EIDD-036

{{Short description|Chemical compound}}

{{Distinguish|Progesterone 3-oxime}}

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| IUPAC_name = (8S,9S,10R,13S,14S,17S)-17-[(Z)-N-hydroxy-C-methylcarbonimidoyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one

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| class = Neurosteroid

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| CAS_number = 211302-60-2

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| PubChem = 86692077

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| synonyms = EPRX-036; Progesterone 20-oxime; P4-20-O; Pregn-4-ene-3,20-dione 20-oxime; 20-(Hydroxyimino)pregn-4-en-3-one

| C=21 | H=31 | N=1 | O=2

| SMILES = C/C(=N/O)/[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

| StdInChI_Ref =

| StdInChI = 1S/C21H31NO2/c1-13(22-24)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19,24H,4-11H2,1-3H3/b22-13-/t16-,17+,18-,19-,20-,21+/m0/s1

| StdInChIKey_Ref =

| StdInChIKey = WGIMTKVWTJMLDA-ODGMAUQTSA-N

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EIDD-036, also known as EPRX-036, as well as progesterone 20-oxime (P4-20-O) or 20-(hydroxyimino)pregn-4-en-3-one, is a synthetic, water-soluble analogue of progesterone, a neurosteroid, and the active metabolite of EIDD-1723 (EPRX-01723), a medication developed for the potential treatment of traumatic brain injury.{{cite journal | vauthors = Wali B, Sayeed I, Guthrie DB, Natchus MG, Turan N, Liotta DC, Stein DG | title = Evaluating the neurotherapeutic potential of a water-soluble progesterone analog after traumatic brain injury in rats | journal = Neuropharmacology | volume = 109 | pages = 148–158 | date = October 2016 | pmid = 27267687 | doi = 10.1016/j.neuropharm.2016.05.017 | 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{{cite journal | vauthors = MacNevin CJ, Atif F, Sayeed I, Stein DG, Liotta DC | title = Development and screening of water-soluble analogues of progesterone and allopregnanolone in models of brain injury | journal = J. Med. Chem. | volume = 52 | issue = 19 | pages = 6012–23 | date = October 2009 | pmid = 19791804 | doi = 10.1021/jm900712n }}{{cite journal | vauthors = 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 | title = Water-soluble progesterone analogues are effective, injectable treatments in animal models of traumatic brain injury | journal = ACS Med Chem Lett | volume = 3 | issue = 5 | pages = 362–6 | date = May 2012 | pmid = 24900479 | pmc = 4025794 | doi = 10.1021/ml200303r }}