EIDD-1723

EIDD-1723, also known as EPRX-01723 or as progesterone 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt, is a synthetic, water-soluble analogue of progesterone and a neurosteroid which was developed for the potential treatment of traumatic brain injury.[1][2] It is a rapidly converted prodrug of EIDD-036 (EPRX-036; progesterone 20-oxime), which is considered to be the active form of the agent.[1] Previous C3 and C20 oxime derivatives of progesterone, such as P1-185 (progesterone 3-O-(L-valine)-E-oxime), were also developed and studied prior to EIDD-1723.[3][4]

EIDD-1723
Clinical data
Other namesProgesterone 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt; Pregn-4-ene-3,20-dione 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt
Drug classNeurosteroid
Identifiers
IUPAC name
  • Pregn-4-ene-3,20-dione 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt
CAS Number
Chemical and physical data
FormulaC22H32NNa2O6P
Molar mass483.452 g·mol−1
3D model (JSmol)
SMILES
  • C/C([C@H]1CC[C@@]2([H])[C@]3([H])CCC4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=N\OCOP([O-])([O-])=O.[Na+].[Na+]
InChI
  • InChI=1S/C22H34NO6P.2Na/c1-14(23-28-13-29-30(25,26)27)18-6-7-19-17-5-4-15-12-16(24)8-10-21(15,2)20(17)9-11-22(18,19)3;;/h12,17-20H,4-11,13H2,1-3H3,(H2,25,26,27);;/q;2*+1/p-2/b23-14+;;/t17-,18+,19-,20-,21-,22+;;/m0../s1
  • Key:SXDGHAWSHQZKQM-ZZSMYOISSA-L

See also

References
  1. Wali B, Sayeed I, Guthrie DB, Natchus MG, Turan N, Liotta DC, Stein DG (October 2016). "Evaluating the neurotherapeutic potential of a water-soluble progesterone analog after traumatic brain injury in rats". Neuropharmacology. 109: 148–158. doi:10.1016/j.neuropharm.2016.05.017. PMID 27267687.
  2. Guthrie, D. B., Lockwood, M. A., Natchus, M. G., Liotta, D. C., Stein, D. G., & Sayeed, I. (2017). U.S. Patent No. 9,802,978. Washington, DC: U.S. Patent and Trademark Office. https://patents.google.com/patent/US9802978B2/en
  3. MacNevin CJ, Atif F, Sayeed I, Stein DG, Liotta DC (October 2009). "Development and screening of water-soluble analogues of progesterone and allopregnanolone in models of brain injury". J. Med. Chem. 52 (19): 6012–23. doi:10.1021/jm900712n. PMID 19791804.
  4. Guthrie DB, Stein DG, Liotta DC, Lockwood MA, Sayeed I, Atif F, Arrendale RF, Reddy GP, Evers TJ, Marengo JR, Howard RB, Culver DG, Natchus MG (May 2012). "Water-soluble progesterone analogues are effective, injectable treatments in animal models of traumatic brain injury". ACS Med Chem Lett. 3 (5): 362–6. doi:10.1021/ml200303r. PMC 4025794. PMID 24900479.


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