56-59-7 Usage
Description
Felypressin, also known as Octapressin, is a synthetic nonapeptide that contains eight amino acids, including cystine. It is a vasopressin 1 agonist with relatively low antidiuretic activity and little oxytocic activity. Felypressin exhibits considerable pressor (vasoconstrictor) activity, which is different from that of epinephrine. It is five times more effective as a vasopressor than lysine vasopressin and is characterized by its white or almost white appearance in the form of powder or flakes.
Uses
Used in Surgery:
Felypressin is used as a vasoconstrictor in surgery to minimize blood flow, particularly in obstetrics and gynecology. Its vasoconstrictor properties make it a valuable tool for controlling bleeding and reducing blood loss during surgical procedures.
Used in Dental Applications:
Felypressin is used as a vasoconstrictor in local anesthetic injections for dental use. Its effectiveness in constricting blood vessels helps to minimize bleeding and swelling, allowing for a more comfortable and successful dental procedure.
Used in Treatment of Mouth Pain and Inflammation:
Felypressin is an ingredient in preparations that have been used for the treatment of pain and inflammation of the mouth. Its vasoconstrictor properties help to reduce swelling and alleviate pain, providing relief to patients suffering from oral discomfort.
Used in Pharmaceutical Industry:
Felypressin, under the brand name PLV-2 by Novartis, is utilized in the pharmaceutical industry for the development of medications targeting various medical conditions that can benefit from its vasoconstrictor properties.
Originator
Octapressin,Sandoz,W. Germany,1967
Manufacturing Process
Preparation of N-Carbobenzoxy-L-Glutaminyl-L.Asparaginyl-S-Benzyl-LCysteinyl-L-Prolyl-ε-N-p-Toluenesulfonyl-L-Lysylglycinamide: 200 parts by
weight of N-carbobenzoxy-L-prolyl-ε-N-p-toluenesulfonyl-L-lysyl-glycinamide
are dissolved in 1,000 parts by volume of anhydrous acetic acid which has
been saturated with HBr, the mixture allowed to stand for 1 hour at 20°C and
then evaporated under reduced pressure at below 40°C. The residue from this
evaporation is carefully washed with diethyl ether and then added to a
solution 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 1,500
parts by volume of dimethylformamide. The mixture is allowed to stand
overnight at 20°C and the mixture is then poured into twice its volume of
acetone. The precipitate which settles out is filtered off, washed with water,
and recrystallized from dimethylformamide-acetone. There are thus obtained
190 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 acetic
acid which is saturated with HBr, and the mixture allowed to stand for 1 hour
at 20°C. After evaporating off the solvent under reduced pressure at a
temperature of 35°C (or another temperature below 40°C), the residue is
carefully washed with diethyl ester, whereupon a solution of 32 parts by
weight of N-carbobenzoxy-S-benzyl-L-cysteinyl-L-phenylalanyl-L-phenylalanylazide
and 70 parts by volume of triethylamine in 500 parts by volume of
dimethylformamide is added.The mixture is allowed to stand for 2 days at 20°C, after which twice its
volume of ethylacetate is added and the resultant precipitate then washed
with 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 is
stirred 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 of
dry liquid ammonia at boiling temperature of the solution, until a stable blue
coloration appears. After the addition of 1.8 parts by weight of ammonium
chloride, the solution is evaporated to dryness. The residue of this evaporation
contains the desired L-cysteinyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-Lasparaginyl-
L-cysteinyl-L-prolyl-L-lysyl-glycinamidePreparation 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 acetic
acid and is then oxidized by passing air into the solution at a pH of 6.5 to 8.0
for 1 hour. The solution, which contains Felypressin, is adjusted to a pH of 4.0
to 5.0, whereupon 100 parts by weight of sodium chloride are added and the
mixture 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 appropriate
solvent. The solution may be used directly or, if desired, after dilution with
water or a sodium chloride solution
Therapeutic Function
Vasoconstrictor
Check Digit Verification of cas no
The CAS Registry Mumber 56-59-7 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 56-59:
(4*5)+(3*6)+(2*5)+(1*9)=57
57 % 10 = 7
So 56-59-7 is a valid CAS Registry Number.
InChI:InChI=1/C46H65N13O11S2/c47-18-8-7-14-29(40(64)52-23-38(51)62)54-45(69)35-15-9-19-59(35)46(70)34-25-72-71-24-28(48)39(63)55-31(20-26-10-3-1-4-11-26)43(67)56-32(21-27-12-5-2-6-13-27)42(66)53-30(16-17-36(49)60)41(65)57-33(22-37(50)61)44(68)58-34/h1-6,10-13,28-35H,7-9,14-25,47-48H2,(H2,49,60)(H2,50,61)(H2,51,62)(H,52,64)(H,53,66)(H,54,69)(H,55,63)(H,56,67)(H,57,65)(H,58,68)
