P1-185
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| Synonyms | (3E)-3-({[(2S)-2-Amino-3-methylbutanoyl]oxy}imino)pregn-4-en-20-one |
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| Formula | C26H40N2O3 |
| Molar mass | 428.61 g/mol |
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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).[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 is somewhat challenging, so oxime conjugates of progesterone of the C20 instead of C3 position have since been developed.[2]
See also[edit]
- List of neurosteroids
- Estradiol sulfamate
- Ganaxolone
- Norelgestromin
- Norethisterone acetate oxime
- Norgestimate
- Pregnenolone
- Quingestrone
References[edit]
- ^ a b 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.
- ^ a b c 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.
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