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
• Affected Organisms: Humans and other mammals
• ATC Code:
  D05AX05: Tazarotene
  D05AX: Other antipsoriatics for topical use
  D05A: ANTIPSORIATICS FOR TOPICAL USE
  D05: ANTIPSORIATICS
  D: DERMATOLOGICALS
• Drug Type: Small molecular drug
• #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: CHEMBL32184
  CAS Number: 118292-40-3
  UNII: 81BDR9Y8PS
  DrugBank ID: DB00799
  TTD ID: D0BM5G
  INTEDE ID: DR1536
• Drug-Molecule Activity Atlas (DMA)NEW: Click to Jump to the Detailed DMA Information of This Drug
• Drug ADMET Endpoint Profile (DAE)NEW: Click to Jump to the Detailed DAE 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]

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

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.