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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.CNCC[C@@H](O)[C@@H]1C[C@@H](CN1)SC2=C(N3[C@@H]([C@@H]([C@@H](C)O)C3=O)[C@H]2C)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

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.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
17.75 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
38.8 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
71.88 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
39 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
40.05 mg/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
31.98 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
66.31 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
120.21 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
65.34 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
68.25 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.54 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
250 mg single, intravenous
dose: 250 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.5 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.41 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1.43 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1.46 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
LENAPENEM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
1000 mg single, intravenous
Highest studied dose
Dose: 1000 mg
Route: intravenous
Route: single
Dose: 1000 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/8089072/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/8089072/
Sources:
https://pubmed.ncbi.nlm.nih.gov/8089072/
500 mg 2 times / day multiple, intravenous
Studied dose
Dose: 500 mg, 2 times / day
Route: intravenous
Route: multiple
Dose: 500 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/8089072/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: FASTED
Sources:
https://pubmed.ncbi.nlm.nih.gov/8089072/
Sources:
https://pubmed.ncbi.nlm.nih.gov/8089072/
PubMed

PubMed

TitleDatePubMed
In vitro and in vivo antibacterial activities of a new carbapenem BO-2727 for use in obstetrics and gynecology.
1998-01-28
Antibacterial properties of BO-2727, a new carbapenem antibiotic.
1997-08
1 beta-Methyl-2-(5-substituted pyrrolidin-3-ylthio)carbapenems. 3. Synthesis and antibacterial activity of BO-2727 and its related compounds.
1997-07
Comparative in vitro pharmacodynamics of BO-2727, meropenem and imipenem against Gram-positive and Gram-negative bacteria.
1997-02
Affinities of BO-2727 for bacterial penicillin-binding proteins and morphological change of gram-negative rods.
1997-02
In vitro and in vivo evaluation of BO-2727 against imipenem- and/or meropenem-resistant Pseudomonas aeruginosa.
1997-02
Comparative stability of carbapenem and penem antibiotics to human recombinant dehydropeptidase-I.
1996-05
In vitro antibacterial activity and beta-lactamase stability of a new carbapenem, BO-2727.
1995-10
In vitro and in vivo antibacterial activities of BO-2727, a new carbapenem.
1995-05
Mechanism of enhanced antipseudomonal activity of BO-2727, a new injectable 1-beta-methyl carbapenem.
1995-03
In vitro activity of a new carbapenem antibiotic, BO-2727, with potent antipseudomonal activity.
1993-12
Patents

Patents

US5534422 A
2

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 HYDROCHLORIDE MONOHYDRATE
Common Name English
LENAPENEM HYDROCHLORIDE HYDRATE
JAN  
Preferred 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
Code System Code Type Description
FDA UNII
N0450C4END
Created by admin on Mon Mar 31 18:09:22 GMT 2025 , Edited by admin on Mon Mar 31 18:09:22 GMT 2025
PRIMARY
PUBCHEM
443100
Created by admin on Mon Mar 31 18:09:22 GMT 2025 , Edited by admin on Mon Mar 31 18:09:22 GMT 2025
PRIMARY
CAS
149882-71-3
Created by admin on Mon Mar 31 18:09:22 GMT 2025 , Edited by admin on Mon Mar 31 18:09:22 GMT 2025
PRIMARY
ACTIVE MOIETY
Structure of LENAPENEM
NIH
NCATS
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