PANIPENEM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H21N3O4S
Molecular Weight	339.41
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H](O)[C@@H]1[C@H]2CC(S[C@H]3CCN(C3)C(C)=N)=C(N2C1=O)C(O)=O

InChI

InChIKey=TYMABNNERDVXID-DLYFRVTGSA-N

InChI=1S/C15H21N3O4S/c1-7(19)12-10-5-11(13(15(21)22)18(10)14(12)20)23-9-3-4-17(6-9)8(2)16/h7,9-10,12,16,19H,3-6H2,1-2H3,(H,21,22)/t7-,9+,10-,12-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C15H21N3O4S
Molecular Weight	339.41
Charge	0
Count

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

Description
Sources: Finch RG, Greenwood D, Whitley RJ, Ragnar Norrby S (2003). Antibiotic and chemotherapy: anti-infective agents and their use in therapy. Elsevier Health Sciences. pp. 269. P.237 ISBN 978-0-443-07129-4
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/12678575

Panipenem is a parenteral carbapenem antibacterial agent with a broad spectrum of in vitro activity covering a wide range of Gram-negative and Gram-positive aerobic and anaerobic bacteria, including Streptococcus pneumoniae and species producing β-lactamases. Panipenem is coadministered with betamipron (Carbenin, Daiichi Sankyo Company) to inhibit panipenem uptake into the renal tubule and prevent nephrotoxicity. In large, randomised clinical trials, panipenem/betamipron demonstrated good clinical and bacteriological efficacy (similar to that of imipenem/cilastatin) in adults with respiratory tract or urinary tract infections.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
beta-lactamase activity 4 Target ID: GO:0008800 Sources: http://aac.asm.org/content/55/11/4943.long	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infection 8 Sources: http://adisinsight.springer.com/drugs/800001168 http://www.ncbi.nlm.nih.gov/pubmed/12678575 https://www.ncbi.nlm.nih.gov/pubmed/18203711	Curative		Approved 8583	Carbenin Approved Use Panipenem has been approved in Japan, China and Korea, it has been used for the treatment of lower respiratory tract, urinary tract, obstetrical/gynecological and surgical infections

C_max

Value	Dose	Co-administered	Analyte	Population
14.26 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	250 mg single, intravenous dose: 250 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
27.51 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
49.27 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6.8 μg/mL OTHER GOV'T https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	125 mg single, intravenous dose: 125 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
23.32 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
26.24 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
50.01 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
44.58 μg/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
23.2 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	250 mg single, intravenous dose: 250 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
45.21 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
84.8 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
11.72 μg × h/mL OTHER GOV'T https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	125 mg single, intravenous dose: 125 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
39.42 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
40.27 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
85.88 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
71.07 μg × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.14 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	250 mg single, intravenous dose: 250 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.19 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	500 mg single, intravenous dose: 500 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.23 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=39 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	1000 mg single, intravenous dose: 1000 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.13 h OTHER GOV'T https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_242/_article/-char/en	125 mg single, intravenous dose: 125 mg route of administration: Intravenous experiment type: SINGLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.07 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.27 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.11 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.35 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=40 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en	1000 mg 2 times / day multiple, intravenous dose: 1000 mg route of administration: Intravenous experiment type: MULTIPLE co-administered: BETAMIPRON	BETAMIPRON	PANIPENEM plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
93% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/2/430574_6139503D1027_2_C11_1F.pdf#page=51 \| https://www.jstage.jst.go.jp/article/chemotherapy1953/39/Supplement3/39_Supplement3_265/_article/-char/en#page=18	500 mg 2 times / day multiple, intravenous dose: 500 mg route of administration: Intravenous experiment type: MULTIPLE co-administered:		PANIPENEM serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
0.5 g 2 times / day multiple, intravenous Recommended Dose: 0.5 g, 2 times / day Route: intravenous Route: multiple Dose: 0.5 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/	Disc. AE: Unconsciousness, Seizure... AEs leading to discontinuation/dose reduction: Unconsciousness (grade 5) Seizure (grade 5) Coma (grade 5) Renal failure (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/
1 g 2 times / day multiple, intravenous Recommended Dose: 1 g, 2 times / day Route: intravenous Route: multiple Dose: 1 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/12111568/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/12111568/	Sources: https://pubmed.ncbi.nlm.nih.gov/12111568/

AEs

AE	Significance	Dose	Population
Coma	grade 5 Disc. AE	0.5 g 2 times / day multiple, intravenous Recommended Dose: 0.5 g, 2 times / day Route: intravenous Route: multiple Dose: 0.5 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/
Renal failure	grade 5 Disc. AE	0.5 g 2 times / day multiple, intravenous Recommended Dose: 0.5 g, 2 times / day Route: intravenous Route: multiple Dose: 0.5 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/
Seizure	grade 5 Disc. AE	0.5 g 2 times / day multiple, intravenous Recommended Dose: 0.5 g, 2 times / day Route: intravenous Route: multiple Dose: 0.5 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/
Unconsciousness	grade 5 Disc. AE	0.5 g 2 times / day multiple, intravenous Recommended Dose: 0.5 g, 2 times / day Route: intravenous Route: multiple Dose: 0.5 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/9695479/

PubMed

Title	Date	PubMed
Panipenem/betamipron.	2003	12678575
[New antimicrobial agent series XLVI: panipenem/betamipron].	1994-03	8182894
Overview of a new carbapenem, panipenem/betamipron.	1994	7758396

Patents

Sample Use Guides

In Vivo Use Guide

panipenem-betamipron 0.5 g every 6 or 8 hours for 7 - 14 days

Route of Administration: Intravenous

In Vitro Use Guide

Panipenem demonstrated the strongest antibacterial activity among the carbapenems with a MIC range of < or =0.06 to 0.12 microg/mL

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:28:15 GMT 2025` Edited by `admin` on `Mon Mar 31 18:28:15 GMT 2025`
Record UNII	W9769W09JF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PANIPENEM

Official Name

English

CS-533

Preferred Name

English

PANIPENEM [JAN]

Common Name

English

panipenem [INN]

Common Name

English

RS-533

Code

English

PANIPENEM [MI]

Common Name

English

(+)-(5R,6S)-3-(((S)-1-ACETIMIDOYL-3-PYRROLIDINYL)THIO)-6-((R)-1-HYDROXYETHYL)-7-OXO-1-AZABICYCLO(3.2.0)HEPT-2-ENE-2-CARBOXYLIC ACID

Systematic Name

English

PANIPENEM [MART.]

Common Name

English

Panipenem [WHO-DD]

Common Name

English

Classification Tree Code System Code

WHO-ATC

J01DH55