Selepressin

Selepressin (INN) (code name FE-202158), also known as [Phe(2),Ile(3), Hgn(4),Orn(iPr)(8)]vasopressin) is a potent, highly selective, short-acting peptide full agonist of the vasopressin 1A receptor and analog of vasopressin which was under development by Ferring Pharmaceuticals for the treatment of vasodilatory hypotension in septic shock.[1][2][3][4]

Selepressin
Clinical data
Other namesH-Cys(1)-Phe-Ile-hGln-Asn-Cys(1)-Pro-Orn(iPr)-Gly-NH2
ATC code
  • None
Identifiers
IUPAC name
  • (2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-10-(4-amino-4-oxobutyl)-7-(2-amino-2-oxoethyl)-16-benzyl-13-[(2S)-butan-2-yl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-5-(propan-2-ylamino)pentan-2-yl]pyrrolidine-2-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC46H73N13O11S2
Molar mass1048.29 g·mol−1
3D model (JSmol)
SMILES
  • CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@H](C(=O)N1)Cc2ccccc2)N)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CCCNC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCCC(=O)N
InChI
  • InChI=1S/C46H73N13O11S2/c1-5-26(4)38-45(69)54-30(14-9-17-35(48)60)41(65)56-32(21-36(49)61)42(66)57-33(24-72-71-23-28(47)39(63)55-31(43(67)58-38)20-27-12-7-6-8-13-27)46(70)59-19-11-16-34(59)44(68)53-29(15-10-18-51-25(2)3)40(64)52-22-37(50)62/h6-8,12-13,25-26,28-34,38,51H,5,9-11,14-24,47H2,1-4H3,(H2,48,60)(H2,49,61)(H2,50,62)(H,52,64)(H,53,68)(H,54,69)(H,55,63)(H,56,65)(H,57,66)(H,58,67)/t26-,28-,29-,30-,31-,32-,33-,34-,38-/m0/s1
  • Key:JCVQBJTWWDYUFQ-MRUTUVJXSA-N

The Phase 2b/3 adaptive trial (SEPSIS-ACT) was terminated in February 2018 for futility. The trial was halted prior to the initiation of the arm for the highest dosing regimen of 5.0 ng/kg/min.[5]

References
  1. Levin JI (24 October 2014). Macrocycles in Drug Discovery. Royal Society of Chemistry. pp. 313–. ISBN 978-1-84973-701-2.
  2. Vincent J (23 September 2012). Annual Update in Intensive Care and Emergency Medicine 2012. Springer Science & Business Media. pp. 80–. ISBN 978-3-642-25716-2.
  3. Vincent JL (2 September 2008). Yearbook of Intensive Care and Emergency Medicine 2008. Springer Science & Business Media. pp. 427–. ISBN 978-3-540-77290-3.
  4. Laporte R, Kohan A, Heitzmann J, Wisniewska H, Toy J, La E, et al. (June 2011). "Pharmacological characterization of FE 202158, a novel, potent, selective, and short-acting peptidic vasopressin V1a receptor full agonist for the treatment of vasodilatory hypotension". The Journal of Pharmacology and Experimental Therapeutics. 337 (3): 786–96. doi:10.1124/jpet.111.178848. PMID 21411496. S2CID 576654.
  5. Clinical trial number NCT02508649 for "Selepressin Evaluation Programme for Sepsis-Induced Shock - Adaptive Clinical Trial" at ClinicalTrials.gov
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