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MedKoo Cat#: 202370 | Name: Pyroxamide
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Description:

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

Pyroxamide is a synthetic derivative of hydroxamic acid with antineoplastic properties, Pyroxamide inhibits histone deacetylases involved in transcription; induces hyperacetylation of core histones, modulating chromatin structure and affecting transcription of some genes that inhibit tumor growth; and induces growth arrest and apoptosis. Pyroxamide is used in clinical studies for cancer chemotherapy.

Chemical Structure

Pyroxamide
Pyroxamide
CAS#382180-17-8

Theoretical Analysis

MedKoo Cat#: 202370

Name: Pyroxamide

CAS#: 382180-17-8

Chemical Formula: C13H19N3O3

Exact Mass: 265.1426

Molecular Weight: 265.31

Elemental Analysis: C, 58.85; H, 7.22; N, 15.84; O, 18.09

Price and Availability

Size Price Availability Quantity
10mg USD 450.00
25mg USD 700.00
50mg USD 1,050.00
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Related CAS #
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Synonym
Pyroxamide
IUPAC/Chemical Name
N1-hydroxy-N8-(pyridin-3-yl)octanediamide
InChi Key
PTJGLFIIZFVFJV-UHFFFAOYSA-N
InChi Code
InChI=1S/C13H19N3O3/c17-12(15-11-6-5-9-14-10-11)7-3-1-2-4-8-13(18)16-19/h5-6,9-10,19H,1-4,7-8H2,(H,15,17)(H,16,18)
SMILES Code
O=C(NO)CCCCCCC(NC1=CC=CN=C1)=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 and DMF
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
More Info
             
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Pyroxamide is an HDAC inhibitor, including HDAC1 (IC50 = 0.1-0.2 μM). It induces growth suppression and cell death of certain types of cancer cells in culture.
In vitro activity:
Pyroxamide induced growth suppression and cell death in human rhabdomyosarcoma cellso. Accumulation of acetylated histones and induction of p21/WAF1 expression were observed in cells exposed to pyroxamide. There was an induction of p21/WAF1 at 15 and 24 h when the cells were cultured with pyroxamide. Pyroxamide increased nuclei with hypodiploid or sub-G(1) fraction in a dose dependent manner. Reference: Clin Cancer Res. 2003 Nov 15;9(15):5749-55. https://pubmed.ncbi.nlm.nih.gov/14654560/
In vivo activity:
Administration of pyroxamide to nude mice caused little evident toxicity significantly suppressed the growth of s.c. CWR22 prostate cancer xenografts. Serum prostate-specific antigen levels in control versus pyroxamide-treated mice were not significantly different. Human CWR22 prostate tumor xenografts from mice treated with pyroxamide showed increased levels of histone acetylation and increased expression of the cell cycle regulator p21/WAF1. Reference: Clin Cancer Res. 2001 Apr;7(4):962-70. https://pubmed.ncbi.nlm.nih.gov/11309347/
Solvent mg/mL mM
Solubility
DMF 2.0 7.54
DMSO 5.0 18.85
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 265.31 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. Xu Y, Fan S, Liu Y, Shi J, Xie X, Wang X, Wang C, Liu X, Xia G. HDAC1 in the Ovarian Granulosa Cells of Tan Sheep Improves Cumulus Cell Expansion and Oocyte Maturation Independently of the EGF-like Growth Factors. Biology (Basel). 2022 Oct 6;11(10):1464. doi: 10.3390/biology11101464. PMID: 36290368; PMCID: PMC9598242. 2. Kutko MC, Glick RD, Butler LM, Coffey DC, Rifkind RA, Marks PA, Richon VM, LaQuaglia MP. Histone deacetylase inhibitors induce growth suppression and cell death in human rhabdomyosarcoma in vitro. Clin Cancer Res. 2003 Nov 15;9(15):5749-55. PMID: 14654560. 3. Einsiedel HG, Kawan L, Eckert C, Witt O, Fichtner I, Henze G, Seeger K. Histone deacetylase inhibitors have antitumor activity in two NOD/SCID mouse models of B-cell precursor childhood acute lymphoblastic leukemia. Leukemia. 2006 Aug;20(8):1435-6. doi: 10.1038/sj.leu.2404282. Epub 2006 Jun 29. PMID: 16810202. 4. Butler LM, Webb Y, Agus DB, Higgins B, Tolentino TR, Kutko MC, LaQuaglia MP, Drobnjak M, Cordon-Cardo C, Scher HI, Breslow R, Richon VM, Rifkind RA, Marks PA. Inhibition of transformed cell growth and induction of cellular differentiation by pyroxamide, an inhibitor of histone deacetylase. Clin Cancer Res. 2001 Apr;7(4):962-70. PMID: 11309347.
In vitro protocol:
1. Xu Y, Fan S, Liu Y, Shi J, Xie X, Wang X, Wang C, Liu X, Xia G. HDAC1 in the Ovarian Granulosa Cells of Tan Sheep Improves Cumulus Cell Expansion and Oocyte Maturation Independently of the EGF-like Growth Factors. Biology (Basel). 2022 Oct 6;11(10):1464. doi: 10.3390/biology11101464. PMID: 36290368; PMCID: PMC9598242. 2. Kutko MC, Glick RD, Butler LM, Coffey DC, Rifkind RA, Marks PA, Richon VM, LaQuaglia MP. Histone deacetylase inhibitors induce growth suppression and cell death in human rhabdomyosarcoma in vitro. Clin Cancer Res. 2003 Nov 15;9(15):5749-55. PMID: 14654560.
In vivo protocol:
1. Einsiedel HG, Kawan L, Eckert C, Witt O, Fichtner I, Henze G, Seeger K. Histone deacetylase inhibitors have antitumor activity in two NOD/SCID mouse models of B-cell precursor childhood acute lymphoblastic leukemia. Leukemia. 2006 Aug;20(8):1435-6. doi: 10.1038/sj.leu.2404282. Epub 2006 Jun 29. PMID: 16810202. 2. Butler LM, Webb Y, Agus DB, Higgins B, Tolentino TR, Kutko MC, LaQuaglia MP, Drobnjak M, Cordon-Cardo C, Scher HI, Breslow R, Richon VM, Rifkind RA, Marks PA. Inhibition of transformed cell growth and induction of cellular differentiation by pyroxamide, an inhibitor of histone deacetylase. Clin Cancer Res. 2001 Apr;7(4):962-70. PMID: 11309347.
1: Wang S, Cui Z, Zhu J, Zhou P, Cao X, Li X, Ma Y, He Q. Colchicine inhibits the proliferation and promotes the apoptosis of papillary thyroid carcinoma cells likely due to the inhibitory effect on HDAC1. Biochem Biophys Res Commun. 2023 Oct 30;679:129-138. doi: 10.1016/j.bbrc.2023.09.006. Epub 2023 Sep 8. PMID: 37690423. 2: Xu Y, Fan S, Liu Y, Shi J, Xie X, Wang X, Wang C, Liu X, Xia G. HDAC1 in the Ovarian Granulosa Cells of Tan Sheep Improves Cumulus Cell Expansion and Oocyte Maturation Independently of the EGF-like Growth Factors. Biology (Basel). 2022 Oct 6;11(10):1464. doi: 10.3390/biology11101464. PMID: 36290368; PMCID: PMC9598242. 3: Haldrup J, Strand SH, Cieza-Borrella C, Jakobsson ME, Riedel M, Norgaard M, Hedensted S, Dagnaes-Hansen F, Ulhoi BP, Eeles R, Borre M, Olsen JV, Thomsen M, Kote-Jarai Z, Sorensen KD. FRMD6 has tumor suppressor functions in prostate cancer. Oncogene. 2021 Jan;40(4):763-776. doi: 10.1038/s41388-020-01548-w. Epub 2020 Nov 28. PMID: 33249427. 4: Garcia-Rodriguez L, Jones L, Chen KM, Datta I, Divine G, Worsham MJ. Causal network analysis of head and neck keloid tissue identifies potential master regulators. Laryngoscope. 2016 Oct;126(10):E319-24. doi: 10.1002/lary.25958. Epub 2016 Mar 18. PMID: 26990118. 5: Einsiedel HG, Kawan L, Eckert C, Witt O, Fichtner I, Henze G, Seeger K. Histone deacetylase inhibitors have antitumor activity in two NOD/SCID mouse models of B-cell precursor childhood acute lymphoblastic leukemia. Leukemia. 2006 Aug;20(8):1435-6. doi: 10.1038/sj.leu.2404282. Epub 2006 Jun 29. PMID: 16810202. 6: Kouraklis G, Theocharis S. Histone deacetylase inhibitors: a novel target of anticancer therapy (review). Oncol Rep. 2006 Feb;15(2):489-94. PMID: 16391874. 7: Kutko MC, Glick RD, Butler LM, Coffey DC, Rifkind RA, Marks PA, Richon VM, LaQuaglia MP. Histone deacetylase inhibitors induce growth suppression and cell death in human rhabdomyosarcoma in vitro. Clin Cancer Res. 2003 Nov 15;9(15):5749-55. PMID: 14654560. 8: Kouraklis G, Theocharis S. Histone deacetylase inhibitors and anticancer therapy. Curr Med Chem Anticancer Agents. 2002 Jul;2(4):477-84. doi: 10.2174/1568011023353921. PMID: 12678732. 9: Daud A, Munster P, Munster P, Spriggs DR. New drugs in gynecologic cancer. Curr Treat Options Oncol. 2001 Apr;2(2):119-28. doi: 10.1007/s11864-001-0054-0. PMID: 12057130. 10: Butler LM, Webb Y, Agus DB, Higgins B, Tolentino TR, Kutko MC, LaQuaglia MP, Drobnjak M, Cordon-Cardo C, Scher HI, Breslow R, Richon VM, Rifkind RA, Marks PA. Inhibition of transformed cell growth and induction of cellular differentiation by pyroxamide, an inhibitor of histone deacetylase. Clin Cancer Res. 2001 Apr;7(4):962-70. PMID: 11309347.

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Justicisaponin I