Octreotida

Base Information

• Chemical Name: Octreotida
• CAS No.: 83150-76-9
• Molecular Formula: C49H66N10O10S2
• Molecular Weight: 1019.26
• Hs Code.: 3004909090
• 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: 83150-76-9.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: white powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.673
• Boiling Point: 1447.228°C at 760 mmHg
• PKA: 12.60±0.70(Predicted)
• 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:

99%min ^*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
• Description: Octreotide is a long-acting somatostatin analog indicated for symptomatic control in acromegaly and gastroenteropancreatic tumors. Other potential uses under investigation include diabetes, psoriasis and Alzheimer's disease.
• Uses: Octreotide Acetate is the acetate salt of a synthetic long-acting cyclic octapeptide with pharmacologic properties mimicking those of the natural hormone somatostatin. It inhibits the secretion of growth hormone, glucagon, insulin, gastrin, vasoactive intestinal peptide, secretin, motilin and pancreatic polypeptide. Octreotide acetate was uses for the treatment of severe diarrhea and flushing associated with malignant carcinoid tumors, acromegaly, and diarrhea associated with VIPoma; and, then in 2010, for the treatment of neuroendocrine tumors.
• Indications: Octreotide acetate (Sandostatin) is a synthetic peptide analogue of the hormone somatostatin. Its actions include inhibition of the pituitary secretion of growth hormone and an inhibition of pancreatic islet cell secretion of insulin and glucagon. Unlike somatostatin, which has a plasma half-life of a few minutes, octreotide has a plasma elimination half-life of 1 to 2 hours. Excretion of the drug is primarily renal.
• Therapeutic Function: Antiulcer, Growth hormone inhibitor
• Biological Functions: Octreotide acetate, a long-acting octapeptide analogue of somatostatin, has a half-life of approximately 100 minutes. A comparison of the primary structures of octreotide and somatostatin suggests little similarity, but from earlier work at the Salk Institute it was known that not all the residues in somatostatin were necessary to elicit its full biological activity. Other studies suggested that the essential fragment for its activity was the tetrapeptide Phe7-Trp8- Lys9-Thr10. These earlier studies helped in the design of the potent drug now known as octreotide acetate. This drug suppresses the secretion of gastroenteropancreatic peptides, such as gastrin, vasoactive intestinal peptide (VIP), insulin, and glucagon, as well as pituitary GH. Furthermore, it is more potent than natural somatostatin in inhibiting the release of glucagon, insulin, and GH.
• Clinical Use: Octreotide acetate is used by SC injection in the palliative treatment of patients with metastatic carcinoid tumors, which are tumors of the endocrine system, GI tract, and lung (gastroenteropancreatic). Carcinoid tumors secrete increasing amounts of vasoactive substances, including histamine, serotonin, bradykinin, and prostaglandins. Octreotide acetate inhibits or suppresses the release of these vasoactive substances and, thus, is useful in treating the severe diarrhea, facial flushing, and wheezing episodes that accompany carcinoid tumors. In addition, it finds use in the palliative management of VIP-secreting tumors (VIPomas, usually pancreatic tumors). Patients with VIPomas suffer a profuse, watery diarrhea syndrome, and octreotide acetate is able to help by decreasing the release of damaging intestinal tumor cell secretions. Octreotide also helps to reduce hypokalemia by correcting electrolyte imbalances.An excessive secretion of GH from the pituitary can cause the disorder known as acromegaly, which is characterized by a progressive enlargement of the head, face, hands, feet, and thorax. Inasmuch as octreotide acetate is able to decrease the secretion of GH from the pituitary, it is used in treating patients with acromegaly who are unresponsive to previous pituitary radiation therapy or surgery. It is used in the treatment of acromegaly, because it reduces the blood levels of both GH and insulin-like growth factor-I (IGF-I). The long-acting repository form of octreotide acetate also is used in treating acromegaly, carcinoid tumors, and VIPomas, but in monthly depot injections.Octreotide for IV injection is used in the treatment of acute bleeding from esophageal varices. Variceal bleeding occurs in about half the patients with cirrhosis of the liver and is responsible for about one-third of deaths in these patients. Octreotide is a potent vasoconstrictor that reduces portal and collateral blood flow by constricting visceral vessels, which leads to reduced portal blood pressure and decreases the bleeding.

Technology Process of Octreotida

There total 10 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: 85.6%

H-D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr-OH → octreotide (83150-76-9)

Guidance literature:

With ammonium acetate; pyrographite; In tetrahydrofuran; water; at 20 ℃;

Reference yield: 80.0%

D-Phe-Cys-Phe-D-Trp-Lys-Thr-Cys-Thr(ol) → octreotide (83150-76-9)

Guidance literature:

In water; at 20 ℃; for 47.5h; pH=7.4; aq. phosphate buffer;

DOI:10.1002/anie.200904276

Reference yield: 76.4%

H-DPhe-Cys(SO3Na)-Phe-DTrp-Lys-Thr-Cys-Thr-ol → octreotide (83150-76-9)

Guidance literature:

for 24 - 72h; pH=3 - 9.2; Product distribution / selectivity;

upstream raw materials:

Boc-D-Phe-OH

Togni's reagent

Togni's reagent II

Refernces

• 1、 Patil, Nitin A.,Karas, John A.,Wade, John D.,Hossain, Mohammed Akhter,Tailhades, Julien. "Rapid Photolysis-Mediated Folding of Disulfide-Rich Peptides". . p. 8599 - 8603. Retrieved 2019/06/04.
• 2、 Tailhades, Julien,Gidel, Marie-Aude,Grossi, Benjamin,Lecaillon, Jennifer,Brunel, Luc,Subra, Gilles,Martinez, Jean,Amblard, Muriel. "Synthesis of peptide alcohols on the basis of an O-N acyl-transfer reaction". experimental part. p. 117 - 120. Retrieved 2010/04/04.