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MedKoo Cat#: 563828 | Name: Oxamflatin
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Description:

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

Oxamflatin is a histone deacetylase (HDAC) inhibitor that exhibits potent anticancer activity by inducing cell differentiation, apoptosis, and growth arrest in various cancer cell lines. It specifically inhibits class I and II HDACs, leading to increased histone acetylation, which alters gene expression and promotes chromatin relaxation. Oxamflatin has been reported to suppress tumor growth in vitro and in vivo, with demonstrated efficacy in leukemia, colon, and lung cancer models. Additionally, it has been shown to enhance the effects of other anticancer agents by modulating epigenetic pathways, making it a potential candidate for combination therapies.

Chemical Structure

Oxamflatin
Oxamflatin
CAS#151720-43-3

Theoretical Analysis

MedKoo Cat#: 563828

Name: Oxamflatin

CAS#: 151720-43-3

Chemical Formula: C17H14N2O4S

Exact Mass: 342.0674

Molecular Weight: 342.37

Elemental Analysis: C, 59.64; H, 4.12; N, 8.18; O, 18.69; S, 9.36

Price and Availability

Size Price Availability Quantity
25mg USD 350.00 2 Weeks
50mg USD 550.00 2 Weeks
100mg USD 950.00 2 Weeks
1g USD 3,850.00 2 Weeks
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Related CAS #
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Synonym
Oxamflatin; Metacept 3; Metacept3; Metacept-3;
IUPAC/Chemical Name
(E)-5-[3-(Benzenesulfonamido)phenyl]-N-hydroxypent-2-en-4-ynamide
InChi Key
QRPSQQUYPMFERG-LFYBBSHMSA-N
InChi Code
InChI=1S/C17H14N2O4S/c20-17(18-21)12-5-4-7-14-8-6-9-15(13-14)19-24(22,23)16-10-2-1-3-11-16/h1-3,5-6,8-13,19,21H,(H,18,20)/b12-5+
SMILES Code
O=C(NO)/C=C/C#CC1=CC=CC(NS(=O)(C2=CC=CC=C2)=O)=C1
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Oxamflatin is a potent HDAC inhibitor with an IC50 of 15.7 nM.
In vitro activity:
Oxamflatin caused an elongated cell shape with filamentous protrusions as well as arrest of the cell cycle at the G1 phase in HeLa cells. These phenotypic changes of HeLa cells were apparently similar to those by trichostatin A (TSA), a specific inhibitor of histone deacetylase (HDAC). The effect of oxamflatin on the transcriptional activity of the cytomegalovirus (CMV) promoter was examined and compared with known HDAC inhibitors, TSA, sodium n-butyrate, and FR901228. Oxamflatin as well as all these inhibitors greatly enhanced the transcriptional activity of the CMV promoter in a dose-dependent manner. Oxamflatin, like TSA, inhibited intracellular HDAC activity, as a result of which marked amounts of acetylated histone species accumulated. Reference: Oncogene. 1999 Apr 15;18(15):2461-70. https://pubmed.ncbi.nlm.nih.gov/10229197/
In vivo activity:
TBD
Solvent mg/mL mM
Solubility
DMF 10.0 29.21
DMF:PBS (pH 7.2) (1:10) 0.1 0.29
DMSO 27.5 80.32
DMSO:PBS (pH 7.2) (1:10) 0.1 0.29
Ethanol 0.5 1.46
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 342.37 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
Formulation protocol:
1. Wang YL, Liui HL, Fu RG, Wang ZW, Ren HT, Dai ZJ, Jing YY, Li Y. HDAC Inhibitor Oxamflatin Induces Morphological Changes and has Strong Cytostatic Effects in Ovarian Cancer Cell Lines. Curr Mol Med. 2016;16(3):232-42. doi: 10.2174/1566524016666160225151408. PMID: 26917266. 2. Kim YB, Lee KH, Sugita K, Yoshida M, Horinouchi S. Oxamflatin is a novel antitumor compound that inhibits mammalian histone deacetylase. Oncogene. 1999 Apr 15;18(15):2461-70. doi: 10.1038/sj.onc.1202564. PMID: 10229197.
In vitro protocol:
1. Wang YL, Liui HL, Fu RG, Wang ZW, Ren HT, Dai ZJ, Jing YY, Li Y. HDAC Inhibitor Oxamflatin Induces Morphological Changes and has Strong Cytostatic Effects in Ovarian Cancer Cell Lines. Curr Mol Med. 2016;16(3):232-42. doi: 10.2174/1566524016666160225151408. PMID: 26917266. 2. Kim YB, Lee KH, Sugita K, Yoshida M, Horinouchi S. Oxamflatin is a novel antitumor compound that inhibits mammalian histone deacetylase. Oncogene. 1999 Apr 15;18(15):2461-70. doi: 10.1038/sj.onc.1202564. PMID: 10229197.
In vivo protocol:
TBD
1: Yang H, Xiao T, Deng Y, Ding C, Zhang M, Li J, Lv Z. JunD functions as a transcription factor of IL-10 to regulate bacterial infectious inflammation in grass carp (Ctenopharyngodon idella). Int J Biol Macromol. 2024 Feb;258(Pt 2):129045. doi: 10.1016/j.ijbiomac.2023.129045. Epub 2023 Dec 28. PMID: 38159700. 2: Hasegawa EH, Farr GH 3rd, Maves L. Comparison of Pronase versus Manual Dechorionation of Zebrafish Embryos for Small Molecule Treatments. J Dev Biol. 2023 Mar 28;11(2):16. doi: 10.3390/jdb11020016. PMID: 37092478; PMCID: PMC10123619. 3: Farr GH 3rd, Morris M, Gomez A, Pham T, Kilroy E, Parker EU, Said S, Henry C, Maves L. A novel chemical-combination screen in zebrafish identifies epigenetic small molecule candidates for the treatment of Duchenne muscular dystrophy. Skelet Muscle. 2020 Oct 15;10(1):29. doi: 10.1186/s13395-020-00251-4. PMID: 33059738; PMCID: PMC7559456. 4: Awada R, Verdier D, Froger S, Brulard E, de Faria Maraschin S, Etienne H, Breton D. An innovative automated active compound screening system allows high- throughput optimization of somatic embryogenesis in Coffea arabica. Sci Rep. 2020 Jan 21;10(1):810. doi: 10.1038/s41598-020-57800-6. PMID: 31965007; PMCID: PMC6972844. 5: Samiec M, Skrzyszowska M. Intrinsic and extrinsic molecular determinants or modulators for epigenetic remodeling and reprogramming of somatic cell-derived genome in mammalian nuclear-transferred oocytes and resultant embryos. Pol J Vet Sci. 2018 Mar;21(1):217-227. doi: 10.24425/119040. PMID: 29624006. 6: Faghihloo E, Araei Y, Mohammadi M, Mirzaei H, Mohammadi HR, Mokhtari-Azad T. The effect of oxamflatin on the E-cadherin expression in gastric cancer cell line. Cancer Gene Ther. 2016 Nov;23(11):396-399. doi: 10.1038/cgt.2016.52. Epub 2016 Oct 21. PMID: 27767089. 7: Wang YL, Liui HL, Fu RG, Wang ZW, Ren HT, Dai ZJ, Jing YY, Li Y. HDAC Inhibitor Oxamflatin Induces Morphological Changes and has Strong Cytostatic Effects in Ovarian Cancer Cell Lines. Curr Mol Med. 2016;16(3):232-42. doi: 10.2174/1566524016666160225151408. PMID: 26917266. 8: Martínez-Bonet M, Clemente MI, Serramía MJ, Moreno S, Muñoz E, Muñoz- Fernández MA. Immunological and pharmacological strategies to reactivate HIV-1 from latently infected cells: a possibility for HIV-1 paediatric patients? J Virus Erad. 2015 Jul 1;1(3):148-52. PMID: 27482406; PMCID: PMC4946732. 9: Mao J, Zhao MT, Whitworth KM, Spate LD, Walters EM, O'Gorman C, Lee K, Samuel MS, Murphy CN, Wells K, Rivera RM, Prather RS. Oxamflatin treatment enhances cloned porcine embryo development and nuclear reprogramming. Cell Reprogram. 2015 Feb;17(1):28-40. doi: 10.1089/cell.2014.0075. Epub 2014 Dec 30. PMID: 25548976; PMCID: PMC4312790. 10: Balliu M, Guandalini L, Romanelli MN, D'Amico M, Paoletti F. HDAC-inhibitor (S)-8 disrupts HDAC6-PP1 complex prompting A375 melanoma cell growth arrest and apoptosis. J Cell Mol Med. 2015 Jan;19(1):143-54. doi: 10.1111/jcmm.12345. Epub 2014 Nov 6. PMID: 25376115; PMCID: PMC4288358. 11: Hou L, Ma F, Yang J, Riaz H, Wang Y, Wu W, Xia X, Ma Z, Zhou Y, Zhang L, Ying W, Xu D, Zuo B, Ren Z, Xiong Y. Effects of histone deacetylase inhibitor oxamflatin on in vitro porcine somatic cell nuclear transfer embryos. Cell Reprogram. 2014 Aug;16(4):253-65. doi: 10.1089/cell.2013.0058. Epub 2014 Jun 24. PMID: 24960409; PMCID: PMC4116115. 12: Guandalini L, Balliu M, Cellai C, Martino MV, Nebbioso A, Mercurio C, Carafa V, Bartolucci G, Dei S, Manetti D, Teodori E, Scapecchi S, Altucci L, Paoletti F, Romanelli MN. Design, synthesis and preliminary evaluation of a series of histone deacetylase inhibitors carrying a benzodiazepine ring. Eur J Med Chem. 2013 Aug;66:56-68. doi: 10.1016/j.ejmech.2013.05.017. Epub 2013 May 31. PMID: 23792316. 13: Park SJ, Park HJ, Koo OJ, Choi WJ, Moon JH, Kwon DK, Kang JT, Kim S, Choi JY, Jang G, Lee BC. Oxamflatin improves developmental competence of porcine somatic cell nuclear transfer embryos. Cell Reprogram. 2012 Oct;14(5):398-406. doi: 10.1089/cell.2012.0007. PMID: 23013534. 14: Ghosh SK, Perrine SP, Williams RM, Faller DV. Histone deacetylase inhibitors are potent inducers of gene expression in latent EBV and sensitize lymphoma cells to nucleoside antiviral agents. Blood. 2012 Jan 26;119(4):1008-17. doi: 10.1182/blood-2011-06-362434. Epub 2011 Dec 7. PMID: 22160379; PMCID: PMC3271713. 15: Su J, Wang Y, Li Y, Li R, Li Q, Wu Y, Quan F, Liu J, Guo Z, Zhang Y. Oxamflatin significantly improves nuclear reprogramming, blastocyst quality, and in vitro development of bovine SCNT embryos. PLoS One. 2011;6(8):e23805. doi: 10.1371/journal.pone.0023805. Epub 2011 Aug 30. PMID: 21912607; PMCID: PMC3166058. 16: Bui HT, Seo HJ, Park MR, Park JY, Thuan NV, Wakayama T, Kim JH. Histone deacetylase inhibition improves activation of ribosomal RNA genes and embryonic nucleolar reprogramming in cloned mouse embryos. Biol Reprod. 2011 Nov;85(5):1048-56. doi: 10.1095/biolreprod.110.089474. Epub 2011 Jul 13. PMID: 21753193. 17: Huber K, Doyon G, Plaks J, Fyne E, Mellors JW, Sluis-Cremer N. Inhibitors of histone deacetylases: correlation between isoform specificity and reactivation of HIV type 1 (HIV-1) from latently infected cells. J Biol Chem. 2011 Jun 24;286(25):22211-8. doi: 10.1074/jbc.M110.180224. Epub 2011 Apr 29. PMID: 21531716; PMCID: PMC3121366. 18: Yin H, Zhang Y, Zhou X, Zhu H. Histonedeacetylase inhibitor Oxamflatin increase HIV-1 transcription by inducing histone modification in latently infected cells. Mol Biol Rep. 2011 Nov;38(8):5071-8. doi: 10.1007/s11033-010-0653-6. Epub 2010 Dec 23. PMID: 21181272. 19: Wang LZ, Chan D, Yeo W, Wan SC, Chan S, Chan A, Lee SC, Lee HS, Goh BC. A sensitive and specific liquid chromatography-tandem mass spectrometric method for determination of belinostat in plasma from liver cancer patients. J Chromatogr B Analyt Technol Biomed Life Sci. 2010 Sep 15;878(26):2409-14. doi: 10.1016/j.jchromb.2010.07.015. Epub 2010 Jul 30. PMID: 20724229. 20: Ono T, Li C, Mizutani E, Terashita Y, Yamagata K, Wakayama T. Inhibition of class IIb histone deacetylase significantly improves cloning efficiency in mice. Biol Reprod. 2010 Dec;83(6):929-37. doi: 10.1095/biolreprod.110.085282. Epub 2010 Aug 4. PMID: 20686182.