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MedKoo Cat#: 202851 | Name: Tasisulam
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Description:

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

Tasisulam, also known as LY573636, is an acyl-sulfonamide with potential antineoplastic activity. Selectively toxic towards tumor cells, tasisulam appears to induce tumor cell apoptosis by a mitochondrial-targeted mechanism involving the loss of mitochondrial membrane potential and induction of reactive oxygen species (ROS). In combination with an angiogenesis inhibitor, this agent may exhibit synergistic antiangiogenic activity.

Chemical Structure

Tasisulam
Tasisulam
CAS#519055-62-0 (free acid)

Theoretical Analysis

MedKoo Cat#: 202851

Name: Tasisulam

CAS#: 519055-62-0 (free acid)

Chemical Formula: C11H6BrCl2NO3S2

Exact Mass: 412.8350

Molecular Weight: 415.10

Elemental Analysis: C, 31.83; H, 1.46; Br, 19.25; Cl, 17.08; N, 3.37; O, 11.56; S, 15.45

Price and Availability

Size Price Availability Quantity
25mg USD 250.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 750.00 2 Weeks
200mg USD 1,250.00 2 Weeks
500mg USD 2,650.00 2 Weeks
1g USD 3,850.00 2 Weeks
2g USD 6,450.00 2 Weeks
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Related CAS #
519055-62-0 (free acid) 519055-63-1 (sodium)
Synonym
LY573636, LY 573636, LY-573636, Tasisulam, Tasisulam sodium
IUPAC/Chemical Name
N-(2,4-Dichlorobenzoyl)-5-bromothiophene-2-sulfonamide
InChi Key
WWONFUQGBVOKOF-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H6BrCl2NO3S2/c12-9-3-4-10(19-9)20(17,18)15-11(16)7-2-1-6(13)5-8(7)14/h1-5H,(H,15,16)
SMILES Code
O=S(C1=CC=C(Br)S1)(NC(C2=CC=C(Cl)C=C2Cl)=O)=O
Appearance
Solid powder
Purity
>98% (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, not in water
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

Preparing Stock Solutions

The following data is based on the product molecular weight 415.10 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.

Recalculate based on batch purity %
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
1: Jang JH, Kim JY, Lee TJ. Recent advances in anticancer mechanisms of molecular glue degraders: focus on RBM39-dgrading synthetic sulfonamide such as indisulam, E7820, tasisulam, and chloroquinoxaline sulfonamide. Genes Genomics. 2024 Sep 13. doi: 10.1007/s13258-024-01565-z. Epub ahead of print. PMID: 39271535. 2: Andresini M, Carret S, Degennaro L, Ciriaco F, Poisson JF, Luisi R. Multistep Continuous Flow Synthesis of Isolable NH2 -Sulfinamidines via Nucleophilic Addition to Transient Sulfurdiimide. Chemistry. 2022 Oct 21;28(59):e202202066. doi: 10.1002/chem.202202066. Epub 2022 Aug 23. PMID: 35861934; PMCID: PMC9804385. 3: Faust TB, Yoon H, Nowak RP, Donovan KA, Li Z, Cai Q, Eleuteri NA, Zhang T, Gray NS, Fischer ES. Structural complementarity facilitates E7820-mediated degradation of RBM39 by DCAF15. Nat Chem Biol. 2020 Jan;16(1):7-14. doi: 10.1038/s41589-019-0378-3. Epub 2019 Nov 4. PMID: 31686031; PMCID: PMC6917914. 4: van der Wildt B , Shen B , Chin FT . Efficient synthesis of carbon-11 labelled acylsulfonamides using [11C]CO carbonylation chemistry. Chem Commun (Camb). 2019 Mar 7;55(21):3124-3127. doi: 10.1039/c8cc09661a. PMID: 30793132; PMCID: PMC7454003. 5: Perkins EJ, Posada M, Kellie Turner P, Chappell J, Ng WT, Twelves C. Physiologically Based Pharmacokinetic Modelling of Cytochrome P450 2C9-Related Tolbutamide Drug Interactions with Sulfaphenazole and Tasisulam. Eur J Drug Metab Pharmacokinet. 2018 Jun;43(3):355-367. doi: 10.1007/s13318-017-0447-5. PMID: 29119333; PMCID: PMC5956062. 6: Han T, Goralski M, Gaskill N, Capota E, Kim J, Ting TC, Xie Y, Williams NS, Nijhawan D. Anticancer sulfonamides target splicing by inducing RBM39 degradation via recruitment to DCAF15. Science. 2017 Apr 28;356(6336):eaal3755. doi: 10.1126/science.aal3755. Epub 2017 Mar 16. Erratum in: Science. 2017 May 26;356(6340):eaan7977. doi: 10.1126/science.aan7977. PMID: 28302793. 7: Steinkamp AD, Schmitt L, Chen X, Fietkau K, Heise R, Baron JM, Bolm C. Synthesis of a Sulfonimidamide-Based Analog of Tasisulam and Its Biological Evaluation in the Melanoma Cell Lines SKMel23 and A375. Skin Pharmacol Physiol. 2016;29(6):281-290. doi: 10.1159/000453042. Epub 2016 Dec 24. PMID: 28013301. 8: Jotte RM, Von Hoff DD, Braiteh F, Becerra CR, Richards DA, Smith DA, Garbo L, Stephenson J, Conkling PR, Robert-Vizcarrondo F, Chen J, Turner PK, Chow KH, Tai DF, Ilaria R Jr. An innovative, multi-arm, complete phase 1b study of the novel anti-cancer agent tasisulam in patients with advanced solid tumors. Invest New Drugs. 2015 Feb;33(1):148-58. doi: 10.1007/s10637-014-0160-z. Epub 2014 Sep 28. PMID: 25260842. 9: Hamid O, Ilaria R Jr, Garbe C, Wolter P, Maio M, Hutson TE, Arance A, Lorigan P, Lee J, Hauschild A, Mohr P, Hahka-Kemppinen M, Kaiser C, Turner PK, Conti I, Grob JJ. A randomized, open-label clinical trial of tasisulam sodium versus paclitaxel as second-line treatment in patients with metastatic melanoma. Cancer. 2014 Jul 1;120(13):2016-24. doi: 10.1002/cncr.28635. Epub 2014 Mar 26. PMID: 24676877. 10: Fujiwara Y, Ando Y, Mukohara T, Kiyota N, Chayahara N, Mitsuma A, Inada- Inoue M, Sawaki M, Ilaria R Jr, Kellie Turner P, Funai J, Maeda K, Minami H. A phase I study of tasisulam sodium using an albumin-tailored dose in Japanese patients with advanced solid tumors. Cancer Chemother Pharmacol. 2013 Apr;71(4):991-8. doi: 10.1007/s00280-013-2092-2. Epub 2013 Feb 1. PMID: 23370664. 11: Gordon MS, Ilaria R Jr, de Alwis DP, Mendelson DS, McKane S, Wagner MM, Look KY, LoRusso PM. A phase I study of tasisulam sodium (LY573636 sodium), a novel anticancer compound, administered as a 24-h continuous infusion in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2013 Jan;71(1):21-7. doi: 10.1007/s00280-012-1917-8. Epub 2012 Dec 11. PMID: 23228983. 12: Schindler K, Schicher N, Kunstfeld R, Pehamberger H, Toepker M, Haitel A, Hoeller C, Harmankaya K. A rare case of primary rhabdoid melanoma of the urinary bladder treated with ipilimumab, an anti-CTLA 4 monoclonal antibody. Melanoma Res. 2012 Aug;22(4):320-5. doi: 10.1097/CMR.0b013e32835566c0. PMID: 22713795. 13: Scagliotti GV, Ilaria R Jr, Novello S, von Pawel J, Fischer JR, Ermisch S, de Alwis DP, Andrews J, Reck M, Crino L, Eschbach C, Manegold C. Tasisulam sodium (LY573636 sodium) as third-line treatment in patients with unresectable, metastatic non-small-cell lung cancer: a phase-II study. J Thorac Oncol. 2012 Jun;7(6):1053-7. doi: 10.1097/JTO.0b013e3182519d79. PMID: 22588156. 14: Ryan CW, Matias C, Agulnik M, Lopez-Pousa A, Williams C, de Alwis DP, Kaiser C, Miller MA, Ermisch S, Ilaria R Jr, Keohan ML. A phase II study of tasisulam sodium (LY573636 sodium) as second-line or third-line treatment for patients with unresectable or metastatic soft tissue sarcoma. Invest New Drugs. 2013 Feb;31(1):145-51. doi: 10.1007/s10637-012-9819-5. Epub 2012 Apr 27. PMID: 22539091. 15: Meier T, Uhlik M, Chintharlapalli S, Dowless M, Van Horn R, Stewart J, Blosser W, Cook J, Young D, Ye X, Evans G, Credille K, Ballard D, Huber L, Capen A, Chedid M, Ilaria R Jr, Smith MC, Stancato L. Tasisulam sodium, an antitumor agent that inhibits mitotic progression and induces vascular normalization. Mol Cancer Ther. 2011 Nov;10(11):2168-78. doi: 10.1158/1535-7163.MCT-11-0323. Epub 2011 Sep 8. PMID: 21903607. 16: Kirkwood JM, Gonzalez R, Reintgen D, Clingan PR, McWilliams RR, de Alwis DP, Zimmermann A, Brown MP, Ilaria RL Jr, Millward MJ. A phase 2 study of tasisulam sodium (LY573636 sodium) as second-line treatment for patients with unresectable or metastatic melanoma. Cancer. 2011 Oct 15;117(20):4732-9. doi: 10.1002/cncr.26068. Epub 2011 Mar 31. PMID: 21456002. 17: Simon GR, Ilaria RL Jr, Sovak MA, Williams CC, Haura EB, Cleverly AL, Sykes AK, Wagner MM, de Alwis DP, Slapak CA, Miller MA, Spriggs DR. A phase I study of tasisulam sodium (LY573636 sodium), a novel anticancer compound in patients with refractory solid tumors. Cancer Chemother Pharmacol. 2011 Nov;68(5):1233-41. doi: 10.1007/s00280-011-1593-0. Epub 2011 Mar 23. PMID: 21431416; PMCID: PMC3215883.

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