Details of the Drug

General Information of Drug (ID: DMWADLM)

Drug Name
Diclofenac glucuronide
Synonyms
Diclofenac acyl glucuronide; Diclofenac glucuronide; CHEBI:59609; Diclofenac beta-D-glucosiduronic acid; UNII-C8BEZ13XEN; C8BEZ13XEN; CHEMBL3527338; 64118-81-6; 1-O-({2-[(2,6-dichlorophenyl)amino]phenyl}acetyl)-beta-D-glucopyranuronic acid; Diclofenac acyl-D-glucuronide; Diclofenac O-glucuronide; Epitope ID:131803; Diclofenac-beta-D-glucuronide; SCHEMBL4258872; Diclofenac-acyl-beta-D-glucuronide; BDBM50088512; ZINC35048352; Q27126801; 2-(2,6-Dichloroanilino)phenylacetic acid beta-D-glucopyranuronosyl ester
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 472.3
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 7
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 9
Chemical Identifiers
Formula
C20H19Cl2NO8
IUPAC Name
(2S,3S,4S,5R,6S)-6-[2-[2-(2,6-dichloroanilino)phenyl]acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Canonical SMILES
C1=CC=C(C(=C1)CC(=O)OC2C(C(C(C(O2)C(=O)O)O)O)O)NC3=C(C=CC=C3Cl)Cl
InChI
InChI=1S/C20H19Cl2NO8/c21-10-5-3-6-11(22)14(10)23-12-7-2-1-4-9(12)8-13(24)30-20-17(27)15(25)16(26)18(31-20)19(28)29/h1-7,15-18,20,23,25-27H,8H2,(H,28,29)/t15-,16-,17+,18-,20+/m0/s1
InChIKey
JXIKYYSIYCILNG-HBWRTXEVSA-N
Cross-matching ID
PubChem CID
16084218
ChEBI ID
CHEMBL3527338
CAS Number
64118-81-6
INTEDE ID
DR2228
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Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Beta-glucuronidase (uidA) DE7Y39R A0A2A5L2J1_LACRH Substrate [1]
Beta-glucuronidase (uidA) DE9EXRN A0A173S5S4_9FIRM Substrate [1]
Beta-glucuronidase (uidA) DECW8T2 A0A076IX12_9BACE Substrate [1]
Beta-glucuronidase (uidA) DEB8PZ0 Q6W7J7_RUMGN Substrate [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Gene/Protein Processing [2]
UDP-glucuronosyltransferase 2B7 OT2Q71VQ UD2B7_HUMAN Biotransformations [3]
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References

1 tructure, function, and inhibition of drug reactivating human gut microbial beta-glucuronidases. Sci Rep. 2019 Jan 29;9(1):825.
2 Toxicological evaluation of acyl glucuronides utilizing half-lives, peptide adducts, and immunostimulation assays. Toxicol In Vitro. 2015 Dec 25;30(1 Pt B):241-9.
3 Effect of UGT2B7*2 and CYP2C8*4 polymorphisms on diclofenac metabolism. Toxicol Lett. 2018 Mar 1;284:70-78. doi: 10.1016/j.toxlet.2017.11.038. Epub 2017 Dec 2.