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MedKoo Cat#: 205750 | Name: XL888
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Description:

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

XL888 is an orally bioavailable, ATP-competitive, small-molecule inhibitor of heat shock protein 90 (Hsp90) with potential antineoplastic activity. Hsp90 inhibitor XL888 specifically binds to Hsp90, inhibiting its chaperone function and promoting the proteasomal degradation of oncogenic signaling proteins involved in tumor cell proliferation and survival; inhibition of tumor cell proliferation may result. Hsp90, a chaperone complex protein upregulated in a variety of tumor cell types, regulates the folding and degradation of many oncogenic signaling proteins, including Her-2 and Met.

Chemical Structure

XL888
XL888
CAS#1149705-71-4

Theoretical Analysis

MedKoo Cat#: 205750

Name: XL888

CAS#: 1149705-71-4

Chemical Formula: C29H37N5O3

Exact Mass: 503.2896

Molecular Weight: 503.64

Elemental Analysis: C, 69.16; H, 7.40; N, 13.91; O, 9.53

Price and Availability

Size Price Availability Quantity
5mg USD 150.00 Ready to ship
10mg USD 250.00 Ready to ship
25mg USD 450.00 Ready to ship
50mg USD 850.00 Ready to ship
100mg USD 1,250.00 Ready to ship
200mg USD 1,750.00 Ready to ship
500mg USD 2,950.00 Ready to ship
1g USD 3,950.00 2 weeks
2g USD 6,950.00 2 weeks
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Related CAS #
No Data
Synonym
XL888; XL-888; XL 888
IUPAC/Chemical Name
5-((R)-sec-butylamino)-N1-((1R,3s,5S)-8-(5-(cyclopropanecarbonyl)pyridin-2-yl)-8-azabicyclo[3.2.1]octan-3-yl)-2-methylterephthalamide
InChi Key
LHGWWAFKVCIILM-CIQXWFTPSA-N
InChi Code
InChI=1S/C29H37N5O3/c1-4-17(3)32-25-14-23(16(2)11-24(25)28(30)36)29(37)33-20-12-21-8-9-22(13-20)34(21)26-10-7-19(15-31-26)27(35)18-5-6-18/h7,10-11,14-15,17-18,20-22,32H,4-6,8-9,12-13H2,1-3H3,(H2,30,36)(H,33,37)/t17-,20-,21-,22+/m1/s1
SMILES Code
O=C(NC1=CC=C(CCN2CC3=C(C=C(OC)C(OC)=C3)CC2)C=C1)C4=CC=CC(/C=C(C(N(C)/C5=C\C6=CC=CC=C6)=O)\NC5=O)=C4
Appearance
White 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 503.64 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: Kumari R, Ghava D, Rathod R, Panda AK, Kumar S, Behera SK. Molecular Dynamics of Adenomatous Polyposis Coli (APC) Protein and Its Inhibitors: A Special Insight to Colorectal Cancer. Crit Rev Oncog. 2025;30(1):91-105. doi: 10.1615/CritRevOncog.v30.i1.110. PMID: 39819437. 2: Abbas EMH, Sabour R, Alsaiari NA, Medrasi HY, Kassem AF, Farghaly TA. Design, Synthesis, and Docking of Novel Tropane Hybrids as Potent Hsp90 Inhibitors with Potential Anti-Breast Cancer Activity. Curr Med Chem. 2024 Sep 13. doi: 10.2174/0109298673313163240829094557. Epub ahead of print. PMID: 39279701. 3: Lee JY, Reyes N, Woo SH, Goel S, Stratton F, Kuang C, Mansfield AS, LaFave LM, Peng T. Senescent fibroblasts in the tumor stroma rewire lung cancer metabolism and plasticity. bioRxiv [Preprint]. 2024 Jul 30:2024.07.29.605645. doi: 10.1101/2024.07.29.605645. PMID: 39131266; PMCID: PMC11312578. 4: Kaplan Ö, Gökşen Tosun N. Molecular pathway of anticancer effect of next- generation HSP90 inhibitors XL-888 and Debio0932 in neuroblastoma cell line. Med Oncol. 2024 Jul 3;41(8):194. doi: 10.1007/s12032-024-02428-z. PMID: 38958814; PMCID: PMC11222184. 5: Khosla S. A pipeline for senolytics. J Clin Invest. 2024 May 1;134(9):e180558. doi: 10.1172/JCI180558. PMID: 38690734; PMCID: PMC11060745. 6: Mansfield CR, Quan B, Chirgwin ME, Eduful B, Hughes PF, Neveu G, Sylvester K, Ryan DH, Kafsack BFC, Haystead TAJ, Leahy JW, Fitzgerald MC, Derbyshire ER. Selective targeting of Plasmodium falciparum Hsp90 disrupts the 26S proteasome. Cell Chem Biol. 2024 Apr 18;31(4):729-742.e13. doi: 10.1016/j.chembiol.2024.02.008. Epub 2024 Mar 15. PMID: 38492573; PMCID: PMC11031320. 7: Lee JY, Reyes NS, Ravishankar S, Zhou M, Krasilnikov M, Ringler C, Pohan G, Wilson C, Ang KK, Wolters PJ, Tsukui T, Sheppard D, Arkin MR, Peng T. An in vivo screening platform identifies senolytic compounds that target p16INK4a+ fibroblasts in lung fibrosis. J Clin Invest. 2024 Mar 7;134(9):e173371. doi: 10.1172/JCI173371. PMID: 38451724; PMCID: PMC11060735. 8: Kaplan Ö. Synergistic induction of apoptosis in liver cancer cells: exploring the combined potential of doxorubicin and XL-888. Med Oncol. 2023 Oct 4;40(11):318. doi: 10.1007/s12032-023-02181-9. PMID: 37794195. 9: Eroglu Z, Chen YA, Smalley I, Li J, Markowitz JK, Brohl AS, Tetteh L, Taylor H, Sondak VK, Khushalani NI, Smalley KSM. Combined BRAF, MEK, and heat-shock protein 90 inhibition in advanced BRAF V600-mutant melanoma. Cancer. 2024 Jan;130(2):232-243. doi: 10.1002/cncr.35029. Epub 2023 Sep 30. PMID: 37776537. 10: Sun C, Bai M, Ke W, Wang X, Zhao X, Lu Z. The HSP90 inhibitor, XL888, enhanced cell apoptosis via downregulating STAT3 after insufficient radiofrequency ablation in hepatocellular carcinoma. Life Sci. 2021 Oct 1;282:119762. doi: 10.1016/j.lfs.2021.119762. Epub 2021 Jun 26. PMID: 34186047. 11: Zhang Y, Ware MB, Zaidi MY, Ruggieri AN, Olson BM, Komar H, Farren MR, Nagaraju GP, Zhang C, Chen Z, Sarmiento JM, Ahmed R, Maithel SK, El-Rayes BF, Lesinski GB. Heat Shock Protein-90 Inhibition Alters Activation of Pancreatic Stellate Cells and Enhances the Efficacy of PD-1 Blockade in Pancreatic Cancer. Mol Cancer Ther. 2021 Jan;20(1):150-160. doi: 10.1158/1535-7163.MCT-19-0911. Epub 2020 Oct 9. PMID: 33037138; PMCID: PMC7790996. 12: Eroglu Z, Chen YA, Gibney GT, Weber JS, Kudchadkar RR, Khushalani NI, Markowitz J, Brohl AS, Tetteh LF, Ramadan H, Arnone G, Li J, Zhao X, Sharma R, Darville LNF, Fang B, Smalley I, Messina JL, Koomen JM, Sondak VK, Smalley KSM. Combined BRAF and HSP90 Inhibition in Patients with Unresectable BRAFV600E-Mutant Melanoma. Clin Cancer Res. 2018 Nov 15;24(22):5516-5524. doi: 10.1158/1078-0432.CCR-18-0565. Epub 2018 Apr 19. PMID: 29674508; PMCID: PMC6195480. 13: Azimi A, Caramuta S, Seashore-Ludlow B, Boström J, Robinson JL, Edfors F, Tuominen R, Kemper K, Krijgsman O, Peeper DS, Nielsen J, Hansson J, Egyhazi Brage S, Altun M, Uhlen M, Maddalo G. Targeting CDK2 overcomes melanoma resistance against BRAF and Hsp90 inhibitors. Mol Syst Biol. 2018 Mar 5;14(3):e7858. doi: 10.15252/msb.20177858. PMID: 29507054; PMCID: PMC5836539. 14: Vido MJ, Aplin AE. The Broad Stroke of Hsp90 Inhibitors: Painting over the RAF Inhibitor Paradox. J Invest Dermatol. 2015 Oct;135(10):2355-2357. doi: 10.1038/jid.2015.239. PMID: 26358385; PMCID: PMC4568562. 15: Phadke M, Gibney GT, Rich CJ, Fedorenko IV, Chen YA, Kudchadkar RR, Sondak VK, Weber J, Messina JL, Smalley KSM. XL888 Limits Vemurafenib-Induced Proliferative Skin Events by Suppressing Paradoxical MAPK Activation. J Invest Dermatol. 2015 Oct;135(10):2542-2544. doi: 10.1038/jid.2015.205. Epub 2015 Jun 3. PMID: 26039542; PMCID: PMC4567904. 16: Rebecca VW, Wood E, Fedorenko IV, Paraiso KH, Haarberg HE, Chen Y, Xiang Y, Sarnaik A, Gibney GT, Sondak VK, Koomen JM, Smalley KS. Evaluating melanoma drug response and therapeutic escape with quantitative proteomics. Mol Cell Proteomics. 2014 Jul;13(7):1844-54. doi: 10.1074/mcp.M113.037424. Epub 2014 Apr 23. PMID: 24760959; PMCID: PMC4083119. 17: Haarberg HE, Paraiso KH, Wood E, Rebecca VW, Sondak VK, Koomen JM, Smalley KS. Inhibition of Wee1, AKT, and CDK4 underlies the efficacy of the HSP90 inhibitor XL888 in an in vivo model of NRAS-mutant melanoma. Mol Cancer Ther. 2013 Jun;12(6):901-12. doi: 10.1158/1535-7163.MCT-12-1003. Epub 2013 Mar 28. PMID: 23538902; PMCID: PMC3683468. 18: Bussenius J, Blazey CM, Aay N, Anand NK, Arcalas A, Baik T, Bowles OJ, Buhr CA, Costanzo S, Curtis JK, DeFina SC, Dubenko L, Heuer TS, Huang P, Jaeger C, Joshi A, Kennedy AR, Kim AI, Lara K, Lee J, Li J, Lougheed JC, Ma S, Malek S, Manalo JC, Martini JF, McGrath G, Nicoll M, Nuss JM, Pack M, Peto CJ, Tsang TH, Wang L, Womble SW, Yakes M, Zhang W, Rice KD. Discovery of XL888: a novel tropane-derived small molecule inhibitor of HSP90. Bioorg Med Chem Lett. 2012 Sep 1;22(17):5396-404. doi: 10.1016/j.bmcl.2012.07.052. Epub 2012 Jul 21. PMID: 22877636. 19: Paraiso KH, Haarberg HE, Wood E, Rebecca VW, Chen YA, Xiang Y, Ribas A, Lo RS, Weber JS, Sondak VK, John JK, Sarnaik AA, Koomen JM, Smalley KS. The HSP90 inhibitor XL888 overcomes BRAF inhibitor resistance mediated through diverse mechanisms. Clin Cancer Res. 2012 May 1;18(9):2502-14. doi: 10.1158/1078-0432.CCR-11-2612. Epub 2012 Feb 20. PMID: 22351686; PMCID: PMC3398738. 20: Lyman SK, Crawley SC, Gong R, Adamkewicz JI, McGrath G, Chew JY, Choi J, Holst CR, Goon LH, Detmer SA, Vaclavikova J, Gerritsen ME, Blake RA. High- content, high-throughput analysis of cell cycle perturbations induced by the HSP90 inhibitor XL888. PLoS One. 2011 Mar 7;6(3):e17692. doi: 10.1371/journal.pone.0017692. Erratum in: PLoS One. 2011;6(3). doi: 10.1371/annotation/73d83e95-8f14-48ed-bb67-2310a33e4ecc. PMID: 21408192; PMCID: PMC3049797.