149647-78-9
Vorinostat
CAS: 149647-78-9
Molecular Formula: C14H20N2O3
149647-78-9 - Names and Identifiers
| Name | Vorinostat |
| Synonyms | M344 CS-1949 Zolinza SAHA cpd Vornostat CCRIS 8456 Vorinostat UNII-58IFB293JI Vorinostat [USAN] Suberanilohydroxamic acid suberoylanilide hydroxamic acid N-Hydroxy-N'-phenyloctanediamide N-Hyrdroxy-N'-phenyloctanediamide Octanediamide, N-hydroxy-N'-phenyl- Octanediamide, N1-hydroxy-N8-phenyl- Zolinza (See Suberoylanilide Hydroxamic Acid) SAHA, N-Hydroxy-Nphenyloctanediamide, Zolinza |
| CAS | 149647-78-9 |
| EINECS | 682-505-1 |
| InChI | InChI=1/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) |
| InChIKey | WAEXFXRVDQXREF-UHFFFAOYSA-N |
149647-78-9 - Physico-chemical Properties
| Molecular Formula | C14H20N2O3 |
| Molar Mass | 264.32 |
| Density | 1.2 |
| Melting Point | 161-162°C |
| Solubility | Soluble in ethanol (3 mg/ml at 25 °C), DMSO (53 mg/ml at 25 °C), DMF (~20 mg/ml). |
| Appearance | White crystalline solid |
| Color | white to tan |
| Merck | 14,10034 |
| pKa | 9.48±0.20(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 6 months. |
| Sensitive | Sensitive to heat |
| Refractive Index | 1.566 |
| MDL | MFCD00945317 |
| Physical and Chemical Properties | Appearance: white to off-white crystalline powder |
| In vitro study | Vorinostat is a small molecular weight (<300) linear oxime acid that inhibits HDAC activity, including the accumulation of acetylated histones and non-histones, inhibits the proliferation of cultured cells, and inhibits tumor growth. Vorinostat inhibits HDAC activity by binding to the active site of the enzyme. Vorinostat inhibits the proliferation of a variety of transformed cells (including lymphoma, multiple myeloma, leukemia, and non-small cell lung cancer) at concentrations ranging from 0.5 to 10 μm for 50% growth compared to controls. Vorinostat acts on lymphoma and leukemia cells, including Burkitt, B- cell acute lymphoblastic leukemia (B-ALL), MCL, DLBCL, ATL, and T-cells, and inhibits cell proliferation to varying degrees. In addition to inhibiting the proliferation of transformed cells, Vorinostat also inhibits normal cell proliferation by comparing Vorinostat's effects on a group of cell lines-normal human non-fibroblasts (WI-38) and SV40 giant T antigen transformed WI-38(VA-13). And get proven. Vorinostat inhibited the proliferation of both cell types in a dose-dependent manner. However, Vorinostat was found to have selective toxicity to transformed cells, including the death of tumor cells, while it only inhibits normal cells and does not cause death. The combination of Genistein and Vorinostat is much more effective than the combination of 5-aza and Vorinostat in inducing cell death. The combination of Genistein and Vorinostat reduces proliferation by 80% in ARCaP-E cells and by more than 60% in ARCaP-M cells. The combination of Genistein and Vorinostat has a synergistic effect on inhibiting cell proliferation. Acting on ARCaP-E cells (820 gene induction and 1046 gene suppression) ARCaP-M cells, Vorinostat affects more genes than Genistein. Vorinostat acts on the surface of tumor cells to increase the level of Fas protein in a dose-dependent manner, and when treated at a dose of 0.75 μm, the increase reached a stable level. Vorinostat inhibited tumor cell growth, including NB4, H460 and HCT-116, with IC50 of 0.7 μm, 3.4 μm and 1.2 μm, respectively. |
| In vivo study | Both Decitabine and Vorinostat have the function of causing tumor regression. However, the combination of Decitabine and Vorinostat had a stronger effect on tumor regression. Without any treatment, no significant difference in lung tumor burden was observed in wild-type and Fasgld mice. However, the combination of Decitabine and Vorinostat treatment of wild-type mice led to greater tumor regression than the treatment of Fas. |
149647-78-9 - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R61 - May cause harm to the unborn child R68 - Possible risk of irreversible effects |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| WGK Germany | 3 |
| RTECS | RG8835000 |
| HS Code | 29280000 |
149647-78-9 - Reference
| Reference Show more | 1. [IF=3.196] Qiushuang Gao et al."Discovery of potent HDAC2 inhibitors based on virtual screening in combination with drug repurposing."J Mol Struct. 2022 Jan;1247:131399 |
149647-78-9 - Reference Information
| anti-tumor drugs | vorinostat is a new type of molecular targeted anti-tumor drugs that inhibit histone deacetylase (histone deacetylase,HDAC) and cause cell cycle arrest and/or apoptosis. It is the first HDAC inhibitor approved by the US FDA for the treatment of cutaneous T-cell lymphoma (CTCL) with obvious skin invasion that has progressed, resistant or relapsed after two systemic treatment regimens. on October 6, 2006, the us food and drug administration (FDA) approved vorinostat capsule (vorinostat) as a new drug for the treatment of skin cancer. This drug is the world's first new anti-cancer drug developed by Merck in the United States to inhibit histone deacetylase. It is used to treat cutaneous T-cell lymphoma (CTCL). The FDA approves it for other drug treatments or after treatment Metastatic cutaneous T-cell tumor that cannot be cured, or worsens, or the condition is repeated. A large number of experimental studies and clinical results show that vorinostat has good curative effect on a variety of tumors and has obvious synergistic effect with other tumor drugs. At present, the research on the treatment of other tumors is still in depth. These results show that vorinostat has broad market prospects. the toxicity of vorinostat is small, and the evidence for its safety and effectiveness comes from two clinical trials, including 107 patients with CTCL who relapsed after receiving other drugs. According to the standard analysis determined by the improvement of skin injury score level, 30% patients receiving Zolinza treatment improved, and the curative effect lasted for 168 days on average. The most common serious adverse reactions were pulmonary embolism, dehydration, deep venous thrombosis and anemia. Common adverse reactions include gastrointestinal symptoms (including diarrhea, nausea, loss of appetite, vomiting and constipation); fatigue, chills and taste disorders. Animal experiments showed that pregnant women banned the drug. |
| preparation method | octanoic acid is dehydrated intramolecularly under the action of acetic anhydride to generate octanoic anhydride, which is cycloamidation with aniline in ethyl acetate at 0 ℃ to obtain octanoic acid monoacylaniline, and then esterified with methanol and hydroxy amine hydrochloride to obtain the anti-tumor drug vorinostat, with a total yield of about 65%. "Chinese Journal of Pharmaceutical Industry", Volume 40, Issue 7, 2009, pages 481-483 |
| The anticancer drug vorinostat can clear the latent HIV virus | Researchers from the University of North Carolina at Chapel Hill published a groundbreaking research paper in the journal Nature on July 25, 2012, it is confirmed that a deacetylase inhibitor drug that can be used to treat certain types of lymphoma-vorinostat (vorinostat)-can clear the latent HIV virus in the patient. Researchers conducted a series of experiments to evaluate the potential of this drug to activate and destroy the latent HIV virus. At first, laboratory experiments measuring the level of active HIV virus in CD4 T cells showed that vorinostat removed the camouflage of latent HIV virus in these cells. Next, eight HIV-infected men who remained medically stable after antiretroviral therapy took vorinotair, and then tested their active HIV levels and compared them with those before taking the drug. the researchers found that the level of HIV virus RNA in CD4 T cells of these patients treated with vorinostat increased by an average of 4.5 times, thus confirming that the HIV virus was removed from disguise. This is the first published study to confirm that deacetylase inhibitors have the potential to break the latency in the latent virus reservoir. This study provides compelling evidence that people may adopt a new strategy to directly attack and eradicate latent HIV infection. Breaking the latent nature of HIV virus is only the first step to cure HIV infection. |
| biological activity | Vorinostat (suberoylanilide hydroxamic acid, SAHA, MK0683) is an HDAC inhibitor with IC50 of ~ 10 nM in cell-free test. Vorinostat will inhibit efficient HPV-18 DNA amplification. |
| Target | Value |
| HDAC (Cell-free assay) | ~10 nM |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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Product Name: Suberoylanilide Hydroxamic Acid Visit Supplier Webpage Request for quotationCAS: 149647-78-9
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
QQ: 3008007409
Wechat: 18301782025
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