| Identification | Back Directory | [Name]
Tiaprofenic acid | [CAS]
33005-95-7 | [Synonyms]
Surgam
FC 3001
RU 15060
Suralgan
Tiaprofen
Surgam SA
Tiaprofenic
TiaprofenicAci
Tiaprofensaeure
Tiaprofenic acid
Acido tiaprofenico
Acide tiaprofenique
Acidum tiaprofenicum
Tiaprofenic acid CRS
(RS)-Tiaprofenic acid
Tiaprofenic acid USP/EP/BP
Acide tiaprofenique [inn-french]
Acido tiaprofenico [inn-spanish]
TIAPROFENIC ACID EPT(CRM STANDARD)
2-(5-Benzyl-2-thienyl)propionsaeure
α-(5-Benzoyl-2-thienyl)propionic Acid
2-(5-benzoylthiophen-2-yl)propanoic acid
2-(5-Benzoylthiophen-2-yl)propionic Acid
5-BENZOYL-α-METHYL-2-THIOPHENEACETIC ACID
2-Thiopheneacetic acid, 5-benzoyl-α-methyl-
5-Benzoyl-alpha-methyl-2-thiopheneacetic acid
2-[5-(Phenylcarbonyl)-2-thienyl]propanoic acid
(2RS)-2-(5-Benzoylthiophen-2-yl)propanoic acid
2-Thiopheneacetic acid, 5-benzoyl-alpha-methyl-
2-Thiopheneacetic acid, 5-benzoyl-a-methyl- (8CI, 9CI) | [EINECS(EC#)]
251-329-3 | [Molecular Formula]
C14H12O3S | [MDL Number]
MFCD00866089 | [MOL File]
33005-95-7.mol | [Molecular Weight]
260.312 |
| Chemical Properties | Back Directory | [Appearance]
White or almost white, crystalline powder. | [Melting point ]
96° (isopropyl ether) | [Boiling point ]
373.57°C (rough estimate) | [density ]
1.2959 (rough estimate) | [refractive index ]
1.5050 (estimate) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
Practically insoluble in water, freely soluble in acetone, in ethanol (96 per cent) and in methylene chloride. | [form ]
neat | [pka]
4.05±0.10(Predicted) | [color ]
White to Almost white | [λmax]
314nm(Phosphate buffer sol.)(lit.) | [Merck ]
14,9422 | [Major Application]
pharmaceutical (small molecule) | [InChI]
InChI=1S/C14H12O3S/c1-9(14(16)17)11-7-8-12(18-11)13(15)10-5-3-2-4-6-10/h2-9H,1H3,(H,16,17) | [InChIKey]
GUHPRPJDBZHYCJ-UHFFFAOYSA-N | [SMILES]
C1(=CC=C(C(C)C(=O)O)S1)C(=O)C1C=CC=CC=1 |
| Hazard Information | Back Directory | [Chemical Properties]
White or almost white, crystalline powder. | [Uses]
Antiinflammatory;Cyclooxygenase inhibitor | [Definition]
ChEBI: An aromatic ketone that is thiophene substituted at C-2 by benzoyl and at C-4 by a 1-carboxyethyl group. | [Originator]
Surgam,Roussel,France,1975 | [Manufacturing Process]
A mixture of 10.3 g of thiophene-2α-methylacetic acid [prepared by process of
Bercot-Vatteroni, et al., Bull. Soc. Chim. (1961) pp. 1820-21], 11.10 g of
benzoyl chloride and a suspension of 23.73 g of aluminum chloride in 110 cc
of chloroform was allowed to stand for 15 minutes and was then poured into a
mixture of ice and hydrochloric acid. The chloroform phase was extracted with
a 10% aqueous potassium carbonate solution and the aqueous alkaline phase
was acidified with N hydrochloric acid and was then extracted with ether. The
ether was evaporated off and the residue was crystallized from carbon
tetrachloride to obtain a 54% yield of 5-benzoyl-thiophene-2α-methylacetic
acid melting at 83°C to 85°C. The product occurred in the form of colorless
crystals soluble in dilute alkaline solutions, alcohol and ether and insoluble in
water. | [Therapeutic Function]
Antiinflammatory | [Clinical Use]
#N/A | [Drug interactions]
Potentially hazardous interactions with other drugs
ACE inhibitors and angiotensin-II antagonists:
antagonism of hypotensive effect; increased risk of
nephrotoxicity and hyperkalaemia.
Analgesics: avoid concomitant use of 2 or more
NSAIDs, including aspirin (increased side effects);
avoid with ketorolac (increased risk of side effects
and haemorrhage).
Antibacterials: possibly increased risk of convulsions
with quinolones.
Anticoagulants: effects of coumarins and
phenindione enhanced; possibly increased risk of
bleeding with heparins, dabigatran and edoxaban -
avoid long term use with edoxaban.
Antidepressants: increased risk of bleeding with
SSRIs and venlaflaxine.
Antidiabetic agents: effects of sulphonylureas
enhanced.
Antiepileptics: possibly increased phenytoin
concentration.
Antivirals: increased risk of haematological toxicity
with zidovudine; concentration increased by
ritonavir.
Ciclosporin: may potentiate nephrotoxicity.
Cytotoxics: reduced excretion of methotrexate;
increased risk of bleeding with erlotinib.
Diuretics: increased risk of nephrotoxicity;
antagonism of diuretic effect; hyperkalaemia with
potassium-sparing diuretics.
Lithium: excretion decreased.
Pentoxifylline: increased risk of bleeding.
Tacrolimus: increased risk of nephrotoxicity. | [Metabolism]
Sparingly metabolised in the liver to two inactive metabolites. Excretion of tiaprofenic acid and its metabolites are mainly in the urine in the form of acyl glucuronides; some is excreted in the bile. |
| Safety Data | Back Directory | [RIDADR ]
UN 2811 6.1/PG III | [WGK Germany ]
WGK 3 | [RTECS ]
XM7580000 | [HS Code ]
2934.99.3000 | [HazardClass ]
6.1 | [PackingGroup ]
III | [Storage Class]
6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | [Hazard Classifications]
Acute Tox. 3 Oral
Repr. 2 |
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