Leuprolide (1-3)

Base Information

• Chemical Name: Leuprolide (1-3)
• CAS No.: 35925-21-4
• Molecular Formula: C22H24N6O5
• Molecular Weight: 452.47
• UNII: 7OI82E72DN
• DSSTox Substance ID: DTXSID40468362
• Nikkaji Number: J370.354A
• Wikidata: Q27268644
• Mol file: 35925-21-4.mol

Synonyms:Leuprolide (1-3);35925-21-4;Leuprolide (m3);Leuprolide (miii);L-Pyroglu-L-his-L-trp;L-Tryptophan, 5-oxo-L-prolyl-L-histidyl-;5-Oxo-L-prolyl-L-histidyl-L-tryptophan;Leuprolide (metabolite miii);LH-RH (1-3);UNII-7OI82E72DN;7OI82E72DN;(Pyro)-L-glutamic acid-L-histidine-L-tryptophan-OH;L-Pyroglutamyl-L-histidyl-L-tryptophan;(2S)-2-[[(2S)-3-(1H-imidazol-5-yl)-2-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]propanoyl]amino]-3-(1H-indol-3-yl)propanoic acid;SCHEMBL10982108;DTXSID40468362;OHCMNYPOVOHMJR-BZSNNMDCSA-N;PYROGLUTAMYLHISTIDYLTRYPTOPHAN;AKOS040752518;N-[N-(5-Oxo-L-Prolyl)-L-Histidyl]-L-Tryptophan;Q27268644

Chemical Property of Leuprolide (1-3)

Chemical Property:

• Boiling Point: 1072.7±65.0 °C(Predicted)
• PSA: 179.54000
• Density: 1.456±0.06 g/cm3(Predicted)
• LogP: 1.96550
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 452.18081789
• Heavy Atom Count: 33
• Complexity: 764

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)NC1C(=O)NC(CC2=CN=CN2)C(=O)NC(CC3=CNC4=CC=CC=C43)C(=O)O
• Isomeric SMILES: C1CC(=O)N[C@@H]1C(=O)N[C@@H](CC2=CN=CN2)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)O
• Uses: L-Pyroglu-L-His-L-Trp is an impurity of Leuprolide(L330590) which is used to treat central precocious puberty. Leuprolide is also used to synthesize drugs that are useful for the treatment endometriosis, hysteromyoma an premenopausal breast cancer.

Technology Process of Leuprolide (1-3)

There total 3 articles about Leuprolide (1-3) 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:

histrelin (76712-82-8) → His-Trp-Ser-Tyr-(D-Nim-bzl-His)-Leu-Arg-Pro-NHEt (134190-11-7) + cyclo(-His-Trp) + Ser-Tyr-(D-Nim-bzl-His)-Leu-Arg-Pro-NHEt (134009-09-9) + 35925-21-4 + L-Pyroglutamic acid (98-79-3)

Guidance literature:

With water; at 87 ℃; for 432h; Product distribution; degradation, var. reaction time, temperature and ph;

DOI:10.1002/jps.2600800316

Reference yield:

gonadorelin (33515-09-2) → luteinizing hormone-releasing hormone (4-10) (51776-33-1) + H-pyroGlu-His-Trp-OH (35925-21-4) + pEHWSYGLRPG + C55H75N17O13

Guidance literature:

With acetate buffer; sodium perchlorate; In water; at 70 ℃; Kinetics; Rate constant; Thermodynamic data; mechanism, ΔE(excit.), other reagents: perchloric acid, borate buffer, carbonate buffer, various temperature, pH, reactant concentration, ionic strength;

DOI:10.1021/js9601187

Reference yield:

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) → L-histidyl-L-tryptophanyldiketopiperazine (18610-65-6,108391-80-6,133397-85-0,18610-64-5) + 103065-82-3 + 53634-19-8 + pGlu-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-OH (35263-73-1) + His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2 (38280-53-4) + 35925-21-4

Guidance literature:

With water; at 50 ℃; for 2160h; Product distribution; pH = 6.5; var. temp. and times of degradation;

DOI:10.1002/jps.2600800504

upstream raw materials:

histrelin

gonadotropin releasing hormone

gonadorelin

Downstream raw materials:

C₆₃H₇₀N₁₀O₁₁

Refernces

• 1、 Oyler,Naldi,Lloyd,Graden,Shaw,Cotter. "Characterization of the solution degradation products of histrelin, a gonadotropin releasing hormone (LH/RH) agonist". . p. 271 - 275. Retrieved 2007/10/02.