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Congestive heart failure BD10 Withdrawn from market [1]
Affected Organisms
Humans and other mammals
ATC Code
C03CC02: Ticrynafen
C03CC: Aryloxyacetic acid derivatives
C03C: HIGH-CEILING DIURETICS
C03: DIURETICS
C: CARDIOVASCULAR SYSTEM
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) 5
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 5
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
CHEMBL9590
CAS Number
40180-04-9
UNII
HC95205SY4
DrugBank ID
DB04831
TTD ID
D0T0TZ
INTEDE ID
DR1593
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Antileukoproteinase (SLPI) OTUNFUU8 SLPI_HUMAN Gene/Protein Processing [4]
Hepatocyte growth factor receptor (MET) OT7K55MU MET_HUMAN Gene/Protein Processing [4]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [4]
Proepiregulin (EREG) OTRM4NQY EREG_HUMAN Gene/Protein Processing [4]
Renin (REN) OT52GZR2 RENI_HUMAN Gene/Protein Processing [5]
Solute carrier family 12 member 2 (SLC12A2) OT3ZJ3LH S12A2_HUMAN Gene/Protein Processing [6]
UDP-glucuronosyltransferase 1A1 OTH1C8OJ UD11_HUMAN Gene/Protein Processing [7]
Molecular Interaction Atlas (MIA) 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 Effects of prostaglandins inhibition on changes in active and inactive renin induced by antihypertensive drugs. Clin Exp Hypertens A. 1982;4(11-12):2435-48. doi: 10.3109/10641968209062401.
6 Azosemide is more potent than bumetanide and various other loop diuretics to inhibit the sodium-potassium-chloride-cotransporter human variants hNKCC1A and hNKCC1B. Sci Rep. 2018 Jun 29;8(1):9877. doi: 10.1038/s41598-018-27995-w.
7 Markers of electrophilic stress caused by chemically reactive metabolites in human hepatocytes. Drug Metab Dispos. 2008 May;36(5):816-23.