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Epelsiban information


Epelsiban
Clinical data
ATC code
  • None
Legal status
Legal status
  • In general: non-regulated
Identifiers
IUPAC name
  • (3R,6R)-3-(2,3-dihydro-1H-inden-2-yl)-1-[(1R)-1-(2,6-dimethylpyridin-3-yl)-2-(morpholin-4-yl)-2-oxoethyl]-6-[(2S)-butan-2-yl]piperazine-2,5-dione
CAS Number
  • 872599-83-2
    1159097-48-9 (besylate)
PubChem CID
  • 11634973
DrugBank
  • DB11934
ChemSpider
  • 9809717
UNII
  • T2EZ19HX73
KEGG
  • D10117 checkY
ChEMBL
  • ChEMBL2037511
CompTox Dashboard (EPA)
  • DTXSID701029864 Edit this at Wikidata
Chemical and physical data
FormulaC30H38N4O4
Molar mass518.658 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CC[C@H](C)[C@@H]1C(=O)N[C@@H](C(=O)N1[C@H](C2=C(N=C(C=C2)C)C)C(=O)N3CCOCC3)C4CC5=CC=CC=C5C4
InChI
  • InChI=1S/C30H38N4O4/c1-5-18(2)26-28(35)32-25(23-16-21-8-6-7-9-22(21)17-23)29(36)34(26)27(24-11-10-19(3)31-20(24)4)30(37)33-12-14-38-15-13-33/h6-11,18,23,25-27H,5,12-17H2,1-4H3,(H,32,35)/t18-,25+,26+,27+/m0/s1
  • Key:UWHCWRQFNKUYCG-QUZACWSFSA-N

Epelsiban (INN,[1] USAN,[2] code name GSK-557,296-B) is an orally bioavailable drug which acts as a selective and potent oxytocin receptor antagonist (Ki = 0.13 nM).[3][4] It was initially developed by GlaxoSmithKline (GSK) for the treatment of premature ejaculation in men[5][6] and then as an agent to enhance embryo or blastocyst implantation in women undergoing embryo or blastocyst transfer associated with in vitro fertilization (IVF).,[7] and was also investigated for use in the treatment of adenomyosis.[8]

  1. ^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names (Rec. INN): List 67" (PDF). World Health Organization. p. 62. Archived from the original (PDF) on October 5, 2016. Retrieved 4 October 2016.
  2. ^ USAN Council (2011). "Statement on a Nonproprietary Name Adopted by the USAN Council" (PDF). Retrieved 2011-10-28.
  3. ^ Borthwick AD, Liddle J, Davies DE, Exall AM, Hamlett C, Hickey DM, Mason AM, Smith IE, Nerozzi F, Peace S, Pollard D, Sollis SL, Allen MJ, Woollard PM, Pullen MA, Westfall TD, Stanislaus DJ (January 2012). "Pyridyl-2,5-diketopiperazines as potent, selective, and orally bioavailable oxytocin antagonists: synthesis, pharmacokinetics, and in vivo potency". Journal of Medicinal Chemistry. 55 (2): 783–96. doi:10.1021/jm201287w. PMID 22239250.
  4. ^ Borthwick AD, Liddle J (January 2013). "Retosiban and Epelsiban: Potent and Selective Orally available Oxytocin Antagonists". In Domling A (ed.). Methods and Principles in Medicinal Chemistry: Protein-Protein Interactions in Drug Discovery. Weinheim: Wiley-VCH. pp. 225–256. doi:10.1002/9783527648207.ch10. ISBN 978-3-527-33107-9.
  5. ^ Clément P, Bernabé J, Compagnie S, Alexandre L, McCallum S, Giuliano F (August 2013). "Inhibition of ejaculation by the non‐peptide oxytocin receptor antagonist GSK 557296: a multi‐level site of action". British Journal of Pharmacology. 169 (7): 1477–1485. doi:10.1111/bph.12198. PMC 3724105. PMID 23530818.
  6. ^ Shinghal R, Barnes A, Mahar KM, Stier B, Giancaterino L, Condreay LD, Black L, McCallum SW (October 2013). "Safety and efficacy of epelsiban in the treatment of men with premature ejaculation: A randomized, double‐blind, placebo‐controlled, fixed‐dose study". The Journal of Sexual Medicine. 10 (10): 2506–2517. doi:10.1111/jsm.12272. PMID 23937679.
  7. ^ Mahar KM, Stier B, Fries M, McCallum SW (November 2015). "A single- and multiple-dose study to investigate the pharmacokinetics of epelsiban and its metabolite, GSK2395448, in healthy female volunteers". Clinical Pharmacology in Drug Development. 4 (6): 418–426. doi:10.1002/cpdd.210. PMID 27137713. S2CID 23903528.
  8. ^ Mahar KM, Enslin MB, Gress A, Amrine-Madsen H, Cooper M (January 2018). "Single‐and Multiple‐Day Dosing Studies to Investigate High‐Dose Pharmacokinetics of Epelsiban and Its Metabolite, GSK2395448, in Healthy Female Volunteers". Clinical Pharmacology in Drug Development. 7 (1): 33–43. doi:10.1002/cpdd.363. PMID 28556598. S2CID 41083332.

and 24 Related for: Epelsiban information

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Epelsiban

Last Update:

Epelsiban (INN, USAN, code name GSK-557,296-B) is an orally bioavailable drug which acts as a selective and potent oxytocin receptor antagonist (Ki =...

Word Count : 1682

Dipeptide

Last Update:

Retrieved 28 July 2014. Borthwick AD, Liddle J (January 2013). "Retosiban and Epelsiban: Potent and Selective Orally available Oxytocin Antagonists". In Domling...

Word Count : 749

Vasopressin

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 3871

Desmopressin

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1518

Oxytocin

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 11640

Atosiban

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1724

Oxytocin receptor

Last Update:

non-selective over vasopressin receptors Peptide Atosiban Barusiban Non-peptide Epelsiban L-368,899 (CAS# 148927-60-0) L-371,257 (CAS# 162042-44-6) – peripherally...

Word Count : 2492

Lithium carbonate

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 2631

Oxytocin receptor agonist

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 264

Carbetocin

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1913

Terlipressin

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 584

Tolvaptan

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 763

Vasopressin receptor

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 974

Vasopressin receptor antagonist

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1059

Demeclocycline

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1043

Neurophysin I

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 407

Vasotocin

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1361

Diketopiperazine

Last Update:

PMID 22709011. Borthwick AD, Liddle J (January 2013). "Retosiban and Epelsiban: Potent and Selective Orally available Oxytocin Antagonists". In Domling...

Word Count : 413

Vasopressin receptor 2

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1740

Uterotonic

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 2321

Conivaptan

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 805

Felypressin

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 130

Lixivaptan

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 1714

Nelivaptan

Last Update:

Antagonists: Peptide: Atosiban Tocinoic acid; Non-peptide: Barusiban Cligosiban Epelsiban Erlosiban IX-01 L-368,899 L-371,257 L-372,662 Nolasiban Retosiban SSR-126768...

Word Count : 259

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