U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula 2C16H17N9O5S3.ClH
Molecular Weight 1059.578
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CEFMENOXIME HYDROCHLORIDE

SMILES

Cl.[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C(O)=O.[H][C@]56SCC(CSC7=NN=NN7C)=C(N5C(=O)[C@H]6NC(=O)C(=N/OC)\C8=CSC(N)=N8)C(O)=O

InChI

InChIKey=MPTNDTIREFCQLK-UNVJPQNDSA-N
InChI=1S/2C16H17N9O5S3.ClH/c2*1-24-16(20-22-23-24)33-4-6-3-31-13-9(12(27)25(13)10(6)14(28)29)19-11(26)8(21-30-2)7-5-32-15(17)18-7;/h2*5,9,13H,3-4H2,1-2H3,(H2,17,18)(H,19,26)(H,28,29);1H/b2*21-8-;/t2*9-,13-;/m11./s1

HIDE SMILES / InChI
Cefmenoxime is a semisynthetic beta-lactam cephalosporin antibiotic with activity similar to that of cefotaxime. Like other 'third-generation' cephalosporins it is active in vitro against most common Gram-positive and Gram-negative pathogens, is a potent inhibitor of Enterobacteriaceae (including beta-lactamase-producing strains), and is resistant to hydrolysis by beta-lactamases. Cefmenoxime has a high rate of clinical efficacy in many types of infection and is at least equal in clinical and bacteriological efficacy to several other cephalosporins in urinary tract infections, respiratory tract infections, postoperative infections and gonorrhoea. The bactericidal activity of cefmenoxime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefmenoxime is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases. Cefmenoxime is marketed in Japan under the brand name Bestron, indicated for the treatment of otitis externa, otitis media, and sinusitis. Cefmenoxime hydrochloride was approved by the U.S. Food and Drug Administration (FDA) on Dec 30, 1987. It was developed and marketed as Cefmax®, but it has being discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
BESTRON

Approved Use

INDICATIONS Cefmenoxime-susceptible strains of Staphylococcus spp., Streptococcus spp., Streptococcus pneumoniae, Moraxella (Branhamella) catarrhalis, Proteus spp., Morganella morganii, Providencia spp., Haemophilus influenzae, Pseudomonas aeruginosa, and Peptostreptococcus spp. Otitis externa, otitis media, and sinusitis (except for cases of severe obstruction in the middle meatus in administration by nebulization with a nebulizer).

Launch Date

1996
Curative
BESTRON

Approved Use

INDICATIONS Cefmenoxime-susceptible strains of Staphylococcus spp., Streptococcus spp., Streptococcus pneumoniae, Moraxella (Branhamella) catarrhalis, Proteus spp., Morganella morganii, Providencia spp., Haemophilus influenzae, Pseudomonas aeruginosa, and Peptostreptococcus spp. Otitis externa, otitis media, and sinusitis (except for cases of severe obstruction in the middle meatus in administration by nebulization with a nebulizer).

Launch Date

1996
Curative
BESTRON

Approved Use

INDICATIONS Cefmenoxime-susceptible strains of Staphylococcus spp., Streptococcus spp., Streptococcus pneumoniae, Moraxella (Branhamella) catarrhalis, Proteus spp., Morganella morganii, Providencia spp., Haemophilus influenzae, Pseudomonas aeruginosa, and Peptostreptococcus spp. Otitis externa, otitis media, and sinusitis (except for cases of severe obstruction in the middle meatus in administration by nebulization with a nebulizer).

Launch Date

1996
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
88.3 μg/mL
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
95.5 μg/mL
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
84 μg × h/mL
15 mg/kg bw single, intravenous
dose: 15 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.34 h
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.14 h
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.06 h
15 mg/kg bw single, intravenous
dose: 15 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
23%
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
23%
10 mg/kg bw single, intravenous
dose: 10 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
CEFMENOXIME plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
150 mg/kg 1 times / day multiple, intravenous
Studied dose
Dose: 150 mg/kg, 1 times / day
Route: intravenous
Route: multiple
Dose: 150 mg/kg, 1 times / day
Sources:
unhealthy, 1-15 years
Health Status: unhealthy
Age Group: 1-15 years
Sources:
12 g 1 times / day multiple, intravenous
Studied dose
Dose: 12 g, 1 times / day
Route: intravenous
Route: multiple
Dose: 12 g, 1 times / day
Sources:
unhealthy, 55.5 years (range: 19-88 years)
n = 2
Health Status: unhealthy
Condition: intra abdominal infection
Age Group: 55.5 years (range: 19-88 years)
Sex: M+F
Population Size: 2
Sources:
PubMed

PubMed

TitleDatePubMed
Cefmenoxime (SCE-1365), a novel broad-spectrum cephalosporin: in vitro and in vivo antibacterial activities.
1981 Jan
Therapeutic efficacy of chloramphenicol, co-trimoxazole (trimethoprim/sulphamethoxazole), cefmenoxime and ceftriaxone in experimental bacteraemia and meningitis caused by ampicillin-resistant Haemophilus influenzae type b.
1988 Nov
Cefmenoxime in corneal organ culture.
1994
Pharmacoeconomic analysis of cefmenoxime dual individualization in the treatment of nosocomial pneumonia.
1994 Mar
[Antibacterial activities of cefmenoxime against recent fresh clinical isolates from patients in sinusitis].
1995 May
Patents

Sample Use Guides

Dissolve the powder in the attached solvent at a final concentration of 10 mg (potency)/1 mL as cefmenoxime hydrochloride, and used as follows: For otitis externa and otitis media, usually instill 6 to 10 drops into the ear and keep the same position for about 10 minutes twice daily. For sinusitis, usually inhale nasally by a nebulizer 2 to 4 mL every other day, 3 times per week or inject 1 mL into the maxillary sinus once per week. The frequency of administration may be adjusted depending on the patient’s symptoms.
Route of Administration: Topical
In Vitro Use Guide
Cefmenoxime showed the most potent activity, the MIC of this drug against all of the 92 strains of Haemophilus influenzae was 0.063 ug/ml.
Name Type Language
CEFMENOXIME HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   WHO-DD  
USAN  
Official Name English
CEFMENOXIME HYDROCHLORIDE [ORANGE BOOK]
Common Name English
CEFMENOXIME HYDROCHLORIDE [USP IMPURITY]
Common Name English
CEFMENOXIME HYDROCHLORIDE [MI]
Common Name English
(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID 7(SUP 2)-(Z)-(O-METHYLOXIME), HYDROCHLORIDE (2:1)
Common Name English
CEFMENOXIME HYDROCHLORIDE [JAN]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-3-(((1-METHYL-1H-TETRAZOL-5-YL)THIO)METHYL)-8-OXO-, HYDROCHLORIDE (2:1), (6R-(6.ALPHA.,7.BETA.(Z)))
Common Name English
CEFMENOXIME HYDROCHLORIDE [MART.]
Common Name English
CEFMENOXIME HCL
Common Name English
NSC-760352
Code English
CEFMENOXIME HYDROCHLORIDE [USAN]
Common Name English
Cefmenoxime hydrochloride [WHO-DD]
Common Name English
SCE-1365 HYDROCHLORIDE
Code English
CEFMAX
Brand Name English
ABBOTT-50192
Code English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C65296
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
PUBCHEM
11954009
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
EVMPD
SUB01117MIG
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
NSC
760352
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
MERCK INDEX
m3196
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY Merck Index
SMS_ID
100000084984
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
278-299-4
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
FDA UNII
NON736D32W
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PRIMARY
DRUG BANK
DBSALT000801
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID0046646
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY
CHEBI
31370
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PRIMARY
ChEMBL
CHEMBL1201224
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PRIMARY
CAS
75738-58-8
Created by admin on Fri Dec 15 16:35:28 GMT 2023 , Edited by admin on Fri Dec 15 16:35:28 GMT 2023
PRIMARY