Penfluridol

  • CAT Number: A000558
  • CAS Number: 26864-56-2
  • Molecular Formula: C28H27ClF5NO
  • Molecular Weight: 523.97
  • Purity: ≥95%
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Penfluridol, also known as R-16341 and Semap, is long-acting anti-psychotic agent used for maintenance or long-term therapy of schizophrenia and other psychotic disorders. Penfluridol distributes extensively in fatty tissues following oral administration. This depot effect produces a very slow release of drug from the tissues, and results in a very long duration of activity. 3. Penfluridol is extensively metabolized by oxidative N-dealkylation to afford, as isolated metabolites, the beta-glucuronide conjugate of the diphenylbutyric acid derivative A1 and the unconjugated basic piperidine moiety B1.

Catalog Number A000558
CAS Number 26864-56-2
Synonyms

26864-56-2; 1-(4,4-bis(4-fluorophenyl)butyl)-4-(4-chloro-3-(trifluoromethyl)phenyl)piperidin-4-ol; Semap; TLP-607; McN-JR-16,341

Molecular Formula

C28H27ClF5NO

Purity 95%
Storage 3 years -20C powder
InChI 1S/C28H27ClF5NO/c29-26-12-7-21(18-25(26)28(32,33)34)27(36)13-16-35(17-14-27)15-1-2-24(19-3-8-22(30)9-4-19)20-5-10-23(31)11-6-20/h3-12,18,24,36H,1-2,13-17H2
InChIKey MDLAAYDRRZXJIF-UHFFFAOYSA-N
SMILES C1CN(CCC1(C2=CC(=C(C=C2)Cl)C(F)(F)F)O)CCCC(C3=CC=C(C=C3)F)C4=CC=C(C=C4)F
Reference

1: Nikvarz N, Vahedian M, Khalili N. Chlorpromazine versus penfluridol for
schizophrenia. Cochrane Database Syst Rev. 2017 Sep 23;9:CD011831. doi:
10.1002/14651858.CD011831.pub2. Review. PubMed PMID: 28940256.
<br>

2: Du J, Shang J, Chen F, Zhang Y, Yin N, Xie T, Zhang H, Yu J, Liu F. A
CRISPR/Cas9-based screening for non-homologous end joining inhibitors reveals
ouabain and penfluridol as radiosensitizers. Mol Cancer Ther. 2017 Sep 1. pii:
molcanther.0090.2017. doi: 10.1158/1535-7163.MCT-17-0090. [Epub ahead of print]
PubMed PMID: 28864683.
<br>

3: Ranjan A, German N, Mikelis C, Srivenugopal K, Srivastava SK. Penfluridol
induces endoplasmic reticulum stress leading to autophagy in pancreatic cancer.
Tumour Biol. 2017 Jun;39(6):1010428317705517. doi: 10.1177/1010428317705517.
PubMed PMID: 28618969.
<br>

4: Ranjan A, Wright S, Srivastava SK. Immune consequences of penfluridol
treatment associated with inhibition of glioblastoma tumor growth. Oncotarget.
2017 Jul 18;8(29):47632-47641. doi: 10.18632/oncotarget.17425. PubMed PMID:
28512255; PubMed Central PMCID: PMC5564593.
<br>

5: Ranjan A, Srivastava SK. Penfluridol suppresses glioblastoma tumor growth by
Akt-mediated inhibition of GLI1. Oncotarget. 2017 May 16;8(20):32960-32976. doi:
10.18632/oncotarget.16515. PubMed PMID: 28380428; PubMed Central PMCID:
PMC5464842.
<br>

6: Hedrick E, Li X, Safe S. Penfluridol Represses Integrin Expression in Breast
Cancer through Induction of Reactive Oxygen Species and Downregulation of Sp
Transcription Factors. Mol Cancer Ther. 2017 Jan;16(1):205-216. doi:
10.1158/1535-7163.MCT-16-0451. Epub 2016 Nov 3. PubMed PMID: 27811009; PubMed
Central PMCID: PMC5222719.
<br>

7: Ranjan A, Srivastava SK. Penfluridol suppresses pancreatic tumor growth by
autophagy-mediated apoptosis. Sci Rep. 2016 May 18;6:26165. doi:
10.1038/srep26165. PubMed PMID: 27189859; PubMed Central PMCID: PMC4870635.

<br>
8: Ranjan A, Gupta P, Srivastava SK. Penfluridol: An Antipsychotic Agent
Suppresses Metastatic Tumor Growth in Triple-Negative Breast Cancer by Inhibiting
Integrin Signaling Axis. Cancer Res. 2016 Feb 15;76(4):877-90. doi:
10.1158/0008-5472.CAN-15-1233. Epub 2015 Dec 1. PubMed PMID: 26627008; PubMed
Central PMCID: PMC4755811.
<br>

9: Wu L, Liu YY, Li ZX, Zhao Q, Wang X, Yu Y, Wang YY, Wang YQ, Luo F. Anti-tumor
effects of penfluridol through dysregulation of cholesterol homeostasis. Asian
Pac J Cancer Prev. 2014;15(1):489-94. PubMed PMID: 24528079.
<br>

10: Soares BG, Lima MS. Penfluridol for schizophrenia. Cochrane Database Syst
Rev. 2006 Apr 19;(2):CD002923. Review. PubMed PMID: 16625563.

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