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22494-42-4

22494-42-4 structure
22494-42-4 structure
  • Name: Diflunisal
  • Chemical Name: diflunisal
  • CAS Number: 22494-42-4
  • Molecular Formula: C13H8F2O3
  • Molecular Weight: 250.198
  • Catalog: API Antipyretic analgesics Non-steroidal anti-inflammatory drugs
  • Create Date: 2018-09-13 14:10:25
  • Modify Date: 2024-01-02 19:31:05
  • Diflunisal (MK-647) is a salicylate derivative with nonsteroidal anti-inflammatory and uricosuric properties, which is used alone as an analgesic and in rheumatoid arthritis patients. The mechanism of action of diflunisal is as a Cyclooxygenase (COX) Inhibitor.
Name diflunisal
Synonyms Dolobil
Difludol
Dolisal
2',4'-Difluoro-4-hydroxy-3-biphenylcarboxylic acid
Flustar
4',6'-difluoro-4-hydroxybiphenyl-3-carboxylic acid
Dolobis
[1,1'-Biphenyl]-3-carboxylic acid, 2',4'-difluoro-4-hydroxy-
Diflunisal
EINECS 245-034-9
Fluodonil
Adomal
[14C]-Diflunisal
MFCD00057834
5-(2,4-difluorophenyl)-2-hydroxybenzoic acid
2-hydroxy-5-(2',4'-difluorophenyl)benzoic acid
Diflunisalum
Fluniget
Dolobid
Flovacil
2',4'-difluoro-4-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
2',4'-Difluoro-4-hydroxybiphenyl-3-carboxylic acid
5-(2,4-Difluorophenyl)salicylic acid
Description Diflunisal (MK-647) is a salicylate derivative with nonsteroidal anti-inflammatory and uricosuric properties, which is used alone as an analgesic and in rheumatoid arthritis patients. The mechanism of action of diflunisal is as a Cyclooxygenase (COX) Inhibitor.
Related Catalog
Target

COX

In Vivo Administration of increasing doses of Diflunisal to rats shows that the effect of the dose on the pharmacokinetics of Diflunisal is quite complicated. The plasma concentrations of Diflunisal decline exponentially with time, albeit with a half-life that increases with increasing dose. The CLP is reduced considerably when the dose increases from 3 to 10 mg/kg and then remains relatively constant over the dose range of 10 to 60 mg/kg. Diflunisal has been shown to be highly bound to rat plasma protein and dependent on concentration. The fraction of unbound Diflunisal is increased about 10-fold over the concentration range of 5 to 300 μg/mL[1]. Diflunisal exhibits activity after oral administration with potency about 25 times greater than that of aspirin, about 3 times that of glafenine and twice that of zomepirac[2].
Animal Admin Rats[1] For the study of dose dependency, Diflunisal is administered by i.a. injection in doses of 3, 10, 30 and 60 mg/kg (1.5, 5, 15 and 30 mg/mL dosing solution in 0.1 M NaHCO3). The infusion studies consist of a bolus injection of Diflunisal followed immediately by a 7-hr infusion at a constant rate. Seven groups of rats are included in the infusion studies. The loading doses used are 2, 3, 5, 10, 25, 50 and 80 mg/kg and their corresponding infusion rates are 3, 4.5, 9, 18, 36, 72 and 144 μg/min (0.576 mL/hr of seven different dosing solutions: 0.31, 0.47, 0.94, 1.88, 3.75, 7.5 and 15 mg/mL in 0.1 M NaHCO3). Blood samples are collected serially at appropriate times for the dose-dependency studies, but collected hourly for the infusion studies. Plasma is obtained immediately by centrifugation of blood samples and extracted with acetonitrile and then frozen (-20°C) until assay[1].
References

[1]. Lin JH, et al. Dose-dependent pharmacokinetics of diflunisal in rats: dual effects of protein binding and metabolism. J Pharmacol Exp Ther. 1985 Nov;235(2):402-6.

[2]. Winter CA, et al. Analgesic activity of diflunisal [MK-647; 5-(2,4-difluorophenyl)salicylic acid] in rats with hyperalgesia induced by Freund's adjuvant. J Pharmacol Exp Ther. 1979 Dec;211(3):678-85.

[3]. Cappon GD, et al. Relationship between cyclooxygenase 1 and 2 selective inhibitors and fetal development when administered to rats and rabbits during the sensitive periods for heart development and midline closure. Birth Defects Res B Dev Reprod Toxicol. 2003 Feb;68(1):47-56.
Density 1.4±0.1 g/cm3
Boiling Point 386.9±42.0 °C at 760 mmHg
Melting Point 32-36 °C
Molecular Formula C13H8F2O3
Molecular Weight 250.198
Flash Point 187.8±27.9 °C
Exact Mass 250.044144
PSA 57.53000
LogP 4.44
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.601
Storage condition Refrigerator

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DV2030000
CHEMICAL NAME :
3-Biphenylcarboxylic acid, 2',4'-difluoro-4-hydroxy-
CAS REGISTRY NUMBER :
22494-42-4
LAST UPDATED :
199806
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C13-H8-F2-O3
MOLECULAR WEIGHT :
250.21
WISWESSER LINE NOTATION :
QVR BQ ER BF DF

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
71 mg/kg/5D-I
TOXIC EFFECTS :
Behavioral - tolerance Liver - jaundice, cholestatic
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
429 mg/kg/17W-I
TOXIC EFFECTS :
Blood - agranulocytosis Nutritional and Gross Metabolic - body temperature increase
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
392 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
159 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
185 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
439 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
124 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
212 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
603 mg/kg
TOXIC EFFECTS :
Behavioral - tremor Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
800 mg/kg/4D-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
9400 mg/kg/14W-I
TOXIC EFFECTS :
Gastrointestinal - other changes Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
520 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
780 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Cytogenetic analysis
TYPE OF TEST :
Sister chromatid exchange

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
350 mg/kg
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 370,1,1996 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X6814 No. of Facilities: 16 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 94 (estimated) No. of Female Employees: 62 (estimated)
Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H302-H315-H319-H335-H361
Precautionary Statements P280-P301 + P312 + P330-P305 + P351 + P338
Personal Protective Equipment Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges
Hazard Codes Xn:Harmful;
Risk Phrases R22;R36/37/38;R63
Safety Phrases S22-S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DV2030000
HS Code 2918290000
89-55-4 structure

89-55-4

144025-03-6 structure

144025-03-6

~93%

22494-42-4 structure

22494-42-4

Literature: DeVasher, Rebecca B.; Moore, Lucas R.; Shaughnessy, Kevin H. Journal of Organic Chemistry, 2004 , vol. 69, # 23 p. 7919 - 7927
59089-67-7 structure

59089-67-7

~%

22494-42-4 structure

22494-42-4

Literature: US4131618 A1, ;
55544-00-8 structure

55544-00-8

~88%

22494-42-4 structure

22494-42-4

Literature: Kim, Seung-Hoi; Kim, Jong-Gyu Bulletin of the Korean Chemical Society, 2011 , vol. 32, # 1 p. 341 - 343
529-28-2 structure

529-28-2

~%

22494-42-4 structure

22494-42-4

Literature: Science (Washington, DC, United States), , vol. 337, # 6102 p. 1644 - 1648,5
148854-10-8 structure

148854-10-8

~%

22494-42-4 structure

22494-42-4

Literature: Science (Washington, DC, United States), , vol. 337, # 6102 p. 1644 - 1648,5
606-45-1 structure

606-45-1

148854-10-8 structure

148854-10-8

~%

22494-42-4 structure

22494-42-4

Literature: Science (Washington, DC, United States), , vol. 337, # 6102 p. 1644 - 1648,5
124-38-9 structure

124-38-9

367-25-9 structure

367-25-9

100-66-3 structure

100-66-3

~%

22494-42-4 structure

22494-42-4

Literature: Journal of Medicinal Chemistry, , vol. 21, p. 1093 - 1100
124-38-9 structure

124-38-9

367-25-9 structure

367-25-9

71-43-2 structure

71-43-2

~%

22494-42-4 structure

22494-42-4

Literature: Journal of Medicinal Chemistry, , vol. 21, p. 1093 - 1100
HS Code 2922299090
Summary 2922299090. other amino-naphthols and other amino-phenols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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