Jump to section
IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyFelypressin
Identification
- Name
- Felypressin
- Accession Number
- DB00093 (BTD00114, BIOD00114)
- Type
- Small Molecule
- Groups
- Experimental
- 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
Structure for Felypressin (DB00093)
- Synonyms
- 2-(L-phenylalanine)-8-L-lysinevasopressin
- Felipresina
- Felypressin
- Felypressine
- Felypressinum
- PLV-2
- International/Other Brands
- Colupressine (Joullie) / Octapressin (Sandoz)
- Categories
- Amino Acids, Peptides, and Proteins
- Cardiovascular Agents
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Lypressin
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary Hormones
- Pituitary Hormones, Posterior
- Proteins
- Vasoconstrictor Agents
- Vasopressin and Analogues
- Vasopressins
- 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[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
Pharmacology
- Indication
For use as an alternative to adrenaline as a localising agent, provided that local ischaemia is not essential.
- 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.
Target Actions Organism AVasopressin V1a receptor agonistHuman - 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
Drug Interaction 3,5-diiodothyropropionic acid The therapeutic efficacy of Felypressin can be increased when used in combination with 3,5-diiodothyropropionic acid. Abaloparatide The therapeutic efficacy of Felypressin can be increased when used in combination with Abaloparatide. Benzylthiouracil The therapeutic efficacy of Felypressin can be increased when used in combination with Benzylthiouracil. Carbimazole The therapeutic efficacy of Felypressin can be increased when used in combination with Carbimazole. Dibromotyrosine The therapeutic efficacy of Felypressin can be increased when used in combination with Dibromotyrosine. Follitropin The therapeutic efficacy of Felypressin can be increased when used in combination with Follitropin. Levothyroxine The therapeutic efficacy of Felypressin can be increased when used in combination with Levothyroxine. Liothyronine The therapeutic efficacy of Felypressin can be increased when used in combination with Liothyronine. Liotrix The therapeutic efficacy of Felypressin can be increased when used in combination with Liotrix. Methimazole The therapeutic efficacy of Felypressin can be increased when used in combination with Methimazole. - 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
- Cecanho R, De Luca LA Jr, Ranali J: Cardiovascular effects of felypressin. Anesth Prog. 2006 Winter;53(4):119-25. [PubMed:17177590]
- External Links
- PubChem Compound
- 14257662
- PubChem Substance
- 46507522
- ChemSpider
- 16736539
- ChEBI
- 60564
- ChEMBL
- CHEMBL3185126
- Therapeutic Targets Database
- DAP000217
- PharmGKB
- PA164744374
- Wikipedia
- Felypressin
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Novartis pharmaceuticals corp
- Packagers
- Not Available
- Dosage forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 222 Boissonnas, R.and Guttmann, S.; U.S. Patent 3,232,923; February 1, 1966: assigned to Sandoz AG, Switzerland. - Predicted Properties
Property Value Source Water Solubility 0.0453 mg/mL ALOGPS logP -1.1 ALOGPS logP -5.8 ChemAxon logS -4.4 ALOGPS pKa (Strongest Acidic) 11.39 ChemAxon pKa (Strongest Basic) 10.18 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 13 ChemAxon Hydrogen Donor Count 12 ChemAxon Polar Surface Area 405.32 Å2 ChemAxon Rotatable Bond Count 19 ChemAxon Refractivity 264.79 m3·mol-1 ChemAxon Polarizability 103.93 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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
- 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]
- 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]
- 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]
- 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 December 01, 2018 19:14