H-DPhe-cyclo[DPen-Tyr-DTrp-Lys-Val-Cys]-Thr-NH2

Base Information

• Chemical Name: H-DPhe-cyclo[DPen-Tyr-DTrp-Lys-Val-Cys]-Thr-NH2
• CAS No.: 108736-35-2
• Molecular Formula: C₅₄H₆₉N₁₁O₁₀S₂
• Molecular Weight: 1096.34
• Hs Code.: 3504009000
• European Community (EC) Number: 689-178-4
• Wikipedia: Lanreotide
• NCI Thesaurus Code: C1523
• RXCUI: 68092
• ChEMBL ID: CHEMBL2079626
• Mol file: 108736-35-2.mol

Synonyms:188Re-lanreotide;2-naphthylalanyl-cyclo(cysteinyl-tyrosyl-tryptophyl-lysyl-valyl-cysteinyl)-threoninamide;3-(2-naphthyl)-D-Ala-Cys-Tyr-D-Trp-Lys-Val-Cys-Thr-NH2;3-(2-naphthyl)alanyl-cystinyl-tyrosyl-tryptophyl-lysyl-valyl-cystinyl-threonine amide;angiopeptin;BIM 23014;BIM 23014 C;BIM 23014C;BIM-23014;BIM-23014 C;D-Nal-Cys-Tyr-Trp-Lys-Val-Cys-Thr-NH2;DC 13-116;DC-13-116;DC13-116;L-Threoninamide, 3-(2-naphthalenyl)-D-alanyl-L-cysteinyl-L-tyrosyl-D-tryptophyl-L-lysyl-L-valyl-L-cysteinyl-, cyclic (2-7)-disulfide;lanreotide;lanreotide acetate;lanreotide-SR;Nal-cyclo(Cys-Tyr-Trp-Lys-Val-Cys)-Thr-NH2;Nal-cyclo(Cys-Tyr-Trp-Lys-Val-Cys)Thr-NH2;naphthalenyl-cyclo(cysteinyl-tyrosyl-tryptophyl-lysyl-valyl-cysteinyl)threoninamide;naphthyl-cyclo(Cys-Tyr-Trp-Lys-Val-Cys)Thr-NH2;Somatulin;Somatulina;Somatuline

Chemical Property of H-DPhe-cyclo[DPen-Tyr-DTrp-Lys-Val-Cys]-Thr-NH2

Chemical Property:

• Boiling Point: 1498.3 °C at 760 mmHg
• PKA: 9.90±0.15(Predicted)
• Flash Point: 859.9 °C
• PSA: 405.68000
• Density: 1.323 g/cm³
• LogP: 5.34830
• Storage Temp.: −20°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 17
• Exact Mass: 1095.46702979
• Heavy Atom Count: 77
• Complexity: 2000

Purity/Quality:

98% ^*data from raw suppliers

Lanreotide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Hormonal Agents
• Canonical SMILES: CC(C)C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)C(CC5=CC6=CC=CC=C6C=C5)N)C(=O)NC(C(C)O)C(=O)N
• Isomeric SMILES: C[C@H]([C@@H](C(=O)N)NC(=O)[C@H]1CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)C(C)C)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=C(C=C4)O)NC(=O)[C@@H](CC5=CC6=CC=CC=C6C=C5)N)O
• Recent ClinicalTrials: Study of Lanreotide in Patients With Metastatic Gastrointestinal Neuroendocrine Tumors Who Are Undergoing Liver-directed Radioembolization With Yttrium-90 Microspheres
• Recent EU Clinical Trials: A randomized, multi-center, open-label, active-controlled Phase 3 trial to assess the efficacy and safety of octreotide subcutaneous depot (CAM2029) versus octreotide LAR or lanreotide ATG in patients with gastroenteropancreatic neuroendocrine tumors.
• Recent NIPH Clinical Trials: JCOG1901: An intergroup phase III study of combination therapy with everolimus and lanreotide versus everolimus monotherapy for unresectable or recurrent gastroenteropancreatic neuroendocrine tumor
• Uses: Antineoplas tic.
• Clinical Use: #N/A

Technology Process of H-DPhe-cyclo[DPen-Tyr-DTrp-Lys-Val-Cys]-Thr-NH2

There total 3 articles about H-DPhe-cyclo[DPen-Tyr-DTrp-Lys-Val-Cys]-Thr-NH2 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:

H-D-β-Nal-Cys-(Acm)-Tyr-D-Trp-Lys-Val-Cys(Acm)-Thr-NH2 (1026080-86-3) → lanreotide (108736-35-2)

Guidance literature:

With iodine; acetic acid; In methanol; at 55 ℃; for 0.25h; Inert atmosphere;

Reference yield:

Fmoc-Tyr(Clt)-OH (350241-80-4) + Fmoc-Val-OH (68858-20-8) + Boc-Lys(Boc)-OH (2483-46-7) + Fmoc-Thr-NH2 + Boc-D-2Nal-OH (76985-10-9) + Fmoc-Trp-OH (35737-15-6) + N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4) → lanreotide (108736-35-2)

Guidance literature:

Fmoc-Thr-NH₂; With benzotriazol-1-ol; diisopropyl-carbodiimide; In 1-methyl-pyrrolidin-2-one; dichloromethane; at 0 - 30 ℃;

With piperidine; In 1-methyl-pyrrolidin-2-one;

Fmoc-Tyr(Clt)-OH; Fmoc-Val-OH; Boc-Lys(Boc)-OH; Boc-D-2Nal-OH; Fmoc-Trp-OH; N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine; Further stages;

Reference yield:

→ lanreotide (108736-35-2)

Guidance literature:

upstream raw materials:

H-D-β-Nal-Cys-(Acm)-Tyr-D-Trp-Lys-Val-Cys(Acm)-Thr-NH₂

Fmoc-Tyr(Clt)-OH

Fmoc-Val-OH

Boc-Lys(Boc)-OH

Refernces

• 1、 -. "Boc and Fmoc solid phase peptide synthesis". Page/Page column 10. . Retrieved 2013/03/26.
• 2、 -. "Pharmaceutical compositions containing growth-hormone inhibitors or their biologically active fragments for the treatment of uterine myomas". . . Retrieved 2008/06/13.