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Identification
NameFelypressin
Accession NumberDB00093  (BIOD00114, BTD00114)
Typesmall molecule
Groupsapproved
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(L-phenylalanine)-8-L-lysinevasopressinNot AvailableNot Available
FelipresinaSpanishINN
FelypressinNot AvailableINN, BAN, USAN
FelypressineFrenchINN
FelypressinumLatinINN
PLV-2Not AvailableNot Available
SaltsNot Available
Brand names
NameCompany
ColupressineJoullie
OctapressinSandoz
Brand mixtures
Brand NameIngredients
Citanest DentalFelypressin + Prilocaine
Citanest Dental OctapressinFelypressin + Prilocaine
Citanest OctapressinFelypressin + Prilocaine
Xylonest OctapressinFelypressin + Prilocaine
Categories
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[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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentPeptides
Alternative parentsNot Available
SubstituentsNot Available
Classification descriptionNot Available
Pharmacology
IndicationFor use as an alternative to adrenaline as a localising agent, provided that local ischaemia is not essential.
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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
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
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption Not Available Not Available
Blood Brain Barrier Not Available Not Available
Caco-2 permeable Not Available Not Available
P-glycoprotein substrate Not Available Not Available
P-glycoprotein inhibitor I Not Available Not Available
P-glycoprotein inhibitor II Not Available Not Available
Renal organic cation transporter Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 1A2 substrate Not Available Not Available
CYP450 2C9 substrate Not Available Not Available
CYP450 2D6 substrate Not Available Not Available
CYP450 2C19 substrate Not Available Not Available
CYP450 3A4 substrate Not Available Not Available
CYP450 inhibitory promiscuity Not Available Not Available
Ames test Not Available Not Available
Carcinogenicity Not Available Not Available
Biodegradation Not Available Not Available
Rat acute toxicity Not Available Not applicable
hERG inhibition (predictor I) Not Available Not Available
hERG inhibition (predictor II) Not Available Not 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 solubility4.53e-02 g/lALOGPS
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 area405.32ChemAxon
rotatable bond count19ChemAxon
refractivity264.79ChemAxon
polarizability103.93ChemAxon
number of rings4ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

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

General Reference
  1. Cecanho R, De Luca LA Jr, Ranali J: Cardiovascular effects of felypressin. Anesth Prog. 2006 Winter;53(4):119-25. Pubmed
External Links
ResourceLink
Therapeutic Targets DatabaseDAP000217
PharmGKBPA164744374
WikipediaFelypressin
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Vasopressin V1a receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Vasopressin V1a receptor P37288 Details

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
  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
  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. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on April 22, 2014 13:18