LENAPENEM HYDROCHLORIDE MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C18H29N3O5S.ClH.H2O
Molecular Weight	453.981
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of LENAPENEM HYDROCHLORIDE MONOHYDRATE

Structure Search

SMILES

O.Cl.[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=FNSICOGCVDQJPU-HCRFUVGVSA-N

InChI=1S/C18H29N3O5S.ClH.H2O/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);1H;1H2/t8-,9-,10+,11+,12-,13-,14-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C18H29N3O5S
Molecular Weight	399.505
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 activity of a new carbapenem antibiotic, BO-2727, with potent antipseudomonal activity.	1993 Dec	8109950
Affinities of BO-2727 for bacterial penicillin-binding proteins and morphological change of gram-negative rods.	1997 Feb	9099223

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:30 GMT 2023` Edited by `admin` on `Fri Dec 15 15:48:30 GMT 2023`
Record UNII	N0450C4END
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LENAPENEM HYDROCHLORIDE MONOHYDRATE

Common Name

English

BO-2727

Code

English

LENAPENEM MONOHYDROCHLORIDE MONOHYDRATE

Common Name

English

LENAPENEM HYDROCHLORIDE HYDRATE [JAN]

Common Name

English

L-739428

Code

English

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

Common Name

English

L 739428

Code

English

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

Common Name

English

BO 2727

Code

English

LENAPENEM HYDROCHLORIDE HYDRATE

Common Name

English

Code System Code Type Description

FDA UNII

N0450C4END

Created by admin on Fri Dec 15 15:48:30 GMT 2023 , Edited by admin on Fri Dec 15 15:48:30 GMT 2023

PRIMARY

PUBCHEM

443100

Created by admin on Fri Dec 15 15:48:30 GMT 2023 , Edited by admin on Fri Dec 15 15:48:30 GMT 2023

PRIMARY

CAS

149882-71-3

Created by admin on Fri Dec 15 15:48:30 GMT 2023 , Edited by admin on Fri Dec 15 15:48:30 GMT 2023

PRIMARY

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					D6NBQ3H12U

LENAPENEM

ACTIVE MOIETY

Details

SMILES

InChI

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

Originator

Approval Year

Targets

Conditions

Approved Use

PubMed

Patents

Sample Use Guides

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