal(1)-4-Cl-Phe(2)-3-Pal(3)-Et2-hArg(6,8)-AlaNH2(10)-;AT42442;DB06785;GnRH, N-Ac-2-Nal(1)-4-Cl-Phe(2)-3-Pal(3)-Et2-hArg(6,8)-AlaNH2(10)-;N-Ac-(2-naphthyl)Ala-2-(4-Cl-Phe)-3-(3-pyridinyl-Ala)-6,8-Et2-hArg-10-AlaNH2-LHRH;DA-63686;LHRH, N-acetyl-2-naphthylalanyl(1)-(4-chlorophenylalanyl)(2)-3-pyrdinylalanyl(3)-diethylhomoarginyl(6,8)-alaninamide(10)-;D08010;EN300-19652012;Q5521314;Ac-D-Nal-[D-(pCl)Phe]-D-Pal-Ser-Tyr-D-Har(Et2)-Leu-Har(Et2)-Pro-DAla-NH2;Ac-D-2Nal-D-Phe(4-Cl)-D-3Pal-Ser-Tyr-D-hArg(Et,Et)-Leu-hArg(Et,Et)-Pro-D-Ala-NH2 3 AcOH;

Chemical Name: (2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]amino]-4-methylpentanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide

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M.F/Formula	C80H113ClN18O13
M.W/Mr.	1570.3
Sequence	One Letter Code:XXXSYXLXPA Three Letter Code:Ac-D-2Nal-D-Phe(4-Cl)-D-3Pal-Ser-Tyr-D-hArg(Et,Et)-Leu-hArg(Et,Et)-Pro-D-Ala-NH2
Labeling Target	Gonadotropin-releasing hormone (GNRH) Receptor
Application	Ganirelix is primarily used in assisted reproduction to control ovulation.
Activity	Antagonist
Biological Activity	Ganirelix is a gonadotropin releasing hormone (GnRH) antagonist. It blocks a natural hormone called GnRH that typically releases other hormones to prepare your body for ovulation (release of an egg from your ovary). By blocking GnRH, ganirelix temporarily delays ovulation. It's used to prevent eggs from being released too early and can help your provider be more successful during your egg retrieval procedure.
Areas of Interest	Endocrinology
Functions	Peptide binding
Target	Gonadotropin-releasing hormone (GnRH)

Source#	Synthetic
Solubility	−20°C
Organism	Human
InChI	InChI=1S/C80H113ClN18O13/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/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)/t50-,60-,61+,62+,63-,64+,65-,66-,67+,68+/m1/s1
InChI Key	GJNXBNATEDXMAK-PFLSVRRQSA-N
Canonical SMILES	CCNC(=NCCCCC(C(=O)NC(CC(C)C)C(=O)NC(CCCCN=C(NCC)NCC)C(=O)N1CCCC1C(=O)NC(C)C(=O)N)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CN=CC=C3)NC(=O)C(CC4=CC=C(C=C4)Cl)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)NC(=O)C)NCC
Isomeric SMILES	CCNC(=NCCCC[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC3=CN=CC=C3)NC(=O)[C@@H](CC4=CC=C(C=C4)Cl)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)NC(=O)C)NCC
BoilingPoint	N/A
References	Use of GnRH antagonists in patients with an a priori poor IVF prognosis results in predictably poor outcomes. Patients without factors predicting poor outcome have acceptable PRs. The pattern of E2 rise immediately after initiation of GnRH antagonists does not predict cycle outcome. Oral contraceptives can be successfully used to schedule antagonist-based IVF cycles but might increase the risk of cycle cancellation in some patient populations. Shapiro, D. B., Mitchell-Leef, D., Carter, M., & Nagy, Z. P. (2005). Ganirelix acetate use in normal-and poor-prognosis patients and the impact of estradiol patterns. Fertility and sterility, 83(3), 666-670. Elevated estradiol (E(2)) levels predispose to development of ovarian hyperstimulation syndrome (OHSS). Since GnRH antagonist is associated with a reduction in E(2) levels, we hypothesized that GnRH-antagonist treatment of women down-regulated with GnRH agonist who are at risk of OHSS might reduce E(2) levels and avoid cycle cancellation. Gustofson, R. L., Segars, J. H., & Larsen, F. W. (2006). Ganirelix acetate causes a rapid reduction in estradiol levels without adversely affecting oocyte maturation in women pretreated with leuprolide acetate who are at risk of ovarian hyperstimulation syndrome. Human Reproduction, 21(11), 2830-2837. Ganirelix is effective, safe, and well tolerated. Compared with leuprolide acetate, ganirelix therapy has a shorter duration and fewer injections but produces a similar pregnancy rate. Fluker, M., Grifo, J., Leader, A., Levy, M., Meldrum, D., Muasher, S. J., ... & Shapiro, D. B. (2001). Efficacy and safety of ganirelix acetate versus leuprolide acetate in women undergoing controlled ovarian hyperstimulation. Fertility and sterility, 75(1), 38-45.
Melting Point	N/A

1. GLP-1, exendin-4 and C-peptide regulate pancreatic islet microcirculation, insulin secretion and glucose tolerance in rats

2. Spatiotemporal delivery of nanoformulated liraglutide for cardiac regeneration after myocardial infarction

3. The spatiotemporal control of signalling and trafficking of the GLP-1R

4. Oleic acid and glucose regulate glucagon-like peptide 1 receptor expression in a rat pancreatic ductal cell line

5. Genetic, cellular, and structural characterization of the membrane potential-dependent cell-penetrating peptide translocation pore

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