Octreotida

Base Information

• Chemical Name: Octreotida
• CAS No.: 79517-01-4
• Molecular Formula: C₂H₄O₂*C₄₉H₆₆N₁₀O₁₀S₂
• Molecular Weight: 1079.31
• Hs Code.: 2937190000
• European Community (EC) Number: 616-695-4
• Wikipedia: Octreotide
• Wikidata: Q63413189
• NCI Thesaurus Code: C711
• RXCUI: 7617
• Metabolomics Workbench ID: 42574
• ChEMBL ID: CHEMBL3182554
• Mol file: 79517-01-4.mol

Synonyms:Compound 201 995;Compound 201-995;Compound 201995;Octreotide;Octreotide Acetate;Octreotide Acetate Salt;SAN 201 995;SAN 201-995;SAN 201995;Sandostatin;Sandostatine;Sandoz 201 995;Sandoz 201-995;Sandoz 201995;SM 201 995;SM 201-995;SM 201995;SMS 201 995;SMS 201-995;SMS 201995

Chemical Property of Octreotida

Chemical Property:

• Appearance/Colour: Colourless to off-white lyophilised solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 153-156oC
• Boiling Point: 1447.228 °C at 760 mmHg
• Flash Point: 829.053 °C
• PSA: 382.82000
• Density: 1.395 g/cm³
• LogP: 3.02100
• Storage Temp.: −20°C
• Solubility.: H2O: soluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 17
• Exact Mass: 1018.44048069
• Heavy Atom Count: 71
• Complexity: 1740

Purity/Quality:

98%, ^*data from raw suppliers

Octreotide Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Hormonal Agents
• Canonical SMILES: CC(C1C(=O)NC(CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)C(CC5=CC=CC=C5)N)C(=O)NC(CO)C(C)O)O
• Isomeric SMILES: C[C@H]([C@@H](CO)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)O)CCCCN)CC2=CNC3=CC=CC=C32)CC4=CC=CC=C4)NC(=O)[C@@H](CC5=CC=CC=C5)N)O
• Recent ClinicalTrials: Efficacy of Octreotide on Blood and Iron Requirements in Patients With Anemia Due to Angiodysplasias
• Recent EU Clinical Trials: Phase 1b/3 global, randomized, controlled, open-label trial comparing treatment with RYZ101 to standard of care (SoC) therapy in subjects with inoperable, advanced, somatostatin receptor expressing (SSTR+), well-differentiated gastro-enteropancreatic neuroendocrine tumors (GEP-NETs) that have progressed following prior treatment with 177Lu-labelled somatostatin analogue (177Lu-SSA) therapy (ACTION-1)
• Recent NIPH Clinical Trials: Study on the Effectiveness of Octreotide Treatment for Chyle Leakage after Neck Dissection
• Uses: Octapeptide analog of Somatostatin. A gastric antisecretory agent. Used in treatment of acromegaly natural hormone somatostatin Octreotide acetate USP (Sandostatin) is used to treat Mestastatic carcinoid tumors; vasoactive intestinal peptide-secretory tumors.
• Indications: Octreotide (Sandostatin) is a synthetic somatostatin analogue. It is used in a variety of situations and must be given subcutaneously or intravenously. Most commonly, it is used as a continuous intravenous infusion in patients hospitalized with bleeding varices, because it decreases splanchnic circulation and therefore reduces portal pressures.A long-acting depot form is approved for the suppression of severe diarrhea and flushing associated with malignant carcinoid syndrome and for the treatment of the profuse watery diarrhea associated with vasoactive intestinal peptide tumor. Octreotide is useful in inhibiting the secretion of various autacoids and peptide hormones by metastatic carcinoid tumors (serotonin) and islet cell carcinomas of the pancreas (gastrin, glucagon, insulin, vasoactive intestinal peptide). The diarrhea and flushing associated with the carcinoid syndrome are improved in 70 to 80% of the patients treated with octreotide. Its side effects, which are usually mild, include nausea and pain at the injection site. Mild transient hypoglycemia or hyperglycemia may result from alterations in insulin, glucagon, or growth hormone secretion.
• Therapeutic Function: Antiulcer, Growth hormone inhibitor
• Clinical Use: Relief of symptoms of gastro-enteropancreatic endocrine tumours and acromegaly
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: ciclosporin concentration reduced.

Technology Process of Octreotida

There total 2 articles about Octreotida 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: 30.21%

Boc-D-Phe-Cys(Trt)-Phe-D-Trp-Lys(Boc)-Thr(OtBu)-Cys(Trt)-Thr-OH + acetic acid (64-19-7,77671-22-8) → octreotide acetate (79517-01-4)

Guidance literature:

Boc-D-Phe-Cys(Trt)-Phe-D-Trp-Lys(Boc)-Thr(OtBu)-Cys(Trt)-Thr-OH; With triethylsilane; methoxybenzene; trifluoroacetic acid; In dichloromethane; at 10 - 30 ℃;

acetic acid; With iodine; In methanol; water; acetonitrile; at 25 - 30 ℃;

Reference yield:

→ Octreotide acetate (79517-01-4)

Guidance literature:

Reference yield: 77.0%

di-tert-butyl dicarbonate (24424-99-5) + 3-(triphenylmethylthio)propionic acid N-hydroxysuccinimide ester (129431-12-5) + octreotide acetate (79517-01-4) → Lys-boc octreotide 3-tritylmercaptopropionamide (1616776-08-9)

Guidance literature:

di-tert-butyl dicarbonate; octreotide acetate; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;

3-(triphenylmethylthio)propionic acid N-hydroxysuccinimide ester; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

upstream raw materials:

acetic acid

Downstream raw materials:

Lys-boc octreotide 3-tritylmercaptopropionamide

Refernces

• 1、 -. "Sustained release pharmaceutical compositions for the parenteral administration of hydrophilic compounds". . . Retrieved 2008/06/13.