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Gonadorelin Acetate

Gonadorelin is a trophic peptide hormone responsible for the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. GnRH is synthesized and released from GnRH neurons within the hypothalamus. The peptide belongs to gonadotropin-releasing hormone family. It constitutes the initial step in the hypothalamic–pituitary–gonadal axis.

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CAT No: 10-101-19

CAS No: 33515-09-2 (net), 34973-08-5 (acetate)

Synonyms/Alias: Gonadorelin acetate;34973-08-5;Gonadorelin (acetate);GnRH-I acetate;Gonadorelin acetate anhydrous;499785-55-6;UNII-Z6TK4T303L;Z6TK4T303L;34973-08-5 (acetate);Hypocrine;LH-RH (Human);Cystorelin;Fertiline;Lutrelef;Lutrepulse;Luprolite acetate;Gonadorelin diacetate;71447-49-9;UNII-K56QT79S2O;Luteinizing;ABBOTT-41070;(2S)-N-[(2S)-5-CARBAMIMIDAMIDO-1-[(2S)-2-(CARBAMOYLMETHYLCARBAMOYL)PYRROLIDIN-1-YL]-1-OXOPENTAN-2-YL]-2-{2-[(2S)-2-[(2S)-3-HYDROXY-2-[(2S)-2-[(2S)-3-(1H-IMIDAZOL-4-YL)-2-{[(2S)-5-OXOPYRROLIDIN-2-YL]FORMAMIDO}PROPANAMIDO]-3-(1H-INDOL-3-YL)PROPANAMIDO]PROPANAMIDO]-3-(4-HYDROXYPHENYL)PROPANAMIDO]ACETAMIDO}-4-METHYLPENTANAMIDE; ACETIC ACID;Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2, Luteinizing Hormone-Releasing Hormone (LH-RH), Luteinising Hormone-Releasing Hormone, L HRH, Gonadorelin;LHRH ACETATE;K56QT79S2O;CHEMBL1200511;DTXSID30198161;PLR-4013-V;N-[1-[[1-[[1-[[1-[[2-[[1-[[1-[2-[[(2-amino-2-oxoethyl)amino]-oxomethyl]-1-pyrrolidinyl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-(4-hydr;PLR-4013;MFCD01742354;AKOS040763976;AC-8924;AT41855;CS-5289;DA-63864;HY-12555;TS-10352;AY-24031?;NS00022081;

Chemical Name: acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]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

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Specification Technical Data Publications Customer reviews and Q&A
M.F/FormulaC57H79N17O15
M.W/Mr.1242.3
SequenceOne Letter Code:XHWSYGLRPG
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2.CH3CO2H
Labeling TargetGonadotropin-releasing hormone (GNRH) Receptor
ApplicationGonadorelin is also known as LHRH. After a transient increase, continuous administration results in downregulation of LH and FSH levels followed by a suppression of ovarian and testicular steroid biosynthesis.
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
ActivityAgonist
Areas of InterestCardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
TargetGonadotropin-releasing hormone receptor
Source#Synthetic
Length10
Long-term Storage ConditionsSoluble in DMSO, not in water
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
InChIInChI=1S/C55H75N17O13.C2H4O2/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36;1-2(3)4/h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60);1H3,(H,3,4)/t36-,37-,38-,39-,40-,41-,42-,43-;/m0./s1
InChI KeyNGCGMRBZPXEPOZ-HBBGHHHDSA-N
Canonical SMILESCC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6.CC(=O)O
Isomeric SMILESCC(C)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)NC(=O)CNC(=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
BoilingPointN/A
ShelfLife>2 years if stored properly
References

Recently, several reports of adverse reactions after pulsatile GnRH (gonadorelin hydrochloride) infusion therapy have appeared in the medical literature. Although the cause of these reactions has been associated with GnRH itself, the contributions of impurities and degradation products in the administered drug have not been determined, suggesting that the use of high-purity material may be advantageous in controlling unwanted side effects. This study evaluates the purity and long-term stability of a new GnRH product, gonadorelin acetate (Lutrepulse, Ortho Pharmaceutical Corporation). Both the purity and potency of the drug substance, the lyophilized product for injection, and the reconstituted material that would be transferred to the infusion pump system were monitored using high-performance liquid chromatography. The gonadorelin acetate drug substance was found to be stable for at least 12 months when stored at 24 degrees C in 50% relative humidity, and showed no degradation even under accelerated storage conditions. Similarly, the lyophilized product also showed excellent stability for at least 18 months when stored at 24 degrees C in 50% relative humidity. Upon reconstitution, gonadorelin acetate was found to be stable for at least 45 days when stored at 24 degrees C or 37 degrees C.

Wong, W., Mercorelli, M., DeLuccia, F., Young, R., Lane, P. A., Hoerig, J., & Turan, A. (1990). Stability and purity profile of gonadorelin acetate: a high-purity gonadotropin-releasing hormone. International journal of fertility, 35(5), 302-309.

Gonadotropin-releasing hormone analogues are generally regarded as safe drugs. Gonadorelin acetate has been widely used for the diagnosis of central precocious puberty, and life-threatening reactions to gonadorelin acetate are extremely rare. Herein, we described - to the best of our knowledge - the first pediatric case in which severe anaphylaxis was encountered after intravenous gonadorelin acetate administration. An 8-year-old girl who was diagnosed with central precocious puberty was receiving triptorelin acetate treatment uneventfully for 6 months. In order to evaluate the efficacy of the treatment, an LH-RH stimulation test with gonadorelin acetate was planned. Within 3 min after intravenous administration of gonadorelin acetate, she lost consciousness and tonic seizures began in her hands and feet. She was immediately treated with epinephrine, diphenhydramine, and fluids. Her vital signs recovered within 30 min. Based on the results, anaphylaxis should be anticipated and the administration of these drugs should be performed in a setting that is equipped to deal with systemic reactions.

Akın, O., Yavuz, S. T., Hacıhamdioğlu, B., Sarı, E., Gürsel, O., & Yeşilkaya, E. (2015). Anaphylaxis to gonadorelin acetate in a girl with central precocious puberty. Journal of Pediatric Endocrinology and Metabolism, 28(11-12), 1387-1389.

Melting PointN/A

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

2. Tachykinin-related peptides modulate immune-gene expression in the mealworm beetle Tenebrio molitor L

3. SERS spectrum of the peptide thymosin‐β4 obtained with Ag nanorod substrate

4. Cell-based adhesion assays for isolation of snake venom’s integrin antagonists

5. Myotropic activity of allatostatins in tenebrionid beetles

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    Carbetocin is a long-acting synthetic agonist analogue of human oxytocin, with antihemorrhagic and uterotonic activities. Upon administration, carbetocin targets, binds to and activates peripheral oxytocin receptors that are present on the smooth musculature of the uterus. This causes uterus contractions and prevents excessive bleeding after childbirth, particularly following Cesarean section, and may be used to decrease blood loss during hysteroscopic myomectomy.

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