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

MedKoo CAT#: 406222

CAS#: 183506-66-3

Description: Apicidin is a a potent histone deacetylases (HDAC) inhibitor with potential anticancer activity.

Chemical Structure

CAS# 183506-66-3

Theoretical Analysis

MedKoo Cat#: 406222
Name: Apicidin
CAS#: 183506-66-3
Chemical Formula: C34H49N5O6
Exact Mass: 623.36828
Molecular Weight: 623.78
Elemental Analysis: C, 65.47; H, 7.92; N, 11.23; O, 15.39

Price and Availability

Size Price Availability Quantity
1.0mg USD 160.0 2 Weeks
5.0mg USD 350.0 2 Weeks
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Synonym: Apicidin

IUPAC/Chemical Name: (3S,6S,9S,15aR)-9-((R)-sec-butyl)-6-((1-methoxy-1H-indol-2-yl)methyl)-3-(6-oxooctyl)decahydro-1H-pyrido[1,2-a][1,4,7,10]tetraazacyclododecine-1,4,7,10(12H)-tetraone


InChi Code: InChI=1S/C34H49N5O6/c1-5-22(3)30-34(44)38-19-13-12-18-29(38)33(43)35-26(16-9-7-8-15-25(40)6-2)31(41)36-27(32(42)37-30)21-24-20-23-14-10-11-17-28(23)39(24)45-4/h10-11,14,17,20,22,26-27,29-30H,5-9,12-13,15-16,18-19,21H2,1-4H3,(H,35,43)(H,36,41)(H,37,42)/t22-,26+,27+,29-,30+/m1/s1

SMILES Code: O=C(N[C@@H](CCCCCC(CC)=O)C(N[C@@H](CC(N1OC)=CC2=C1C=CC=C2)C(N[C@H]3[C@H](C)CC)=O)=O)[C@](CCCC4)([H])N4C3=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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 623.78 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: Choi JH, Lee JY, Choi AY, Hwang KY, Choe W, Yoon KS, Ha J, Yeo EJ, Kang I. Retraction Note: Apicidin induces endoplasmic reticulum stress- and mitochondrial dysfunction-associated apoptosis via phospholipase Cγ1- and Ca2+-dependent pathway in mouse Neuro-2a neuroblastoma cells. Apoptosis. 2022 Dec;27(11-12):1060. doi: 10.1007/s10495-022-01771-8. Epub 2022 Sep 28. PMID: 36169758.

2: Parlet CP, Kavanaugh JS, Crosby HA, Raja HA, El-Elimat T, Todd DA, Pearce CJ, Cech NB, Oberlies NH, Horswill AR. Apicidin Attenuates MRSA Virulence through Quorum-Sensing Inhibition and Enhanced Host Defense. Cell Rep. 2019 Apr 2;27(1):187-198.e6. doi: 10.1016/j.celrep.2019.03.018. PMID: 30943400; PMCID: PMC7224364.

3: Ahn MY, Ahn SG, Yoon JH. Apicidin, a histone deaceylase inhibitor, induces both apoptosis and autophagy in human oral squamous carcinoma cells. Oral Oncol. 2011 Nov;47(11):1032-8. doi: 10.1016/j.oraloncology.2011.07.027. PMID: 21856210.

4: Choi JH, Lee JY, Choi AY, Hwang KY, Choe W, Yoon KS, Ha J, Yeo EJ, Kang I. Apicidin induces endoplasmic reticulum stress- and mitochondrial dysfunction- associated apoptosis via phospholipase Cγ1- and Ca(2+)-dependent pathway in mouse Neuro-2a neuroblastoma cells. Apoptosis. 2012 Dec;17(12):1340-58. doi: 10.1007/s10495-012-0755-9. Retraction in: Apoptosis. 2022 Dec;27(11-12):1060. Erratum in: Apoptosis. 2019 Feb;24(1-2):198-199. PMID: 22926926.

5: Luo B, Chen J, Zhou GF, Xie XY, Tang J, Wen QX, Song L, Xie SQ, Long Y, Chen GJ, Hu XT. Apicidin attenuates memory deficits by reducing the Aβ load in APP/PS1 mice. CNS Neurosci Ther. 2023 May;29(5):1300-1311. doi: 10.1111/cns.14102. Epub 2023 Jan 27. PMID: 36708130; PMCID: PMC10068467.

6: Witte TE, Harris LJ, Nguyen HDT, Hermans A, Johnston A, Sproule A, Dettman JR, Boddy CN, Overy DP. Apicidin biosynthesis is linked to accessory chromosomes in Fusarium poae isolates. BMC Genomics. 2021 Aug 4;22(1):591. doi: 10.1186/s12864-021-07617-y. PMID: 34348672; PMCID: PMC8340494.

7: Zhang J, Lai Z, Huang W, Ling H, Lin M, Tang S, Liu Y, Tao Y. Apicidin Inhibited Proliferation and Invasion and Induced Apoptosis via Mitochondrial Pathway in Non-small Cell Lung Cancer GLC-82 Cells. Anticancer Agents Med Chem. 2017;17(10):1374-1382. doi: 10.2174/1871520617666170419120044. PMID: 28425856.

8: Jung ID, Lee JS, Jeong YI, Lee CM, Chang JH, Jeong SK, Chun SH, Park WS, Han J, Shin YK, Park YM. Apicidin, the histone deacetylase inhibitor, suppresses Th1 polarization of murine bone marrow-derived dendritic cells. Int J Immunopathol Pharmacol. 2009 Apr-Jun;22(2):501-15. doi: 10.1177/039463200902200227. PMID: 19505402.

9: Hsu WC, Le HN, Lin YJ, Chen MC, Wang TF, Li CC, Kuo WW, Mahalakshmi B, Singh CH, Chen MC, Huang CY. Calmodulin/CaMKII-γ mediates prosurvival capability in apicidin-persistent hepatocellular carcinoma cells via ERK1/2/CREB/c-fos signaling pathway. J Cell Biochem. 2021 Jun;122(6):612-625. doi: 10.1002/jcb.29892. Epub 2021 Jan 18. PMID: 33459431.

10: Jin JM, Lee S, Lee J, Baek SR, Kim JC, Yun SH, Park SY, Kang S, Lee YW. Functional characterization and manipulation of the apicidin biosynthetic pathway in Fusarium semitectum. Mol Microbiol. 2010 Apr;76(2):456-66. doi: 10.1111/j.1365-2958.2010.07109.x. Epub 2010 Mar 10. PMID: 20233305.

11: Ahn MY, Ahn JW, Kim HS, Lee J, Yoon JH. Apicidin inhibits cell growth by downregulating IGF-1R in salivary mucoepidermoid carcinoma cells. Oncol Rep. 2015 Apr;33(4):1899-907. doi: 10.3892/or.2015.3776. Epub 2015 Feb 2. PMID: 25647264.

12: Hsu HH, Cheng LH, Ho TJ, Kuo WW, Lin YM, Chen MC, Lee NH, Tsai FJ, Tsai KH, Huang CY. Apicidin-resistant HA22T hepatocellular carcinoma cells massively promote pro-survival capability via IGF-IR/PI3K/Akt signaling pathway activation. Tumour Biol. 2014 Jan;35(1):303-13. doi: 10.1007/s13277-013-1041-3. Epub 2013 Aug 30. PMID: 23990456.

13: Han JW, Ahn SH, Park SH, Wang SY, Bae GU, Seo DW, Kwon HK, Hong S, Lee HY, Lee YW, Lee HW. Apicidin, a histone deacetylase inhibitor, inhibits proliferation of tumor cells via induction of p21WAF1/Cip1 and gelsolin. Cancer Res. 2000 Nov 1;60(21):6068-74. PMID: 11085529.

14: Ueda T, Takai N, Nishida M, Nasu K, Narahara H. Apicidin, a novel histone deacetylase inhibitor, has profound anti-growth activity in human endometrial and ovarian cancer cells. Int J Mol Med. 2007 Feb;19(2):301-8. PMID: 17203205.

15: Kwon SH, Ahn SH, Kim YK, Bae GU, Yoon JW, Hong S, Lee HY, Lee YW, Lee HW, Han JW. Apicidin, a histone deacetylase inhibitor, induces apoptosis and Fas/Fas ligand expression in human acute promyelocytic leukemia cells. J Biol Chem. 2002 Jan 18;277(3):2073-80. doi: 10.1074/jbc.M106699200. Epub 2001 Nov 6. PMID: 11698395.

16: Hu XT, Zhu BL, Zhao LG, Wang JW, Liu L, Lai YJ, He L, Deng XJ, Chen GJ. Histone deacetylase inhibitor apicidin increases expression of the α-secretase ADAM10 through transcription factor USF1-mediated mechanisms. FASEB J. 2017 Apr;31(4):1482-1493. doi: 10.1096/fj.201600961RR. Epub 2016 Dec 21. PMID: 28003340.

17: Kim JS, Jeung HK, Cheong JW, Maeng H, Lee ST, Hahn JS, Ko YW, Min YH. Apicidin potentiates the imatinib-induced apoptosis of Bcr-Abl-positive human leukaemia cells by enhancing the activation of mitochondria-dependent caspase cascades. Br J Haematol. 2004 Jan;124(2):166-78. doi: 10.1046/j.1365-2141.2003.04759.x. PMID: 14687026.

18: Ahn MY. HDAC inhibitor apicidin suppresses murine oral squamous cell carcinoma cell growth in vitro and in vivo via inhibiting HDAC8 expression. Oncol Lett. 2018 Nov;16(5):6552-6560. doi: 10.3892/ol.2018.9468. Epub 2018 Sep 20. PMID: 30405794; PMCID: PMC6202526.

19: Ansari D, Urey C, Hilmersson KS, Bauden MP, Ek F, Olsson R, Andersson R. Apicidin sensitizes pancreatic cancer cells to gemcitabine by epigenetically regulating MUC4 expression. Anticancer Res. 2014 Oct;34(10):5269-76. PMID: 25275019.

20: Kim SH, Ahn S, Han JW, Lee HW, Lee HY, Lee YW, Kim MR, Kim KW, Kim WB, Hong S. Apicidin is a histone deacetylase inhibitor with anti-invasive and anti- angiogenic potentials. Biochem Biophys Res Commun. 2004 Mar 19;315(4):964-70. doi: 10.1016/j.bbrc.2004.01.149. PMID: 14985106.

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