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P1-185

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
P1-185
Clinical data
Other names(3E)-3-({[(2S)-2-Amino-3-methylbutanoyl]oxy}imino)pregn-4-en-20-one
Drug classProgestogen;Neurosteroid
Identifiers
  • [(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
PubChemCID
ChemSpider
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC26H40N2O3
Molar mass428.617 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 asprogesterone 3-O-(L-valine)-E-oxime or aspregn-4-ene-3,20-dione 3-O-(L-valine)-E-oxime, is asyntheticprogestogen andneurosteroid and anoximeesteranalogue andprodrug ofprogesterone (and by extension ofallopregnanolone).[1][2] It was developed as an improvedwater-soluble version of progesterone such that it could be formulated as anaqueous preparation and easily and rapidly administeredintravenously as a potential therapy fortraumatic brain injury.[1][2] However, thechemical synthesis of P1-185 was described as somewhat challenging, so oxime conjugates of progesterone of the C20 instead of C3 position, such asEIDD-1723 andEIDD-036, have since been developed.[2][3][4]

See also

[edit]

References

[edit]
  1. ^abMacNevin 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.
  2. ^abcGuthrie 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.
  3. ^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.
  4. ^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

[edit]
  • Media related toP1-185 at Wikimedia Commons
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PRTooltip Progesterone receptor
Agonists
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(SPRMsTooltip Selective progesterone receptor modulators)
Antagonists
mPRTooltip Membrane progesterone receptor
(PAQRTooltip Progestin and adipoQ receptor)
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