Cannabaceae

thcscience_admin
Not to be confused with diisopropyl methylphosphonate.
DIMP
Clinical data
Other namesRo 7-8117; N-(3,5-Dimethyl-4-isoxazolylmethyl)phthalimide
Drug classNonsteroidal antiandrogen
Identifiers
  • 2-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-2,3-dihydro-1H-isoindole-1,3-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC14H12N2O3
Molar mass256.261 g·mol−1
3D model (JSmol)
  • CC1=C(C(=NO1)C)CN2C(=O)C3=CC=CC=C3C2=O
  • InChI=1S/C14H12N2O3/c1-8-12(9(2)19-15-8)7-16-13(17)10-5-3-4-6-11(10)14(16)18/h3-6H,7H2,1-2H3
  • Key:SHPRUADECKZSMQ-UHFFFAOYSA-N

DIMP (developmental code name Ro 7-8117), or N-(3,5-dimethyl-4-isoxazolylmethyl)phthalimide, is a nonsteroidal antiandrogen (NSAA) structurally related to thalidomide (which also binds to and antagonizes the androgen receptor (AR))[1][2][3] that was first described in 1973 and was never marketed.[4] Along with flutamide, it was one of the earliest NSAAs to be discovered,[5] and for this reason, has been described as a "classical" NSAA.[1][2][3] The drug is a selective, competitive, silent antagonist of the AR,[4][6] although it is described as an "only relatively weak competitor".[7][8] Its relative binding affinity for the androgen receptor is about 2.6% of that of metribolone.[9] DIMP possesses no androgenic, estrogenic, progestogenic, or antigonadotropic activity,[4] but it does reverse the antigonadotropic effects of testosterone, indicating that, like other pure AR antagonists, it is progonadotropic.[4]

DIMP is the lead antiandrogen of the phthalimide group of nonsteroidal AR ligands, and a variety of AR ligands with higher affinity for the AR have been derived from DIMP and thalidomide.[10][11]

See also[edit]

References[edit]

  1. ^ a b Hashimoto Y, Tanatani A, Nagasawa K, Miyachi H (2004). "Thalidomide as a multitarget drug and its application as a template for drug design". Drugs of the Future. 29 (4): 383. doi:10.1358/dof.2004.029.04.792298. ISSN 0377-8282.
  2. ^ a b Liu B, Su L, Geng J, Liu J, Zhao G (October 2010). "Developments in nonsteroidal antiandrogens targeting the androgen receptor". ChemMedChem. 5 (10): 1651–1661. doi:10.1002/cmdc.201000259. PMID 20853390. S2CID 23228778.
  3. ^ a b Hashimoto Y (July 2003). "Structural development of synthetic retinoids and thalidomide-related molecules". Cancer Chemotherapy and Pharmacology. 52 (Suppl 1): S16–S23. doi:10.1007/s00280-003-0590-3. PMID 12819930. S2CID 22663471.
  4. ^ a b c d Boris A, Scott JW, DeMartino L, Cox DC (March 1973). "Endocrine profile of a nonsteroidal antiandrogen N-(3,5-dimethyl-4-isoxazolylmethyl)phthalimide (DIMP)". Acta Endocrinologica. 72 (3): 604–614. doi:10.1530/acta.0.0720604. PMID 4739363.
  5. ^ Singhal RL, Thomas JA (1 January 1976). Cellular Mechanisms Modulating Gonadal Action. University Park Press. p. 239. ISBN 978-0-8391-0776-7.
  6. ^ Ahlin K, Forsberg JG, Jacobsohn D, Thore-Berger B (1975). "The male genital tract and the nipples of male and female offspring of rats given the non-steroidal antiandrogens DIMP and Sch 13521, during pregnancy". Archives d'Anatomie Microscopique et de Morphologie Expérimentale. 64 (1): 27–44. PMID 1217898.
  7. ^ Heyns W, Verhoeven G, De Moor P (May 1976). "Androgen binding in rat uterus cytosol. Study of the specificity". Journal of Steroid Biochemistry. 7 (5): 335–343. doi:10.1016/0022-4731(76)90092-3. PMID 180344.
  8. ^ Rasmusson GH (January 1986). "Chemical control of androgen action.". In Daily PM, Pawsen PA (eds.). Annual Reports in Medicinal Chemistry. Vol. 21. Academic Press. pp. 179-188 (182). ISBN 978-0-08-058365-5.
  9. ^ Wakeling AE, Furr BJ, Glen AT, Hughes LR (December 1981). "Receptor binding and biological activity of steroidal and nonsteroidal antiandrogens". Journal of Steroid Biochemistry. 15: 355–359. doi:10.1016/0022-4731(81)90297-1. PMID 7339263.
  10. ^ Gao W, Bohl CE, Dalton JT (September 2005). "Chemistry and structural biology of androgen receptor". Chemical Reviews. 105 (9): 3352–3370. doi:10.1021/cr020456u. PMC 2096617. PMID 16159155.
  11. ^ Kaur P, Khatik GL (2016). "Advancements in Non-steroidal Antiandrogens as Potential Therapeutic Agents for the Treatment of Prostate Cancer". Mini Reviews in Medicinal Chemistry. 16 (7): 531–546. doi:10.2174/1389557516666160118112448. PMID 26776222.
source: https://en.wikipedia.org/wiki/DIMP_(antiandrogen)

One thought on “Cannabaceae”

  1. Well, that’s interesting to know that Psilotum nudum are known as whisk ferns. Psilotum nudum is the commoner species of the two. While the P. flaccidum is a rare species and is found in the tropical islands. Both the species are usually epiphytic in habit and grow upon tree ferns. These species may also be terrestrial and grow in humus or in the crevices of the rocks.
    View the detailed Guide of Psilotum nudum: Detailed Study Of Psilotum Nudum (Whisk Fern), Classification, Anatomy, Reproduction

Leave a Reply