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40180-04-9 molecular structure
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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 and InChIs

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

Cite this record

CBID:4375 http://www.chembase.cn/molecule-4375.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
40180-04-9
PubChem SID
160967807
46505485
PubChem CID
38409

DATA SOURCES

DATA SOURCES

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Data Source Data ID Price
TRC
T438750 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.2171626  H Acceptors
H Donor LogD (pH = 5.5) 1.612726 
LogD (pH = 7.4) 0.4315071  Log P 3.8738816 
Molar Refractivity 75.6808 cm3 Polarizability 29.518778 Å3
Polar Surface Area 63.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.09  LOG S -5.12 
Solubility (Water) 2.54e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO expand Show data source
Ethanol expand Show data source
Methanol expand Show data source
Apperance
Pale Beige Solid expand Show data source
Melting Point
148-149°C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
Download expand Show data source

DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB04831 external link
Item Information
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 external link
Tienilic Acid is a heterocyclic derivative of phenoxyacetic acid. Tienilic acid is used as diuretic, uricosuric, antihypertensive.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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