Tiaprofenic Acid

Modify Date: 2025-08-26 17:32:47

Tiaprofenic Acid Structure
Tiaprofenic Acid structure
 Common Name Tiaprofenic Acid
CAS Number 33005-95-7 Molecular Weight 260.30800
Density 1.29 g/cm3 Boiling Point 450.3ºC at 760 mmHg
Molecular Formula C14H12O3S Melting Point 96° (isopropyl ether)
MSDS N/A Flash Point 226.1ºC

 Use of Tiaprofenic Acid


Tiaprofenic acid is an orally active nonsteroidal anti-inflammatory drug (NSAID) with anti-inflammatory and analgesic potency. Tiaprofenic acid inhibits prostaglandin synthesis by suppressing cyclo-oxygenase (COX). Tiaprofenic acid can be used in the treatment of rheumatic diseases[1].

 Names

Name Tiaprofenic Acid
Synonym More Synonyms

 Tiaprofenic Acid Biological Activity

Description Tiaprofenic acid is an orally active nonsteroidal anti-inflammatory drug (NSAID) with anti-inflammatory and analgesic potency. Tiaprofenic acid inhibits prostaglandin synthesis by suppressing cyclo-oxygenase (COX). Tiaprofenic acid can be used in the treatment of rheumatic diseases[1].
Related Catalog
In Vivo Female Lewis rats received either Tiaprofenic acid (as an intravenous (iv.) bolus injection of 15 mg/kg and constant infusion of 0.02 mg/min) for 6 h. Tiaprofenic acid results in a significant decrease in serum sulfate concentrations and increase in sulfate clearance ratio. There is also a significant decrease in the fraction of sulfate reabsorbed by the kidneys[2].
References

[1]. G L Plosker, et al. Tiaprofenic Acid. A Reappraisal of Its Pharmacological Properties and Use in the Management of Rheumatic Diseases. Drugs. 1995 Dec;50(6):1050-75.

[2]. L J Benincosa, et al. Tiaprofenic Acid Inhibits the Renal Reabsorption of Sulfate in Rats. Prostaglandins Leukot Essent Fatty Acids. 1993 Jul;49(1):503-8.

 Chemical & Physical Properties

Density 1.29 g/cm3
Boiling Point 450.3ºC at 760 mmHg
Melting Point 96° (isopropyl ether)
Molecular Formula C14H12O3S
Molecular Weight 260.30800
Flash Point 226.1ºC
Exact Mass 260.05100
PSA 82.61000
LogP 3.16720
Index of Refraction 1.612
InChIKey GUHPRPJDBZHYCJ-UHFFFAOYSA-N
SMILES CC(C(=O)O)c1ccc(C(=O)c2ccccc2)s1
Water Solubility Practically insoluble in water, freely soluble in acetone, in ethanol (96 per cent) and in methylene chloride.

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XM7580000
CHEMICAL NAME :
2-Thiopheneacetic acid, 5-benzoyl-alpha-methyl-
CAS REGISTRY NUMBER :
33005-95-7
BEILSTEIN REFERENCE NO. :
1380662
LAST UPDATED :
199612
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C14-H12-O3-S
MOLECULAR WEIGHT :
260.32
WISWESSER LINE NOTATION :
T5SJ BY1&VQ EVR

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
168 mg/kg/14D-I
TOXIC EFFECTS :
Vascular - shock Lungs, Thorax, or Respiration - other changes Gastrointestinal - ulceration or bleeding from small intestine
REFERENCE :
MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 158,647,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
672 mg/kg/7W-I
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - anorexia (human) Liver - other changes
REFERENCE :
LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 1,803,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
16 mg/kg/2D-I
TOXIC EFFECTS :
Behavioral - wakefulness Behavioral - hallucinations, distorted perceptions Behavioral - excitement
REFERENCE :
CMAJAX Canadian Medical Association Journal. (Canadian Medical Assoc., POB 8650, Ottawa, ON K1G 0G8, Canada) V.1- 1911- Volume(issue)/page/year: 137,1022,1987
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
257 mg/kg/30D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Kidney, Ureter, Bladder - inflammation, necrosis, or scarring of bladder
REFERENCE :
MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 160,123,1994
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
720 mg/kg/60D-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - other changes in urine composition Kidney, Ureter, Bladder - inflammation, necrosis, or scarring of bladder
REFERENCE :
MJAUAJ Medical Journal of Australia. (Australasian Medical Pub. Co. Ltd., 71-79 Arundel St., Glebe, N.S.W., Australia) V.1- 1914- Volume(issue)/page/year: 160,123,1994
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
181 mg/kg
TOXIC EFFECTS :
Behavioral - antipsychotic
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 9,715,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
225 mg/kg
TOXIC EFFECTS :
Behavioral - antipsychotic
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 9,715,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
215 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,688,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
690 mg/kg
TOXIC EFFECTS :
Behavioral - antipsychotic
REFERENCE :
OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 9,715,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
355 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4159986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
675 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 15,688,1984 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2190 mg/kg/1Y-I
TOXIC EFFECTS :
Lungs, Thorax, or Respiration - other changes Related to Chronic Data - death Related to Chronic Data - changes in ovarian weight
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,1743,1980 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1800 mg/kg
SEX/DURATION :
male 10 week(s) pre-mating female 2 week(s) pre-mating - 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 6,195,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7200 mg/kg
SEX/DURATION :
male 10 week(s) pre-mating female 2 week(s) pre-mating - 6 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 6,195,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
200 mg/kg
SEX/DURATION :
female 6-15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
JZKEDZ Jitchuken Zenrinsho Kenkyuho. Central Institute for Experimental Animals, Research Reports. (Jikken Dobutsu Chuo Kenkyusho, 1433 Nogawa, Takatsu-ku, Kawasaki 211, Japan) V.1- 1975- Volume(issue)/page/year: 6,205,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
975 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,1773,1980

 Safety Information

RIDADR UN 2811 6.1/PG III
RTECS XM7580000
Packaging Group III

 Synthetic Route

2-(THIOPHEN-2-YL)PROPANOIC ACID structure

2-(THIOPHEN-2-Y...

CAS#:54955-39-4

Benzoyl chloride structure

Benzoyl chloride

CAS#:98-88-4

~95%

Tiaprofenic Acid Structure

Tiaprofenic Acid

CAS#:33005-95-7

Literature: Zhang, Shuguang; Huang, Shuang; Feng, Chengliang; Cai, Jin; Chen, Junqing; Ji, Min Journal of Chemical Research, 2013 , vol. 37, # 7 p. 406 - 408
methyl α-methylthio-α-(5-benzoyl-2-thienyl)propionate structure

methyl α-methyl...

CAS#:67355-14-0

Sodium thiomethoxide structure

Sodium thiomethoxide

CAS#:5188-07-8

~65%

Tiaprofenic Acid Structure

Tiaprofenic Acid

CAS#:33005-95-7

Literature: Sagami Chemical Research Center Patent: US4242519 A1, 1980 ;

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 Synonyms

2-(5-Benzoylthiophen-2-yl)propanoic acid
Tiaprofenic acid
2-(5-Benzoylthiophen-2-yl)propionic Acid
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