cephalexin   Click here for help

GtoPdb Ligand ID: 4832

Synonyms: cefalexin | Ceporex® | Keflex®
Approved drug
cephalexin is an approved drug (FDA (1971, prior history not available))
Compound class: Synthetic organic
Comment: Cephalexin is a cephalosporin antibacterial.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 138.03
Molecular weight 347.09
XLogP -2.19
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES NC(c1ccccc1)C(=O)NC1C(=O)N2C1SCC(=C2C(=O)O)C
Isomeric SMILES N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
InChI InChI=1S/C16H17N3O4S/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23)/t10-,11-,15-/m1/s1
1. Anand BS, Patel J, Mitra AK. (2003)
Interactions of the dipeptide ester prodrugs of acyclovir with the intestinal oligopeptide transporter: competitive inhibition of glycylsarcosine transport in human intestinal cell line-Caco-2.
J Pharmacol Exp Ther, 304 (2): 781-91. [PMID:12538834]
2. Covitz KM, Amidon GL, Sadée W. (1996)
Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells.
Pharm Res, 13 (11): 1631-4. [PMID:8956326]
3. Fujimoto Y, Ishizaka Y, Tahira T, Sone H, Takahashi H, Enomoto K, Mori M, Sugimura T, Nagao M. (1991)
Possible involvement of c-myc but not ras genes in hepatocellular carcinomas developing after spontaneous hepatitis in LEC rats.
Mol Carcinog, 4 (4): 269-74. [PMID:1714740]
4. 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]
5. 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]
6. Tanihara Y, Masuda S, Sato T, Katsura T, Ogawa O, Inui K. (2007)
Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters.
Biochem Pharmacol, 74 (2): 359-71. [PMID:17509534]
7. Terada T, Saito H, Mukai M, Inui K. (1997)
Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells.
Am J Physiol, 273 (5 Pt 2): F706-11. [PMID:9374833]
8. Terada T, Saito H, Mukai M, Inui KI. (1996)
Identification of the histidine residues involved in substrate recognition by a rat H+/peptide cotransporter, PEPT1.
FEBS Lett, 394 (2): 196-200. [PMID:8843163]