P1-185 Other names (3E )-3-({[(2S )-2-Amino-3-methylbutanoyl]oxy}imino)pregn-4-en-20-one Drug class Progestogen ; Neurosteroid
[(E )-[(8S ,9S ,10R ,13S ,14S ,17S )-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a ]phenanthren-3-ylidene]amino] (2S )-2-amino-3-methylbutanoate
CAS Number PubChem CID ChemSpider ChEMBL Formula C 26 H 40 N 2 O 3 Molar mass 428.617 g·mol−1 3D model (JSmol )
CC(C)[C@@H](C(=O)O/N=C/1\CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@@H]4C(=O)C)C)C)N
InChI=1S/C26H40N2O3/c1-15(2)23(27)24(30)31-28-18-10-12-25(4)17(14-18)6-7-19-21-9-8-20(16(3)29)26(21,5)13-11-22(19)25/h14-15,19-23H,6-13,27H2,1-5H3/b28-18+/t19-,20+,21-,22-,23-,25-,26+/m0/s
Key:JFIPYWOCXPCAFX-NPRMJFGVSA-N
P1-185 , also known as progesterone 3-O -(L -valine)-E -oxime or as pregn-4-ene-3,20-dione 3-O -(L -valine)-E -oxime , is a synthetic progestogen and neurosteroid and an oxime ester analogue and prodrug of progesterone (and by extension of allopregnanolone ).[1] [2] It was developed as an improved water-soluble version of progesterone such that it could be formulated as an aqueous preparation and easily and rapidly administered intravenously as a potential therapy for traumatic brain injury .[1] [2] However, the chemical synthesis of P1-185 was described as somewhat challenging, so oxime conjugates of progesterone of the C20 instead of C3 position, such as EIDD-1723 and EIDD-036 , have since been developed.[2] [3] [4]
See also [ ]
List of neurosteroids § Inhibitory > Synthetic > Pregnanes
List of progestogen esters § Oximes of progesterone derivatives
References [ ]
^ a b MacNevin CJ, Atif F, Sayeed I, Stein DG, Liotta DC (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 .
^ a b c 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 (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 .
^ 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 .
^ 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
External links [ ]
Media related to P1-185 at Wikimedia Commons
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