vorinostat Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
histone deacetylase inhibitors 4124 149647-78-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • vorinostat
  • suberoylanilide hydroxamic acid
A hydroxamic acid and anilide derivative that acts as a HISTONE DEACETYLASE inhibitor. It is used in the treatment of CUTANEOUS T-CELL LYMPHOMA and SEZARY SYNDROME.
  • Molecular weight: 264.33
  • Formula: C14H20N2O3
  • CLOGP: 0.99
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 3
  • TPSA: 78.43
  • ALOGS: -3.57
  • ROTB: 8

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 43 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.50 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 28 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.29 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.76 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Oct. 6, 2006 FDA MERCK

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 240.95 49.80 54 335 10828 2346868
Dehydration 119.63 49.80 36 353 22259 2335437
Vomiting 91.64 49.80 40 349 71562 2286134
Sepsis 90.98 49.80 28 361 18460 2339236
Nausea 86.14 49.80 44 345 112145 2245551
Thrombocytopenia 85.82 49.80 27 362 19104 2338592
Platelet count decreased 82.19 49.80 25 364 15788 2341908
Diarrhoea 73.34 49.80 36 353 83528 2274168
Pyrexia 68.35 49.80 30 359 53678 2304018
Cutaneous T-cell lymphoma 62.33 49.80 10 379 312 2357384
Neutrophil count decreased 59.26 49.80 16 373 6551 2351145
Haematotoxicity 55.48 49.80 11 378 1156 2356540
Fatigue 55.28 49.80 30 359 84843 2272853
Decreased appetite 52.95 49.80 21 368 28870 2328826

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Febrile neutropenia 132.11 42.91 39 438 11061 1735243
Anaemia 119.55 42.91 46 431 29411 1716893
Lymphopenia 104.21 42.91 23 454 2010 1744294
Thrombocytopenia 96.04 42.91 36 441 21213 1725091
Platelet count decreased 70.83 42.91 27 450 16496 1729808
Nausea 65.66 42.91 36 441 51160 1695144
Pneumonia 63.42 42.91 34 443 46148 1700156
Dehydration 58.59 42.91 24 453 17634 1728670
Activated partial thromboplastin time prolonged 56.87 42.91 13 464 1317 1744987
Pyrexia 52.19 42.91 30 447 46370 1699934
Product use in unapproved indication 49.79 42.91 18 459 9404 1736900
Decreased appetite 48.52 42.91 23 454 23848 1722456
Cutaneous T-cell lymphoma 48.22 42.91 9 468 333 1745971
Sepsis 46.56 42.91 21 456 19417 1726887
Death 45.70 42.91 35 442 87408 1658896

Pharmacologic Action:

SourceCodeDescription
ATC L01XX38 ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
ANTINEOPLASTIC AGENTS
OTHER ANTINEOPLASTIC AGENTS
Other antineoplastic agents
FDA EPC N0000175588 Histone Deacetylase Inhibitor
MeSH PA D000970 Antineoplastic Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D056572 Histone Deacetylase Inhibitors
CHEBI has role CHEBI:35610 antineoplastic agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Primary cutaneous T-cell lymphoma indication 400122007
Hypocalcemia contraindication 5291005
Dehydration contraindication 34095006
Hypokalemia contraindication 43339004
Diarrhea contraindication 62315008
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Prolonged QT interval contraindication 111975006
Deep venous thrombosis contraindication 128053003
Hypomagnesemia contraindication 190855004
Pulmonary thromboembolism contraindication 233935004
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Thromboembolic disorder contraindication 371039008
Breastfeeding (mother) contraindication 413712001
Vomiting contraindication 422400008
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.34 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
100MG ZOLINZA MERCK N021991 Oct. 6, 2006 RX CAPSULE ORAL 7732490 March 4, 2023 TREATMENT OF CUTANEOUS MANIFESTATIONS IN PATIENTS WTIH CUTANEOUS T-CELL LYMPHOMA (CTCL)
100MG ZOLINZA MERCK N021991 Oct. 6, 2006 RX CAPSULE ORAL 8067472 March 4, 2023 TREATMENT OF CUTANEOUS MANIFESTATIONS IN PATIENTS WTIH CUTANEOUS T-CELL LYMPHOMA (CTCL)
100MG ZOLINZA MERCK N021991 Oct. 6, 2006 RX CAPSULE ORAL 8101663 March 4, 2023 TREATMENT OF CUTANEOUS MANIFESTATIONS IN PATIENTS WTIH CUTANEOUS T-CELL LYMPHOMA (CTCL)
100MG ZOLINZA MERCK N021991 Oct. 6, 2006 RX CAPSULE ORAL 7851509 Feb. 21, 2024 TREATMENT OF CUTANEOUS MANIFESTATIONS IN PATIENTS WTIH CUTANEOUS T-CELL LYMPHOMA (CTCL)
100MG ZOLINZA MERCK N021991 Oct. 6, 2006 RX CAPSULE ORAL 7399787 Feb. 9, 2025 TREATMENT OF CUTANEOUS MANIFESTATIONS IN PATIENTS WTIH CUTANEOUS T-CELL LYMPHOMA (CTCL)
100MG ZOLINZA MERCK N021991 Oct. 6, 2006 RX CAPSULE ORAL 8450372 March 18, 2028 TREATMENT OF CUTANEOUS MANIFESTATIONS IN PATIENTS WTIH CUTANEOUS T-CELL LYMPHOMA (CTCL)

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Histone deacetylase 3 Enzyme INHIBITOR Ki 8.30 CHEMBL CHEMBL
Histone deacetylase 1 Enzyme INHIBITOR Ki 8.89 CHEMBL CHEMBL
Histone deacetylase 2 Enzyme INHIBITOR Ki 8.80 CHEMBL CHEMBL
Histone deacetylase 6 Enzyme INHIBITOR Ki 9 CHEMBL CHEMBL
Histone deacetylase 11 Enzyme Ki 7.89 CHEMBL
Histone deacetylase Enzyme IC50 8 CHEMBL
Histone deacetylase 8 Enzyme Ki 6.76 CHEMBL
Histone deacetylase 1/3/5/8 Enzyme IC50 6.96 CHEMBL
Histone deacetylase 3/NCoR1 Transcription factor Ki 7.92 CHEMBL
Lysine-specific demethylase 4E Enzyme IC50 4.85 CHEMBL
Histone deacetylase 9 Enzyme Ki 7.31 CHEMBL
Histone deacetylase 4 Enzyme Ki 7.80 CHEMBL
Histone deacetylase 5 Enzyme Ki 7.48 CHEMBL
Histone deacetylase (HDAC1 and HDAC2) Enzyme IC50 8 CHEMBL
Histone deacetylase 7 Enzyme Ki 6.89 CHEMBL
Histone deacetylase 3/Nuclear receptor corepressor 2 (HDAC3/NCoR2) Transcription factor Ki 8.70 CHEMBL
Histone deacetylase 10 Enzyme Ki 7.30 CHEMBL
Histone deacetylase Enzyme IC50 7.55 CHEMBL
Histone deacetylase Enzyme IC50 7 CHEMBL
Histone deacetylase 1 Enzyme IC50 6.95 CHEMBL
Histone deacetylase Enzyme IC50 7.23 CHEMBL
HD2 type histone deacetylase HDA106; Histone deacetylase 2b; Uncharacterized protein Enzyme IC50 7.30 CHEMBL
Histone deacetylase Enzyme IC50 6.78 CHEMBL
Histone deacetylase-like amidohydrolase Enzyme Kd 6.52 CHEMBL

External reference:

IDSource
D000077337 MESH_DESCRIPTOR_UI
4025777 VUID
N0000179580 NUI
C0672708 UMLSCUI
D06320 KEGG_DRUG
58IFB293JI UNII
8661 INN_ID
422523009 SNOMEDCT_US
22259 MMSL
d05891 MMSL
194337 RXNORM
4025777 VANDF
422505001 SNOMEDCT_US
011760 NDDF
CHEMBL98 ChEMBL_ID
DB02546 DRUGBANK_ID
CHEBI:45716 CHEBI
5311 PUBCHEM_CID
6852 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
ZOLINZA HUMAN PRESCRIPTION DRUG LABEL 1 0006-0568 CAPSULE 100 mg ORAL NDA 19 sections