Exisulind | CAS#59973-80-7 | antineoplastic

MedKoo Cat#: 584399 | Name: Exisulind

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Exisulind, also known as CP248, is a sulfated analog of indomethacin that inhibits K-ras-dependent cyclooxygenase-2 and acts as an antineoplastic agent that fosters microtubule depolymerization.

Chemical Structure

Exisulind

CAS#59973-80-7

Theoretical Analysis

MedKoo Cat#: 584399

Name: Exisulind

CAS#: 59973-80-7

Chemical Formula: C20H17FO4S

Exact Mass: 372.0832

Molecular Weight: 372.41

Elemental Analysis: C, 64.50; H, 4.60; F, 5.10; O, 17.18; S, 8.61

Price and Availability

Size	Price	Availability
50mg	USD 350.00	2 Weeks
100mg	USD 600.00	2 Weeks
250mg	USD 1,050.00	2 Weeks

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Synonym

Exisulind; Sulindac sulfone; Aptosyn; Prevatec; FGN-1; FGN 1; FGN1; CP248; C P248; CP-248; NSC719619; NSC 719619; NSC-719619;

IUPAC/Chemical Name

1H-Indene-3-acetic acid, 5-fluoro-2-methyl-1-((4-(methylsulfonyl)phenyl)methylene)-, (1Z)-

InChi Key

MVGSNCBCUWPVDA-MFOYZWKCSA-N

InChi Code

InChI=1S/C20H17FO4S/c1-12-17(9-13-3-6-15(7-4-13)26(2,24)25)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-

SMILES Code

O=C(O)CC(C1=C/2C=CC(F)=C1)=C(C)C2=C\C3=CC=C(S(=O)(C)=O)C=C3

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

TBD

In vitro activity:

The influence of Exisulind on the viability and apoptosis of CD34(+) stem cells from patients with advanced myelodysplastic syndrome (MDS) and acute myeloid leukaemia (AML)/MDS was investigated. In eight out of 10 patient samples Exisulind reduced the fraction of viable cells by inducing apoptosis Reference: Br J Haematol. 2006 Nov;135(3):355-7. https://pubmed.ncbi.nlm.nih.gov/16978222/

In vivo activity:

Over the 30 week duration of this experiment, a total of 10.53±1.72 tumors/tumor bearing mouse were recorded in the UVB-irradiated group while only 5±0.80 tumors were recorded in the NO-exisulind-treated animals (Fig. 2A & B). NO-exisulind treatment also resulted in significant tumor reduction and delay of tumor incidence when compared at early time points with UVB alone positive controls. However, tumor incidence at the 28th week was 80% and increased to 100% by the 30th week in both NO-exisulind treated and UVB-alone irradiated treatment groups (Fig. 2C). Similarly, NO-exisulind significantly reduced tumor volume when assessed in terms of mean tumor volume/mouse (p<0.05) as shown in Fig. 2D. Application of NO-exisulind also slightly increased the latency period of tumor induction. Reference: Photochem Photobiol. 2012 Sep; 88(5): 1141–1148. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3368998/

Preparing Stock Solutions

The following data is based on the product molecular weight 372.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Czibere A, Prall WC, Zerbini LF, Jäger M, Kobbe G, Knipp S, Libermann TA, Haas R, Aivado M. Exisulind induces apoptosis in advanced myelodysplastic syndrome (MDS) and acute myeloid leukaemia/MDS. Br J Haematol. 2006 Nov;135(3):355-7. doi: 10.1111/j.1365-2141.2006.06298.x. Epub 2006 Sep 15. PMID: 16978222. 2. Czibere A, Prall WC, Zerbini LF, Grall F, Craigie EC, Ulrich SD, Giagounidis AA, Haas R, Libermann TA, Aivado M. The nonsteroidal anti-inflammatory drug Exisulind selectively induces apoptosis via JNK in secondary acute myeloid leukemia after myelodysplastic syndrome. Cell Cycle. 2005 Jun;4(6):812-7. doi: 10.4161/cc.4.6.1722. Epub 2005 Jun 8. PMID: 15970671. 3. Singh T, Chaudhary SC, Kapur P, Weng Z, Elmets CA, Kopelovich L, Athar M. Nitric oxide donor exisulind is an effective inhibitor of murine photocarcinogenesis. Photochem Photobiol. 2012 Sep-Oct;88(5):1141-8. doi: 10.1111/j.1751-1097.2012.01093.x. Epub 2012 Feb 24. PMID: 22364235; PMCID: PMC3368998.

In vitro protocol:

In vivo protocol:

1. Singh T, Chaudhary SC, Kapur P, Weng Z, Elmets CA, Kopelovich L, Athar M. Nitric oxide donor exisulind is an effective inhibitor of murine photocarcinogenesis. Photochem Photobiol. 2012 Sep-Oct;88(5):1141-8. doi: 10.1111/j.1751-1097.2012.01093.x. Epub 2012 Feb 24. PMID: 22364235; PMCID: PMC3368998.

1: Singh T, Chaudhary SC, Kapur P, Weng Z, Elmets CA, Kopelovich L, Athar M. Nitric oxide donor exisulind is an effective inhibitor of murine photocarcinogenesis. Photochem Photobiol. 2012 Sep-Oct;88(5):1141-8. doi: 10.1111/j.1751-1097.2012.01093.x. Epub 2012 Feb 24. PubMed PMID: 22364235; PubMed Central PMCID: PMC3368998. 2: Weight CJ, Kim SP, Karnes RJ, Bergstralh EJ, Cheville JC, Leibovich BC. A prospective, controlled phase II study of neoadjuvant exisulind therapy before radical prostatectomy: effect on apoptosis. Urology. 2012 Aug;80(2):484.e17-22. doi: 10.1016/j.urology.2012.02.027. Epub 2012 Apr 13. PubMed PMID: 22503761. 3: Griffiths GJ. Exisulind Cell Pathways. Curr Opin Investig Drugs. 2000 Nov;1(3):386-91. Review. PubMed PMID: 11249724. 4: Lim JT, Joe AK, Suzui M, Shimizu M, Masuda M, Weinstein IB. Sulindac sulfide and exisulind inhibit expression of the estrogen and progesterone receptors in human breast cancer cells. Clin Cancer Res. 2006 Jun 1;12(11 Pt 1):3478-84. PubMed PMID: 16740773. 5: Piazza GA, Thompson WJ, Pamukcu R, Alila HW, Whitehead CM, Liu L, Fetter JR, Gresh WE Jr, Klein-Szanto AJ, Farnell DR, Eto I, Grubbs CJ. Exisulind, a novel proapoptotic drug, inhibits rat urinary bladder tumorigenesis. Cancer Res. 2001 May 15;61(10):3961-8. PubMed PMID: 11358813. 6: Lim SJ, Lee YJ, Park DH, Lee E, Choi MK, Park W, Chun KH, Choi HG, Cho JS. Alpha-tocopheryl succinate sensitizes human colon cancer cells to exisulind-induced apoptosis. Apoptosis. 2007 Feb;12(2):423-31. PubMed PMID: 17191116. 7: Kim JY, Yang HM, Lee JE, Kim BK, Jin S, Lee J, Park KW, Cho HJ, Kwon YW, Lee HY, Kang HJ, Oh BH, Park YB, Kim HS. Activation of Protein Kinase G (PKG) Reduces Neointimal Hyperplasia, Inhibits Platelet Aggregation, and Facilitates Re-endothelialization. Sci Rep. 2016 Nov 11;6:36979. doi: 10.1038/srep36979. PubMed PMID: 27833146; PubMed Central PMCID: PMC5105062. 8: Jones SF, Kuhn JG, Greco FA, Raefsky EL, Hainsworth JD, Dickson NR, Thompson DS, Willcutt NT, White MB, Burris HA 3rd. A phase I/II study of exisulind in combination with docetaxel/carboplatin in patients with metastatic non-small-cell lung cancer. Clin Lung Cancer. 2005 May;6(6):361-6. PubMed PMID: 15943897. 9: Liu L, Li H, Underwood T, Lloyd M, David M, Sperl G, Pamukcu R, Thompson WJ. Cyclic GMP-dependent protein kinase activation and induction by exisulind and CP461 in colon tumor cells. J Pharmacol Exp Ther. 2001 Nov;299(2):583-92. PubMed PMID: 11602670. 10: Lim SJ, Lee YJ, Lee E. p38MAPK inhibitor SB203580 sensitizes human SNU-C4 colon cancer cells to exisulind-induced apoptosis. Oncol Rep. 2006 Nov;16(5):1131-5. PubMed PMID: 17016604. 11: Joe AK, Liu H, Xiao D, Soh JW, Pinto JT, Beer DG, Piazza GA, Thompson WJ, Weinstein IB. Exisulind and CP248 induce growth inhibition and apoptosis in human esophageal adenocarcinoma and squamous carcinoma cells. J Exp Ther Oncol. 2003 Mar-Apr;3(2):83-94. PubMed PMID: 12822514. 12: Pitari GM, Li T, Baksh RI, Waldman SA. Exisulind and guanylyl cyclase C induce distinct antineoplastic signaling mechanisms in human colon cancer cells. Mol Cancer Ther. 2006 May;5(5):1190-6. PubMed PMID: 16731751. 13: Goluboff ET, Shabsigh A, Saidi JA, Weinstein IB, Mitra N, Heitjan D, Piazza GA, Pamukcu R, Buttyan R, Olsson CA. Exisulind (sulindac sulfone) suppresses growth of human prostate cancer in a nude mouse xenograft model by increasing apoptosis. Urology. 1999 Feb;53(2):440-5. PubMed PMID: 9933075. 14: Witta SE, Gustafson DL, Pierson AS, Menter A, Holden SN, Basche M, Persky M, O'Bryant CL, Zeng C, Baron A, Long ME, Gibbs A, Kelly K, Bunn PA Jr, Chan DC, Pallansch P, Eckhardt SG. A phase I and pharmacokinetic study of exisulind and docetaxel in patients with advanced solid tumors. Clin Cancer Res. 2004 Nov 1;10(21):7229-37. PubMed PMID: 15534096. 15: Goluboff ET. Exisulind, a selective apoptotic antineoplastic drug. Expert Opin Investig Drugs. 2001 Oct;10(10):1875-82. Review. PubMed PMID: 11772293. 16: Ryan CW, Stadler WM, Vogelzang NJ. A phase I/II dose-escalation study of exisulind and docetaxel in patients with hormone-refractory prostate cancer. BJU Int. 2005 May;95(7):963-8. PubMed PMID: 15839914. 17: Chan DC, Earle KA, Zhao TL, Helfrich B, Zeng C, Baron A, Whitehead CM, Piazza G, Pamukcu R, Thompson WJ, Alila H, Nelson P, Bunn PA Jr. Exisulind in combination with docetaxel inhibits growth and metastasis of human lung cancer and prolongs survival in athymic nude rats with orthotopic lung tumors. Clin Cancer Res. 2002 Mar;8(3):904-12. PubMed PMID: 11895925. 18: Bunn PA Jr, Chan DC, Earle K, Zhao TL, Helfrich B, Kelly K, Piazza G, Whitehead CM, Pamukcu R, Thompson W, Alila H. Preclinical and clinical studies of docetaxel and exisulind in the treatment of human lung cancer. Semin Oncol. 2002 Feb;29(1 Suppl 4):87-94. Review. PubMed PMID: 11894018. 19: Exisulind: Aptosyn, FGN 1, Prevatac, sulindac sulfone. Drugs R D. 2004;5(4):220-6. Review. PubMed PMID: 15230629. 20: Weiss GJ, Vokes EE, Bunn PA Jr, Magree L, Rusk J, Albert D, Kelly K. Docetaxel and exisulind in previously treated non-small cell lung cancer (NSCLC) patients: a multicenter, phase II clinical trial. J Thorac Oncol. 2007 Oct;2(10):933-8. PubMed PMID: 17909356.