Pasireotide acetate

Base Information

• Chemical Name: Pasireotide acetate
• CAS No.: 396091-73-9
• Molecular Formula: C58H66N10O9
• Molecular Weight: 1047.21
• European Community (EC) Number: 686-178-6
• UNII: 662X0VFR9L
• Wikipedia: Pasireotide
• Wikidata: Q27263939

Synonyms:Pasireotide acetate;Pasireotide (acetate);Pasireotide acetate salt [MI];396091-76-2;UNII-662X0VFR9L;662X0VFR9L;Cyclo((2S)-2-phenylglycyl-D-tryptophyl-L-lysyl-O-(phenylmethyl)-L-tyrosyl-L-phenylalanyl-(4R)-4-((((2-aminoethyl)amino)carbonyl)oxy)-L-prolyl), monoacetate;SOM230 (acetate);396091-73-9;396091-76-2 (acetate);HY-16381A;MFCD08067735;AKOS040764247;MS-31971;CS-0082819;Q27263939;acetic acid;[(3S,6S,9S,12R,15S,18S,20R)-9-(4-aminobutyl)-3-benzyl-12-(1H-indol-3-ylmethyl)-2,5,8,11,14,17-hexaoxo-15-phenyl-6-[(4-phenylmethoxyphenyl)methyl]-1,4,7,10,13,16-hexazabicyclo[16.3.0]henicosan-20-yl] N-(2-aminoethyl)carbamate

Chemical Property of Pasireotide acetate

Chemical Property:

• Boiling Point: 1351.4±65.0 °C(Predicted)
• PKA: 11.86±0.46(Predicted)
• PSA: 281.20000
• Density: 1.36±0.1 g/cm3(Predicted)
• LogP: 6.74190
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 18
• Exact Mass: 1106.52255309
• Heavy Atom Count: 81
• Complexity: 1970

Purity/Quality:

99% ^*data from raw suppliers

PasireotideTFASalt ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)O.C1C(CN2C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C2=O)CC3=CC=CC=C3)CC4=CC=C(C=C4)OCC5=CC=CC=C5)CCCCN)CC6=CNC7=CC=CC=C76)C8=CC=CC=C8)OC(=O)NCCN
• Isomeric SMILES: CC(=O)O.C1[C@H](CN2[C@@H]1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C2=O)CC3=CC=CC=C3)CC4=CC=C(C=C4)OCC5=CC=CC=C5)CCCCN)CC6=CNC7=CC=CC=C76)C8=CC=CC=C8)OC(=O)NCCN
• Recent EU Clinical Trials: Efficacy and feasibility of pasireotide to reduce clinically relevant digestive leakage after complete cytoreductive surgery (CRS) plus Hyperthermic Intra-Peritoneal Chemotherapy (HIPEC) for peritoneal carcinomatosis – a phase II randomized multicentric trial
• Description: In April 2012, the European Commission approved pasireotide for the treatment of Cushing’s Disease (CD) in adult patients who have not responded to surgical interventionor forwhomsurgery is not anoption.Pasireotide was approved for the same indication by the US FDA in December of 2012. Pasireotide (also known as SOM230) is a cyclohexapeptide that acts as a somatostatin analogue to inhibit the release of ACTH. Somatostatins are cyclic peptides of 14 and 28 amino acids that play animportant role inregulating endocrineandexocrine release inmany tissues through an inhibitory mechanism. There are five known subtypes of somatostatin receptors (SSTRs). Natural somatostatins bind with high affinity to all five subtypes, however, their therapeutic use is limited by rapid degradation in plasma. Pasireotide arose fromefforts to identify a somatostatinmimetic with long-lasting inhibitory effects. Starting with a 14-amino acid somatostatin peptide, a systematic alanine scan revealed residues that were essential for receptor sub-type binding, including key b-turn regions and adjacent residues. Placing the key structural elements as unnatural amino acids in a cyclohexapeptide backbone gave pasireotide.
• Uses: Pasireotide can be used in biological study of long-term treatment of Cushing''s disease with pasireotide, 5-yr results from open-label extension study of Phase III trial.
• Clinical Use: Pasireotide, also known as SOM230, is a cyclic, hexameric peptide developed by Novartis which exhibits somatostatin-like activity as an antisecretory agent used in the treatment of Cushing’s disease. Pasireotide activates a broad range of somatostatin receptors, and in particular displays a significantly higher binding affinity for somatostatin receptors 1, 3, and 5 than its competitor somatostatin-mimic octreotide in vitro, as well as a comparable binding affinity for somatostatin receptor 2. Pasireotide is more potent than somatostatin in inhibiting the secretion of human growth hormone (HGH), glucagon, and insulin.
• Drug interactions: Potentially hazardous interactions with other drugs Antifungals: avoid with ketoconazole. Ciclosporin: possibly reduces ciclosporin concentration.

Technology Process of Pasireotide acetate

There total 2 articles about Pasireotide acetate 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:

cyclo[Pro(4-OCO-NH-CH2-CH2-NH-Boc)-Phg-D-Trp(BoC)-Lys(Boc)-Tyr(Bzl)-Phe] (842149-91-1) → pasireotide (396091-73-9)

Guidance literature:

With chlorotriisopropylsilane; trifluoroacetic acid; In water; at 5 - 10 ℃; for 1h;

Reference yield:

bis(trichloromethyl) carbonate (32315-10-9) + N-BOC-1,2-diaminoethane (57260-73-8) + cyclo(Phe-Pro(4-OH)-Phg-D-Trp(Boc)-Lys(Boc)-Tyr(Bzl)) → pasireotide (396091-73-9)

Guidance literature:

bis(trichloromethyl) carbonate; cyclo(Phe-Pro(4-OH)-Phg-D-Trp(Boc)-Lys(Boc)-Tyr(Bzl)); In tetrahydrofuran; for 1h;

N-BOC-1,2-diaminoethane; With dmap; In tetrahydrofuran; at 20 ℃;

With chlorotriisopropylsilane; trifluoroacetic acid; In water; for 2h;

upstream raw materials:

cyclo[Pro(4-OCO-NH-CH₂-CH₂-NH-Boc)-Phg-D-Trp(BoC)-Lys(Boc)-Tyr(Bzl)-Phe]

bis(trichloromethyl) carbonate

N-BOC-1,2-diaminoethane

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