Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2413)
Drug Name
Cefadroxil
Synonyms
Cefadroxil (JP15); Cefadroxil anhydrous; Cefadroxilo; Cefadroxilo [INN-Spanish]; Cefadroxilum; Cefadroxilum [INN-Latin]; Cephadroxil; Curisafe (TN); D-Cefadroxil; BL-S 578; BL-S578; MJF-11567-3; Sumacef; Sumacef (TN); (6R,7R)-7-((R)-2-Amino-2-(p-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid; (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; (6R,7R)-7-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7beta-{[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino}-3,4-didehydrocepham-4-carboxylic acid; CDX; S 578; S-578
Indication Acute tonsillitis [ICD11: CA03] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 363.4 Topological Polar Surface Area 158
Heavy Atom Count 25 Rotatable Bond Count 4
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
47965
PubChem SID
9095 ; 7847323 ; 7978892 ; 8149235 ; 10990583 ; 11335584 ; 11360823 ; 11362958 ; 11365520 ; 11368082 ; 11373871 ; 11376244 ; 11461795 ; 11466462 ; 11467582 ; 11483750 ; 11486123 ; 11487903 ; 11492081 ; 11493918 ; 14852631 ; 16050996 ; 24892921 ; 25622160 ; 34712894 ; 46509128 ; 47440185 ; 47515253 ; 47515254 ; 47959665 ; 48035040 ; 48334422 ; 48415709 ; 49699087 ; 50124273 ; 57654040 ; 75439952 ; 85279381 ; 87322627 ; 90451718 ; 92125414 ; 93576133 ; 93576712 ; 99301497 ; 103620148 ; 103914339 ; 104133801 ; 104354273 ; 121363085 ; 124766005
ChEBI ID
CHEBI:3479
CAS Number
66592-87-8
TTD Drug ID
D0X9ZC
Formula
C16H17N3O5S
Canonical SMILES
CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O
InChI
1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)/t10-,11-,15-/m1/s1
InChIKey
BOEGTKLJZSQCCD-UEKVPHQBSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
Cefadroxil M1 PDM007137 N. A. Hydrolysis - Hydrolysis of cyclic tertiary carboxamide 1 Human
Cefadroxil M2 PDM007138 N. A. Conjugation - Glycine conjugation 1 Human
Cefadroxil M3 PDM007139 N. A. Conjugation - Aromatic OH-glucuronidation 1 Human
Cefadroxil M4 PDM007140 N. A. Conjugation - O-Glucuronidation of aliphatic acid 1 Human
Cefadroxil M5 PDM007141 N. A. Conjugation - Carnitine conjugation 1 Human
Cefadroxil M6 PDM007142 N. A. Reduction - Reduction of alpha,beta-unsaturated carbon-carbon double bond adjacent to electron withdrawing group 1 Gut microbial environment
Cefadroxil M7 PDM007143
2666
Reduction - 4'-Dehydroxylation of substituted benzene 1 Gut microbial environment
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
N-acylhomoserine lactone acylase (lacA) DME1021 Acidovorax ebreus
A0A0A1VBK6_9BURK
3.5.1.97
[2]
References
1 Cefadroxil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 A novel quorum-quenching N-acylhomoserine lactone acylase from Acidovorax sp. strain MR-S7 mediates antibiotic resistance. Appl Environ Microbiol. 2017 Jun 16;83(13). pii: e00080-17.

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