Felypressin CAS 56-59-7
Introduction：Basic information about Felypressin CAS 56-59-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Felypressin Basic information
| Product Name: | Felypressin |
| Synonyms: | FELYPRESSIN;H-CYS-PHE-PHE-GLN-ASN-CYS-PRO-LYS-GLY-NH2, CYS1,6, CYCLIC;[PHE2,LYS8]-VASOPRESSIN;2-L-Phenylalanine-8-L-lysine-vasopressin;N-[5-Amino-1-(carbamoylmethylcarbamoyl)pentyl]-1-[19-amino-13,16-dibenzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]pyrrolidine-2-carboxamide;Octapressin;Phelypressin;PLV-2 |
| CAS: | 56-59-7 |
| MF: | C46H65N13O11S2 |
| MW: | 1040.22 |
| EINECS: | 200-282-7 |
| Product Categories: | Inhibitors;Amino Acids & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Vasopressin and Oxytocin receptor |
| Mol File: | 56-59-7.mol |
Felypressin Chemical Properties
| Melting point | >197oC (dec.) |
| Boiling point | 1571.3±65.0 °C(Predicted) |
| density | 1.288±0.06 g/cm3(Predicted) |
| storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| solubility | Freely soluble in water, practically insoluble in acetone and ethanol (96 per cent). It dissolves in dilute solutions of alkali hydroxides. |
| pka | 12.82±0.70(Predicted) |
| form | Solid |
| color | White |
| Sequence | H-[Cys-Phe-Phe-Gln-Asn-Cys]-Pro-Lys-Gly-NH2，(Disulfide bridge: Cys-Cys) |
| CAS DataBase Reference | 56-59-7(CAS DataBase Reference) |
Safety Information
| WGK Germany | 3 |
| Chemical Properties | White or almost white, powder or flakes |
| Originator | Octapressin,Sandoz,W. Germany,1967 |
| Uses | Felypressin(Octapressin) is a vasopressin 1 agonist and a peptide containing eight amino acids including cystine. Felypressin is used as a vasoconstrictor. |
| Definition | ChEBI: A synthetic nonapeptide comprising cysteinyl, phenylalanyl, phenylalanyl, glutaminyl, asparaginyl, cysteinyl, prolyl, lysyl, and glycinamide residues in sequence, with a disulfide bridge joining the two cysteine residues. Its antidiuretic effects are less han those of vasopressin. It is used as a vasoconstrictor in local anaesthetic injections for dental use, and is an ingredient of preparations that have been used for treatment of pain and inflammation of the mouth. |
| Manufacturing Process | Preparation of N-Carbobenzoxy-L-Glutaminyl-L.Asparaginyl-S-Benzyl-LCysteinyl-L-Prolyl-ε-N-p-Toluenesulfonyl-L-Lysylglycinamide: 200 parts byweight of N-carbobenzoxy-L-prolyl-ε-N-p-toluenesulfonyl-L-lysyl-glycinamideare dissolved in 1,000 parts by volume of anhydrous acetic acid which hasbeen saturated with HBr, the mixture allowed to stand for 1 hour at 20°C andthen evaporated under reduced pressure at below 40°C. The residue from thisevaporation is carefully washed with diethyl ether and then added to asolution of 185 parts by weight of N-carbobenzoxy-L-glutaminyl-L-asparaginyl-S-benzyl-L-cysteinyl-azide and 48 parts by volume of triethylamine in 1,500parts by volume of dimethylformamide. The mixture is allowed to standovernight at 20°C and the mixture is then poured into twice its volume ofacetone. The precipitate which settles out is filtered off, washed with water,and recrystallized from dimethylformamide-acetone. There are thus obtained190 parts by weight of N-carbobenzoxy-L-glutaminyl-L-asparaginyl-S-benzyl-Lcysteinyl-L-prolyl-ε-N-p-toluenesulfonyl-L-lysyl-glycinamide; MP 165°C(decomposition). Preparation of N-Carbobenzoxy-S-Benzyl-L-Cysteinyl-L-Phenylalanyl-LPhenylalanyl-L-Glutaminyl-L-Asparaginyl-S-Benzyl-L-Cysteinyl-L-Prolyl-ε-N-p-Toluenesulfonyl-L-Lysyl-Glycinamide: 50 parts by weight of N-carbobenzoxy-Lglutaminyl-L-asparaginyl-S-benzyl-L-cysteinyl-L-prolyl-ε-N-p-toluenesulfonyl-Llysyl-glycinamide are dissolved in 400 parts by volume of anhydrous aceticacid which is saturated with HBr, and the mixture allowed to stand for 1 hourat 20°C. After evaporating off the solvent under reduced pressure at atemperature of 35°C (or another temperature below 40°C), the residue iscarefully washed with diethyl ester, whereupon a solution of 32 parts byweight of N-carbobenzoxy-S-benzyl-L-cysteinyl-L-phenylalanyl-L-phenylalanylazideand 70 parts by volume of triethylamine in 500 parts by volume ofdimethylformamide is added. The mixture is allowed to stand for 2 days at 20°C, after which twice itsvolume of ethylacetate is added and the resultant precipitate then washedwith warm methanol. There are obtained 45 parts by weight of Ncarbobenzoxy-S-benzyl-L-cysteinyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-S-benzyl-L-cysteinyl-L-prolyl-ε-N-p-toluenesulfonyl-L-lysylglycinamide;MP 222°C. Preparation of L-Cysteinyl-L-Phenylalanyl-L-Phenylalanyl-L-Glutaminyl-LAsparaginyl-L-Cysteinyl-L-Prolyl-L-Lysyl-Glycinamide: Metallic potassium isstirred into a solution of 10 parts by weight of N-carbobenzoxy-S-benzyl-Lcysteinyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-S-benzyl-Lcysteinyl-L-prolyl-ε-N-p-toluenesulfonyl-L-lysyl-glycinamide in 2,500 parts ofdry liquid ammonia at boiling temperature of the solution, until a stable bluecoloration appears. After the addition of 1.8 parts by weight of ammoniumchloride, the solution is evaporated to dryness. The residue of this evaporationcontains the desired L-cysteinyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-Lasparaginyl-L-cysteinyl-L-prolyl-L-lysyl-glycinamide Preparation of Felypressin: The aforesaid residue, containing the L-cysteinyl-Lphenylalanyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-Llysyl-glycinamide, is dissolved in 20,000parts by volume of 0.01 normal aceticacid and is then oxidized by passing air into the solution at a pH of 6.5 to 8.0for 1 hour. The solution, which contains Felypressin, is adjusted to a pH of 4.0to 5.0, whereupon 100 parts by weight of sodium chloride are added and themixture evaporated to dryness, yielding a dry powder of good stability. It can be stored, and yields a clear solution, e.g., in water or other appropriatesolvent. The solution may be used directly or, if desired, after dilution withwater or a sodium chloride solution |
| Brand name | PLV-2 (Novartis). |
| Therapeutic Function | Vasoconstrictor |
| General Description | Felypressin, 2-L-phenylalanine-8-L-lysinevasopressin, has relatively low antidiuretic activity and littleoxytocic activity. It has considerable pressor (i.e., vasoconstrictor)activity, which differs from that of epinephrine (i.e.,following capillary constriction in the intestine it lowers thepressure in the vena portae, whereas epinephrine raises theportal pressure). Felypressin also causes increased renalblood flow in the cat, whereas epinephrine brings about afall in renal blood flow. Felypressin is five times more effectiveas a vasopressor than is lysine vasopressin and is recommendedin surgery to minimize blood flow, especially inobstetrics and gynecology. |
Felypressin Preparation Products And Raw materials
| Raw materials | Ammonia-->Acetic acid-->Hydrogen bromide-->Oxygen |
