OPK-88004

OPK-88004
Legal status
Legal status
Identifiers
IUPAC name
  • propan-2-yl N-[(2S)-7-cyano-4-(pyridin-2-ylmethyl)-2,3-dihydro-1H-cyclopenta[b]indol-2-yl]carbamate
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H22N4O2
Molar mass374.4 g·mol−1
3D model (JSmol)
SMILES
  • CC(C)OC(=O)N[C@H]1CC2=C(C1)N(C3=C2C=C(C=C3)C#N)CC4=CC=CC=N4
InChI
  • InChI=1S/C22H22N4O2/c1-14(2)28-22(27)25-17-10-19-18-9-15(12-23)6-7-20(18)26(21(19)11-17)13-16-5-3-4-8-24-16/h3-9,14,17H,10-11,13H2,1-2H3,(H,25,27)/t17-/m0/s1
  • Key:IHIWYQYVBNODSV-KRWDZBQOSA-N

OPK-88004 (formerly known as LY-2452473 or TT-701) is a non-steroidal indole derivative which acts as a selective androgen receptor modulator (SARM). It has been investigated by OPKO Health for the treatment of erectile dysfunction and symptoms associated with benign prostate hyperplasia.[1][2][3]

Research

The compound advanced to a phase II trial in benign prostatic hyperplasia, but it was terminated due to difficulty in measuring prostate size, the trial's primary endpoint.[4]

It was also tried in a study to improve quality of life in patients with prostate cancer. Although it did not cause progression of the disease and increased lean body mass, the drug did not improve sexual function.[3]

See also

References

  1. ↑ Yi P, Rehmel JF, Cassidy K, Hadden C, Campanale K, Patel N, Johnson J (December 2012). "Disposition and metabolism of LY2452473, a selective androgen receptor modulator, in humans". Drug Metabolism and Disposition. 40 (12): 2354–2364. doi:10.1124/dmd.112.047613. PMID 22961682. S2CID 6942291.
  2. ↑ Noey EL, Yang Z, Li Y, Yu H, Richey RN, Merritt JM, et al. (June 2017). "Origins of Regioselectivity in the Fischer Indole Synthesis of a Selective Androgen Receptor Modulator". The Journal of Organic Chemistry. 82 (11): 5904–5909. doi:10.1021/acs.joc.7b00878. PMID 28467062.
  3. 1 2 Pencina KM, Burnett AL, Storer TW, Guo W, Li Z, Kibel AS, et al. (July 2021). "A Selective Androgen Receptor Modulator (OPK-88004) in Prostate Cancer Survivors: A Randomized Trial". The Journal of Clinical Endocrinology and Metabolism. 106 (8): 2171–2186. doi:10.1210/clinem/dgab361. PMC 8277210. PMID 34019661.
  4. ↑ Christiansen AR, Lipshultz LI, Hotaling JM, Pastuszak AW (March 2020). "Selective androgen receptor modulators: the future of androgen therapy?". Translational Andrology and Urology. 9 (Suppl 2): S135–S148. doi:10.21037/tau.2019.11.02. PMC 7108998. PMID 32257854.
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