Identification

Name
Felypressin
Accession Number
DB00093  (BTD00114, BIOD00114)
Type
Small Molecule
Groups
Approved
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.

Structure
Thumb
Synonyms
  • 2-(L-phenylalanine)-8-L-lysinevasopressin
  • Felipresina
  • Felypressin
  • Felypressine
  • Felypressinum
  • PLV-2
International/Other Brands
Colupressine (Joullie) / Octapressin (Sandoz)
Categories
UNII
17N2918V6G
CAS number
56-59-7
Weight
Average: 1040.219
Monoisotopic: 1039.436791367
Chemical Formula
C46H65N13O11S2
InChI Key
SFKQVVDKFKYTNA-DZCXQCEKSA-N
InChI
InChI=1S/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-/m0/s1
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
SMILES
NCCCC[[email protected]](NC(=O)[[email protected]@H]1CCCN1C(=O)[[email protected]@H]1CSSC[[email protected]](N)C(=O)N[[email protected]@H](CC2=CC=CC=C2)C(=O)N[[email protected]@H](CC2=CC=CC=C2)C(=O)N[[email protected]@H](CCC(N)=O)C(=O)N[[email protected]@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O

Pharmacology

Indication

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

Structured Indications
Not Available
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.

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.

TargetActionsOrganism
AVasopressin V1a receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference

Boissonnas, R.and Guttmann, S.; U.S. Patent 3,232,923; February 1, 1966: assigned to Sandoz AG, Switzerland.

General References
  1. Cecanho R, De Luca LA Jr, Ranali J: Cardiovascular effects of felypressin. Anesth Prog. 2006 Winter;53(4):119-25. [PubMed:17177590]
External Links
ChemSpider
16736539
ChEBI
60564
ChEMBL
CHEMBL3185126
Therapeutic Targets Database
DAP000217
PharmGKB
PA164744374
Wikipedia
Felypressin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Novartis pharmaceuticals corp
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)222Boissonnas, R.and Guttmann, S.; U.S. Patent 3,232,923; February 1, 1966: assigned to Sandoz AG, Switzerland.
Predicted Properties
PropertyValueSource
Water Solubility0.0453 mg/mLALOGPS
logP-1.1ALOGPS
logP-5.8ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)11.39ChemAxon
pKa (Strongest Basic)10.18ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area405.32 Å2ChemAxon
Rotatable Bond Count19ChemAxon
Refractivity264.79 m3·mol-1ChemAxon
Polarizability103.93 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Cyclic peptides / Proline and derivatives / Macrolactams / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Pyrrolidinecarboxamides / N-acylpyrrolidines / Benzene and substituted derivatives / N-acyl amines / Tertiary carboxylic acid amides
show 10 more
Substituents
Alpha-oligopeptide / Cyclic alpha peptide / N-acyl-alpha amino acid or derivatives / Proline or derivatives / Macrolactam / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / N-acylpyrrolidine / Pyrrolidine carboxylic acid or derivatives
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
heterodetic cyclic peptide (CHEBI:60564)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Vasopressin receptor activity
Specific Function
Receptor for arginine vasopressin. The activity of this receptor is mediated by G proteins which activate a phosphatidyl-inositol-calcium second messenger system. Has been involved in social behavi...
Gene Name
AVPR1A
Uniprot ID
P37288
Uniprot Name
Vasopressin V1a receptor
Molecular Weight
46799.105 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Manning M, Stoev S, Chini B, Durroux T, Mouillac B, Guillon G: Peptide and non-peptide agonists and antagonists for the vasopressin and oxytocin V1a, V1b, V2 and OT receptors: research tools and potential therapeutic agents. Prog Brain Res. 2008;170:473-512. doi: 10.1016/S0079-6123(08)00437-8. [PubMed:18655903]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Drug created on June 13, 2005 07:24 / Updated on October 02, 2017 04:31