2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid

• ChemBase ID: 4375
• Molecular Formular: C13H8Cl2O4S
• Molecular Mass: 331.17122
• Monoisotopic Mass: 329.9520351
• SMILES: Clc1c(ccc(OCC(=O)O)c1Cl)C(=O)c1sccc1
• Canonical SMILES: OC(=O)COc1ccc(c(c1Cl)Cl)C(=O)c1cccs1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid
• IUPAC Traditional name: ticrynafen; 2,3-dichloro-4-(thiophene-2-carbonyl)phenoxyacetic acid
• Brand Name: Diflurex; Selacryn; Ticrex
• Synonyms: 2-[2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy]acetic Acid; [2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy]acetic Acid; 2,3-Dichloro-4-(2-thenoyl)phenoxyacetic Acid; 4-(2-Thenoyl)-2,3-dichlorophenoxyacetic Acid; 4-(2-Thienylcarbonyl)-2,3-dichlorophenoxyacetic Acid; ANP 3624; CE 3624; Difluorex; FR 3068; SKF 62698; Selacryn; Ticrynafen; Tienylic Acid; Tienilic Acid; Tienilic acid; (2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid; 4-(2-Theonyl)-2,3-dichlorphenoxyessigsaeure [German]; (2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acid; (2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy)acetic acid; 4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acid; Acide tienilique [inn-french]; Acidum tienilicum [inn-latin]; Acido tienilico [inn-spanish]; Thienylic acid; Tienilico acido [spanish]; Ticrynafen

Database IDs

• CAS Number: 40180-04-9
• PubChem SID: 46505485; 160967807
• PubChem CID: 38409

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.2171626
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 1.612726
• LogD (pH = 7.4): 0.4315071
• Log P: 3.8738816
• Molar Refractivity: 75.6808 cm^3
• Polarizability: 29.518778 Å^3
• Polar Surface Area: 63.6 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.09
• LOG S: -5.12
• Solubility (Water): 2.54e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: Pale Beige Solid
• Melting Point: 148-149°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB04831

• Drug Groups: withdrawn
• Description: Ticrynafen, or tienilic acid, is a diuretic drug with uric acid-lowering (uricosuric) action, formerly marketed for the treatment of hypertension. It was withdrawn in 1982, shortly after its introduction to the market, after case reports in the United States indicated a link between the use of ticrynafen and hepatitis. (Manier et al., 1982)
• Indication: For the treatment of hypertension.
• Affected Organisms: Humans and other mammals
• References: 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]
• External Links: Wikipedia

Toronto Research Chemicals - T438750

Tienilic Acid is a heterocyclic derivative of phenoxyacetic acid. Tienilic acid is used as diuretic, uricosuric, antihypertensive.

REFERENCES

• 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
• Kerremans, A.L., et al.: Eur. J. Clin. Pharmacol., 22, 515 (1982)
• Manier, J.W., et al.: Am. J. Gastroenterol., 77, 401 (1982)