EIDD-036

EIDD-036, also known as EPRX-036, as well as progesterone 20-oxime (P4-20-O) or 20-(hydroxyimino)pregn-4-en-3-one, is a synthetic, water-soluble analogue of progesterone, a neurosteroid, and the active metabolite of EIDD-1723 (EPRX-01723), a medication developed for the potential treatment of traumatic brain injury.[1][2][3][4]

Not to be confused with Progesterone 3-oxime.
EIDD-036
Clinical data
Other namesEPRX-036; Progesterone 20-oxime; P4-20-O; Pregn-4-ene-3,20-dione 20-oxime; 20-(Hydroxyimino)pregn-4-en-3-one
Drug classNeurosteroid
Identifiers
IUPAC name
  • (8S,9S,10R,13S,14S,17S)-17-[(Z)-N-hydroxy-C-methylcarbonimidoyl]-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
PubChem CID
Chemical and physical data
FormulaC21H31NO2
Molar mass329.484 g·mol−1
3D model (JSmol)
SMILES
  • C/C(=N/O)/[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
InChI
  • InChI=1S/C21H31NO2/c1-13(22-24)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19,24H,4-11H2,1-3H3/b22-13-/t16-,17+,18-,19-,20-,21+/m0/s1
  • Key:WGIMTKVWTJMLDA-ODGMAUQTSA-N

See also

References
  1. 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.
  2. Guthrie, D. B., Lockwood, M. A., Natchus, M. G., Liotta, D. C., Stein, D. G., & Sayeed, I. (2017). U.S. Patent No. 9,802,978. Washington, DC: U.S. Patent and Trademark Office. https://patents.google.com/patent/US9802978B2/en
  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". J. Med. Chem. 52 (19): 6012–23. doi:10.1021/jm900712n. PMID 19791804.
  4. 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.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.