2-(pyrrolidin-1-yl)ethan-1-ol; 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid

• ChemBase ID: 126991
• Molecular Formular: C20H24Cl2N2O3
• Molecular Mass: 411.32216
• Monoisotopic Mass: 410.116398
• SMILES: O=C(O)Cc1ccccc1Nc1c(Cl)cccc1Cl.OCCN1CCCC1
• Canonical SMILES: OC(=O)Cc1ccccc1Nc1c(Cl)cccc1Cl.OCCN1CCCC1
• InChI: InChI=1S/C14H11Cl2NO2.C6H13NO/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(18)19;8-6-5-7-3-1-2-4-7/h1-7,17H,8H2,(H,18,19);8H,1-6H2
• InChIKey: DCERVXIINVUMKU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(pyrrolidin-1-yl)ethan-1-ol; 2-{2-[(2,6-dichlorophenyl)amino]phenyl}acetic acid
• IUPAC Traditional name: diclofenac; epolamine
• Brand Name: Aclonac, Cataflam, Voltaren
• Synonyms: Diclofenac

Database IDs

• CAS Number: 15307-86-5
• PubChem SID: 162221314
• PubChem CID: 3033; 114753
• CHEBI ID: 47381
• ATC CODE: M02AA15; M01AB05; S01BC03; D11AX18
• CHEMBL: 139
• Chemspider ID: 2925
• DrugBank ID: DB00586
• IUPHAR ligand ID: 2714
• KEGG ID: D07816
• Unique Ingredient Identifier: 144O8QL0L1
• Wikipedia Title: Diclofenac
• Medline Plus: a689002

CALCULATED PROPERTIES

• Acid pKa: 3.995652
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 2.7453504
• LogD (pH = 7.4): 1.0974493
• Log P: 4.2590094
• Molar Refractivity: 75.4614 cm^3
• Polarizability: 29.034273 Å^3
• Polar Surface Area: 49.33 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: oral, rectal, intramuscular, intravenous (renal- and gallstones), topical
• Excretion: biliary, only 1% in urine
• Half Life: 1.2-2 hr (35% of the drug enters enterohepatic recirculation)
• Metabolism: hepatic, no active metabolites exist
• Protein Bound: more than 99%
• Legal Status: P (UK); Rx-only most preparations/countries, limited OTC in some countries, manufacture and veterinary use is banned in India, Nepal and Pakistan due to imminent extinction of local vultures
• Pregnancy Category: C (1st. and 2nd. trimenon), D (third trimenon); C (Australia)