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Progesterone 3-oxime (P4-3-O), also known as 3-(hydroxyimino)pregn-4-en-3-one, is a progesterone derivative which was never marketed.[1] It is a progestogen oxime – specifically, the C3 oxime of the progestogen progesterone.[1] Progesterone C3 and C20 oxime conjugates, like progesterone 3-(O-carboxymethyl)oxime, have been found to be water-soluble prodrugs of progesterone and pregnane neurosteroids.[2][3][4][5]

See also

References

  1. ^ a b Shoppee CW, Lack RE, Newman BC (1964). "640. Aza-steroids. Part VII. 3-aza-A-homopregn-4a-ene and related compounds". Journal of the Chemical Society (Resumed): 3388–3392. doi:10.1039/jr9640003388. ISSN 0368-1769.
  2. ^ 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". Journal of Medicinal Chemistry. 52 (19): 6012–6023. doi:10.1021/jm900712n. PMID 19791804.
  3. ^ Guthrie DB, Stein DG, Liotta DC, Lockwood MA, Sayeed I, Atif F, et al. (May 2012). "Water-soluble progesterone analogues are effective, injectable treatments in animal models of traumatic brain injury". ACS Medicinal Chemistry Letters. 3 (5): 362–366. doi:10.1021/ml200303r. PMC 4025794. PMID 24900479.
  4. ^ 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.
  5. ^ Basu K, Mitra AK (1990). "Effects of 3-hydrazone modification on the metabolism and protein binding of progesterone". International Journal of Pharmaceutics. 65 (1–2): 109–114. doi:10.1016/0378-5173(90)90015-V. ISSN 0378-5173.
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