Felypressin

Felypressin is a non-catecholamine vasoconstrictor that is chemically related to vasopressin, the posterior pituitary hormone. It is added to some local anaesthetics such as prilocaine in a concentration of 0.03 IU/ml. Felypressin is a Vasopressin 1 agonist, and will thus have effects at all Arginine vasopressin receptor 1As. It will, however, have its main physiological effects on vascular SMC's due to the form in which it is administered.

Felypressin
Names
IUPAC name
1-[19-Amino-13,16-dibenzyl-10-(2-carbamoyl-ethyl)-7-carbamoylmethyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaaza-cycloeicosane-4-carbonyl]-pyrrolidine-2-carboxylic acid [5-amino-1-(carbamoylmethyl-carbamoyl)-pentyl]-amide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.257
PubChem CID
UNII
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 Y
    Key: SFKQVVDKFKYTNA-DZCXQCEKSA-N Y
  • 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-/m0/s1
    Key: SFKQVVDKFKYTNA-DZCXQCEKBI
SMILES
  • NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@@H]1CCCN1C(=O)[C@H]4NC(=O)[C@@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H](N)CSSC4)CC(N)=O
Properties
Chemical formula
 C46H65N13O11S2
Molar mass 1040.22 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

V1 receptors are found in various sites around the body. The major points include the CNS, Liver, Anterior Pituitary, Muscle (both vascular and non-vascular smooth muscle), and Platelets (CLAMP).

Another example of a V1 agonist is terlipressin - which is used in oesophageal varices.

References
    • "Vasopressin analogues and treatments", Prof Buckingham, Imperial College School of Medicine (ICSM) - adapted by JHPatel


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