Vorinostat

Vorinostat
Clinical data
Pronunciation	/vɒˈrɪnoʊstæt/ vorr-IN-oh-stat
Trade names	Zolinza
AHFS/Drugs.com	Monograph
MedlinePlus	a607050
License data	US FDA: Vorinostat;
Routes of; administration	Oral (capsules)
ATC code	L01XH01 (WHO) ;
Legal status
Legal status	US: ℞-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	1.8–11%
Protein binding	~71%
Metabolism	Hepatic glucuronidation and β-oxidation; CYP system not involved
Metabolites	vorinostat O-glucuronide, 4-anilino-4-oxobutanoic acid (both inactive)
Elimination half-life	~2 hours (vorinostat and O-glucuronide), 11 hours (4-anilino-4-oxobutanoic acid)
Excretion	Renal (negligible)
Identifiers
	IUPAC name N-Hydroxy-N'-phenyloctanediamide;
CAS Number	149647-78-9 ;
PubChem CID	5311;
IUPHAR/BPS	6852;
DrugBank	DB02546 ;
ChemSpider	5120 ;
UNII	58IFB293JI;
KEGG	D06320 ;
ChEBI	CHEBI:45716 ;
ChEMBL	ChEMBL98 ;
CompTox Dashboard (EPA)	DTXSID6041133 ;
ECHA InfoCard	100.207.822
Chemical and physical data
Formula	C14H20N2O3
Molar mass	264.325 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Nc1ccccc1)CCCCCCC(=O)NO;
	InChI 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) ; Key:WAEXFXRVDQXREF-UHFFFAOYSA-N ;
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Vorinostat (rINN),^[3] also known as suberoylanilide hydroxamic acid (suberoyl+anilide+hydroxamic acid abbreviated as SAHA), is a member of a larger class of compounds that inhibit histone deacetylases (HDAC). Histone deacetylase inhibitors (HDI) have a broad spectrum of epigenetic activities.

Vorinostat is marketed under the name Zolinza (/zoʊˈlɪnzə/ zoh-LIN-zə) by Merck for the treatment of cutaneous manifestations in patients with cutaneous T cell lymphoma (CTCL) when the disease persists, gets worse, or comes back during or after two systemic therapies.^[2]^[4] The compound was developed by Columbia University chemist Ronald Breslow and Memorial Sloan-Kettering researcher Paul Marks.^[5]^[6]

^ "Withdrawal Assessment Report for Vorinostat MSD 100 mg Hard Capsules (vorinostat)" (PDF). European Medicines Agency. 23 October 2008. p. 9. Archived from the original (PDF) on 15 September 2016. Retrieved 1 September 2016.
^ ^a ^b "Zolinza (vorinostat) Capsules. Full Prescribing Information" (PDF). Merck & Co., Inc., Whitehouse Station, NJ 08889, USA. Retrieved 1 September 2016.
^ "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 56" (PDF). WHO Drug Information. 20 (3): 232. 2006. Archived from the original (PDF) on July 5, 2011. Retrieved 1 September 2016.
^ "ZOLINZA, Merck's Investigational Medicine for Advanced Cutaneous T-Cell Lymphoma (CTCL), To Receive Priority Review from U.S. Food and Drug Administration" (Press release). Merck & Co. June 7, 2006. Archived from the original on September 14, 2006. Retrieved October 6, 2006.
^ Lee JH, Mahendran A, Yao Y, Ngo L, Venta-Perez G, Choy ML, et al. (September 2013). "Development of a histone deacetylase 6 inhibitor and its biological effects". Proceedings of the National Academy of Sciences of the United States of America. 110 (39): 15704–15709. Bibcode:2013PNAS..11015704L. doi:10.1073/pnas.1313893110. PMC 3785767. PMID 24023063.
^ Marks PA, Breslow R (January 2007). "Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug". Nature Biotechnology. 25 (1): 84–90. doi:10.1038/nbt1272. PMID 17211407. S2CID 12656582.

[1] "Withdrawal Assessment Report for Vorinostat MSD 100 mg Hard Capsules (vorinostat)" (PDF). European Medicines Agency. 23 October 2008. p. 9. Archived from the original (PDF) on 15 September 2016. Retrieved 1 September 2016.

[Zolinza_PI-2] "Zolinza (vorinostat) Capsules. Full Prescribing Information" (PDF). Merck & Co., Inc., Whitehouse Station, NJ 08889, USA. Retrieved 1 September 2016.

[3] "International Nonproprietary Names for Pharmaceutical Substances (INN). Recommended International Nonproprietary Names: List 56" (PDF). WHO Drug Information. 20 (3): 232. 2006. Archived from the original (PDF) on July 5, 2011. Retrieved 1 September 2016.

[4] "ZOLINZA, Merck's Investigational Medicine for Advanced Cutaneous T-Cell Lymphoma (CTCL), To Receive Priority Review from U.S. Food and Drug Administration" (Press release). Merck & Co. June 7, 2006. Archived from the original on September 14, 2006. Retrieved October 6, 2006.

[5] Lee JH, Mahendran A, Yao Y, Ngo L, Venta-Perez G, Choy ML, et al. (September 2013). "Development of a histone deacetylase 6 inhibitor and its biological effects". Proceedings of the National Academy of Sciences of the United States of America. 110 (39): 15704–15709. Bibcode:2013PNAS..11015704L. doi:10.1073/pnas.1313893110. PMC 3785767. PMID 24023063.

[:0-6] Marks PA, Breslow R (January 2007). "Dimethyl sulfoxide to vorinostat: development of this histone deacetylase inhibitor as an anticancer drug". Nature Biotechnology. 25 (1): 84–90. doi:10.1038/nbt1272. PMID 17211407. S2CID 12656582.

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