Tienilic acid

Identification

Name
Tienilic acid
Accession Number
DB04831
Description

Tienilic acid, or ticrynafen, is a diuretic drug with uric acid-lowering action which was marketed for the treatment of hypertension. It was withdrawn in 1982 after case reports in the United States suggested a link between ticrynafen and hepatitis. (Manier et al., 1982)

Type
Small Molecule
Groups
Withdrawn
Structure
Thumb
Weight
Average: 331.171
Monoisotopic: 329.952034848
Chemical Formula
C13H8Cl2O4S
Synonyms
  • (2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid
  • (2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acid
  • 4-(2-Theonyl)-2,3-dichlorphenoxyessigsäure
  • 4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acid
  • Acide tiénilique
  • ácido tienilico
  • Acidum tienilicum
  • Thienylic acid
  • Ticrynafen
  • Tienilic acid
  • Tienilico acido

Pharmacology

Indication

For the treatment of hypertension.

Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

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Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirTienilic acid may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy.
AcarboseTienilic acid may increase the excretion rate of Acarbose which could result in a lower serum level and potentially a reduction in efficacy.
AcebutololAcebutolol may increase the hypotensive activities of Tienilic acid.
AceclofenacThe therapeutic efficacy of Tienilic acid can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Tienilic acid can be decreased when used in combination with Acemetacin.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Tienilic acid.
AcetaminophenTienilic acid may increase the excretion rate of Acetaminophen which could result in a lower serum level and potentially a reduction in efficacy.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Tienilic acid.
Acetylsalicylic acidAcetylsalicylic acid may decrease the excretion rate of Tienilic acid which could result in a higher serum level.
AclidiniumTienilic acid may increase the excretion rate of Aclidinium which could result in a lower serum level and potentially a reduction in efficacy.
Additional Data Available
  • Extended Description
    Extended Description
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  • Severity
    Severity
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  • Action
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Food Interactions
Not Available

Products

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International/Other Brands
Diflurex / Selacryn / Ticrex

Categories

ATC Codes
C03CC02 — Tienilic acid
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl compounds
Direct Parent
Aryl-phenylketones
Alternative Parents
Chlorophenoxyacetates / Thiophene carboxylic acids and derivatives / Phenoxy compounds / Phenol ethers / Dichlorobenzenes / Benzoyl derivatives / Alkyl aryl ethers / Aryl chlorides / Vinylogous halides / Heteroaromatic compounds
show 5 more
Substituents
1,2-dichlorobenzene / Alkyl aryl ether / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Aryl-phenylketone / Benzenoid / Benzoyl / Carboxylic acid / Carboxylic acid derivative
show 18 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
aromatic ether, monocarboxylic acid, thiophenes, dichlorobenzene, aromatic ketone (CHEBI:9590)

Chemical Identifiers

UNII
HC95205SY4
CAS number
40180-04-9
InChI Key
AGHANLSBXUWXTB-UHFFFAOYSA-N
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)
IUPAC Name
2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid
SMILES
OC(=O)COC1=C(Cl)C(Cl)=C(C=C1)C(=O)C1=CC=CS1

References

Synthesis Reference

Harold Graboyes, "Method for preparing ticrynafen." U.S. Patent US4107179, issued April, 1977.

US4107179
General References
  1. Manier JW, Chang WW, Kirchner JP, Beltaos E: Hepatotoxicity associated with ticrynafen--a uricosuric diuretic. Am J Gastroenterol. 1982 Jun;77(6):401-4. [PubMed:7091125]
KEGG Drug
D02386
KEGG Compound
C11702
PubChem Compound
38409
PubChem Substance
46505485
ChemSpider
35204
BindingDB
50090674
ChEBI
9590
ChEMBL
CHEMBL267744
ZINC
ZINC000000002166
Wikipedia
Ticrynafen

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)149 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00254 mg/mLALOGPS
logP4.09ALOGPS
logP3.87ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.22ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity75.68 m3·mol-1ChemAxon
Polarizability30.45 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.913
Blood Brain Barrier+0.8914
Caco-2 permeable-0.5564
P-glycoprotein substrateNon-substrate0.6678
P-glycoprotein inhibitor INon-inhibitor0.8785
P-glycoprotein inhibitor IINon-inhibitor0.9398
Renal organic cation transporterNon-inhibitor0.875
CYP450 2C9 substrateNon-substrate0.7168
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6863
CYP450 1A2 substrateNon-inhibitor0.5326
CYP450 2C9 inhibitorNon-inhibitor0.6725
CYP450 2D6 inhibitorNon-inhibitor0.908
CYP450 2C19 inhibitorNon-inhibitor0.8257
CYP450 3A4 inhibitorNon-inhibitor0.9104
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.638
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.8764
BiodegradationNot ready biodegradable0.5809
Rat acute toxicity2.5618 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9848
hERG inhibition (predictor II)Non-inhibitor0.9193
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Enzymes

Details
1. Cytochrome P450 2C9
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Hutzler JM, Balogh LM, Zientek M, Kumar V, Tracy TS: Mechanism-based inactivation of cytochrome P450 2C9 by tienilic acid and (+/-)-suprofen: a comparison of kinetics and probe substrate selection. Drug Metab Dispos. 2009 Jan;37(1):59-65. doi: 10.1124/dmd.108.023358. Epub 2008 Oct 6. [PubMed:18838506]

Drug created on September 11, 2007 14:55 / Updated on June 12, 2020 10:52

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