CEFLUPRENAM

Details

Stereochemistry	EPIMERIC
Molecular Formula	C20H25FN8O6S2
Molecular Weight	556.591
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC[N+](C)(C\C=C\C1=C(N2[C@H](SC1)[C@H](NC(=O)C(=N/OCF)\C3=NSC(N)=N3)C2=O)C([O-])=O)CC(N)=O

InChI

InChIKey=XAKKNLNAJBNLPC-MAYKBZFQSA-N

InChI=1S/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H25FN8O6S2
Molecular Weight	556.591
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/9311195
Curator's Comment: description was created based on several sources, including, http://www.ncbi.nlm.nih.gov/pubmed/1622167, http://www.ncbi.nlm.nih.gov/pubmed/8270493

Cefluprenam is an anti-bacterial agent of broad spectrum. It was active in vitro against different bacteria strains with MIC values from 0.78 ug/ml to 3.13 ug/ml. The drug exerts its bactericidal activity through inhibition of penicillin-binding proteins, showing high affinity to all four subtypes. Cefluprenam was tested for the treatment of respiratory tract infections in phase III study, however the drug development was stopped.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: http://www.ncbi.nlm.nih.gov/pubmed/8270493	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Respiratory tract infections 85 Sources: http://www.ncbi.nlm.nih.gov/pubmed/9743906	Curative		Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
155.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9743906/	20 mg/kg bw 3 times / day multiple, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFLUPRENAM serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
153 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9743906/	20 mg/kg bw 3 times / day multiple, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFLUPRENAM serum	Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
111.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9743906/	20 mg/kg bw 3 times / day multiple, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFLUPRENAM serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
81 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9743906/	20 mg/kg bw 3 times / day multiple, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFLUPRENAM serum	Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.43 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9743906/	20 mg/kg bw 3 times / day multiple, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFLUPRENAM serum	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN
1.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9743906/	20 mg/kg bw 3 times / day multiple, intravenous dose: 20 mg/kg bw route of administration: Intravenous experiment type: MULTIPLE co-administered:		CEFLUPRENAM serum	Homo sapiens population: UNHEALTHY age: NEWBORN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2000 mg 2 times / day multiple, intravenous Highest studied dose Dose: 2000 mg, 2 times / day Route: intravenous Route: multiple Dose: 2000 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7876395/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7876395/	Sources: https://pubmed.ncbi.nlm.nih.gov/7876395/

PubMed

Title	Date	PubMed
beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter.	2000-01-21	10636865
[Pharmacokinetic and clinical studies with cefluprenam in the pediatric field. Pediatric Study Group of Gefluprenam].	1997-07	9743906
Therapeutic effects of cefluprenam (CFLP) on polymicrobial infections associated with Enterococcus faecalis in rat pyometra model.	1997-02	18611779
Affinity of E1077, a new cephalosporin, for penicillin-binding proteins of Staphylococcus aureus and its antistaphylococcal activity.	1993-11	8270493
In vitro and in vivo antibacterial activities of E1077, a novel parenteral cephalosporin.	1993-01	8431019
In vitro and in vivo antibacterial activities of E1077, a novel parenteral cephalosporin with a broad antibacterial spectrum.	1992-09	1416879
In vitro evaluation of E1077, a new cephalosporin with a broad antibacterial spectrum.	1992-03	1622167

Patents

Sample Use Guides

In Vivo Use Guide

20 to 40 mg (potency)/kg

Route of Administration: Intravenous

In Vitro Use Guide

Cefluprenam was tested against different bacteria strains. The MIC was determined by visual inspection for lack of turbidity after 24 h of incubation at 37°C. MIC90 for S. aureus and Staphylococcus epidermidis were 0.78 to 1.56 ug/ml. MIC50 for E. faecalis was 1.56 ug/ml. Enterobacteriaceae was inhibited at 0.78 ug/ml. P. vulgaris - at 3.13 ug/ml (MIC90). The MIC90s of the drug for E. cloacae, E. aerogenes, and C. freundii were 0.78, 0.05, and 0.39 ug/ml, respectively. Against S. marcescens the drug was active with MIC90 value of 3.13 ug/ml. MIC50 for P. aeruginosa was 3.13 ug/ml, etc.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:33:38 GMT 2025` Edited by `admin` on `Mon Mar 31 18:33:38 GMT 2025`
Record UNII	098633Q42P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFLUPRENAM [JAN]

Preferred Name

English

CEFLUPRENAM

Official Name

English

CEFLUPRENAM [MART.]

Common Name

English

cefluprenam [INN]

Common Name

English

(-)-((E)-3-((6R,7R)-7-(2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)GLYOXYLAMIDO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO (4.2.0)OCT-2-EN-3-YL)ALLYL)(CARBAMOYLMETHYL)ETHYLMETHYLAMMONIUM HYDROXIDE, INNER SALT, 7(SUP 2)-(Z)-(O-(FLUOROMETHYL)OXIME)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357