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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

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
In vitro antibacterial activity and beta-lactamase stability of a new carbapenem, BO-2727.
1995 Oct
In vitro and in vivo evaluation of BO-2727 against imipenem- and/or meropenem-resistant Pseudomonas aeruginosa.
1997 Feb
Patents

Patents

Sample Use Guides

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
  • Download
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
JAN  
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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