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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H18N4O4S
Molecular Weight 350.393
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIAPENEM

SMILES

[H][C@]12[C@@H](C)C(SC3CN4C=NC=[N+]4C3)=C(N1C(=O)[C@]2([H])[C@@H](C)O)C([O-])=O

InChI

InChIKey=MRMBZHPJVKCOMA-YJFSRANCSA-N
InChI=1S/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1

HIDE SMILES / InChI
Biapenem (INN) is a carbapenem antibiotic. It has in vitro activity against anaerobes. Approved in Japan in 2001. Biapenem is a carbopenems antibiotic which suppresses bacterial growth by inhibiting the enzymes responsible for bacterial cell wall synthesis, and shows broad-spectrum antibacterial activity both against gram-positive bacteria and gram-negative bacteria. Biapenem is stable to dehaloperoxidase-I (DHP-I) and can not be administered together with DHP-I inhibitor. This product is applicable to the treatment of a variety of infections caused by sensitive bacteria: septicemia, pneumonia, lung abscess, secondary infections resulting from chronic respiratory disease, cystitis, pyelonephritis, peritonitis, appendagitis, etc. Biapenem is generally well tolerated. The most common adverse events in clinical trials were skin eruptions/rashes, nausea and diarrhoea.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Optimal dosing regimen of biapenem in Chinese patients with lower respiratory tract infections based on population pharmacokinetic/pharmacodynamic modelling and Monte Carlo simulation.
2016 Mar
Patents

Patents

Sample Use Guides

For adults is 0.6 g/d, given over approximately 30-60 minutes in twice administration per day. Dosage can be adjusted according to the physical condition such as age and symptom of each individual, but should not exceed 1.2 g/d.
Route of Administration: Intravenous
In Vitro Use Guide
Curator's Comment: biapenem is clinically effective in the treatment of infection caused with P. aeruginosa.
For the carbapenems, the rank order of activity was meropenem (MIC50, 1 microg/ml)=biapenem (1 microg/ml)>imipenem (2 microg/m)>panipenem (8 microg/ml).
Name Type Language
BIAPENEM
INN   JAN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
6-[[(4R,5S,6S)-2-Carboxy-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]thio]-6,7-dihydro-5H-pyrazolo[1,2-a]-S-triazol-4-ium hydroxide, inner salt
Systematic Name English
Biapenem [WHO-DD]
Common Name English
biapenem [INN]
Common Name English
BIAPENEM [JAN]
Common Name English
CL 186,815
Code English
LJ-C10627
Code English
BIAPENEM [MART.]
Common Name English
6-(((4R,5S,6S)-2-CARBOXY-6-((1R)-1-HYDROXYETHYL)-4-METHYL-7-OXO-1-AZABICYCLO(3.2.0)HEPT-2-EN-3-YL)THIO)-6,7-DIHYDRO-5H-PYRAZOLO(1,2-A)(1,2,4)TRIAZOL-4-IUM INNER SALT
Systematic Name English
L-627
Code English
5H-PYRAZOLO(1,2-A)(1,2,4)TRIAZOL-4-IUM, 6-((2-CARBOXY-6-(1-HYDROXYETHYL)-4-METHYL-7-OXO-1-AZABICYCLO(3.2.0)HEPT-2-EN-3-YL)THIO)-6,7-DIHYDRO-, HYDROXIDE, INNER SALT, (4R-(4.ALPHA.,5.BETA.,6.BETA.(R*)))-
Systematic Name English
BIAPENEM [MI]
Common Name English
CL-186815
Code English
OMEGACIN
Brand Name English
BIAPENEM [USAN]
Common Name English
LJC-10627
Code English
LJ C10,627
Code English
Classification Tree Code System Code
WHO-VATC QJ01DH05
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
WHO-ATC J01DH05
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
NCI_THESAURUS C260
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
Code System Code Type Description
PUBCHEM
71339
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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DRUG BANK
DB13028
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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CAS
120410-24-4
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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CHEBI
3089
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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MESH
C065257
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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MERCK INDEX
m2471
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
PRIMARY Merck Index
SMS_ID
100000085876
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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FDA UNII
YR5U3L9ZH1
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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WIKIPEDIA
BIAPENEM
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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NCI_THESAURUS
C72620
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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EVMPD
SUB05813MIG
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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INN
7074
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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USAN
EE-66
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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EPA CompTox
DTXSID5046435
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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ChEMBL
CHEMBL285347
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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DRUG CENTRAL
365
Created by admin on Fri Dec 15 15:43:09 GMT 2023 , Edited by admin on Fri Dec 15 15:43:09 GMT 2023
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