Tienilic Acid

HCID 38409CAS 40180-04-9
Substructure searchFind similar structures

Basic information

Standard SMILES
O=C(O)COc1ccc(C(=O)c2cccs2)c(Cl)c1Cl
InChIKey
AGHANLSBXUWXTB-UHFFFAOYSA-N
Molecular formula
C13H8Cl2O4S
Average molar mass
331.2 g/mol
Monoisotopic mass
329.9520351

Overview

Tienilic acid is an aromatic ketone that is 2,3-dichlorophenoxyacetic acid in which the hydrogen at position 4 on the benzene ring is replaced by a thiophenecarbonyl group. A loop diuretic used to treat hypertension, it was withdrawn from the market in 1982 due to links with hepatitis. It has a role as an antihypertensive agent, a hepatotoxic agent and a loop diuretic. It is a dichlorobenzene, a monocarboxylic acid, a member of thiophenes, an aromatic ether and an aromatic ketone.

Names & identifiers

Preferred name
Tienilic Acid
IUPAC
2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid
English name
TICRYNAFEN
Molecular formula
C13H8Cl2O4S
Molecular weight
331.17

Names & synonyms

TicrynafenTienilic acid40180-04-9Thienylic acid2-(2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acidAcido tienilicoAcide tieniliqueAcidum tienilicum2-[2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acidDTXSID4023670ANP 3624(2,3-Dichloro-4-(2-thenoyl)phenoxy)acetic acid
Show more names
TienilicTienilic Acid - Ticrynafanticrexfr3068ce3624ANP 362anp3624diflurexskf62698selacryn
4-(2-Thienylketo)-2,3-dichlorophenoxyacetic acidSKF 62698[2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]acetic acid(2,3-Dichloro-4-(2-thiophenecarbonyl)phenoxy)acetic acidSK&F 62698HC95205SY4(2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy)acetic acid4-(2-Theonyl)-2,3-dichlorphenoxyessigsaeure

Database identifiers

CAS
40180-04-9
PubChem CID
38409
DTXSID
DTXSID4023670
ChEMBL
CHEMBL267744
ChEBI
CHEBI:9590
UNII
HC95205SY4
EC Number
254-826-3
Nikkaji
J16.869F

Properties

Computed structural properties

XLogP
4.1
Topological polar surface area
91.8 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
5
Heavy atoms
20

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point
148 · 148-149oC
Boiling point
534.6 · 534.6±50.0 °C(Predicted)
Density
1.532 · 1.532
storage temp.
-20 °C · -20°C
solubility
5 mg/mL · DMSO: soluble5mg/mL (clear solution)
pka
2.79 · 2.79±0.10(Predicted)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSTOT SE 3 (100%)

Toxicology

Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Ticrynafen

vMost-DILI-concern

8

Withdrawn

DOI:10.1016/j.drudis.2016.02.015

Safety data

wgk
3
rtecs
AG9300000
Toxicity
LD50 in mice (mg/kg): 225 i.v., 1275 orally (US 3758506)
risk_code
22
Signal word
Warning
Symbol(GHS)
GHS07

Chemistry & industry

Pharmacology

ATC Code · 2 items

C - Cardiovascular system

QC - Cardiovascular system

Metabolism/MetabolitesTicrynafen has known human metabolites that include Thiophene-4,5-epoxide and Tienilic acid-s-oxide.
MeSH Pharmacological Classification · 3 items

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Agents that promote the excretion of urine through their effects on kidney function.

Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma.

Applications · 3 items

DescriptionCytochrome P450 enzymes function to metabolize both endogenous and exogenous compounds. Both the 3A and 2C isoforms are present in human liver of which CYP2C9 seems most highly expressed. Tienilic acid is a specific suicide substrate for CYP2C9 and CYP2C10 whereby its oxidation inactivates the enzyme. The time required to inactivate one half of the CYP2C10 enzyme at the maximal rate (t½max) is 3.4 minutes, with a dissociation constant (KI) value of 4.3 μM.

UsesA heterocycloc derivative of phenoxyacetic Acid. Uses as a diuretic, uricosuric, anhtihypertensive

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

Suppliers50 total

苏州道澜生物医药科技有限公司15952404857 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Hangzhou Collab Medicine Co.,Ltd.+86-15936229464 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
Additional notes · 1 item

DefinitionChEBI: An aromatic ketone that is 2,3-dichlorophenoxyacetic acid in which the hydrogen at position 4 on the benzene ring is replaced by a thiophenecarbonyl group. A loop diuretic used to treat hypertension, it was withdrawn from the market in 1982 due to links wi h hepatitis.

Related reactions

4 records
New reaction record

Linked notes

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