ChemicalBook > CAS DataBase List > TICRYNAFEN

TICRYNAFEN

Product Name
TICRYNAFEN
CAS No.
40180-04-9
Chemical Name
TICRYNAFEN
Synonyms
Tienilic;Tienilic Acid - Ticrynafan;ticrex;fr3068;ce3624;ANP 362;anp3624;diflurex;skf62698;selacryn
CBNumber
CB8500854
Molecular Formula
C13H8Cl2O4S
Formula Weight
331.17
MOL File
40180-04-9.mol
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TICRYNAFEN Property

Melting point:
148-149oC
Boiling point:
534.6±50.0 °C(Predicted)
Density 
1.532
storage temp. 
-20°C
solubility 
DMSO: soluble5mg/mL (clear solution)
pka
2.79±0.10(Predicted)
form 
powder
color 
white to beige
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
SMILES
C(O)(=O)COC1=CC=C(C(C2SC=CC=2)=O)C(Cl)=C1Cl
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
RTECS 
AG9300000
Toxicity
LD50 in mice (mg/kg): 225 i.v., 1275 orally (US 3758506)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0505
Product name
Tienilic Acid
Purity
≥98% (HPLC)
Packaging
5mg
Price
$97.1
Updated
2025/07/31
Sigma-Aldrich
Product number
SML0505
Product name
Tienilic Acid
Purity
≥98% (HPLC)
Packaging
25mg
Price
$397
Updated
2025/07/31
Cayman Chemical
Product number
10008517
Product name
Tienilic Acid
Purity
≥99%
Packaging
5mg
Price
$72
Updated
2024/03/01
Cayman Chemical
Product number
10008517
Product name
Tienilic Acid
Purity
≥99%
Packaging
10mg
Price
$120
Updated
2024/03/01
Cayman Chemical
Product number
10008517
Product name
Tienilic Acid
Purity
≥99%
Packaging
25mg
Price
$319
Updated
2024/03/01
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TICRYNAFEN Chemical Properties,Usage,Production

Description

Cytochrome 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.

Chemical Properties

Pale Beige Solid

Uses

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

Uses

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

Definition

ChEBI: 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.

brand name

Tienilic Acid is INN and BAN;Anp 3624;Diflarex;Fr 3068;Selcryn;Skf-62698;Ticrynafen;Ticrynapen.

World Health Organization (WHO)

Tienilic acid, a diuretic agent with uricosuric and antihypertensive activity, was introduced in 1976. By 1979 its use had been associated with cases of hepatic toxicity, some of which were fatal, which led to the withdrawal of the drug in most countries in which it was marketed. In France, however, precautions regarding the use of tienilic acid were issued by the Pharmacovigilance Commission and the drug remained available for another decade. In 1991, it was eventually also withdrawn there since cases of hepatitis, some of which were fulminant, had continued to occur.

Biochem/physiol Actions

Tienilic Acid (Ticrynafen) is a P450 inhibitor, a specific suicide substrate for CYP2C9 and CYP2C10. It was once used as a loop diuretic drug with uric acid-lowering (uricosuric) actvity, but was removed from market because of hepatotoxicity.

References

[1] ANNAH MANCY. The Substrate Binding Site of Human Liver Cytochrome P450 2C9: An Approach Using Designed Tienilic Acid Derivatives and Molecular Modeling[J]. Biochemistry Biochemistry, 1995, 34 33: 10365-10375. DOI: 10.1021/bi00033a007
[2] De Souza, F.I., Zumiotti, A.V., and Da Silva, C.F. Neuregulins 1-α and 1-β on the regeneration the peripheral nerves[J]. Acta Ortop Bras.
[3] M. PILAR LOPEZ-GARCIA  Daniel M  Patrick M Dansette. Thiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: Inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid[J]. Biochemistry Biochemistry, 1994, 33 1: 166-175. DOI: 10.1021/bi00167a022

TICRYNAFEN Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from TICRYNAFEN manufacturers

Dideu Industries Group Limited
Product
TICRYNAFEN 40180-04-9
Price
US $1.10/g
Min. Order
1g
Purity
99.00%
Supply Ability
100 Tons Min
Release date
2021-07-06

40180-04-9, TICRYNAFENRelated Search:


  • Tienilic Acid - Ticrynafan
  • ANP 362
  • ce3624
  • diflurex
  • fr3068
  • selacryn
  • skf62698
  • thienylicacid
  • ticrex
  • (2,3-dichloro-4-(2-thenoyl)phenoxy)aceticacid
  • (2,3-dichloro-4-(2-thienylcarbonyl)phenoxy)-aceticaci
  • (2,3-dichloro-4-(2-thienylcarbonyl)phenoxy)aceticacid
  • (2,3-dichloro-4-(2-thiophenecarbonyl)phenoxy)aceticacid
  • 4-(2-theonyl)-2,3-dichlorphenoxyessigsaeure
  • 4-(2-thienylketo)-2,3-dichlorophenoxyaceticacid
  • anp3624
  • tienilicacid
  • [2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy]aceticAcid,TienilicAcid,ThienylicAcid,ANP-3624,CE-3624,SKF-62698,Dif
  • [2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy]acetic Acid, Tienilic Acid, Thienylic Acid, ANP-3624, CE-3624, SKF-62698, Diflurex, Selacryn
  • Tienilic
  • TIENILIC ACID(TICRYNAFEN)
  • 4-(2-Thienylcarbonyl)-2,3-dichlorophenoxyacetic acid
  • Difluorex
  • Tienylic acid
  • 2-[2,3-Dichloro-4-(2-thienylcarbonyl)phenoxy]acetic Acid
  • 4-(2-Thenoyl)-2,3-dichlorophenoxyacetic Acid
  • 2-{2,3-dichloro-4-[(thiophen-2-yl)carbonyl]phenoxy}acetic acid
  • 2-(2,3-dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid
  • Acetic acid, 2-[2,3-dichloro-4-(2-thienylcarbonyl)phenoxy]-
  • Tienilic Acid Solution, 100ppm
  • TICRYNAFEN USP/EP/BP
  • TICRYNAFEN ISO 9001:2015 REACH
  • Ticrynafen, Tienilic acid
  • ANP 3624,Tienilic Acid,Inhibitor,Uricosuric,Diuretic,inhibit,Hepatotoxicity,ANP3624,Ticrynafen,ANP-3624
  • ienilicaci
  • Tinic acid(Axitinib Impurity 18)
  • 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid(Tienilic Acid)
  • Tienilic Acid, 10 mM in DMSO
  • 2,3-dichloro-4-[(thiophen-2-yl)carbonyl]phenoxyacetic acid - [AC79977]
  • 40180-04-9
  • Aromatics
  • Sulfur & Selenium Compounds
  • Heterocyclic Compounds
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals