Vorinostat
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MedKoo CAT#: 100940

CAS#: 149647-78-9

Description: Vorinostat, also known as suberanilohydroxamic acid, MK-0683 and SAHA, is a potent and selective inhibitor of histone deacetylases (HDACs). Vorinostat has been shown to bind to the active site of histone deacetylases and act as a chelator for Zinc ions also found in the active site of histone deacetylases. Vorinostat's inhibition of histone deacetylases results in the accumulation of acetylated histones and acetylated proteins, including transcription factors crucial for the expression of genes needed to induce cell differentiation. Vorinostat was approved for the treatment of cutaneous T cell lymphoma (CTCL) when the disease persists, gets worse, or comes back during or after treatment with other medicines.

Chemical Structure

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Vorinostat
CAS# 149647-78-9
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 100940
Name: Vorinostat
CAS#: 149647-78-9
Chemical Formula: C14H20N2O3
Exact Mass: 264.15
Molecular Weight: 264.320
Elemental Analysis: C, 63.62; H, 7.63; N, 10.60; O, 18.16

Price and Availability

Size Price Availability Quantity
1g USD 110 Ready to ship
2g USD 190 Ready to ship
5g USD 350 Ready to ship
10g USD 650 Ready to ship
20g USD 1050 Ready to ship
50g USD 2450 Ready to ship
100g USD 4250 2 Weeks
200g USD 6350 2 weeks
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Synonym: MK-0683, MK 0683, MK0683, SAHA, M344, CCRIS 8456, HSDB 7930, Vorinostat, suberoylanilide hydroxamic acid, Zolinza

IUPAC/Chemical Name: N1-hydroxy-N8-phenyloctanediamide

InChi Key: WAEXFXRVDQXREF-UHFFFAOYSA-N

InChi Code: InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)

SMILES Code: O=C(NO)CCCCCCC(NC1=CC=CC=C1)=O

Appearance: White to off-white 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: >2 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:          

Biological target: Vorinostat (SAHA) is a potent and orally active pan-inhibitor of HDAC1, HDAC2 and HDAC3 (Class I), HDAC7 (Class II) and HDAC11 (Class IV), with ID50 values of 10 nM and 20 nM for HDAC1 and HDAC3, respectively.
In vitro activity: Vorinostat efficiently suppressed MES-SA cell growth at a low dosage (3 microM) already after 24 hours treatment. Decrease of cell survival was even more pronounced after prolonged treatment and reached 9% and 2% after 48 and 72 hours of treatment, respectively. Colony forming capability of MES-SA cells treated with 3 microM vorinostat for 24 and 48 hours was significantly diminished and blocked after 72 hours. HDACs class I (HDAC2 and 3) as well as class II (HDAC7) were preferentially affected by this treatment. Vorinostat significantly increased p21(WAF1) expression and apoptosis. Reference: Mol Cancer. 2010 Mar 4;9:49. https://pubmed.ncbi.nlm.nih.gov/20202195/
In vivo activity: Nude mice injected with 5 x 106 MES-SA cells were treated for 21 days with vorinostat (50 mg/kg/day) and, in comparison to placebo group, a tumor growth reduction of more than 50% was observed. Results obtained by light- and electron-microscopy suggested pronounced activation of apoptosis in tumors isolated from vorinostat-treated mice. Reference: Mol Cancer. 2010 Mar 4;9:49. https://pubmed.ncbi.nlm.nih.gov/20202195/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO, not in water 100.0 378.33

Preparing Stock Solutions

The following data is based on the product molecular weight 264.32 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. Hrzenjak A, Moinfar F, Kremser ML, Strohmeier B, Petru E, Zatloukal K, Denk H. Histone deacetylase inhibitor vorinostat suppresses the growth of uterine sarcomas in vitro and in vivo. Mol Cancer. 2010 Mar 4;9:49. doi: 10.1186/1476-4598-9-49. PMID: 20202195; PMCID: PMC2843655. 2. Lautz TB, Jie C, Clark S, Naiditch JA, Jafari N, Qiu YY, Zheng X, Chu F, Madonna MB. The effect of vorinostat on the development of resistance to doxorubicin in neuroblastoma. PLoS One. 2012;7(7):e40816. doi: 10.1371/journal.pone.0040816. Epub 2012 Jul 19. PMID: 22829886; PMCID: PMC3400660. 3. Hrzenjak A, Moinfar F, Kremser ML, Strohmeier B, Petru E, Zatloukal K, Denk H. Histone deacetylase inhibitor vorinostat suppresses the growth of uterine sarcomas in vitro and in vivo. Mol Cancer. 2010 Mar 4;9:49. doi: 10.1186/1476-4598-9-49. PMID: 20202195; PMCID: PMC2843655. 4. More SS, Itsara M, Yang X, Geier EG, Tadano MK, Seo Y, Vanbrocklin HF, Weiss WA, Mueller S, Haas-Kogan DA, Dubois SG, Matthay KK, Giacomini KM. Vorinostat increases expression of functional norepinephrine transporter in neuroblastoma in vitro and in vivo model systems. Clin Cancer Res. 2011 Apr 15;17(8):2339-49. doi: 10.1158/1078-0432.CCR-10-2949. Epub 2011 Mar 18. PMID: 21421857; PMCID: PMC3247296.
In vitro protocol: 1. Hrzenjak A, Moinfar F, Kremser ML, Strohmeier B, Petru E, Zatloukal K, Denk H. Histone deacetylase inhibitor vorinostat suppresses the growth of uterine sarcomas in vitro and in vivo. Mol Cancer. 2010 Mar 4;9:49. doi: 10.1186/1476-4598-9-49. PMID: 20202195; PMCID: PMC2843655. 2. Lautz TB, Jie C, Clark S, Naiditch JA, Jafari N, Qiu YY, Zheng X, Chu F, Madonna MB. The effect of vorinostat on the development of resistance to doxorubicin in neuroblastoma. PLoS One. 2012;7(7):e40816. doi: 10.1371/journal.pone.0040816. Epub 2012 Jul 19. PMID: 22829886; PMCID: PMC3400660.
In vivo protocol: 1. Hrzenjak A, Moinfar F, Kremser ML, Strohmeier B, Petru E, Zatloukal K, Denk H. Histone deacetylase inhibitor vorinostat suppresses the growth of uterine sarcomas in vitro and in vivo. Mol Cancer. 2010 Mar 4;9:49. doi: 10.1186/1476-4598-9-49. PMID: 20202195; PMCID: PMC2843655. 2. More SS, Itsara M, Yang X, Geier EG, Tadano MK, Seo Y, Vanbrocklin HF, Weiss WA, Mueller S, Haas-Kogan DA, Dubois SG, Matthay KK, Giacomini KM. Vorinostat increases expression of functional norepinephrine transporter in neuroblastoma in vitro and in vivo model systems. Clin Cancer Res. 2011 Apr 15;17(8):2339-49. doi: 10.1158/1078-0432.CCR-10-2949. Epub 2011 Mar 18. PMID: 21421857; PMCID: PMC3247296.

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 1: Duvic M, Dimopoulos M. The safety profile of vorinostat (suberoylanilide hydroxamic acid) in hematologic malignancies: A review of clinical studies. Cancer Treat Rev. 2016 Feb;43:58-66. doi: 10.1016/j.ctrv.2015.04.003. Epub 2015 Apr 9. Review. PubMed PMID: 26827693.

2: Afifi S, Michael A, Azimi M, Rodriguez M, Lendvai N, Landgren O. Role of Histone Deacetylase Inhibitors in Relapsed Refractory Multiple Myeloma: A Focus on Vorinostat and Panobinostat. Pharmacotherapy. 2015 Dec;35(12):1173-88. doi: 10.1002/phar.1671. Review. PubMed PMID: 26684557.

3: Iwamoto M, Friedman EJ, Sandhu P, Agrawal NG, Rubin EH, Wagner JA. Clinical pharmacology profile of vorinostat, a histone deacetylase inhibitor. Cancer Chemother Pharmacol. 2013 Sep;72(3):493-508. doi: 10.1007/s00280-013-2220-z. Epub 2013 Jul 3. Review. PubMed PMID: 23820962.

4: Lynch DR Jr, Washam JB, Newby LK. QT interval prolongation and torsades de pointes in a patient undergoing treatment with vorinostat: a case report and review of the literature. Cardiol J. 2012;19(4):434-8. Review. PubMed PMID: 22825908.

5: Prebet T, Vey N. Vorinostat in acute myeloid leukemia and myelodysplastic syndromes. Expert Opin Investig Drugs. 2011 Feb;20(2):287-95. doi: 10.1517/13543784.2011.542750. Epub 2010 Dec 31. Review. PubMed PMID: 21192773.

6: Richon VM. Targeting histone deacetylases: development of vorinostat for the treatment of cancer. Epigenomics. 2010 Jun;2(3):457-65. doi: 10.2217/epi.10.20. Review. PubMed PMID: 22121904.

7: Kavanaugh SM, White LA, Kolesar JM. Vorinostat: A novel therapy for the treatment of cutaneous T-cell lymphoma. Am J Health Syst Pharm. 2010 May 15;67(10):793-7. doi: 10.2146/ajhp090247. Review. Erratum in: Am J Health Syst Pharm. 2010 Jul 15;67(14):1136. Kavanaugh, Shannon A [corrected to Kavanaugh, Shannon M]. PubMed PMID: 20479100.

8: Zirlik K, Nashan D, Veelken H. [Vorinostat in the treatment of cutaneous T-cell lymphomas. Treatment with histone deacetylases inhibitors]. Pharm Unserer Zeit. 2010 May;39(3):190-6. doi: 10.1002/pauz.201000365. Review. German. PubMed PMID: 20425773.

9: Siegel D, Hussein M, Belani C, Robert F, Galanis E, Richon VM, Garcia-Vargas J, Sanz-Rodriguez C, Rizvi S. Vorinostat in solid and hematologic malignancies. J Hematol Oncol. 2009 Jul 27;2:31. doi: 10.1186/1756-8722-2-31. Review. PubMed PMID: 19635146; PubMed Central PMCID: PMC2731787.

10: Richon VM, Garcia-Vargas J, Hardwick JS. Development of vorinostat: current applications and future perspectives for cancer therapy. Cancer Lett. 2009 Aug 8;280(2):201-10. doi: 10.1016/j.canlet.2009.01.002. Epub 2009 Jan 31. Review. PubMed PMID: 19181442.

11: Heymann WR. Treatment of cutaneous T-cell lymphoma: focus on vorinostat. J Am Acad Dermatol. 2008 Oct;59(4):696-7. doi: 10.1016/j.jaad.2008.03.006. Review. PubMed PMID: 18793938.

12: Duvic M, Vu J. Vorinostat in cutaneous T-cell lymphoma. Drugs Today (Barc). 2007 Sep;43(9):585-99. Review. PubMed PMID: 17940636.

13: Duvic M, Vu J. Vorinostat: a new oral histone deacetylase inhibitor approved for cutaneous T-cell lymphoma. Expert Opin Investig Drugs. 2007 Jul;16(7):1111-20. Review. PubMed PMID: 17594194.

14: Marks PA, Breslow R. Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug. Nat Biotechnol. 2007 Jan;25(1):84-90. Review. PubMed PMID: 17211407.

Zhang Y, Zhou L, Safran H, Borsuk R, Lulla R, Tapinos N, Seyhan AA, El-Deiry WS. EZH2i EPZ-6438 and HDACi vorinostat synergize with ONC201/TIC10 to activate integrated stress response, DR5, reduce H3K27 methylation, ClpX and promote apoptosis of multiple tumor types including DIPG. Neoplasia. 2021 Aug;23(8):792-810. doi: 10.1016/j.neo.2021.06.007. Epub 2021 Jul 8. PMID: 34246076; PMCID: PMC8274300.