Details of the Drug

General Information of Drug (ID: DM8SMD1)

Drug Name
Tazarotene
Synonyms
Avage; Suretin; Tazaroteno; Tazarotenum; Tazorac; Tazoral; Zorac; AGN 190168; AGN-190168; Avage (TN); Tazarotene [USAN:INN]; Tazorac (TN); Zorac (TN); Tazarotene (JAN/USAN/INN); Tazorac, Avage, Zora, Tazarotene; Ethyl 6-((4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate; Ethyl 6-(2-(4,4-dimethylthiochroman-6-yl)ethynyl)nicotinate; Ethyl 6-[(4,4-dimethyl-3,4-dihydro-2H-thiochromen-6-yl)ethynyl]nicotinate; Ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate; 3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-, ethyl ester; 3-Pyridinecarboxylic acid, 6-((3,4-dihydro-4,4-dimethyl-2H-1-benzothiopyran-6-yl)ethynyl)-,ethyl ester
Indication
Disease Entry ICD 11 Status REF
Acne vulgaris ED80 Approved [1]
Psoriasis EA90 Approved [1]
Psoriasis vulgaris EA90 Approved [2]
Therapeutic Class
Dermatologic Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 351.5
Logarithm of the Partition Coefficient (xlogp) 4.9
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 4
ADMET Property
Clearance
The drug present in the plasma can be removed from the body at the rate of 37.2 mL/min/kg [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 6.22 hours [3]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 3.55 L/kg [3]
Chemical Identifiers
Formula
C21H21NO2S
IUPAC Name
ethyl 6-[2-(4,4-dimethyl-2,3-dihydrothiochromen-6-yl)ethynyl]pyridine-3-carboxylate
Canonical SMILES
CCOC(=O)C1=CN=C(C=C1)C#CC2=CC3=C(C=C2)SCCC3(C)C
InChI
InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
InChIKey
OGQICQVSFDPSEI-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
5381
ChEBI ID
CHEBI:32184
CAS Number
118292-40-3
DrugBank ID
DB00799
TTD ID
D0BM5G
INTEDE ID
DR1536
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor gamma (RARG) TT1Q3IE RARG_HUMAN Binder [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C8 (CYP2C8)
Main DME 		DES5XRU CP2C8_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [6]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [6]
Caspase-3 (CASP3) OTIJRBE7 CASP3_HUMAN Gene/Protein Processing [7]
Potassium voltage-gated channel subfamily H member 2 (KCNH2) OTZX881H KCNH2_HUMAN Gene/Protein Processing [8]
Sodium/iodide cotransporter (SLC5A5) OTU7E9G7 SC5A5_HUMAN Gene/Protein Processing [9]
Steryl-sulfatase (STS) OTXTJQPC STS_HUMAN Gene/Protein Processing [10]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

ICD Disease Classification 14 Disease of the skin
Disease Class ICD-11: EA90 Psoriasis
The Studied Tissue Skin
The Studied Disease Psoriasis [ICD-11:EA90]
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Retinoic acid receptor gamma (RARG) DTT RARG 2.11E-08 -0.77 -0.93
Cytochrome P450 2C8 (CYP2C8) DME CYP2C8 4.73E-03 3.91E-02 2.20E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Tazarotene FDA Label
2 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6952).
3 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4 Recent developments in receptor-selective retinoids. Curr Pharm Des. 2000 Jun;6(9):919-31.
5 Cytochrome P450 2C8 and flavin-containing monooxygenases are involved in the metabolism of tazarotenic acid in humans. Drug Metab Dispos. 2003 Apr;31(4):476-81.
6 [Effects of all-trans-retinoic acid, acitretin and tazarotene on apoptosis and Bax/Bcl-2 expressions of human melanoma cells A375 and the significance]. Di Yi Jun Yi Da Xue Xue Bao. 2005 Aug;25(8):972-4, 978.
7 Effects of ATRA, acitretin and tazarotene on growth and apoptosis of Tca8113 cells. J Huazhong Univ Sci Technolog Med Sci. 2005;25(4):393-6. doi: 10.1007/BF02828205.
8 Why are most phospholipidosis inducers also hERG blockers?. Arch Toxicol. 2017 Dec;91(12):3885-3895. doi: 10.1007/s00204-017-1995-9. Epub 2017 May 27.
9 Enhancement of sodium/iodide symporter expression in thyroid and breast cancer. Endocr Relat Cancer. 2006 Sep;13(3):797-826. doi: 10.1677/erc.1.01143.
10 Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways. J Cell Biochem. 2006 Feb 1;97(2):327-50. doi: 10.1002/jcb.20579.