Apicidin
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MedKoo CAT#: 406222

CAS#: 183506-66-3

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


Chemical Structure

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Apicidin
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 Key: ROUDRKBLRFRFCY-VWIQTCEGSA-N

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: Buoncervello M, Borghi P, Romagnoli G, Spadaro F, Belardelli F, Toschi E, Gabriele L. Apicidin and docetaxel combination treatment drives CTCFL expression and HMGB1 release acting as potential antitumor immune response inducers in metastatic breast cancer cells. Neoplasia. 2012 Sep;14(9):855-67. PubMed PMID: 23019417; PubMed Central PMCID: PMC3459281.

2: 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. PubMed PMID: 22926926.

3: Ahn MY, Kang DO, Na YJ, Yoon S, Choi WS, Kang KW, Chung HY, Jung JH, Min do S, Kim HS. Histone deacetylase inhibitor, apicidin, inhibits human ovarian cancer cell migration via class II histone deacetylase 4 silencing. Cancer Lett. 2012 Dec 28;325(2):189-99. doi: 10.1016/j.canlet.2012.06.017. Epub 2012 Jul 7. PubMed PMID: 22781396.

4: 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. PubMed PMID: 21856210.

5: Keleş E, Lianeri M, Jagodziński PP. Apicidin suppresses transcription of 17β-hydroxysteroid dehydrogenase type 1 in endometrial adenocarcinoma cells. Mol Biol Rep. 2011 Jun;38(5):3355-60. doi: 10.1007/s11033-010-0441-3. Epub 2010 Nov 18. PubMed PMID: 21086175.

6: Durczak M, Jagodzinski PP. Apicidin upregulates PHD2 prolyl hydroxylase gene expression in cervical cancer cells. Anticancer Drugs. 2010 Jul;21(6):619-24. PubMed PMID: 20527723.

7: Ahn MY, Chung HY, Choi WS, Lee BM, Yoon S, Kim HS. Anti-tumor effect of apicidin on Ishikawa human endometrial cancer cells both in vitro and in vivo by blocking histone deacetylase 3 and 4. Int J Oncol. 2010 Jan;36(1):125-31. PubMed PMID: 19956841.

8: Noh JH, Song JH, Eun JW, Kim JK, Jung KH, Bae HJ, Xie HJ, Ryu JC, Ahn YM, Wee SJ, Park WS, Lee JY, Nam SW. Systemic cell-cycle suppression by Apicidin, a histone deacetylase inhibitor, in MDA-MB-435 cells. Int J Mol Med. 2009 Aug;24(2):205-26. PubMed PMID: 19578794.

9: Lai JP, Sandhu DS, Moser CD, Cazanave SC, Oseini AM, Shire AM, Shridhar V, Sanderson SO, Roberts LR. Additive effect of apicidin and doxorubicin in sulfatase 1 expressing hepatocellular carcinoma in vitro and in vivo. J Hepatol. 2009 Jun;50(6):1112-21. doi: 10.1016/j.jhep.2008.12.031. Epub 2009 Mar 9. PubMed PMID: 19376607; PubMed Central PMCID: PMC2756527.

10: Park SJ, Kim MJ, Kim HB, Sohn HY, Bae JH, Kang CD, Kim SH. Cotreatment with apicidin overcomes TRAIL resistance via inhibition of Bcr-Abl signaling pathway in K562 leukemia cells. Exp Cell Res. 2009 Jul 1;315(11):1809-18. doi: 10.1016/j.yexcr.2009.02.024. Epub 2009 Mar 4. PubMed PMID: 19268463.



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