Felypressin

Identification

Name
Felypressin
Accession Number
DB00093
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 a non-catecholamine vasoconstrictor used 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.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 1040.219
Monoisotopic: 1039.436791367
Chemical Formula
C46H65N13O11S2
Synonyms
  • 2-(L-phenylalanine)-8-L-lysinevasopressin
  • Felipresina
  • Felypressin
  • Felypressine
  • Felypressinum
  • PLV-2

Pharmacology

Indication

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

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Felypressin is a synthetic analog of lypressin or vasopressin with a greater vasoconstrictor activity than antidiuretic action. It is used primarily as a hemostatic.

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
Humans
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
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
LevothyroxineLevothyroxine may increase the vasoconstricting activities of Felypressin.
LidocaineThe risk or severity of hypertension can be increased when Felypressin is combined with Lidocaine.
LiothyronineLiothyronine may increase the vasoconstricting activities of Felypressin.
LiotrixLiotrix may increase the vasoconstricting activities of Felypressin.
Patent BlueThe risk or severity of hypotension can be increased when Patent Blue is combined with Felypressin.
Thyroid, porcineThyroid, porcine may increase the vasoconstricting activities of Felypressin.
Thyrotropin alfaThyrotropin alfa may increase the vasoconstricting activities of Felypressin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

    Learn more
  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

Products

International/Other Brands
Colupressine (Joullie) / Octapressin (Sandoz)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Amine / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
heterodetic cyclic peptide (CHEBI:60564)

Chemical Identifiers

UNII
17N2918V6G
CAS number
56-59-7
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

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]
PubChem Compound
14257662
PubChem Substance
46507522
ChemSpider
16736539
RxNav
4319
ChEBI
60564
ChEMBL
CHEMBL3185126
Therapeutic Targets Database
DAP000217
PharmGKB
PA164744374
Wikipedia
Felypressin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentDental Extraction / Maxillary Teeth / Overcoming the Failure of Anaesthesia1

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

Targets

Kind
Protein
Organism
Humans
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 September 03, 2020 19:00

Logo pink
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
Logo pink
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates