Pyroxamide
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MedKoo CAT#: 202370

CAS#: 382180-17-8

Description: 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

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Pyroxamide
CAS# 382180-17-8

Theoretical Analysis

MedKoo Cat#: 202370
Name: Pyroxamide
CAS#: 382180-17-8
Chemical Formula: C13H19N3O3
Exact Mass: 265.14
Molecular Weight: 265.310
Elemental Analysis: C, 58.85; H, 7.22; N, 15.84; O, 18.09

Price and Availability

Size Price Availability Quantity
10mg USD 240
25mg USD 450
50mg USD 790
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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:
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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 2.0 7.54
DMSO 5.0 18.85

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.

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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. Epub 2006 Jun 29. PubMed PMID: 16810202.

2: Kouraklis G, Theocharis S. Histone deacetylase inhibitors: a novel target of anticancer therapy (review). Oncol Rep. 2006 Feb;15(2):489-94. Review. PubMed PMID: 16391874.

3: 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. PubMed PMID: 14654560.

4: Kouraklis G, Theocharis S. Histone deacetylase inhibitors and anticancer therapy. Curr Med Chem Anticancer Agents. 2002 Jul;2(4):477-84. Review. PubMed PMID: 12678732.

5: Daud A, Munster P, Munster P, Spriggs DR. New drugs in gynecologic cancer. Curr Treat Options Oncol. 2001 Apr;2(2):119-28. Review. PubMed PMID: 12057130.

6: 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. PubMed PMID: 11309347.