Chemistry:Progesterone 3-oxime

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Short description: Chemical compound
Progesterone 3-oxime
Progesterone 3-oxime.svg
Clinical data
Other namesProgesterone 3-oxime; P4-3-O; Pregn-4-ene-3,20-dione 3-oxime; 20-(Hydroxyimino)pregn-4-en-3-one
Identifiers
CAS Number
Chemical and physical data
FormulaC21H30NO2
Molar mass328.476 g·mol−1
3D model (JSmol)

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. 1.0 1.1 "640. Aza-steroids. Part VII. 3-aza-A-homopregn-4a-ene and related compounds". Journal of the Chemical Society (Resumed): 3388–3392. 1964. doi:10.1039/jr9640003388. ISSN 0368-1769. 
  2. "Development and screening of water-soluble analogues of progesterone and allopregnanolone in models of brain injury". Journal of Medicinal Chemistry 52 (19): 6012–6023. October 2009. doi:10.1021/jm900712n. PMID 19791804. 
  3. "Water-soluble progesterone analogues are effective, injectable treatments in animal models of traumatic brain injury". ACS Medicinal Chemistry Letters 3 (5): 362–366. May 2012. doi:10.1021/ml200303r. PMID 24900479. 
  4. "Evaluating the neurotherapeutic potential of a water-soluble progesterone analog after traumatic brain injury in rats". Neuropharmacology 109: 148–158. October 2016. doi:10.1016/j.neuropharm.2016.05.017. PMID 27267687. 
  5. "Effects of 3-hydrazone modification on the metabolism and protein binding of progesterone". International Journal of Pharmaceutics 65 (1–2): 109–114. 1990. doi:10.1016/0378-5173(90)90015-V. ISSN 0378-5173.