Progesterone 3-oxime

Progesterone 3-oxime
Clinical data
Other names	Progesterone 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	51652-28-9;
Chemical and physical data
Formula	C21H30NO2
Molar mass	328.476 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

^ ^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.
^ 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.
^ 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.
^ 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.
^ 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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