Leuprorelin

Base Information

• Chemical Name: Leuprorelin
• CAS No.: 53714-56-0
• Deprecated CAS: 102586-10-7,72648-87-4
• Molecular Formula: C59H84N16O12
• Molecular Weight: 1209.42
• European Community (EC) Number: 633-395-9
• UNII: EFY6W0M8TG
• DSSTox Substance ID: DTXSID50872411
• Nikkaji Number: J34.477J
• Wikipedia: Leuprorelin
• Wikidata: Q907160
• NCI Thesaurus Code: C62042
• RXCUI: 42375
• Pharos Ligand ID: SQKL7HTUSTU5
• Metabolomics Workbench ID: 49623
• ChEMBL ID: CHEMBL1201199
• Mol file: 53714-56-0.mol

Synonyms:A 43818;A-43818;A43818;Acetate, Leuprolide;Enantone;Leuprolide;Leuprolide Acetate;Leuprolide Monoacetate;Leuprolide, (DL-Leu)-Isomer;Leuprolide, (L-Leu)-Isomer;Leuprorelin;Lupron;Monoacetate, Leuprolide;TAP 144;TAP-144;TAP144

Chemical Property of Leuprorelin

Chemical Property:

• Appearance/Colour: Fluffy solid.
• Refractive Index: 1.681
• PKA: 9.82±0.15(Predicted)
• PSA: 466.34000
• Density: 1.44 g/cm³
• LogP: 3.44730
• Storage Temp.: −20°C
• Water Solubility.: Soluble in water at 1mg/ml
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 15
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 32
• Exact Mass: 1208.64546218
• Heavy Atom Count: 87
• Complexity: 2390

Purity/Quality:

98% ^*data from raw suppliers

Leuprolide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(CC(C)C)NC(=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
• Isomeric SMILES: CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=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
• Recent ClinicalTrials: Ipilimumab + Androgen Depravation Therapy in Prostate Cancer
• Recent EU Clinical Trials: Short versus long-term androgen deprivation therapy combined with salvage radiotherapy in prostate cancer patients with biochemical recurrence after prostatectomy: a multicentre phase III randomised controlled trial
• Description: Leuprorelin(Leuprolide?) is a synthetic water-soluble nonapeptide with both ends closed, and also a highly active analogue of luteinizing hormone releasing hormone (LHRH or GnRH) produced by the hypothalamus. It can stimulate the pituitary gland to secrete gonadotropins and induce the production of steroids in the reproductive organs.
• Uses: Leuprorelin is a nonapeptide synthetic analogue of gonadotropin (GnRH), which can promote the release of luteinizing hormone (LHRH) and follicle stimulating hormone (FSH) from the anterior pituitary, regulate the secretion of gonadal hormones, and increase the serum levels of testosterone and dihydrotestosterone. Concentration, so as to achieve the function of treating reproductive system diseases. It is used to treat prostate cancer, uterine fibroids, ovarian cysts, breast cancer and cryptorchidism in children. Highly active luteinizing hormone releasing hormone (LHRH) agonist Gonadotropin releasing hormone (gonadorelin) analogue; treatment of prostate cancer.
• Indications: Leuprolide is a potent LH-RH agonist for the first several days to a few weeks after initiation of therapy, and therefore, it initially stimulates testicular and ovarian steroidogenesis. Because of this initial stimulation of testosterone production, it is recommended that patients with prostatic cancer be treated concurrently with leuprolide and the antiandrogen flutamide (discussed earlier). Leuprolide is generally well tolerated, with hot flashes being the most common side effect.
• Therapeutic Function: Antineoplastic

Technology Process of Leuprorelin

There total 8 articles about Leuprorelin 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:

pGlu-His(Trt)-Trp-Ser(tBu)-Tyr(tBu)-D-Leu-Leu-Arg(Pbf)-Pro-NHEt (914200-76-3) → Leuprolide (53714-56-0)

Guidance literature:

With chlorotriisopropylsilane; ethane-1,2-dithiol; trifluoroacetic acid; at 20 ℃; for 2h;

Reference yield:

pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg(Mds)-Pro-NH-Et → Leuprolide (53714-56-0)

Guidance literature:

With methyl-phenyl-thioether; trifluoroacetic acid; at 50 ℃; for 1h; Yield given;

DOI:10.1039/c39800000668

Reference yield:

pGlu-His(Trt)-Trp(Boc)-Ser(tBu)-Tyr(tBu)-D-Leu-Leu-Arg(Pbf)-Pro-NHEt → Leuprolide (53714-56-0)

Guidance literature:

With chlorotriisopropylsilane; water; trifluoroacetic acid; at 20 - 60 ℃;

DOI:10.1039/C8CC07935H

upstream raw materials:

pGlu-His(Trt)-Trp-Ser(tBu)-Tyr(tBu)-D-Leu-Leu-Arg(Pbf)-Pro-NHEt

Refernces

• 1、 Ishiyama, Takashi,Kanai, Motomu,Maruyama, Katsuya,Oisaki, Kounosuke,Sakai, Kentaro,Seki, Yohei,Togo, Takaya. "Protein Modification at Tyrosine with Iminoxyl Radicals". supporting information. p. 19844 - 19855. Retrieved 2021/11/30.
• 2、 Matsumoto, Takuya,Sasamoto, Koki,Hirano, Ryo,Oisaki, Kounosuke,Kanai, Motomu. "A catalytic one-step synthesis of peptide thioacids: the synthesis of leuprorelin via iterative peptide-fragment coupling reactions". supporting information. p. 12222 - 12225. Retrieved 2018/12/01.