Diclofenac

Modify Date: 2024-01-01 18:19:39

Diclofenac Structure
Diclofenac structure
 Common Name Diclofenac
CAS Number 15307-86-5 Molecular Weight 296.149
Density 1.4±0.1 g/cm3 Boiling Point 412.0±45.0 °C at 760 mmHg
Molecular Formula C14H11Cl2NO2 Melting Point 156-158ºC
MSDS N/A Flash Point 203.0±28.7 °C

 Use of Diclofenac


Diclofenac is a potent and nonselective anti-inflammatory agent, acts as a COX inhibitor, with IC50s of 4 nM, 1.3 nM for human COX-1 and COX-2 in CHO cells, and 5.1, 0.84 μM for ovine COX-1 and COX-2, respectively.

 Names

Name diclofenac
Synonym More Synonyms

 Diclofenac Biological Activity

Description Diclofenac is a potent and nonselective anti-inflammatory agent, acts as a COX inhibitor, with IC50s of 4 nM, 1.3 nM for human COX-1 and COX-2 in CHO cells, and 5.1, 0.84 μM for ovine COX-1 and COX-2, respectively.
Related Catalog
Target

Human COX-2:1.3 nM (IC50, in CHO cells)

Human COX-1:4 nM (IC50, in CHO cells)

Ovine COX-2:0.84 μM (IC50)

Ovine COX-1:5.1 μM (IC50)

In Vitro Diclofenac is a potent COX inhibitor, with IC50s of 4 nM and 1.3 nM for human COX-1 and COX-2 in the CHO cells, respectively. Diclofenac effectively blocks COX-1 mediated prostanoid production from U937 cell microsomes, with an IC50 of 7 ± 3 nM[1]. Diclofenac sodium exihibits inhibition on COX-1 and COX-2 enzyme with IC50s of 5.1 and 0.84 μM, respectively[2].
In Vivo Diclofenac (3 mg/kg, b.i.d., for 5 days) significantly increases faecal 51Cr excretion in rats, and such effect is also observed in squirrel monkeys after administrated of 1 mg/kg twice daily for 4 days[1]. Diclofenac (10 mg/kg) shows anti-inflammatory activity in mice[2]. Diclofenac (10 mg/kg) decreases oxidized low-densitylipoprotein (Ox-LDL), but shows no effects on the kinetics parameters of catalase and glutathione peroxidase via intramuscularly injection into rats[3].
Animal Admin Rats[1] Male Sprague-Dawley rats (150 ± 200 g) are dosed orally with Diclofenac either once (acute dosing) or twice daily for 5 days (chronic dosing). A plasma sample is obtained 1 h after the morning dose on day 4 for measurement of Diclofenac concentration. Immediately after the administration of the last dose on day 5, the rats are injected via a tail vein with 0.5 mL of 51Cr-labelled red blood cells from a donor rat after incubation with sodium 51chromate. The rats are placed individually in metabolism cages with food and water ad libitum. Faeces are collected for a 48 h period and 51Cr faecal excretion is calculated as a % of total injected dose (20 mCi per animal)[1]. Squirrel monkeys[1] Squirrel monkeys (Saimiri sciureus; 0.8 ± 1.4 kg) are dosed orally with Diclofenac twice daily for 1 ± 5 days. One hour after administration of the last dose, 51CrCl3 in sterile saline (1 mL/kg, 4 ± 5 mCi per animal) is injected via a saphenous vein and plasma samples are obtained for measurement of Diclofenac concentration. The monkeys are then housed individually in metabolism cages. Faeces are collected for a 24 h period and 51Cr faecal excretion is calculated as a % of total injected dose[1].
References

[1]. Riendeau D, et al. Biochemical and pharmacological profile of a tetrasubstituted furanone as a highly selective COX-2 inhibitor. Br J Pharmacol. 1997 May;121(1):105-17.

[2]. Labib MB, et al. Design, synthesis of novel isoindoline hybrids as COX-2 inhibitors: Anti-inflammatory, analgesic activities and docking study. Bioorg Chem. 2018 Oct;80:70-80.

[3]. Curcelli EC, et al. Beneficial effects of diclofenac therapy on serum lipids, oxidized low-density lipoprotein and antioxidant defenses in rats. Life Sci. 2008 Apr 9;82(15-16):892-8.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 412.0±45.0 °C at 760 mmHg
Melting Point 156-158ºC
Molecular Formula C14H11Cl2NO2
Molecular Weight 296.149
Flash Point 203.0±28.7 °C
Exact Mass 295.016693
PSA 49.33000
LogP 4.06
Vapour Pressure 0.0±1.0 mmHg at 25°C
Index of Refraction 1.662

 MSDS

2-(2,6-Dichloroanilino)phenylacetic Acid Revision number: 5
SAFETY DATA SHEET
Section1. IDENTIFICATION
Product name:2-(2,6-Dichloroanilino)phenylacetic Acid

Revision number:5
Section2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDSNot classified
HEALTH HAZARDS
Acute toxicity (Oral)Category 3
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal wordDanger
Hazard statementsToxic if swallowed
Precautionary statements:
[Prevention]Do not eat, drink or smoke when using this product.
Wash hands thoroughly after handling.
IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. Rinse
[Response]
mouth.
Store locked up.
[Storage]
[Disposal]Dispose of contents/container through a waste management company authorized by
the local government.
Section3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture:Substance
Components:2-(2,6-Dichloroanilino)phenylacetic Acid
Percent:>98.0%(GC)(T)
CAS Number:15307-86-5
Synonyms:Diclofenac
Chemical Formula:C14H11Cl2NO2
Section4. FIRST AID MEASURES
Inhalation:Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact:Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
2-(2,6-Dichloroanilino)phenylacetic Acid
Section4. FIRST AID MEASURES
Eye contact:Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion:Immediately call a POISON CENTER or doctor/physician. Rinse mouth.
Protection of first-aiders:A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.
Section5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical:generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protectiveWhen extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:
Section6. ACCIDENTAL RELEASE MEASURES
Personal precautions,Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep
protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should
emergency procedures: be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.
Section7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures:Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a closed system if possible. Use a local exhaust if dust or aerosol will be
generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions:Keep container tightly closed. Store in a cool and dark place.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material:Comply with laws.
Section8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls:Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Impervious gloves.
Hand protection:
Eye protection:Safety goggles. A face-shield, if the situation requires.
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.
Section9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C):Solid
Form:Crystal- Powder
White - Very pale yellow
Colour:
2-(2,6-Dichloroanilino)phenylacetic Acid
Section9. PHYSICAL AND CHEMICAL PROPERTIES
Odour:No data available
pH: No data available
Melting point/freezing point:158°C (dec.)
Boiling point/range:No data available
Flash point:No data available
Flammability or explosive
limits:
Lower:No data available
Upper:No data available
Relative density:No data available
Solubility(ies):
[Water]No data available
[Other solvents]
Soluble:Methanol
Log Pow:3.03
Section10. STABILITY AND REACTIVITY
Chemical stability:Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen chloride
products:
Section11. TOXICOLOGICAL INFORMATION
Acute Toxicity:orl-rat LD50:62500 ug/kg
ipr-mus LD50:345 mg/kg
Skin corrosion/irritation: No data available
Serious eyeNo data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC =No data available
NTP =No data available
Reproductive toxicity:No data available
RTECS Number:AG6310000
Section12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
Crustacea:No data available
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobility in soil
Log Pow:3.03
No data available
Soil adsorption (Koc):
Henry's LawNo data available
constant(PaM3/mol):
Section13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.
2-(2,6-Dichloroanilino)phenylacetic Acid
Section14. TRANSPORT INFORMATION
Hazards Class:6.1: Toxic substance.
UN-No:2811
Proper shipping name:Toxic solid, organic, n.o.s.
Packing group:III
Section15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

SECTION 16 - ADDITIONAL INFORMATION
N/A

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AG6310000
CHEMICAL NAME :
Acetic acid, (o-(2,6-dichloroanilino)phenyl)-
CAS REGISTRY NUMBER :
15307-86-5
LAST UPDATED :
199612
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C14-H11-Cl2-N-O2
MOLECULAR WEIGHT :
296.16
WISWESSER LINE NOTATION :
QV1R BMR BG FG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
1070 ug/kg
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 117,1058,1992
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
62500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 30,1398,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PHARAT Pharmazie. (VEB Verlag Volk und Gesundheit, Neue Gruenstr. 18, Berlin DDR-1020, Ger. Dem. Rep.) V.1- 1946- Volume(issue)/page/year: 37,148,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
345 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 43,44,1993 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
4 mg/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
JCGBDF Journal of Craniofacial Genetics and Developmental Biology. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 10,83,1990
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
DOSE :
4 mg/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue)
REFERENCE :
JCGBDF Journal of Craniofacial Genetics and Developmental Biology. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1980- Volume(issue)/page/year: 10,83,1990

 Safety Information

Hazard Codes Xi
RIDADR 3249
Packaging Group III
Hazard Class 6.1(b)
HS Code 2942000000

 Synthetic Route

 Customs

HS Code 2922499990
Summary HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

 Synonyms

2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
Benzeneacetic acid, 2-((2,6-dichlorophenyl)amino)-
2-(2-((2,6-dichlorophenyl)amino)phenyl)acetic acid
Acetic acid, (o-(2,6-dichloroanilino)phenyl)-
2-[[2,6-Dichlorophenyl]amino]benzeneacetic acid
MFCD00451393
2-((2,6-dichlorophenyl)amino)benzeneacetic acid
Diclofenac acid
2-[2-[(2,6-dichlorophenyl)amino]phenyl]acetic acid
N-(2,6-Dichlorophenyl)-o-aminophenylacetic Acid
Zorvolex
EINECS 239-348-5
{2-[(2,6-Dichlorophenyl)amino]phenyl}acetic acid
[2-(2,6-dichloroanilino)phenyl]acetic acid
Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-
Motifene
(o-(2,6-Dichloroanilino)phenyl)acetic Acid
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