EIDD-1723

EIDD-1723
Clinical data
Other names	Progesterone 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt; Pregn-4-ene-3,20-dione 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt
Drug class	Neurosteroid
Identifiers
	IUPAC name Pregn-4-ene-3,20-dione 20E-[O-[(phosphonooxy)methyl]oxime] sodium salt;
CAS Number	1659302-89-2;
Chemical and physical data
Formula	C22H32NNa2O6P
Molar mass	483.452 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

^ ^a ^b 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. S2CID 19906601.
^ 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
^ 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.
^ 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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[pmid27267687-1] 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. S2CID 19906601.

[US9802978B2-2] 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

[pmid19791804-3] 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.

[pmid24900479-4] 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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[2]

[3]

[4]

EIDD-1723

See also

References