Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- TO-901317
- DrugBank Accession Number
- DB07080
- Background
TO-901317 is an LXRalpha and LXRbeta agonist.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for TO-901317 (DB07080)
- Weight
- Average: 481.333
Monoisotopic: 481.03941779 - Chemical Formula
- C17H12F9NO3S
- Synonyms
- Not Available
- External IDs
- J1.503.100J
- T-0901317
- T-1317
- TO 901317
- TO-901317
- TO901317
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UOxysterols receptor LXR-beta Not Available Humans UNuclear receptor coactivator 2 Not Available Humans URetinoic acid receptor RXR-beta Not Available Humans UOxysterols receptor LXR-alpha Not Available Humans UNuclear receptor coactivator 1 Not Available Humans UNuclear receptor subfamily 1 group I member 2 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as sulfanilides. These are organic aromatic compounds containing a sulfanilide moiety, with the general structure RS(=O)(=O)NC1=CC=CC=C1.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Sulfanilides
- Direct Parent
- Sulfanilides
- Alternative Parents
- Benzenesulfonamides / Benzenesulfonyl compounds / Organosulfonamides / Tertiary alcohols / Aminosulfonyl compounds / Fluorohydrins / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Organic oxides show 3 more
- Substituents
- Alcohol / Alkyl fluoride / Alkyl halide / Aminosulfonyl compound / Aromatic alcohol / Aromatic homomonocyclic compound / Benzenesulfonamide / Benzenesulfonyl group / Fluorohydrin / Halohydrin show 16 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- sulfonamide (CHEBI:39976)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- A07663A39I
- CAS number
- 293754-55-9
- InChI Key
- SGIWFELWJPNFDH-UHFFFAOYSA-N
- InChI
- InChI=1S/C17H12F9NO3S/c18-14(19,20)10-27(31(29,30)13-4-2-1-3-5-13)12-8-6-11(7-9-12)15(28,16(21,22)23)17(24,25)26/h1-9,28H,10H2
- IUPAC Name
- N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-N-(2,2,2-trifluoroethyl)benzenesulfonamide
- SMILES
- OC(C1=CC=C(C=C1)N(CC(F)(F)F)S(=O)(=O)C1=CC=CC=C1)(C(F)(F)F)C(F)(F)F
References
- General References
- Not Available
- External Links
- KEGG Compound
- C15630
- PubChem Compound
- 447912
- PubChem Substance
- 99443551
- ChemSpider
- 394870
- BindingDB
- 19993
- ChEMBL
- CHEMBL62136
- ZINC
- ZINC000001550221
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- 444
- PDB Entries
- 1pqc / 1uhl / 1upv / 1upw / 2o9i / 4nb6 / 5ejv / 5k3l / 5ntq
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00867 mg/mL ALOGPS logP 3.83 ALOGPS logP 4.77 Chemaxon logS -4.7 ALOGPS pKa (Strongest Acidic) 7.45 Chemaxon pKa (Strongest Basic) -6.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 57.61 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 90.51 m3·mol-1 Chemaxon Polarizability 35.14 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9535 Caco-2 permeable - 0.5297 P-glycoprotein substrate Non-substrate 0.884 P-glycoprotein inhibitor I Non-inhibitor 0.6938 P-glycoprotein inhibitor II Inhibitor 0.5726 Renal organic cation transporter Non-inhibitor 0.8139 CYP450 2C9 substrate Non-substrate 0.6479 CYP450 2D6 substrate Non-substrate 0.7953 CYP450 3A4 substrate Non-substrate 0.5883 CYP450 1A2 substrate Inhibitor 0.5124 CYP450 2C9 inhibitor Inhibitor 0.5544 CYP450 2D6 inhibitor Non-inhibitor 0.8282 CYP450 2C19 inhibitor Inhibitor 0.7733 CYP450 3A4 inhibitor Inhibitor 0.6695 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.7248 Ames test Non AMES toxic 0.7107 Carcinogenicity Non-carcinogens 0.5682 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.3437 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9499 hERG inhibition (predictor II) Non-inhibitor 0.6337
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-006x-5965400000-f6a819110ff9ef0384f6 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0000900000-008ce7806af04f26c340 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0000900000-041a471b31af96fc56c6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001l-1400900000-fca5181850d87d85eee7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0900600000-46cae6a03bd2697deccb Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-032c-9220100000-a8b8b07a6fbf79b79f98 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-00dl-0902000000-4fadd85a51026274ef0f Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 190.98286 predictedDeepCCS 1.0 (2019) [M+H]+ 193.37843 predictedDeepCCS 1.0 (2019) [M+Na]+ 199.29097 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor that exhibits a ligand-dependent transcriptional activation activity (PubMed:25661920). Binds preferentially to double-stranded oligonucleotide direct repeats having the consensus half-site sequence 5'-AGGTCA-3' and 4-nt spacing (DR-4). Regulates cholesterol uptake through MYLIP-dependent ubiquitination of LDLR, VLDLR and LRP8; DLDLR and LRP8. Interplays functionally with RORA for the regulation of genes involved in liver metabolism (By similarity). Induces LPCAT3-dependent phospholipid remodeling in endoplasmic reticulum (ER) membranes of hepatocytes, driving SREBF1 processing and lipogenesis (By similarity). Via LPCAT3, triggers the incorporation of arachidonate into phosphatidylcholines of ER membranes, increasing membrane dynamics and enabling triacylglycerols transfer to nascent very low-density lipoprotein (VLDL) particles (By similarity). Via LPCAT3 also counteracts lipid-induced ER stress response and inflammation, likely by modulating SRC kinase membrane compartmentalization and limiting the synthesis of lipid inflammatory mediators (By similarity). Plays an anti-inflammatory role during the hepatic acute phase response by acting as a corepressor: inhibits the hepatic acute phase response by preventing dissociation of the N-Cor corepressor complex (PubMed:20159957)
- Specific Function
- Apolipoprotein a-i receptor binding
- Gene Name
- NR1H2
- Uniprot ID
- P55055
- Uniprot Name
- Oxysterols receptor LXR-beta
- Molecular Weight
- 50973.375 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcriptional coactivator for steroid receptors and nuclear receptors (PubMed:23508108, PubMed:8670870, PubMed:9430642). Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1) (PubMed:23508108, PubMed:8670870, PubMed:9430642). Required with NCOA1 to control energy balance between white and brown adipose tissues (PubMed:23508108, PubMed:8670870, PubMed:9430642). Critical regulator of glucose metabolism regulation, acts as a RORA coactivator to specifically modulate G6PC1 expression (PubMed:23508108, PubMed:8670870, PubMed:9430642). Involved in the positive regulation of the transcriptional activity of the glucocorticoid receptor NR3C1 by sumoylation enhancer RWDD3 (PubMed:23508108). Positively regulates the circadian clock by acting as a transcriptional coactivator for the CLOCK-BMAL1 heterodimer (By similarity)
- Specific Function
- Aryl hydrocarbon receptor binding
- Gene Name
- NCOA2
- Uniprot ID
- Q15596
- Uniprot Name
- Nuclear receptor coactivator 2
- Molecular Weight
- 159155.645 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE)
- Specific Function
- Dna-binding transcription activator activity, rna polymerase ii-specific
- Gene Name
- RXRB
- Uniprot ID
- P28702
- Uniprot Name
- Retinoic acid receptor RXR-beta
- Molecular Weight
- 56921.38 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor that exhibits a ligand-dependent transcriptional activation activity (PubMed:19481530, PubMed:25661920, PubMed:37478846). Interaction with retinoic acid receptor (RXR) shifts RXR from its role as a silent DNA-binding partner to an active ligand-binding subunit in mediating retinoid responses through target genes defined by LXRES (PubMed:37478846). LXRES are DR4-type response elements characterized by direct repeats of two similar hexanuclotide half-sites spaced by four nucleotides (By similarity). Plays an important role in the regulation of cholesterol homeostasis, regulating cholesterol uptake through MYLIP-dependent ubiquitination of LDLR, VLDLR and LRP8 (PubMed:19481530). Interplays functionally with RORA for the regulation of genes involved in liver metabolism (By similarity). Induces LPCAT3-dependent phospholipid remodeling in endoplasmic reticulum (ER) membranes of hepatocytes, driving SREBF1 processing and lipogenesis (By similarity). Via LPCAT3, triggers the incorporation of arachidonate into phosphatidylcholines of ER membranes, increasing membrane dynamics and enabling triacylglycerols transfer to nascent very low-density lipoprotein (VLDL) particles. Via LPCAT3 also counteracts lipid-induced ER stress response and inflammation, likely by modulating SRC kinase membrane compartmentalization and limiting the synthesis of lipid inflammatory mediators (By similarity)
- Specific Function
- Cholesterol binding
- Gene Name
- NR1H3
- Uniprot ID
- Q13133
- Uniprot Name
- Oxysterols receptor LXR-alpha
- Molecular Weight
- 50395.34 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear receptors, such as for steroids (PGR, GR and ER), retinoids (RXRs), thyroid hormone (TRs) and prostanoids (PPARs). Also involved in coactivation mediated by STAT3, STAT5A, STAT5B and STAT6 transcription factors. Displays histone acetyltransferase activity toward H3 and H4; the relevance of such activity remains however unclear. Plays a central role in creating multisubunit coactivator complexes that act via remodeling of chromatin, and possibly acts by participating in both chromatin remodeling and recruitment of general transcription factors. Required with NCOA2 to control energy balance between white and brown adipose tissues. Required for mediating steroid hormone response. Isoform 2 has a higher thyroid hormone-dependent transactivation activity than isoform 1 and isoform 3
- Specific Function
- Chromatin binding
- Gene Name
- NCOA1
- Uniprot ID
- Q15788
- Uniprot Name
- Nuclear receptor coactivator 1
- Molecular Weight
- 156755.44 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes
- Specific Function
- Dna-binding transcription activator activity, rna polymerase ii-specific
- Gene Name
- NR1I2
- Uniprot ID
- O75469
- Uniprot Name
- Nuclear receptor subfamily 1 group I member 2
- Molecular Weight
- 49761.245 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:18 / Updated at June 12, 2020 16:52