Felypressin

Synonyms :
2-(L-phenylalanine)-8-L-lysinevasopressin, Felipresina, Felypressin, Felypressine, Felypressinum, PLV-2

Status : approved

Category

Vasoconstrictor Agents

Description

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 than 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. [ChEBI]

Used

For use as an alternative to adrenaline as a localising agent, provided that local ischaemia is not essential.

Mechanism Of Action

Felypressin binds to the vasopressin receptor V1a. This causes contraction of the smooth muscle in the vascular bed, especially capillaries, small arterioles and venules.

Pharmacodynamics

Felypressin is a synthetic analog of lypressin or vasopressin with more vasoconstrictor activity than antidiuretic action. It is used primarily as a hemostatic. Felypressin is a non-catecholamine vasoconstrictor that is chemically related to vasopressin, the posterior pituitary hormone.

Chemical Classification

This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.

Cyclic peptides

Organic compounds

Organic acids and derivatives

Carboxylic acids and derivatives

Amino acids, peptides, and analogues

Chemical Name

2-(L-phenylalanine)-8-L-lysinevasopressin

Calculated Property

kind Value Source
logP -1.1 ALOGPS
logS -4.4 ALOGPS
Water Solubility 4.53e-02 g/l ALOGPS
logP -5.8 ChemAxon
IUPAC Name (2S)-6-amino-2-{[(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-13,16-dibenzyl-10-(2-carbamoylethyl)-7-(carbamoylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosane-4-carbonyl]pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)hexanamide ChemAxon
Traditional IUPAC Name felypressin ChemAxon
Molecular Weight 1040.219 ChemAxon
Monoisotopic Weight 1039.436791367 ChemAxon
SMILES NCCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CC2=CC=CC=C2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O ChemAxon
Molecular Formula C46H65N13O11S2 ChemAxon
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)/t28-,29-,30-,31-,32-,33-,34-,35-/s2 ChemAxon
InChIKey InChIKey=SFKQVVDKFKYTNA-YVGXZPIDNA-N ChemAxon
Polar Surface Area (PSA) 405.32 ChemAxon
Refractivity 264.79 ChemAxon
Polarizability 103.93 ChemAxon
Rotatable Bond Count 19 ChemAxon
H Bond Acceptor Count 13 ChemAxon
H Bond Donor Count 12 ChemAxon
pKa (strongest acidic) 11.39 ChemAxon
pKa (strongest basic) 10.18 ChemAxon
Physiological Charge 2 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 1 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Vasopressin V1a receptor : in Human