CEFMENOXIME HYDROCHLORIDE

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 Search

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

Description
Sources: http://www.kyorin-pharm.co.jp/prodinfo/medicine/pdf/BESTRON.pdf | https://www.drugs.com/international/cefmenoxime.html | https://www.ncbi.nlm.nih.gov/pubmed/3304966

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6941742	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Otitis externa 20 Sources: http://www.kyorin-pharm.co.jp/prodinfo/medicine/pdf/BESTRON.pdf	Curative	Approved 8429	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
Sinusitis 26 Sources: http://www.kyorin-pharm.co.jp/prodinfo/medicine/pdf/BESTRON.pdf	Curative	Approved 8429	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
Otitis media 41 Sources: http://www.kyorin-pharm.co.jp/prodinfo/medicine/pdf/BESTRON.pdf	Curative	Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
88.3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6098220	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6098220	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

Value	Dose	Co-administered	Analyte	Population
84 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6095752	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

T_1/2

Value	Dose	Analyte	Population
1.34 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6098220	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6098220	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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6095752	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

F_unbound

Value	Dose	Co-administered	Analyte	Population
23% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6098220	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% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6098220	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/3865630	unhealthy, 1-15 years Health Status: unhealthy Age Group: 1-15 years Sources: https://pubmed.ncbi.nlm.nih.gov/3865630	Sources: https://pubmed.ncbi.nlm.nih.gov/3865630
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: https://pubmed.ncbi.nlm.nih.gov/6097122	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: https://pubmed.ncbi.nlm.nih.gov/6097122	Sources: https://pubmed.ncbi.nlm.nih.gov/6097122

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:55490	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:55490
ChemicalBook	CB7771510	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7771510
MolPort	MolPort-019-999-936	https://www.molport.com/shop/molecule-link/MolPort-019-999-936
ZINC	ZINC000003830413	http://zinc15.docking.org/substances/ZINC000003830413

PubMed

Title	Date	PubMed
Cefmenoxime (SCE-1365), a novel broad-spectrum cephalosporin: in vitro and in vivo antibacterial activities.	1981 Jan	6941742
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	3264831
Cefmenoxime in corneal organ culture.	1994	7816419
Pharmacoeconomic analysis of cefmenoxime dual individualization in the treatment of nosocomial pneumonia.	1994 Mar	8193431
[Antibacterial activities of cefmenoxime against recent fresh clinical isolates from patients in sinusitis].	1995 May	7637194

Patents

Sample Use Guides

In Vivo Use Guide

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

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