Gonadorelin acetate

Base Information

• Chemical Name: Gonadorelin acetate
• CAS No.: 33515-09-2
• Deprecated CAS: 66036-44-0
• Molecular Formula: C55H75N17O13
• Molecular Weight: 1182.31
• Hs Code.: 2942000000
• European Community (EC) Number: 251-553-1,636-116-9,683-628-3
• DSSTox Substance ID: DTXSID30198161
• Wikipedia: Gonadorelin
• NCI Thesaurus Code: C65814
• ChEMBL ID: CHEMBL1200511
• Mol file: 33515-09-2.mol

Synonyms:Cystorelin;Dirigestran;Factrel;FSH Releasing Hormone;FSH-Releasing Hormone;Gn-RH;GnRH;Gonadoliberin;Gonadorelin;Gonadorelin Acetate;Gonadorelin Hydrochloride;Gonadotropin Releasing Hormone;Gonadotropin-Releasing Hormone;Kryptocur;LFRH;LH FSH Releasing Hormone;LH Releasing Hormone;LH-FSH Releasing Hormone;LH-Releasing Hormone;LH-RH;LHFSH Releasing Hormone;LHFSHRH;LHRH;Luliberin;Luteinizing Hormone Releasing Hormone;Luteinizing Hormone-Releasing Hormone;Releasing Hormone, LHFSH

Chemical Property of Gonadorelin acetate

Chemical Property:

• Appearance/Colour: COA
• PKA: 9.82±0.15(Predicted)
• PSA: 472.13000
• Density: 1.54 g/cm³
• LogP: 1.10740
• Solubility.: ≥118.2 mg/mL in DMSO with ultrasonic; insoluble in EtOH; ≥28.7 mg/mL in H2O
• Hydrogen Bond Donor Count: 17
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 31
• Exact Mass: 1241.59415488
• Heavy Atom Count: 89
• Complexity: 2420

Purity/Quality:

99% ^*data from raw suppliers

Gonadorelin European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(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 SMILES: CC(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
• Recent ClinicalTrials: Hormonal Mechanisms of Sleep Restriction - Axis Study
• Recent EU Clinical Trials: Optimizing the fertility potential of bilateral cryptorchidism by treatment
• Uses: Gonad-stimulating principle. Gonadorein is a Gonadotropin-releasing hormone. Gonadorelin agonist treatment for men with locoregional prostate cancer may be associated with an increased risk of incident diabetes and ardiovascular disease.

Technology Process of Gonadorelin acetate

There total 22 articles about Gonadorelin acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

luteinizing hormone-releasing hormone (4-10) (51776-33-1) + Glp-His-Trp-OEt (105823-83-4) → gonadorelin (33515-09-2)

Guidance literature:

With potassium hydroxide; potassium chloride; α-chymotrypsin; In dimethyl sulfoxide; at -15 ℃; for 1h; Product distribution; other time, temperature;

DOI:10.1016/S0040-4039(00)78861-7

Reference yield: 68.0%

Gly-Leu-Arg-Pro-Gly-NH2 + (S)-2-{(S)-3-Hydroxy-2-[(S)-2-{(S)-3-(3H-imidazol-4-yl)-2-[((S)-5-oxo-pyrrolidine-2-carbonyl)-amino]-propionylamino}-3-(1H-indol-3-yl)-propionylamino]-propionylamino}-3-(4-hydroxy-phenyl)-propionic acid carbamoylmethyl ester → gonadorelin (33515-09-2)

Guidance literature:

With α-chymotrypsin; In water; at 25 ℃; Tris-HCl buffer, pH 7.8;

DOI:10.1016/S0968-0896(98)00046-7

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Leu-OH (35661-60-0) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + Fmoc-Tyr(tBu)-OH (71989-38-3,118488-18-9,204384-67-8) + Fmoc-His(Trt)-OH (109425-51-6) + N-fluoren-9-ylmethyloxycarbonyl-L-pyroglutamine (109425-56-1,106982-77-8) + 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester (143824-78-6,163619-04-3) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → gonadotropin releasing hormone (33515-09-2,51988-59-1,53634-19-8,53634-20-1,53634-21-2,53634-22-3,53728-75-9,64693-15-8,70920-45-5,103065-82-3)

Guidance literature:

N-(fluoren-9-ylmethoxycarbonyl)glycine; With N-ethyl-N,N-diisopropylamine; at 90 ℃; for 0.0833333h; Automated synthesizer;

With pyrrolidine; at 95 ℃; for 0.0138889h;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Leu-OH; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-Tyr(tBu)-OH; Fmoc-His(Trt)-OH; N-fluoren-9-ylmethyloxycarbonyl-L-pyroglutamine; 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester; Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; Further stages;

upstream raw materials:

L-Leucyl-L-arginyl-L-prolylglycinamide Formate

L-Pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycine Hydrazine

N₅-[imino(nitroamino)methyl]-N₂-[(phenylmethoxy)carbonyl]-L-ornithine

N^α-tert-butoxycarbonylseryltyrosine methyl ester

Downstream raw materials:

L-histidyl-L-tryptophanyldiketopiperazine

pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-OH

Refernces

• 1、 Schuster,Aaviksaar,Jakubke. "α-Chymotrypsin-catalyzed (3 + 7) segment synthesis of the luteinizing hormone releasing hormone". . p. 2799 - 2802. Retrieved 1992.
• 2、 Nakaie, Clovis R.,Oliveira, Eliandre,Vicente, Eduardo F.,Jubilut, Guita N.,Souza, Sinval E.G.,Marchetto, Reinaldo,Cilli, Eduardo M.. "Solid-phase peptide synthesis in highly loaded conditions". experimental part. p. 101 - 109. Retrieved 2011/06/25.