Icatibant

Base Information

• Chemical Name: Icatibant
• CAS No.: 130308-48-4
• Molecular Formula: C₅₉H₈₉N₁₉O₁₃S
• Molecular Weight: 1304.54
• European Community (EC) Number: 863-000-7
• UNII: 7PG89G35Q7
• DSSTox Substance ID: DTXSID20903963
• Nikkaji Number: J389.307C
• Wikipedia: Icatibant
• Wikidata: Q902379
• NCI Thesaurus Code: C98883
• RXCUI: 1148138
• Pharos Ligand ID: C9RJ35J68WZH
• Metabolomics Workbench ID: 149668
• ChEMBL ID: CHEMBL2028850
• Mol file: 130308-48-4.mol

Synonyms:D-Arg(Hyp(3)-Thi(5)-D-Tic(7)-Oic(8))BK;D-Arg(Hyp(3)-Thi(5)-L-Tic(7)-Oic(8))BK;Firazyr;HOE 140;HOE-140;HOE140;Hoechst 140;Hoechst-140;icatibant;icatibant acetate;JE 049;JE-049;WIN 65365;WIN-65365

Chemical Property of Icatibant

Chemical Property:

• Appearance/Colour: White solid
• Refractive Index: 1.742
• PKA: 3.60±0.21(Predicted)
• PSA: 544.46000
• Density: 1.6 g/cm³
• LogP: 1.58520
• Storage Temp.: −20°C
• XLogP3: -6.4
• Hydrogen Bond Donor Count: 15
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 30
• Exact Mass: 1303.66079514
• Heavy Atom Count: 92
• Complexity: 2720

Purity/Quality:

99% ^*data from raw suppliers

HOE 140 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)CC(N2C(=O)C3CC4=CC=CC=C4CN3C(=O)C(CO)NC(=O)C(CC5=CC=CS5)NC(=O)CNC(=O)C6CC(CN6C(=O)C7CCCN7C(=O)C(CCCN=C(N)N)NC(=O)C(CCCN=C(N)N)N)O)C(=O)NC(CCCN=C(N)N)C(=O)O
• Isomeric SMILES: C1CC[C@H]2[C@@H](C1)C[C@H](N2C(=O)[C@H]3CC4=CC=CC=C4CN3C(=O)[C@H](CO)NC(=O)[C@H](CC5=CC=CS5)NC(=O)CNC(=O)[C@@H]6C[C@H](CN6C(=O)[C@@H]7CCCN7C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](CCCN=C(N)N)N)O)C(=O)N[C@@H](CCCN=C(N)N)C(=O)O
• Recent ClinicalTrials: Prevention of Intradialytic Hypotension by Inhibiting Bradykinin B2 Receptor
• Recent EU Clinical Trials: Evaluation of the effects of bradykinin antagonists on pulmonary manifestations of COVID-19 infections.
• Recent NIPH Clinical Trials: A study on the efficacy of icatibant for sweating-induced dermal pain
• Uses: Antagonist (bradykinin).

Technology Process of Icatibant

There total 3 articles about Icatibant 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: 70.0%

Fmoc-(D)Arg(Pbf)-Arg(Pbf)-Pro-Hyr(tBu)-Gly-OH + Fmoc-Ser(tBu)-OH (71989-33-8) + N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (130309-33-0) + 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid (130309-37-4,1217512-55-4,134526-62-8) + Fmoc-β-(2-thienyl)-L-alanine (130309-35-2,134439-24-0) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) → D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg (130308-48-4)

Guidance literature:

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; With dmap; acetic anhydride; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

With piperidine; In N,N-dimethyl-formamide; at 20 ℃;

Fmoc-(D)Arg(Pbf)-Arg(Pbf)-Pro-Hyr(tBu)-Gly-OH; Fmoc-Ser(tBu)-OH; N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; Fmoc-β-(2-thienyl)-L-alanine; Further stages;

Reference yield:

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-Pro-OH (71989-31-6) + Fmoc-Ser(tBu)-OH (71989-33-8) + (2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid (268729-12-0) + N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (130309-33-0) + 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid (130309-37-4,1217512-55-4,134526-62-8) + Fmoc-β-(2-thienyl)-L-alanine (130309-35-2,134439-24-0) + Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine (187618-60-6) + N-α-[(9H-fluoren-9-ylmethoxy)carbonyl]-NG-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine (187618-60-6) → D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg (130308-48-4)

Guidance literature:

Nα-(9-fluorenylmethyloxycarbonyl)-Nγ-2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl-L-arginine; With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃;

With methanol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

N-(fluoren-9-ylmethoxycarbonyl)glycine; Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; (2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid; N-Fmoc-D-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid; 1‐fluorenylmethoxycarbonyl-(2S,3aS,7aS)‐octahydroindole‐2‐carboxylic acid; Fmoc-β-(2-thienyl)-L-alanine; N-α-[(9H-fluoren-9-ylmethoxy)carbonyl]-N^G-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-D-arginine; Reagent/catalyst; Temperature;

Reference yield:

→ D-Arg-Arg-Pro-Hyp-Gly-Thi-Ser-D-Tic-Oic-Arg (130308-48-4)

Guidance literature:

upstream raw materials:

N-(fluoren-9-ylmethoxycarbonyl)glycine

Fmoc-Pro-OH

Fmoc-Ser(tBu)-OH

(2S,4R)-4-tert-butoxy-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carboxylic acid

Refernces

• 1、 -. "A METHOD FOR PRODUCTION OF HIGH PURITY ICATIBANT". Page/Page column 13-16. . Retrieved 2019/11/12.
• 2、 -. "BRADYKININ ANTAGONISTS". . . Retrieved 2008/06/13.