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15307-86-5 molecular structure
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2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid

ChemBase ID: 468
Molecular Formular: C14H11Cl2NO2
Molecular Mass: 296.14864
Monoisotopic Mass: 295.01668396
SMILES and InChIs

SMILES:
Clc1c(Nc2c(CC(=O)O)cccc2)c(Cl)ccc1
Canonical SMILES:
OC(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl
InChI:
InChI=1S/C14H11Cl2NO2/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19/h1-7,17H,8H2,(H,18,19)
InChIKey:
DCOPUUMXTXDBNB-UHFFFAOYSA-N

Cite this record

CBID:468 http://www.chembase.cn/molecule-468.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
IUPAC Traditional name
diclofenac
Brand Name
Allvoran
Apo-Diclo
Assaren
Benfofen
Cataflam
Delphimix
Dichlofenac
Dichronic
Diclo-Phlogont
Diclo-Puren
Diclobenin
Diclord
Dicloreum
Dolobasan
Duravolten
Ecofenac
Effekton
Kriplex
Neriodin
Novapirina
Novo-Difenac
Novo-Difenac SR
Nu-Diclo
Pennsaid
Primofenac
Prophenatin
Rhumalgan
Solaraze
Solaraze T
Tsudohmin
Valetan
Voldal
Voltaren
Voltaren Ophtha
Voltaren Ophthalmic
Voltaren Rapide
Voltaren SR
Voltaren-XR
Voltarol
Xenid
Dyloject
ProSorb-D
Synonyms
Diclofenac Sodium
Diclofenac Potassium
Diclofenac Acid
ISV-205
Diclofenac
2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
2-(2-((2,6-Dichlorophenyl)amino)phenyl)acetic acid
CAS Number
15307-86-5
MDL Number
MFCD00451393
MFCD00056694
PubChem SID
160963931
46504644
PubChem CID
3033

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.995652  H Acceptors
H Donor LogD (pH = 5.5) 2.7453504 
LogD (pH = 7.4) 1.0974493  Log P 4.2590094 
Molar Refractivity 75.4614 cm3 Polarizability 29.034273 Å3
Polar Surface Area 49.33 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 4.98  LOG S -4.82 
Solubility (Water) 4.47e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Product Information Bioassay(PubChem)
Solubility
50 mg/mL (sodium salt) [Sigma Aldrich] expand Show data source
Hydrophobicity(logP)
3.9 expand Show data source
4.726 expand Show data source
Purity
95% expand Show data source
95+% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00586 external link
Item Information
Drug Groups approved
Description A non-steroidal anti-inflammatory agent (NSAID) with antipyretic and analgesic actions. It is primarily available as the sodium salt. [PubChem]
Indication For the acute and chronic treatment of signs and symptoms of osteoarthritis and rheumatoid arthritis.
Pharmacology Diclofenac is an acetic acid nonsteroidal antiinflammatory drug (NSAID) with analgesic and antipyretic properties. Diclofenac is used to treat pain, dysmenorrhea, ocular inflammation, osteoarthritis, rheumatoid arthritis, ankylosing spondylitis, and actinic keratosis
Toxicity Symptoms of overdose include loss of consciousness, increased intracranial pressure, and aspiration pneumonitis. LD50=390mg/kg (orally in mice)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Completely absorbed from the gastrointestinal tract.
Half Life 2 hours
Protein Binding More than 99%
Elimination Diclofenac is eliminated through metabolism and subsequent urinary and biliary excretion of the glucuronide and the sulfate conjugates of the metabolites. Little or no free unchanged diclofenac is excreted in the urine. Approximately 65% of the dose is excreted in the urine and approximately 35% in the bile as conjugates of unchanged diclofenac plus metabolites.
Distribution * 1.3 L/kg
Clearance * oral cl=622 mL/min [healthy]
* renal cl <1 mL/min [healthy]
References
Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [Pubmed]
Solomon DH, Avorn J, Sturmer T, Glynn RJ, Mogun H, Schneeweiss S: Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum. 2006 May;54(5):1378-89. [Pubmed]
FitzGerald GA, Patrono C: The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med. 2001 Aug 9;345(6):433-42. [Pubmed]
Graham DJ: COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA. 2006 Oct 4;296(13):1653-6. Epub 2006 Sep 12. [Pubmed]
Brater DC: Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage. 2002 Apr;23(4 Suppl):S15-20; discussion S21-3. [Pubmed]
Sigma Aldrich [Link]
Gan TJ: Diclofenac: an update on its mechanism of action and safety profile. Curr Med Res Opin. 2010 Jul;26(7):1715-31. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Sigma Aldrich Link
  • • Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. Pubmed
  • • Solomon DH, Avorn J, Sturmer T, Glynn RJ, Mogun H, Schneeweiss S: Cardiovascular outcomes in new users of coxibs and nonsteroidal antiinflammatory drugs: high-risk subgroups and time course of risk. Arthritis Rheum. 2006 May;54(5):1378-89. Pubmed
  • • FitzGerald GA, Patrono C: The coxibs, selective inhibitors of cyclooxygenase-2. N Engl J Med. 2001 Aug 9;345(6):433-42. Pubmed
  • • Graham DJ: COX-2 inhibitors, other NSAIDs, and cardiovascular risk: the seduction of common sense. JAMA. 2006 Oct 4;296(13):1653-6. Epub 2006 Sep 12. Pubmed
  • • Brater DC: Renal effects of cyclooxygyenase-2-selective inhibitors. J Pain Symptom Manage. 2002 Apr;23(4 Suppl):S15-20; discussion S21-3. Pubmed
  • • Gan TJ: Diclofenac: an update on its mechanism of action and safety profile. Curr Med Res Opin. 2010 Jul;26(7):1715-31. Pubmed
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PATENTS

PATENTS

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