Alvespimycin
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MedKoo CAT#: 584518

CAS#: 467214-20-6

Description: Alvespimycin is a heat shock protein 90 (Hsp90) inhibitor and promising therapeutic agent for cancer.


Chemical Structure

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Alvespimycin
CAS# 467214-20-6

Theoretical Analysis

MedKoo Cat#: 584518
Name: Alvespimycin
CAS#: 467214-20-6
Chemical Formula: C32H48N4O8
Exact Mass: 616.3472
Molecular Weight: 616.756
Elemental Analysis: C, 62.32; H, 7.84; N, 9.08; O, 20.75

Price and Availability

Size Price Availability Quantity
1.0mg USD 210.0 2 Weeks
5.0mg USD 385.0 2 Weeks
10.0mg USD 615.0 2 Weeks
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Synonym: Alvespimycin; KOS 1022; KOS-1022; KOS1022; 17-DMAG

IUPAC/Chemical Name: ((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-dimethylaminoethylamino)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo(16.3.1)docosa-4,6,10,18,21-pentaen-9-yl) carbamate

InChi Key: KUFRQPKVAWMTJO-LMZWQJSESA-N

InChi Code: InChI=1S/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25+,26+,28-,30+/m1/s1

SMILES Code: NC(O[C@@H](/C(C)=C/[C@H](C)[C@@H](O)[C@@H](OC)C[C@H](C)CC1=C2NCCN(C)C)[C@@H](OC)/C=C\C=C(C)\C(NC(C1=O)=CC2=O)=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

Shelf Life: >3 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: 2934.99.03.00

Preparing Stock Solutions

The following data is based on the product molecular weight 616.756 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

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1: Hu ZY, Lu J, Zhao Y. A physiologically based pharmacokinetic model of alvespimycin in mice and extrapolation to rats and humans. Br J Pharmacol. 2014 Jun;171(11):2778-89. doi: 10.1111/bph.12609. PubMed PMID: 24471734; PubMed Central PMCID: PMC4243854.

2: Hu Y, Bobb D, He J, Hill DA, Dome JS. The HSP90 inhibitor alvespimycin enhances the potency of telomerase inhibition by imetelstat in human osteosarcoma. Cancer Biol Ther. 2015;16(6):949-57. doi: 10.1080/15384047.2015.1040964. Epub 2015 Apr 28. PubMed PMID: 25920748; PubMed Central PMCID: PMC4622625.

3: Gao L, Zhao G, Fang JS, Yuan TY, Liu AL, Du GH. Discovery of the neuroprotective effects of alvespimycin by computational prioritization of potential anti-Parkinson agents. FEBS J. 2014 Feb;281(4):1110-22. doi: 10.1111/febs.12672. Epub 2014 Jan 9. PubMed PMID: 24304935.

4: Schulze K, Imbeaud S, Letouzé E, Alexandrov LB, Calderaro J, Rebouissou S, Couchy G, Meiller C, Shinde J, Soysouvanh F, Calatayud AL, Pinyol R, Pelletier L, Balabaud C, Laurent A, Blanc JF, Mazzaferro V, Calvo F, Villanueva A, Nault JC, Bioulac-Sage P, Stratton MR, Llovet JM, Zucman-Rossi J. Exome sequencing of hepatocellular carcinomas identifies new mutational signatures and potential therapeutic targets. Nat Genet. 2015 May;47(5):505-511. doi: 10.1038/ng.3252. Epub 2015 Mar 30. PubMed PMID: 25822088; PubMed Central PMCID: PMC4587544.

5: Jhaveri K, Miller K, Rosen L, Schneider B, Chap L, Hannah A, Zhong Z, Ma W, Hudis C, Modi S. A phase I dose-escalation trial of trastuzumab and alvespimycin hydrochloride (KOS-1022; 17 DMAG) in the treatment of advanced solid tumors. Clin Cancer Res. 2012 Sep 15;18(18):5090-8. doi: 10.1158/1078-0432.CCR-11-3200. Epub 2012 Jul 10. PubMed PMID: 22781552.

6: Maddocks K, Hertlein E, Chen TL, Wagner AJ, Ling Y, Flynn J, Phelps M, Johnson AJ, Byrd JC, Jones JA. A phase I trial of the intravenous Hsp90 inhibitor alvespimycin (17-DMAG) in patients with relapsed chronic lymphocytic leukemia/small lymphocytic lymphoma. Leuk Lymphoma. 2016 Sep;57(9):2212-5. doi: 10.3109/10428194.2015.1129536. Epub 2016 Jan 14. PubMed PMID: 26764527; PubMed Central PMCID: PMC5455147.

7: Lancet JE, Gojo I, Burton M, Quinn M, Tighe SM, Kersey K, Zhong Z, Albitar MX, Bhalla K, Hannah AL, Baer MR. Phase I study of the heat shock protein 90 inhibitor alvespimycin (KOS-1022, 17-DMAG) administered intravenously twice weekly to patients with acute myeloid leukemia. Leukemia. 2010 Apr;24(4):699-705. doi: 10.1038/leu.2009.292. Epub 2010 Jan 28. PubMed PMID: 20111068.

8: Pacey S, Wilson RH, Walton M, Eatock MM, Hardcastle A, Zetterlund A, Arkenau HT, Moreno-Farre J, Banerji U, Roels B, Peachey H, Aherne W, de Bono JS, Raynaud F, Workman P, Judson I. A phase I study of the heat shock protein 90 inhibitor alvespimycin (17-DMAG) given intravenously to patients with advanced solid tumors. Clin Cancer Res. 2011 Mar 15;17(6):1561-70. doi: 10.1158/1078-0432.CCR-10-1927. Epub 2011 Jan 28. PubMed PMID: 21278242; PubMed Central PMCID: PMC3060938.

9: Smith MA, Morton CL, Phelps DA, Kolb EA, Lock R, Carol H, Reynolds CP, Maris JM, Keir ST, Wu J, Houghton PJ. Stage 1 testing and pharmacodynamic evaluation of the HSP90 inhibitor alvespimycin (17-DMAG, KOS-1022) by the pediatric preclinical testing program. Pediatr Blood Cancer. 2008 Jul;51(1):34-41. doi: 10.1002/pbc.21508. PubMed PMID: 18260120.

10: Yang DS. Novel prediction of anticancer drug chemosensitivity in cancer cell lines: evidence of moderation by microRNA expressions. Conf Proc IEEE Eng Med Biol Soc. 2014;2014:4780-6. doi: 10.1109/EMBC.2014.6944693. PubMed PMID: 25571061.

11: Ambade A, Catalano D, Lim A, Kopoyan A, Shaffer SA, Mandrekar P. Inhibition of heat shock protein 90 alleviates steatosis and macrophage activation in murine alcoholic liver injury. J Hepatol. 2014 Oct;61(4):903-11. doi: 10.1016/j.jhep.2014.05.024. Epub 2014 May 22. PubMed PMID: 24859453; PubMed Central PMCID: PMC4169725.

12: Nanduri P, Hao R, Fitzpatrick T, Yao TP. Chaperone-mediated 26S proteasome remodeling facilitates free K63 ubiquitin chain production and aggresome clearance. J Biol Chem. 2015 Apr 10;290(15):9455-64. doi: 10.1074/jbc.M114.627950. Epub 2015 Feb 24. PubMed PMID: 25713068; PubMed Central PMCID: PMC4392251.

13: Lazaro I, Oguiza A, Recio C, Mallavia B, Madrigal-Matute J, Blanco J, Egido J, Martin-Ventura JL, Gomez-Guerrero C. Targeting HSP90 Ameliorates Nephropathy and Atherosclerosis Through Suppression of NF-κB and STAT Signaling Pathways in Diabetic Mice. Diabetes. 2015 Oct;64(10):3600-13. doi: 10.2337/db14-1926. Epub 2015 Jun 26. PubMed PMID: 26116697.

14: Iguchi N, Malykhina AP, Wilcox DT. Inhibition of HIF Reduces Bladder Hypertrophy and Improves Bladder Function in Murine Model of Partial Bladder Outlet Obstruction. J Urol. 2016 Apr;195(4 Pt 2):1250-6. doi: 10.1016/j.juro.2015.08.001. Epub 2016 Feb 28. PubMed PMID: 26926557; PubMed Central PMCID: PMC5505069.

15: Safavi S, Järnum S, Vannas C, Udhane S, Jonasson E, Tomic TT, Grundevik P, Fagman H, Hansson M, Kalender Z, Jauhiainen A, Dolatabadi S, Stratford EW, Myklebost O, Eriksson M, Stenman G, Schneider-Stock R, Ståhlberg A, Åman P. HSP90 inhibition blocks ERBB3 and RET phosphorylation in myxoid/round cell liposarcoma and causes massive cell death in vitro and in vivo. Oncotarget. 2016 Jan 5;7(1):433-45. doi: 10.18632/oncotarget.6336. PubMed PMID: 26595521; PubMed Central PMCID: PMC4808009.

16: Tsai YC, Lam KK, Peng YJ, Lee YM, Yang CY, Tsai YJ, Yen MH, Cheng PY. Heat shock protein 70 and AMP-activated protein kinase contribute to 17-DMAG-dependent protection against heat stroke. J Cell Mol Med. 2016 Oct;20(10):1889-97. doi: 10.1111/jcmm.12881. Epub 2016 May 31. PubMed PMID: 27241357; PubMed Central PMCID: PMC5020632.

17: Wang YL, Shen HH, Cheng PY, Chu YJ, Hwang HR, Lam KK, Lee YM. 17-DMAG, an HSP90 Inhibitor, Ameliorates Multiple Organ Dysfunction Syndrome via Induction of HSP70 in Endotoxemic Rats. PLoS One. 2016 May 25;11(5):e0155583. doi: 10.1371/journal.pone.0155583. eCollection 2016. PubMed PMID: 27224288; PubMed Central PMCID: PMC4880344.

18: Yang WL, Lee YE, Chen MH, Chao KM, Huang CY. In-silico drug screening and potential target identification for hepatocellular carcinoma using Support Vector Machines based on drug screening result. Gene. 2013 Apr 10;518(1):201-8. doi: 10.1016/j.gene.2012.11.030. Epub 2012 Dec 6. PubMed PMID: 23220021.

19: Liu Y, Yu Y, Chu H, Bing D, Wang S, Zhou L, Chen J, Chen Q, Pan C, Sun Y, Cui Y. 17-DMAG induces Hsp70 and protects the auditory hair cells from kanamycin ototoxicity in vitro. Neurosci Lett. 2015 Feb 19;588:72-7. doi: 10.1016/j.neulet.2014.12.060. Epub 2014 Dec 31. PubMed PMID: 25556684.

20: Seo YH. Organelle-specific Hsp90 inhibitors. Arch Pharm Res. 2015 Sep;38(9):1582-90. doi: 10.1007/s12272-015-0636-1. Epub 2015 Jul 22. Review. PubMed PMID: 26195286.