ACITRETIN

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Search structure


Trade Names	ACITRETIN SORIATANE
Synonyms	Acitretin Etretin Neotigason RO 10-1670 RO 10-1670/000 RO-101670000 Soriatane
Status
Molecule Category	UNKNOWN
ATC	D05BB02
UNII	LCH760E9T7
EPA CompTox	DTXSID6022553


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	IHUNBGSDBOWDMA-AQFIFDHZSA-N
Smiles	COc1cc(C)c(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)c(C)c1C
InChI	InChI=1S/C21H26O3/c1-14(8-7-9-15(2)12-21(22)23)10-11-19-16(3)13-20(24-6)18(5)17(19)4/h7-13H,1-6H3,(H,22,23)/b9-7+,11-10+,14-8+,15-12+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C21H26O3
Molecular Weight	326.44
AlogP	5.17
Hydrogen Bond Acceptor	2.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	6.0
Polar Surface Area	46.53
Molecular species	ACID
Aromatic Rings	1.0
Heavy Atoms	24.0

Bioactivity

Mechanism of Action	Action	Reference
Retinoid receptor agonist	AGONIST	PubMed PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Primary active transporter ATP-binding cassette ABCB subfamily	-	18200-38200	-	-	-
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	49000	-	-	-

Assay Description	Organism	Bioactivity	Reference
Antioxidant activity assessed as inhibition of AAPH-induced lipid peroxidation at 100 uM	None	85.0 %
Inhibition of soybean lipoxygenase assessed as conversion of sodium linoleate to 13-hydroperoxylinoleate at 100 uM	Glycine max	1.0 %
Antiinflammatory activity in Fisher 344 rat assessed as inhibition of carrageenan-induced paw edema at 0.01 mmol/Kg, ip administered simultaneously with carrageenan measured after 3.5 hrs relative to control	Rattus norvegicus	63.0 %
PUBCHEM_BIOASSAY: High Throughput Screen to Identify Inhibitors of Mycobacterium tuberculosis H37Rv. (Class of assay: confirmatory)	None	488.0 nM
Inhibition of soybean lipoxygenase at 0.1 mM	Glycine max	1.0 %
Antioxidant activity against AAPH-induced lipid peroxidation assessed as inhibition of conjugated diene hydroperoxide production at 0.1 mM by UV spectrophotometry	None	85.0 %
Antiinflammatory activity in Fisher rat assessed as inhibition of carrageenan-induced paw oedema at 0.01 mmol/kg, po measured after 3.5 hrs	Rattus norvegicus	63.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600)	Staphylococcus aureus subsp. aureus	-32.23 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600)	Escherichia coli	4.27 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600)	Klebsiella pneumoniae	7.64 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600)	Pseudomonas aeruginosa	5.45 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600	Acinetobacter baumannii	8.14 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630	Candida albicans	3.07 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570)	Cryptococcus neoformans	-7.56 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-2.83 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.73 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-15.11 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.2 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.08 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.2 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.08 %

Related Entries

Cross References

Resources	Reference
ChEBI	50173
ChEMBL	CHEMBL1131
DrugBank	DB00459
DrugCentral	78
FDA SRS	LCH760E9T7
Guide to Pharmacology	7598
PubChem	5284513
SureChEMBL	SCHEMBL3759
ZINC	ZINC000003798734

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).