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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

Molecular Formula C15H18N4O4S
Molecular Weight 350.393
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 4 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:43:09 UTC 2023
Edited
by admin
on Fri Dec 15 15:43:09 UTC 2023
Record UNII
YR5U3L9ZH1
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
WHO-ATC J01DH05
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
NCI_THESAURUS C260
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
Code System Code Type Description
PUBCHEM
71339
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
DRUG BANK
DB13028
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
CAS
120410-24-4
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
CHEBI
3089
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
MESH
C065257
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
MERCK INDEX
m2471
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY Merck Index
SMS_ID
100000085876
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
FDA UNII
YR5U3L9ZH1
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
WIKIPEDIA
BIAPENEM
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
NCI_THESAURUS
C72620
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
EVMPD
SUB05813MIG
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
INN
7074
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
USAN
EE-66
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046435
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
ChEMBL
CHEMBL285347
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
DRUG CENTRAL
365
Created by admin on Fri Dec 15 15:43:09 UTC 2023 , Edited by admin on Fri Dec 15 15:43:09 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY