Progesterone dioxime

Progesterone dioxime
Clinical data
Other names	Progesterone 3,20-dioxime; P4-3,20-DO; Pregn-4-ene-3,20-dione 3,20-dioxime; 3,20-Di(hydroxyimino)pregn-4-en-3-one
Identifiers
	IUPAC name (NZ)-N-[1-[(3E,8S,9S,10R,13S,14S,17S)-3-hydroxyimino-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethylidene]hydroxylamine;
CAS Number	26144-38-7;
PubChem CID	91692079;
ChemSpider	7875670;
Chemical and physical data
Formula	C21H32N2O2
Molar mass	344.499 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	238–242 °C (460–468 °F) (recrystallized from alcohol)
	SMILES C/C(=N/O)/[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=C/C(=N/O)/CC[C@]34C)C;
	InChI InChI=1S/C21H32N2O2/c1-13(22-24)17-6-7-18-16-5-4-14-12-15(23-25)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19,24-25H,4-11H2,1-3H3/b22-13-,23-15+/t16-,17+,18-,19-,20-,21+/m0/s1; Key:JKENIRSEIALBGX-GWUBATFGSA-N;

Progesterone dioxime, or progesterone 3,20-dioxime (P4-3,20-DO), also known as 3,20-di(hydroxyimino)pregn-4-en-3-one, is a progesterone derivative which was never marketed.^[1] It is a progestogen oxime – specifically, the C3 and C20 dioxime of the progestogen progesterone.^[1] Progesterone C3 and C20 oxime conjugates have been found to be water-soluble prodrugs of progesterone and pregnane neurosteroids.^[2]^[3]^[4]^[5]

References

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 1024–. ISBN 978-1-4757-2085-3.
^ 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.

This article about a steroid is a stub. You can help Wikipedia by expanding it.

This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it.