Diclofenac
- diclofenac
- 15307-86-5
- Diclofenac acid
- dichlofenac
- Diclophenac
- Create:2005-03-25
- Modify:2025-01-04
- Dichlofenal
- Diclofenac
- Diclofenac Potassium
- Diclofenac Sodium
- Diclofenac, Sodium
- Diclonate P
- Diclophenac
- Dicrofenac
- Feloran
- GP 45,840
- GP-45,840
- GP45,840
- Novapirina
- Orthofen
- Orthophen
- Ortofen
- Sodium Diclofenac
- SR 38
- SR-38
- SR38
- Voltaren
- Voltarol
- diclofenac
- 15307-86-5
- Diclofenac acid
- dichlofenac
- Diclophenac
- Diclofenaco
- Diclofenacum
- 2-(2-((2,6-Dichlorophenyl)amino)phenyl)acetic acid
- ProSorb-D
- Diclofenac resinate
- Voltarol
- Diclofenac free acid
- Zorovolex
- Zorvolex
- Diclofenamic acid
- 2-(2,6-Dichloroanilino)phenylacetic Acid
- 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
- Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-
- 2-[2-(2,6-dichloroanilino)phenyl]acetic acid
- 2-((2,6-Dichlorophenyl)amino)benzeneacetic acid
- CHEBI:47381
- HSDB 7234
- Benzeneacetic acid, 2-((2,6-dichlorophenyl)amino)-
- EINECS 239-348-5
- Solaraze
- UNII-144O8QL0L1
- BRN 2146636
- 2-[2-(2,6-dichlorophenyl)aminophenyl]ethanoic acid
- Voltaren-XR
- ACETIC ACID, (o-(2,6-DICHLOROANILINO)PHENYL)-
- 144O8QL0L1
- LAS41007
- LAS-41007
- MFCD00056694
- 2-[(2,6-Dichlorophenyl)amino]benzeneacetic acid
- CHEMBL139
- {2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
- 2-[2,6-DICHLOROPHENYL)AMINO]BENZENEACETIC ACID
- [2-(2,6-Dichloroanilino)phenyl]acetic acid
- DTXSID6022923
- EC 239-348-5
- 15307-86-5 (free)
- Olfen
- Dicrofenac
- Solaraze (TN)
- DICLOFENAC (MART.)
- DICLOFENAC [MART.]
- (O-(2,6-DICHLOROANILINO)PHENYL)ACETIC ACID
- Enfenamic acid; N-Phenethylanthranilic acid; RH 8
- 2-[2-[(2,6-dichlorophenyl)amino]phenyl]acetic acid
- (2-((2,6-DICHLOROPHENYL)AMINO)PHENYL)ACETIC ACID
- 2-[2-[(2,6-Dichlorophenyl)amino]phenyl]acetic Acid (Diclofenac)
- Diclofenacum [INN-Latin]
- Diclofenaco [INN-Spanish]
- DIF
- (2-(2,6-dichloroanilino)phenyl)acetic acid
- ACECLOFENAC IMPURITY A (EP IMPURITY)
- ACECLOFENAC IMPURITY A [EP IMPURITY]
- (2-((2,6-Dichlorophenyl)amino-phenyl)acetic acid (HD)
- Diclofenac [USAN:INN:BAN]
- ISV-205
- Zorvolex (TN)
- 57 - Pharmaceuticals
- Spectrum_000930
- DICLOFENAC [MI]
- S17 - Pharmaceuticals
- DICLOFENAC [INN]
- 128402-48-2
- Diclofenac (USAN/INN)
- Prestwick0_000594
- Prestwick1_000594
- Prestwick2_000594
- Prestwick3_000594
- Spectrum2_000991
- Spectrum3_000385
- Spectrum4_000506
- Spectrum5_000867
- DICLOFENAC [HSDB]
- DICLOFENAC [USAN]
- DICLOFENAC [VANDF]
- Epitope ID:116873
- AM01 - Analgesic mixture
- SCHEMBL2799
- DICLOFENAC [WHO-DD]
- Lopac0_000441
- Oprea1_011155
- BSPBio_000468
- BSPBio_002169
- KBioGR_001051
- KBioGR_002306
- KBioSS_001410
- KBioSS_002308
- MLS006011795
- BIDD:GT0380
- DivK1c_000272
- DivK1c_000402
- SPBio_001081
- SPBio_002687
- BPBio1_000516
- DTXCID802923
- GTPL2714
- DICLOFENAC [ORANGE BOOK]
- BDBM13066
- HMS501E04
- KBio1_000272
- KBio1_000402
- KBio2_001410
- KBio2_002306
- KBio2_003978
- KBio2_004874
- KBio2_006546
- KBio2_007442
- KBio3_001389
- KBio3_002786
- M01AB05
- M02AA15
- S01BC03
- 2b17
- cMAP_000014
- NINDS_000272
- NINDS_000402
- HMS2090C10
- HMS3886F09
- BCP09087
- BCP13860
- s6073
- STK984493
- AKOS001579542
- DB00586
- KS-1258
- IDI1_000272
- IDI1_000402
- NCGC00021125-01
- NCGC00021125-02
- NCGC00021125-11
- AC-27673
- DA-72738
- HY-15036
- o-(2,6-dichloroanilino)phenylacetic acid
- SMR001550371
- SY038623
- SBI-0051341.P003
- Diclofenac 1000 microg/mL in Acetonitrile
- D3748
- NS00000212
- UNM000001216103
- [2-(2,6-Dichloroanilino)phenyl]acetic acid #
- C01690
- D07816
- D30801
- EN300-119509
- H10425
- [o-(2,6-dichloro-anilino)-phenyl]-acetic acid
- 2-[(2,6-dichlorophenyl)amino]phenylacetic acid
- AB01275502-01
- AB01275502_02
- 2-(2-(2,6-dichlorophenylamino)phenyl)acetic acid
- 2-[(2,6-dichlorophenyl)amino]-benzeneacetic acid
- 2-[(2,6-dichlorophenyl)amino]-phenyl-acetic acid
- Q244408
- [2-(2,6-dichloro-phenylamino)-phenyl]-acetic acid
- 2-[(2,6-dichlorophenyl)-amino]-benzeneacetic acid
- 2-[(2,6-dichlorophenyl)-amino]-phenyl-acetic acid
- 2-[2-(2,6-dichlorophenylamino)phenyl]-acetic acid
- SR-01000003041-3
- 2-[2-(2,6-dichlorophenylamino)-phenyl]-acetic acid
- BRD-K08252256-224-02-9
- BRD-K08252256-236-05-6
- BRD-K08252256-236-17-1
- BRD-K08252256-236-32-0
- BRD-K08252256-236-33-8
- BRD-K08252256-237-02-1
- Z57664869
- F0722-0745
151.48 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
155.98 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
166.89 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
163.79 Ų [M+Na]+
162.87 Ų [M-H]-
156.92 Ų [M+H]+
214.0 99.99
216.0 40.27
242.0 39.02
295.0 38.54
215.0 27.73
214 99.99
216 40.27
242 39.02
295 38.54
215 27.73
250.0196 100
214.0429 6.48
294.0095 3.01
178.0662 1.42
214.04355 100
215.0549 98.71
250.02229 14.01
180.07977 2.95
179.07552 1.99
214.04112 999
214.04071 943
250.01779 457
215.04993 194
278.01395 149
250.02 999
294.00948 25
178.06718 12
214.04329 11
250.02022 999
252.01657 396
251.02315 157
221.15451 157
236.10519 129
214.04253 999
250.01901 459
215.05005 180
278.01413 157
296.02386 66
D - Dermatologicals
D11 - Other dermatological preparations
D11A - Other dermatological preparations
D11AX - Other dermatologicals
D11AX18 - Diclofenac
M - Musculo-skeletal system
M02 - Topical products for joint and muscular pain
M02A - Topical products for joint and muscular pain
M02AA - Antiinflammatory preparations, non-steroids for topical use
M02AA15 - Diclofenac
Diclofenac has known human metabolites that include (2S,3S,4S,5R)-6-[2-[2-(2,6-Dichloroanilino)phenyl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid, 4'-hydroxydiclofenac, and 5-hydroxydiclofenac.
Diclofenac is a known human metabolite of aceclofenac.
- Cytoplasm
- Extracellular
- Membrane
Use (kg) in Switzerland (2009): >5000
Use (kg; approx.) in Germany (2009): >75000
Use (kg; exact) in Germany (2009): 91583
Use (kg) in USA (2002): 9480
Use (kg) in France (2004): 9896
Consumption (g per capita) in Switzerland (2009): 0.64
Consumption (g per capita; approx.) in Germany (2009): 0.92
Consumption (g per capita; exact) in Germany (2009): 1.1
Consumption (g per capita) in the USA (2002): 0.034
Consumption (g per capita) in France (2004): 0.16
Excretion rate: 0.16
Calculated removal (%): 86.6
H301 (98.4%): Toxic if swallowed [Danger Acute toxicity, oral]
H311 (85.9%): Toxic in contact with skin [Danger Acute toxicity, dermal]
H315 (84.4%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (84.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (84.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
Aggregated GHS information provided per 64 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Acute Tox. 3 (98.4%)
Acute Tox. 3 (85.9%)
Skin Irrit. 2 (84.4%)
Eye Irrit. 2 (84.4%)
STOT SE 3 (84.4%)
Acute Tox. 3 (29.5%)
Acute Tox. 4 (40.9%)
Repr. 2 (21.6%)
Repr. 2 (12.5%)
STOT RE 1 (31.8%)
Aquatic Chronic 2 (51.1%)
IMAP assessments - Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-: Human health tier I assessment
IMAP assessments - Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-: Environment tier I assessment
Elevated serum aminotransferase levels have been reported in up to 15% of patients taking oral diclofenac chronically, but are greater than 3 times the upper limit of normal in only 2% to 4% (Cases 1 and 2). Clinically apparent and symptomatic liver disease with jaundice due to diclofenac is rare (1 to 5 cases per 100,000 prescriptions, occurring in 1 to 5 persons per 10,000 exposed). Nevertheless, more than a hundred instances of clinically apparent liver injury due to diclofenac have been reported in the literature and, in most case series, diclofenac ranks in the top 10 causes of drug induced liver injury. The time to onset of liver injury varies from within a week to over a year after starting. The majority of cases present within 2 to 6 months (Cases 3 and 4), and the more severe cases tend to present earlier. The pattern of injury is almost exclusively hepatocellular, although cases presenting with mixed patterns have been reported. The clinical picture is that of jaundice preceded by anorexia, nausea, vomiting and malaise. Fever and rash occur in 25% of cases and some cases have immunoallergic features, while others resemble chronic hepatitis and have autoimmune features. In most cases, liver histology reveals an acute lobular hepatitis. However, a cases with prolonged latency diclofenac hepatotoxicity can have clinical and histologic features of chronic hepatitis (Case 2). There seems to be greater susceptibility for diclofenac liver injury among women than men. The injury can be severe, and several cases of acute liver failure have been attributed to diclofenac.
Likelihood score: A (well known cause of clinically apparent liver injury).
Topical forms of diclofenac (solutions, gels, creams, patches) have been associated with only a low rate of serum enzyme elevations (generally less than 1%) that may be no greater than occurs with placebo or vehicle application. However, product labels for topical diclofenac mention the possibility of liver injury and at least one case of clinically apparent liver injury attributed to topical diclofenac has been reported in the literature. Nevertheless, clinically apparent liver injury due to topical forms of diclofenac must be exceedingly rare.
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
◉ Summary of Use during Lactation
Data on excretion of diclofenac into milk are poor, but the drug has a short half-life and little glucuronide metabolite formation. Levels in milk appear to be quite low. Most reviewers consider diclofenac to be acceptable during breastfeeding. Other agents having more published information may be preferred, especially while nursing a newborn or preterm infant.
Maternal use of diclofenac topical gel or eye drops would not be expected to cause any adverse effects in breastfed infants. To substantially diminish the amount of drug that reaches the breastmilk after using eye drops, place pressure over the tear duct by the corner of the eye for 1 minute or more, then remove the excess solution with an absorbent tissue.
◉ Effects in Breastfed Infants
In one study, 30 mothers undergoing elective cesarean section were allowed to use 25 mg diclofenac suppositories along with either spinal or spinal and epidural anesthesia with a local anesthetic after delivery. The spinal anesthetic group used an average of 56 mg of diclofenac on the day of delivery and 33 mg on the next day whereas the women receiving both spinal and epidural anesthesia used 21 and 18 mg. No mention was made of adverse effects on the breastfed infants.
A breastfed infant developed urticaria on day 15 of life. Her mother had been taking diclofenac (dosage unspecified) for pain since her cesarean section delivery. Diclofenac is a possible cause of the urticaria; however, the infant had also received hepatitis B vaccination 7 days before and the authors thought that it was a more likely cause of the reaction.
◉ Effects on Lactation and Breastmilk
A randomized, double-blind study was performed in pregnant women scheduled for cesarean section under spinal anesthesia with bupivacaine and fentanyl. Patients received either 100 mg diclofenac (n = 100), 100 mg tramadol (n = 100) or placebo (glycerin suppositories) n = 100, all given as rectal suppositories every 8 hours for the first 24 hours after surgery. The time to initiate breastfeeding was significantly shorter among mothers who received diclofenac than a placebo, 1.5 vs 4.1 hours with breastfeeding support and 3.5 vs 6.2 hours without support. Diclofenac was slightly more effective than tramadol among mothers who received no support (3.5 vs 3.7 hours).
- US6407079
- US8217078
- US8546450
- US8618164
- US8741956
- US5985850
- US5792753
- US5914322
- US5607690
- US6974595
- US7482377
- US7759394
- US8097651
- US8927604
- US6365180
- US7662858
- US7884095
- US7939518
- US8110606
- US8623920
- US6287594
- US8946292
- US9180095
- US9186328
- US8999387
- US9173854
- US9180096
- US9017721
- US8679544
- US8252838
- US8563613
- US8871809
- US9132110
- US9220784
- US9101591
- US9168305
- US9066913
- US9168304
- US9561200
- US9370501
- US9375412
- US9339552
- US9539335
- US9415029
- US9339551
- US9827197
- US11351133
- US11344520
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=DCOPUUMXTXDBNB-UHFFFAOYSA-N
- Avoid excessive or chronic alcohol consumption. Co-administration with alcohol may increase the risk of gastrointestinal side effects, such as ulceration.
- Take with food. Food reduces gastric irritation.
- Australian Industrial Chemicals Introduction Scheme (AICIS)Benzeneacetic acid, 2-[(2,6-dichlorophenyl)amino]-https://services.industrialchemicals.gov.au/search-assessments/
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusDiclofenac [USAN:INN:BAN]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0015307865ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useDiclofenachttps://www.drugbank.ca/drugs/DB00586
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- European Chemicals Agency (ECHA)LICENSEUse of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.https://echa.europa.eu/web/guest/legal-noticeDiclofenachttps://chem.echa.europa.eu/100.035.7552-((2,6-Dichlorophenyl)amino)benzeneacetic acidhttps://echa.europa.eu/substance-information/-/substanceinfo/100.107.4842-((2,6-Dichlorophenyl)amino)benzeneacetic acid (EC: 616-599-2)https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/6249Diclofenac (EC: 239-348-5)https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/62870
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- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-lawDiclofenachttp://www.nist.gov/srd/nist1a.cfm
- SpectraBaseDiclofenac -H2O (277)https://spectrabase.com/spectrum/JolUAuY5v8cDCOPUUMXTXDBNB-UHFFFAOYSA-Nhttps://spectrabase.com/spectrum/8BZVzGLqW3g
- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlUSP drug classificationhttp://www.genome.jp/kegg-bin/get_htext?br08302.kegAnatomical Therapeutic Chemical (ATC) classificationhttp://www.genome.jp/kegg-bin/get_htext?br08303.kegTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.kegRisk category of Japanese OTC drugshttp://www.genome.jp/kegg-bin/get_htext?br08312.keg
- Kruve Lab, Ionization & Mass Spectrometry, Stockholm Universitydiclofenac
- MassBank Europe
- Metabolomics Workbench
- Natural Product Activity and Species Source (NPASS)
- Nature Chemical Biology
- NIPH Clinical Trials Search of Japan
- NLM RxNorm TerminologyLICENSEThe RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.htmldiclofenachttps://rxnav.nlm.nih.gov/id/rxnorm/3355
- NMRShiftDB
- WHO Anatomical Therapeutic Chemical (ATC) ClassificationLICENSEUse of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.https://www.whocc.no/copyright_disclaimer/
- PharmGKBLICENSEPharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).https://www.pharmgkb.org/page/policies
- PharosLICENSEData accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.https://pharos.nih.gov/about
- Protein Data Bank in Europe (PDBe)
- RCSB Protein Data Bank (RCSB PDB)LICENSEData files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.https://www.rcsb.org/pages/policies
- Springer Nature
- Thieme ChemistryLICENSEThe Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc-nd/4.0/
- WikidataDiclofenachttps://www.wikidata.org/wiki/Q244408
- WikipediaDiclofenachttps://en.wikipedia.org/wiki/Diclofenac
- Wiley
- Medical Subject Headings (MeSH)LICENSEWorks produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.https://www.nlm.nih.gov/copyright.htmlAnti-Inflammatory Agents, Non-Steroidalhttps://www.ncbi.nlm.nih.gov/mesh/68000894Cyclooxygenase Inhibitorshttps://www.ncbi.nlm.nih.gov/mesh/68016861
- PubChem
- GHS Classification (UNECE)GHS Classification Treehttp://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
- EPA Substance Registry ServicesEPA SRS List Classificationhttps://sor.epa.gov/sor_internet/registry/substreg/LandingPage.do
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
- PATENTSCOPE (WIPO)SID 403461915https://pubchem.ncbi.nlm.nih.gov/substance/403461915
- NCBI