P1-185

{{Short description|Chemical compound}}

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| IUPAC_name = [(E)-[(8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ylidene]amino] (2S)-2-amino-3-methylbutanoate

| image = P1-185.svg

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| class = Progestogen; Neurosteroid

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| CAS_number = 1185297-01-1

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| PubChem = 44219330

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| ChemSpiderID = 25052147

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| ChEMBL = 565873

| C=26 | H=40 | N=2 | O=3

| SMILES = CC(C)[C@@H](C(=O)O/N=C/1\CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@@H]4C(=O)C)C)C)N

| StdInChI_Ref =

| StdInChI = 1S/C26H40N2O3/c1-15(2)23(27)24(30)31-28-18-10-12-25(4)17(14-18)6-7-19-21-9-8-20(16(3)29)26(21,5)13-11-22(19)25/h14-15,19-23H,6-13,27H2,1-5H3/b28-18+/t19-,20+,21-,22-,23-,25-,26+/m0/s

| StdInChIKey_Ref =

| StdInChIKey = JFIPYWOCXPCAFX-NPRMJFGVSA-N

| synonyms = (3E)-3-({[(2S)-2-Amino-3-methylbutanoyl]oxy}imino)pregn-4-en-20-one

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P1-185, also known as progesterone 3-O-(L-valine)-E-oxime or as pregn-4-ene-3,20-dione 3-O-(L-valine)-E-oxime, is a synthetic progestogen and neurosteroid and an oxime ester analogue and prodrug of progesterone (and by extension of allopregnanolone).{{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 | year = 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 | year = 2012 | pmid = 24900479 | pmc = 4025794 | doi = 10.1021/ml200303r }} It was developed as an improved water-soluble version of progesterone such that it could be formulated as an aqueous preparation and easily and rapidly administered intravenously as a potential therapy for traumatic brain injury. However, the chemical synthesis of P1-185 was described as somewhat challenging, so oxime conjugates of progesterone of the C20 instead of C3 position, such as EIDD-1723 and EIDD-036, have since been developed.{{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