cefetamet   Click here for help

GtoPdb Ligand ID: 12416

Synonyms: Ro 15-8074
Compound class: Synthetic organic
Comment: Cefetamet is a semisynthetic, broad-spectrum, third generation cephalosporin and belongs to the β-lactam class of antibacterial compounds. To provide acceptable bioavailability for oral use it is formulated as a pivoxil ester prodrug (cefetamet pivoxil, PubChem CID 5486182) [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 6
Topological polar surface area 197.28
Molecular weight 397.43
XLogP -2.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC1=C(C(=O)O)N2C(=O)[C@H]([C@H]2SC1)NC(=O)/C(=N\OC)/C3=CSC(=N3)N
Isomeric SMILES CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)O
InChI InChI=1S/C14H15N5O5S2/c1-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24-2)6-4-26-14(15)16-6/h4,8,12H,3H2,1-2H3,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
InChI Key MQLRYUCJDNBWMV-GHXIOONMSA-N
References
1. Blouin RA, Stoeckel K. (1993)
Cefetamet pivoxil clinical pharmacokinetics.
Clin Pharmacokinet, 25 (3): 172-88. [PMID:8222459]
2. Bryson HM, Brogden RN. (1993)
Cefetamet pivoxil. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use.
Drugs, 45 (4): 589-621. [PMID:7684677]
3. Fass RJ, Helsel VL. (1986)
In vitro activities of Ro 19-5247 and Ro 15-8074, new oral cephalosporins.
Antimicrob Agents Chemother, 30 (3): 429-34. [PMID:3777906]
4. Ng WS, Chau PY, Leung YK, Wong PC. (1985)
In vitro activity of Ro 15-8074, a new oral cephalosporin, against Neisseria gonorrhoeae.
Antimicrob Agents Chemother, 28 (3): 461-3. [PMID:3935045]
5. Wise R, Andrews JM, Piddock LJ. (1986)
In vitro activity of Ro 15-8074 and Ro 19-5247, two orally administered cephalosporin metabolites.
Antimicrob Agents Chemother, 29 (6): 1067-72. [PMID:3729361]