BIAPENEM

Possibly Marketed Outside US

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

SMILES

C[C@@H](O)[C@@H]1[C@H]2[C@@H](C)C(SC3CN4C=NC=[N+]4C3)=C(N2C1=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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	4 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

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

Condition	Modality	Targets	Highest Phase	Product
Variety of infections 1	Curative		Approved 8,583	Unknown

C_max

Value	Dose	Analyte	Population
8.8 μg/mL	150 mg single, intravenous	BIAPENEM plasma	Homo sapiens
17.3 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
32.4 μg/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
15.6 μg/mL	300 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
14.7 μg/mL	300 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
32.6 μg/mL	600 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
35.3 μg/mL	600 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
20.2 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
17.4 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
14.2 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
40.2 μg/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
33.8 μg/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
33.2 μg/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
25.6 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
24 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
12.8 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
24.8 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
19 μg/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
5.43 mg/L	250 mg single, intravenous	BIAPENEM plasma	Homo sapiens
5.71 mg/L	250 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
16.3 mg/L	500 mg single, intravenous	BIAPENEM plasma	Homo sapiens
16.6 mg/L	500 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
22.6 mg/L	750 mg single, intravenous	BIAPENEM plasma	Homo sapiens
20.8 mg/L	750 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
39.8 mg/L	1000 mg single, intravenous	BIAPENEM plasma	Homo sapiens
38.2 mg/L	1000 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
52.3 mg/L	1250 mg single, intravenous	BIAPENEM plasma	Homo sapiens
44.8 mg/L	1250 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
14.7 μg × h/mL	150 mg single, intravenous	BIAPENEM plasma	Homo sapiens
29.2 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
55.4 μg × h/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
26.2 μg × h/mL	300 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
23.4 μg × h/mL	300 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
56.7 μg × h/mL	600 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
57.1 μg × h/mL	600 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
44.6 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
34.5 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
26.6 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
91.9 μg × h/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
70.1 μg × h/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
66.1 μg × h/mL	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
68 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
61.1 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
46.6 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
52.7 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
120 μg × h/mL	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
17.5 mg × h/L	250 mg single, intravenous	BIAPENEM plasma	Homo sapiens
18.4 mg × h/L	250 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
52.4 mg × h/L	500 mg single, intravenous	BIAPENEM plasma	Homo sapiens
49.4 mg × h/L	500 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
68.3 mg × h/L	750 mg single, intravenous	BIAPENEM plasma	Homo sapiens
70 mg × h/L	750 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
123 mg × h/L	1000 mg single, intravenous	BIAPENEM plasma	Homo sapiens
115 mg × h/L	1000 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
148 mg × h/L	1250 mg single, intravenous	BIAPENEM plasma	Homo sapiens
146 mg × h/L	1250 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
0.97 h	150 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.03 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.04 h	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
0.96 h	300 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
0.85 h	300 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
1.03 h	600 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
1.01 h	600 mg 2 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
1.75 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.82 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.51 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.59 h	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.45 h	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
2.19 h	600 mg single, intravenous	BIAPENEM plasma	Homo sapiens
2.28 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.82 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.95 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
3.33 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
3.92 h	300 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.1 h	250 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.06 h	250 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
1.3 h	500 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.13 h	500 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
1.03 h	750 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.2 h	750 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
1.21 h	1000 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.42 h	1000 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens
1.31 h	1250 mg single, intravenous	BIAPENEM plasma	Homo sapiens
1.63 h	1250 mg 3 times / day multiple, intravenous	BIAPENEM plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
93.4%			BIAPENEM plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
300 mg 3 times / day multiple, intravenous Recommended	unhealthy, ADULT	Other AEs: Liver disorder, Nausea...
500 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT	Disc. AE: Trombocytopenia, Drug fever...

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AEs

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AE	Significance	Dose	Population
Liver disorder	12%	300 mg 3 times / day multiple, intravenous Recommended	unhealthy, ADULT
Nausea	4%	300 mg 3 times / day multiple, intravenous Recommended	unhealthy, ADULT
Drug fever	1.7% Disc. AE	500 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT
Oedema	1.7% Disc. AE	500 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT
Trombocytopenia	1.7% Disc. AE	500 mg 3 times / day multiple, intravenous Studied dose	unhealthy, ADULT

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1,087			inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT3 747 OAT1 725 CYP19A1 429 OCT2 779	OAT3 391 OAT1 395 OCT2 434 P-gp 2,052

Drug as perpetrator

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Target	Modality	Activity
OAT3 749	inhibitor 4,027	mild [IC50 >500 uM]
CYP19A1 430	inhibitor 4,027	no
CYP3A4 2,633	inducer 1,966	no
OAT1 730	inhibitor 4,027	no
OCT2 782	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity
OAT1 395	substrate 4,014	no
OCT2 434	substrate 4,014	no
P-gp 2,052	substrate 4,014	no
OAT3 391	substrate 4,014	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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PubMed

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Title	Date	PubMed
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	26895604

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Patents

Sample Use Guides

In Vivo Use Guide

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

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
Record UNII	YR5U3L9ZH1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BIAPENEM

Official Name

English

OMEGACIN

Preferred 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

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Classification Tree

Code System

Code

Carbapenems

WHO-VATC

QJ01DH05

Carbapenems

WHO-ATC

J01DH05

Antibiotic

NCI_THESAURUS

C260

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Code System

Code

Type

Description

PUBCHEM

71339

PRIMARY

DRUG BANK

DB13028

PRIMARY

CAS

120410-24-4

PRIMARY

CHEBI

3089

PRIMARY

MESH

C065257

PRIMARY

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Related Record

Type

Details


					YR5U3L9ZH1

BIAPENEM

ACTIVE MOIETY

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SMILES

InChI

Description<div class="info-popup-container"><div><span class="pop-sub-key ">Sources:&nbsp;</span><span class="pop-sub-val"><span class="ext-link"><a target="_self" href="http://www.ncbi.nlm.nih.gov/pubmed/12381221">http://www.ncbi.nlm.nih.gov/pubmed/12381221</a></span></span></div></div>

Approval Year

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

Description

C_max

T_1/2

F_unbound

Drug as perpetrator