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Tienilic acid

Tienilic acid structure

CAS No:
40180-04-9
Formula:
C13H8Cl2O4S
Chemical Name:
Tienilic acid
Synonyms:
Acetic acid,2-[2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]-;Acetic acid,[2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]-;2-[2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy]acetic acid;2,3-Dichloro-4-(2-thenoyl)phenoxyacetic acid;Tienilic acid;Ticrynafen;SKF 62698;4-(2-Thenoyl)-2,3-dichlorophenoxyacetic acid;4-(2-Thienylcarbonyl)-2,3-dichlorophenoxyacetic acid;FR 3068;Selacryn;ANP 3624;Tienylic acid;Thienylic acid;Difluorex;CE 3624;2-[2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy]acetic acid
Categories:
Pharmaceutical Intermediates > Heterocyclic Compound

Description

Pale Beige Solid

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 A loop diuretic used to treat hypertension, it was withdrawn from the market in 1982 due to links with hepatitis.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 a loop diuretic, an antihypertensive agent and a hepatotoxic agent. It is a member of thiophenes, an aromatic ketone, an aromatic ether, a monocarboxylic acid and a dichlorobenzene.|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 It was withdrawn in 1982 after case reports in the United States suggested a link between ticrynafen and hepatitis.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)|A novel diuretic with uricosuric action. It has been proposed as an antihypertensive agent.

Tienilic acid Basic Attributes

Molecular Weight：

331.163

Exact Mass：

331.17

EC Number：

254-826-3

UNII：

HC95205SY4

DSSTox ID：

DTXSID4023670

ATC Code：

C - Cardiovascular system

HScode：

2934999090

Characteristics

PSA：

91.8

XLogP3：

3.07

Density：

1.5±0.1 g/cm3

Melting Point：

149 °C

Boiling Point：

534.6±50.0 °C at 760 mmHg

Flash Point：

277.1±30.1 °C

Refractive Index：

1.632

Storage Conditions：

-20ºC Freezer

Toxicity：

LD50 in mice (mg/kg): 225 i.v., 1275 orally ( US 3758506 )

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

RTECS Number：

AG9300000

Marks：

Precautionary statement(s)：

P261, P271, P304+P340, P312, P403+P233, P405, P501

Hazard Statements：

H335

GHS Classification：

|Warning|H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]|P261, P271, P304+P340, P312, P403+P233, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

Drug Indication：

For the treatment of hypertension.

MeSH：

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. (See all compounds classified as Antihypertensive Agents.)|Gout suppressants that act directly on the renal tubule to increase the excretion of uric acid, thus reducing its concentrations in plasma. (See all compounds classified as Uricosuric Agents.)|Agents that promote the excretion of urine through their effects on kidney function. (See all compounds classified as Diuretics.)

Metabolism/Metabolites：

Ticrynafen has known human metabolites that include Thiophene-4,5-epoxide and Tienilic acid-s-oxide.

MeSH Entry Terms：

Acid, Thienylic

Tienilic acid Use and Manufacturing

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

Computed Properties

Molecular Weight:331.2
XLogP3:4.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:329.9520353
Monoisotopic Mass:329.9520353
Topological Polar Surface Area:91.8
Heavy Atom Count:20
Complexity:379
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of Tienilic acid

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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