33005-95-7 Usage
Chemical Properties
White or almost white, crystalline powder.
Originator
Surgam,Roussel,France,1975
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 33005-95-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,0,0 and 5 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 33005-95:
(7*3)+(6*3)+(5*0)+(4*0)+(3*5)+(2*9)+(1*5)=77
77 % 10 = 7
So 33005-95-7 is a valid CAS Registry Number.
InChI:InChI=1/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)
33005-95-7Relevant articles and documents
Preparation method for tiaprofenic acid
-
, (2018/04/02)
The invention relates to a preparation method for tiaprofenic acid. The method comprises the following steps: by taking 2-thiophenecarboxaldehyde as an initial raw material, reacting with methyl magnesium bromide, thereby compounding 1-(2-thienyl) alcohol; reacting with thionyl chloride for substituting chlorine group, cyaniding and hydrolyzing; and finally, performing Friedel-Crafts acylation reaction on the acquired product and benzoyl chloride, thereby acquiring tiaprofenic acid. The preparation method for tiaprofenic acid has the advantages that the common, low-cost and safe raw materialsare adopted for replacing rare, precious and dangerous raw materials, so that the serious pollution problem is avoided and the production cost is greatly lowered, besides, the process route adopted bythe invention is simple, the reaction period is short, the reaction condition is stable, the yield is high and reaches up to 90% or above, the purity of the acquired product after the reaction is high and the purity can reach up to 99% or above, so that the preparation method is suitable for industrial production.
Synthetic process of tiaprofenic acid
-
, (2018/04/01)
The invention relates to a synthetic process of tiaprofenic acid. The synthetic process comprises the following steps: adopting 2-thiotolene as a starting raw material, enabling 2-thiotolene to reactwith trimethylsilyl cyanide to synthesize 2-thiopheneacetonitrile by virtue of bromation, then enabling the 2-thiopheneacetonitrile to react with dimethyl carbonate to be methylated, hydrolyzing cyanogroups, and finally performing F-K reaction with benzoyl chloride, and preparing tiaprofenic acid. The synthetic process has the advantages that the conventional safe raw materials low in price are used for substituting the rare expensive and dangerous raw materials, so that the severe pollution problem is avoided, and the production cost is greatly decreased; and in addition, the process route adopted by the invention is simple, the reaction period is short, the reaction condition is stable, the yield is high and can reach more than 90 percent, the produce obtained after the reaction is highin purity, and the purity can reach more than 99 percent, so that the synthetic process is suitable for the industrialized production.
Novel preparation of tiaprofenic acid
Zhang, Shuguang,Huang, Shuang,Feng, Chengliang,Cai, Jin,Chen, Junqing,Ji, Min
, p. 406 - 408 (2013/09/12)
A new synthesis of the nonsteroidal anti-inflammatory drug tiaprofenic acid starting from thiophene is described. The sequence involves five steps, and the acylation with benzoyl chloride was catalysed by zinc oxide under solventfree conditions at room temperature. This method uses a much cheaper starting material and has a higher total yield (78.4%) than other methods. It is suitable for industrial production.
