cefadroxil   Click here for help

GtoPdb Ligand ID: 4831

Synonyms: Duricef®
Approved drug
cefadroxil is an approved drug (FDA (1978))
Compound class: Synthetic organic
Comment: Cefadroxil is a cephalosporin antibiotic. Like penicillin it is a β-lactam compound.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 4
Rotatable bonds 5
Topological polar surface area 158.26
Molecular weight 363.09
XLogP -2.6
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C(C(c1ccc(cc1)O)N)NC1C(=O)N2C1SCC(=C2C(=O)O)C
Isomeric SMILES O=C([C@@H](c1ccc(cc1)O)N)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
InChI 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
InChI Key BOEGTKLJZSQCCD-UEKVPHQBSA-N
References
1. Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH. (1995)
Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2.
J Biol Chem, 270 (43): 25672-7. [PMID:7592745]
2. Luckner P, Brandsch M. (2005)
Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1.
Eur J Pharm Biopharm, 59 (1): 17-24. [PMID:15567297]
3. Tamai I, Nakanishi T, Hayashi K, Terao T, Sai Y, Shiraga T, Miyamoto K, Takeda E, Higashida H, Tsuji A. (1997)
The predominant contribution of oligopeptide transporter PepT1 to intestinal absorption of beta-lactam antibiotics in the rat small intestine.
J Pharm Pharmacol, 49 (8): 796-801. [PMID:9379359]
4. Wang Y, Li P, Song F, Yang X, Weng Y, Ma Z, Wang L, Jiang H. (2019)
Substrate Transport Properties of the Human Peptide/Histidine Transporter PHT2 in Transfected MDCK Cells.
J Pharm Sci, 108 (10): 3416-3424. [PMID:31254495]
5. Wenzel U, Gebert I, Weintraut H, Weber WM, Clauss W, Daniel H. (1996)
Transport characteristics of differently charged cephalosporin antibiotics in oocytes expressing the cloned intestinal peptide transporter PepT1 and in human intestinal Caco-2 cells.
J Pharmacol Exp Ther, 277 (2): 831-9. [PMID:8627565]