LENAPENEM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H29N3O5S
Molecular Weight	399.505
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12[C@@H](C)C(S[C@@H]3CN[C@@]([H])(C3)[C@H](O)CCNC)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C(O)=O

InChI

InChIKey=PZLOCBSBEUDCPF-YJIVIRPOSA-N

InChI=1S/C18H29N3O5S/c1-8-14-13(9(2)22)17(24)21(14)15(18(25)26)16(8)27-10-6-11(20-7-10)12(23)4-5-19-3/h8-14,19-20,22-23H,4-7H2,1-3H3,(H,25,26)/t8-,9-,10+,11+,12-,13-,14-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9301984
Curator's Comment: description was created based on several sources, including, https://www.ncbi.nlm.nih.gov/pubmed/9099223

Lenapenem is an anti-bacterial agent that was tested in late 90's in phase II clinical trials against bacterial infections. Lenapenem was shown to be active against both Gram-positive and Gram-negative bacteria and exerted its therapeutic effect by inhibiting penicillin binding proteins. The development of the drug was terminated due to the safety reason.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9099223	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9301984	Curative		Phase II 1132	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
In vitro and in vivo antibacterial activities of BO-2727, a new carbapenem.	1995 May	7625784
In vitro antibacterial activity and beta-lactamase stability of a new carbapenem, BO-2727.	1995 Oct	8619591
Comparative stability of carbapenem and penem antibiotics to human recombinant dehydropeptidase-I.	1996 May	8737157
Antibacterial properties of BO-2727, a new carbapenem antibiotic.	1997 Aug	9301984
Comparative in vitro pharmacodynamics of BO-2727, meropenem and imipenem against Gram-positive and Gram-negative bacteria.	1997 Feb	11864079
Affinities of BO-2727 for bacterial penicillin-binding proteins and morphological change of gram-negative rods.	1997 Feb	9099223
In vitro and in vivo evaluation of BO-2727 against imipenem- and/or meropenem-resistant Pseudomonas aeruginosa.	1997 Feb	9099222
1 beta-Methyl-2-(5-substituted pyrrolidin-3-ylthio)carbapenems. 3. Synthesis and antibacterial activity of BO-2727 and its related compounds.	1997 Jul	9711251
In vitro and in vivo antibacterial activities of a new carbapenem BO-2727 for use in obstetrics and gynecology.	1998 Jan-Feb	9444403

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Intravenous

In Vitro Use Guide

Lenapenam was tested against different strains of bacteria. The MIC50 values were: 0.1 ug/ml (Staphylococcus aureus, methicillin susceptibl), 0.05 ug/ml (Staphylococcus epidermidis), <0.006 ug/ml (Streptococcus pyogenes), 0.025 ug/ml (Streptococcus pneumoniae), 0.05 ug/ml (E.coli, Kiebsiella pneumoniae, Enterobacter cloacae), 0.012 ug/ml (Branhamella catarrhalis), etc.

Name

Type

Language

LENAPENEM

Official Name

English

(+)-(4R,5S,6S)-6-((R)-1-HYDROXYETHYL)-3-(((3S,5S)-5-((R)-1-HYDROXY-3-(METHYLAMINO)PROPYL)-3-PYRROLIDINYL)THIO)-4-METHYL-7-OXO-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID

Systematic Name

English

lenapenem [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C260