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Identification
NameFelypressin
Accession NumberDB00093  (BTD00114, BIOD00114)
TypeSmall Molecule
GroupsApproved
DescriptionA 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]
Structure
Thumb
Synonyms
2-(L-phenylalanine)-8-L-lysinevasopressin
Felipresina
Felypressin
Felypressine
Felypressinum
PLV-2
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ColupressineJoullie
OctapressinSandoz
Brand mixturesNot Available
SaltsNot Available
Categories
UNII17N2918V6G
CAS number56-59-7
WeightAverage: 1040.219
Monoisotopic: 1039.436791367
Chemical FormulaC46H65N13O11S2
InChI KeySFKQVVDKFKYTNA-YVGXZPIDNA-N
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
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)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[[email protected]](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
Pharmacology
IndicationFor use as an alternative to adrenaline as a localising agent, provided that local ischaemia is not essential.
Structured Indications Not Available
PharmacodynamicsFelypressin 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 actionFelypressin binds to the vasopressin receptor V1a. This causes contraction of the smooth muscle in the vascular bed, especially capillaries, small arterioles and venules.
TargetKindPharmacological actionActionsOrganismUniProt ID
Vasopressin V1a receptorProteinyes
agonist
HumanP37288 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot 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
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET featuresNot Available
Pharmacoeconomics
Manufacturers
  • Novartis pharmaceuticals corp
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point222Boissonnas, 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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • N-acylpyrrolidine
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Cyclic alcohol
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Organic disulfide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

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 behaviors, including affiliation and attachment.
Gene Name:
AVPR1A
Uniprot ID:
P37288
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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23