Progesterone 3-oxime

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]

Not to be confused with Progesterone 20-oxime.
Progesterone 3-oxime
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
IUPAC name
  • 1-((8S,9S,10R,13S,14S,17S,E)-3-(hydroxyimino)-10,13-dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one
CAS Number
Chemical and physical data
FormulaC21H30NO2
Molar mass328.476 g·mol−1
3D model (JSmol)
SMILES
  • O=C(C)[C@H]1CC[C@]2([H])[C@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=C/C(CC[C@]34C)=N/O
InChI
  • InChI=1S/C21H31NO2/c1-13(23)17-6-7-18-16-5-4-14-12-15(22-24)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19,24H,4-11H2,1-3H3/b22-15+/t16-,17+,18-,19-,20-,21+/m0/s1
  • Key:FPSIMALNSFTZTF-MJRGJNICSA-N

See also

References
  1. Shoppee, C. W.; Lack, Ruth E.; Newman, B. C. (1964). "640. Aza-steroids. Part VII. 3-aza-A-homopregn-4a-ene and related compounds". Journal of the Chemical Society (Resumed): 3388. 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". J. Med. Chem. 52 (19): 6012–23. doi:10.1021/jm900712n. PMID 19791804.
  3. 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 (May 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.
  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, Krishnakali; Mitra, Ashim K. (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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