ritipenem   Click here for help

GtoPdb Ligand ID: 10854

Synonyms: FCE-22101 | FCE22101
Compound class: Synthetic organic
Comment: Ritipenem (FCE 22101) is a penem antibacterial compound belonging to the β-lactam group and exhibits broad-spectrum bacteriolytic activity [3-4]. Its activity profile is similar to that of imipenem, but it shows no activity against Pseudomonas aeruginosa. It is delivered as the orally bioavailable prodrug ritipenem acoxyl (Penemac®, FCE-22891).
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 5
Topological polar surface area 155.46
Molecular weight 288.04
XLogP -1.49
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 NC(=O)OCC1=C(C(=O)O)N2[C@H](S1)[C@H](C2=O)[C@H](O)C
Isomeric SMILES NC(=O)OCC1=C(C(=O)O)N2[C@H](S1)[C@H](C2=O)[C@H](O)C
InChI InChI=1S/C10H12N2O6S/c1-3(13)5-7(14)12-6(9(15)16)4(19-8(5)12)2-18-10(11)17/h3,5,8,13H,2H2,1H3,(H2,11,17)(H,15,16)/t3-,5+,8-/m1/s1
InChI Key IKQNRQOUOZJHTR-UWBRJAPDSA-N
References
1. Afonso A, Hon F, Weinstein J, Gentles M, Shapiro E, Ganguly A, Naples L, Hare R, Miller G. (1993)
Penems containing amino acid derived substituents at C-2.
Bioorg Med Chem Lett, 3: 2177-2182. DOI: 10.1016/S0960-894X(01)80921-5
2. Altamura M, Perrotta E, Sbraci P, Pestellini V, Arcamone F, Cascio G, Lorenzi L, Satta G, Morandotti G, Sperning R. (1995)
2-Substituted penems with amino acid-related side chains: synthesis and antibacterial activity of a new series of beta-lactam antibiotics.
J Med Chem, 38 (21): 4244-56. [PMID:7473551]
3. Inui T, Oshida T, Endo T, Matsushita T. (1999)
Potent bacteriolytic activity of ritipenem associated with a characteristic profile of affinities for penicillin-binding proteins of Haemophilus influenzae.
Antimicrob Agents Chemother, 43 (10): 2534-7. [PMID:10508039]
4. Poggesi I, Spinelli R, Frigerio E, Strolin Benedetti M, Carra L, Sassella D, Rimoldi R. (1997)
A study of the pharmacokinetics and tolerability of ritipenem acoxil in healthy volunteers following multiple oral dosing.
J Antimicrob Chemother, 40 (2): 291-4. [PMID:9301999]