Details of the Drug

General Information of Drug (ID: DMLFSTR)

Drug Name

Ticrynafen

Synonyms

Ticrynafen; Tienilic acid; 40180-04-9; Thienylic acid; Selacryn; Diflurex; Ticrex; Acido tienilico; Acide tienilique; Acidum tienilicum; Tienilico acido; Tienilico acido [Spanish]; Ticrynafen [USAN]; Acido tienilico [INN-Spanish]; Acide tienilique [INN-French]; Acidum tienilicum [INN-Latin]; ANP 3624; C13H8Cl2O4S; SKF 62698; UNII-HC95205SY4; 2-(2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid; (2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid; CCRIS 5489; 4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acid

Indication

Disease Entry	ICD 11	Status	REF
Congestive heart failure	BD10	Withdrawn from market	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

331.2

Logarithm of the Partition Coefficient (xlogp)

4.1

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]

Chemical Identifiers

Formula: C13H8Cl2O4S
IUPAC Name: 2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid
Canonical SMILES: C1=CSC(=C1)C(=O)C2=C(C(=C(C=C2)OCC(=O)O)Cl)Cl
InChI: InChI=1S/C13H8Cl2O4S/c14-11-7(13(18)9-2-1-5-20-9)3-4-8(12(11)15)19-6-10(16)17/h1-5H,6H2,(H,16,17)
InChIKey: AGHANLSBXUWXTB-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 38409
ChEBI ID: CHEBI:9590
CAS Number: 40180-04-9
DrugBank ID: DB04831
TTD ID: D0T0TZ
INTEDE ID: DR1593

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2C9 (CYP2C9)_{Main DME}	DE5IED8	CP2C9_HUMAN	Substrate	[3]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Antileukoproteinase (SLPI)	OTUNFUU8	SLPI_HUMAN	Gene/Protein Processing	[4]
Bone morphogenetic protein 6 (BMP6)	OT9WN536	BMP6_HUMAN	Gene/Protein Processing	[4]
Cystine/glutamate transporter (SLC7A11)	OTKJ6PXW	XCT_HUMAN	Gene/Protein Processing	[4]
Cytochrome P450 2B6 (CYP2B6)	OTOYO4S7	CP2B6_HUMAN	Gene/Protein Processing	[5]
Heme oxygenase 1 (HMOX1)	OTC1W6UX	HMOX1_HUMAN	Gene/Protein Processing	[6]
Hepatocyte growth factor receptor (MET)	OT7K55MU	MET_HUMAN	Gene/Protein Processing	[4]
Interleukin-1 alpha (IL1A)	OTPSGILV	IL1A_HUMAN	Gene/Protein Processing	[4]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[4]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[4]
Proepiregulin (EREG)	OTRM4NQY	EREG_HUMAN	Gene/Protein Processing	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3	Cytochrome P450 enzymes and UDP-glucuronosyltransferases as hepatocellular autoantigens. Mol Biol Rep. 1996;23(3-4):235-42.
4	An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
5	Direct and metabolism-dependent cytochrome P450 inhibition assays for evaluating drug-drug interactions. J Appl Toxicol. 2013 Feb;33(2):100-8.
6	Markers of electrophilic stress caused by chemically reactive metabolites in human hepatocytes. Drug Metab Dispos. 2008 May;36(5):816-23.