P1-185
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).[1][2] 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.[1][2] 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.[2][3][4]
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| Other names | (3E)-3-({[(2S)-2-Amino-3-methylbutanoyl]oxy}imino)pregn-4-en-20-one |
| Drug class | Progestogen; Neurosteroid |
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| Chemical and physical data | |
| Formula | C26H40N2O3 |
| Molar mass | 428.617 g·mol−1 |
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See also
References
- MacNevin CJ, Atif F, Sayeed I, Stein DG, Liotta DC (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 (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.
- 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
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