Aceclofenac
- Iupac Name：2-[2-[2-(2,6-dichloroanilino)phenyl]acetyl]oxyacetic acid
- CAS No.: 89796-99-6
- Molecular Weight：354.18472
- Modify Date.: 2022-11-25 02:23
- Introduction: Aceclofenac is a non-steroidal anti-inflammatory drug (NSAIDs) that is commonly prescribed for people with painful rheumatic conditions such as rheumatoid arthritis, osteoarthritis, and ankylosing spondylitis.The drug should not be given to children, breastfeeding mothers, and people with porphyria. Pregnant women should not also be given aceclofenac as they risk developing patent ductus arteriosus in the neonate.
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1. Names and Identifiers
- 1.1 Name
- Aceclofenac
- 1.2 Synonyms
[2-(2,6-Dichloro-phenylamino)-phenyl]-acetic acid carboxymethyl ester [2-[(2,6-Dichlorophenyl)amino]phenyl]acetoxyacetic acid 2-[[2-[(2,6-Dichlorophenyl)amino]phenyl]acetoxy]acetic acid 2-[2-[2-(2,6-Dichloroanilino)phenyl]acetyl]oxyacetic acid Aceclo Aceclo Plus Aceclofar Aceclofenac BP Acepac Airtal Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-, carboxymethyl ester Biofenac Bristaflam Dolokind Falcol Flexidol Gerbin Glycolic acid 2-[o-(2,6-dichloroanilino)phenyl]acetate Hifenac Hifenac-TL PR 82/3 Preservex Tresquim Zerodol
- 1.3 CAS No.
- 89796-99-6
- 1.4 CID
- 71771
- 1.5 Molecular Formula
- C16H13Cl2NO4 (isomer)
- 1.6 Inchi
- InChI=1S/C16H13Cl2NO4/c17-11-5-3-6-12(18)16(11)19-13-7-2-1-4-10(13)8-15(22)23-9-14(20)21/h1-7,19H,8-9H2,(H,20,21)
- 1.7 InChkey
- MNIPYSSQXLZQLJ-UHFFFAOYSA-N
- 1.8 Canonical Smiles
- C1=CC=C(C(=C1)CC(=O)OCC(=O)O)NC2=C(C=CC=C2Cl)Cl
- 1.9 Isomers Smiles
- C1=CC=C(C(=C1)CC(=O)OCC(=O)O)NC2=C(C=CC=C2Cl)Cl
2. Properties
- 2.1 Density
- 1.455
- 2.1 Melting point
- 149-153℃
- 2.1 Boiling point
- 486 °C at 760 mmHg
- 2.1 Refractive index
- 1.639
- 2.1 Flash Point
- 247.7 °C
- 2.1 Precise Quality
- 353.02200
- 2.1 PSA
- 75.63000
- 2.1 logP
- 3.98030
- 2.1 Solubility
- Soluble in DMSO
- 2.2 Appearance
- white or off-white crystalline powder
- 2.3 Storage
- -20°C Freezer
- 2.4 Chemical Properties
- White Crystalline Solid
- 2.5 Color/Form
- off-white to light tan
- 2.6 pKa
- 2.60±0.10(Predicted)
- 2.7 Water Solubility
- H2O: Insoluble
- 2.8 StorageTemp
- -20°C Freezer
3. Use and Manufacturing
- 3.1 Definition
- ChEBI: A monocarboxylic acid that is the carboxymethyl ester of diclofenac. A non-steroidal anti-inflammatory drug related to diclofenac, it is used in the management of osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis.
- 3.2 Methods of Manufacturing
- Add 500 g of t-butyl aceclofenac to a 2 L three-necked flask, add 500 ml of acetic acid, 25 ml of concentrated hydrochloric acid solution (mass fraction: 37percent), 500 ml of acetic anhydride, and warm to 60 ° C for 3 h.Cooling to 10-30 ° C, stirring and crystallization for 2 h, suction filtration, filter cake with appropriate amount of purified water rinse, vacuum drying at 50 ° C for 8 h, Obtained 418.3g of white solid, which is aceclofenac, yield97.1percent, The HPLC purity was 99.80percent. The largest single impurity was 0.04percent t-butyl aceclofenac. Add 418.3 g of crude aceclofenac to a 2 L three-necked flask, 840 ml of acetic acid, heat until the solid dissolves, dissolve and addInto 8.4g of activated carbon, stirred for 1h, heat filtered, the filtrate was cooled to 25 ° C, stirred and crystallization for 4 h, After suction filtration, the filter cake was rinsed to neutral with an appropriate amount of purified water, and dried under vacuum at 50 ° C for 24 h.The white solid had a dry weight of 412.0 g.It is an aceclofenac refined product with a refined yield of 98.5percent.The HPLC purity was 99.96percent, and the maximum mono-aceclofenac t-butyl ester was 0.005percent.
- 3.3 Usage
- Labeled Aceclofenac, intended for use as an internal standard for the quantification of Aceclofenac by GC- or LC-mass spectrometry.
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- 25-36-50/53
- 4.1 Safety Statements
- S26; S36
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 6.1
- 4.1 Hazard Declaration
- H301-H319-H410
- 4.1 RIDADR
- UN 2811 6.1 / PGIII
- 4.1 Caution Statement
- P273-P301 + P310-P305 + P351 + P338-P501
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- CY1577900
- 4.1 Safety
-
It should not be given to people with porphyria or breast-feeding mothers, and is not recommended for children.
- 4.2 Specification
-
?Aceclofenac , its cas register number is 89796-99-6. It also can be called Aceclofenac [INN:BAN] ; 2-((2,6-Dichlorophenyl)amino)benzeneacetic acid carboxymethyl ester ; 2-(o-(2,6-Dichloranilino)phenylacetoxy)essigsaeure ; Aceclofenaco ; Aceclofenacum ; Glycolic acid, (o-(2,6-dichloroanilino)phenyl)acetate (ester) ; Benzeneacetic acid, 2-((2,6-dichlorophenyl)amino)-, carboxymethyl ester ; Glycolic acid, (o-(2,6-dichloroanilino)phenyl)acetate (ester) . It is a white crystalline solid. Also it is a non-steroidal anti-inflammatory drug and it is manufactured by Intas Biopharmaceuticals.
- 4.3 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| rat |
LD50 |
oral |
130mg/kg (130mg/kg) |
? |
Arzneimittel-Forschung. Drug Research. Vol. 41, Pg. 1265, 1991. |
| women |
TDLo |
oral |
20mg/kg/5D-I (20mg/kg) |
VASCULAR: STRICTIRA; CJAMGES OM VESSE;S
LUNGS, THORAX, OR RESPIRATION: SPUTUM
SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE" |
Annals of Pharmacotherpy. Vol. 29, Pg. 1168, 1995. |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
no data available
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | no data available |
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
2.3 Other hazards which do not result in classification
no data available
6. Synthesis Route
89796-99-6Total: 3 Synthesis Route
8. Other Information
- 8.0 Storage Conditions
- Add 500 g of t-butyl aceclofenac to a 2 L three-necked flask, add 500 ml of acetic acid, 25 ml of concentrated hydrochloric acid solution (mass fraction: 37percent), 500 ml of acetic anhydride, and warm to 60 ° C for 3 h.Cooling to 10-30 ° C, stirring and crystallization for 2 h, suction filtration, filter cake with appropriate amount of purified water rinse, vacuum drying at 50 ° C for 8 h, Obtained 418.3g of white solid, which is aceclofenac, yield97.1percent, The HPLC purity was 99.80percent. The largest single impurity was 0.04percent t-butyl aceclofenac. Add 418.3 g of crude aceclofenac to a 2 L three-necked flask, 840 ml of acetic acid, heat until the solid dissolves, dissolve and addInto 8.4g of activated carbon, stirred for 1h, heat filtered, the filtrate was cooled to 25 ° C, stirred and crystallization for 4 h, After suction filtration, the filter cake was rinsed to neutral with an appropriate amount of purified water, and dried under vacuum at 50 ° C for 24 h.The white solid had a dry weight of 412.0 g.It is an aceclofenac refined product with a refined yield of 98.5percent.The HPLC purity was 99.96percent, and the maximum mono-aceclofenac t-butyl ester was 0.005percent.
- 8.1 Mesh
- Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions.They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)
- 8.2 Absorption
- Aceclofenac is rapidly and completely absorbed from the gastrointestinal tract and circulates mainly as unchanged drug following oral administration. Peak plasma concentrations are reached around 1.25 to 3 hours post-ingestion, and the drug penetrates into the synovial fluid where the concentration may reach up to 60% of that in the plasma. There is no accumulation in regular dosing, with similar maximum plasma concentration (Cmax) and time to reach peak plasma concentration (Tmax) after single and multiple doses.|The main route of elimination is via the urine where the elimination accounts for 70-80% of clearance of the drug. Approximately two thirds of the administered dose is excreted via the urine, mainly as glucuronidated and hydroxylated forms of aceclofenac. About 20% of the dose is excreted into feces.|The volume of distribution is approximately 25 L.|The mean clearance rate is approximately 5 L/h.
- 8.3 Metabolism
- 4'-hydroxyaceclofenac is the main metabolite detected in plasma however other minor metabolites include diclofenac, 5-hydroxyaceclofenac, 5-hydroxydiclofenac, and 4'-hydroxydiclofenac. It is probable that the metabolism of aceclofenac is mediated by CYP2C9.|Aceclofenac has known human metabolites that include 4'-hydroxy-aceclofenac, 5-hydroxy-aceclofenac, and diclofenac.
- 8.4 Biological Half Life
- The mean plasma elimination half-life is approximately 4 hours.
- 8.5 Mesh Entry Terms
- 2-((2,6-dichlorophenyl)amino)phenylacetoxyacetic acid
- 8.6 Usage
- A non-steroidal, anti-inflammatory drug (NSAID) with potent inhibitory activity in several models of inflammation
9. Computational chemical data
- Molecular Weight: 354.18472g/mol
- Molecular Formula: C16H13Cl2NO4
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 353.0221633
- Monoisotopic Mass: 353.0221633
- Complexity: 411
- Rotatable Bond Count: 7
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 5
- Topological Polar Surface Area: 75.6
- Heavy Atom Count: 23
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccB6OAAGAAAAAAAAAAAAAAAAAAAAAAAwYAAAAAAAAAABQAAAHgIQCAAADAqhmCIwyILABgCIAiTSSAKCAAAhBwAIiAFAZogJIHLBl5XGIAhk0AHLyAe8yKCOAAAAAACCABAAAAAAAQQAIAAAAAAAAA==
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aceclofenac
- Purity:99%Packing: 200kg/bag FOB
- Price: 10 USD/kilogram
- Time: 2023/05/31
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