CEFMATILEN HYDROCHLORIDE MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H14N8O5S4.ClH.H2O
Molecular Weight	569.058
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of CEFMATILEN HYDROCHLORIDE MONOHYDRATE

Structure Search

SMILES

O.Cl.NC1=NC(=CS1)C(=N\O)\C(=O)N[C@H]2[C@H]3SCC(SCSC4=CNN=N4)=C(N3C2=O)C(O)=O

InChI

InChIKey=LBWIJMWZWJRRMO-AWXOXGPMSA-N

InChI=1S/C15H14N8O5S4.ClH.H2O/c16-15-18-5(2-30-15)8(21-28)11(24)19-9-12(25)23-10(14(26)27)6(3-29-13(9)23)31-4-32-7-1-17-22-20-7;;/h1-2,9,13,28H,3-4H2,(H2,16,18)(H,19,24)(H,26,27)(H,17,20,22);1H;1H2/b21-8-;;/t9-,13-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	C15H14N8O5S4
Molecular Weight	514.582
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11400319
Curator's Comment: description was created based on several sources, including http://google.com/patents/EP0467647B1 | https://www.ncbi.nlm.nih.gov/pubmed/11400306 | https://www.ncbi.nlm.nih.gov/pubmed/8585742 | https://www.ncbi.nlm.nih.gov/pubmed/9612604

Cefmatilen (codenamed S-1090) is an orally-active cephalosporin antibiotic, that shows high activity against a variety of Gram-positive and Gram-negative bacteria, including Streptococcus pyogenes and Neisseria gonorrhoeae.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: https://ncim-stage.nci.nih.gov/ncimbrowser/ConceptReport.jsp?dictionary=NCI%20Metathesaurus&code=C0964022	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17983256	Curative		Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
2.79 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.78 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.01 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.58 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.1 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.25 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
6.1 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.98 μg/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

AUC

Value	Dose	Analyte	Population
20.35 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
25.51 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
11.37 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
15.06 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
19.25 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
27.52 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
39.53 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
24.89 μg × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Analyte	Population
3.23 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.77 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.89 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.99 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	75 mg single, oral dose: 75 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.84 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.08 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.08 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
2.53 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/29681381/	200 mg 2 times / day multiple, oral dose: 200 mg route of administration: Oral experiment type: MULTIPLE co-administered:	CEFMATILEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED

F_unbound

Value	Dose	Co-administered	Analyte	Population
2.7% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29681381/			CEFMATILEN plasma	Homo sapiens

Doses

Dose	Population	Adverse events
400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/	Other AEs: ALT increased... Other AEs: ALT increased (33%) Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/
400 mg single, oral Highest studied dose Dose: 400 mg Route: oral Route: single Dose: 400 mg Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/	Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/

AEs

AE	Significance	Dose	Population
ALT increased	33%	400 mg 2 times / day multiple, oral Highest studied dose Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FED Sources: https://pubmed.ncbi.nlm.nih.gov/29681381/

PubMed

Title	Date	PubMed
[Toxicity study of cefmatilen hydrochloride hydrate (S-1090) (5)--Six-month repeated oral dose toxicity study and supplement study in rats].	2001-05	11400319

Patents

Sample Use Guides

In Vivo Use Guide

200 mg 2 x/day for 8 days

Route of Administration: Oral

In Vitro Use Guide

The bactericidal activities of S-1090 and the other agents at four times the MIC for Escherichia coli ATCC 25922 were determined. An overnight culture in Mueller-Hinton broth was inoculated into fresh broth, and the mixture was incubated, with constant shaking, until the viability reached 2 3 10^6 to 3 3 10^6 CFU/ml. After the addition of antibiotics, the cultures were incubated at 358C and the number of viable cells was determined.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:29:40 GMT 2025` Edited by `admin` on `Mon Mar 31 21:29:40 GMT 2025`
Record UNII	PA4O9CKP1M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFMATILEN HYDROCHLORIDE HYDRATE

Preferred Name

English

CEFMATILEN HYDROCHLORIDE MONOHYDRATE

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL)(HYDROXYIMINO)ACETYL)AMINO)-8-OXO-3-(((1H-1,2,3-TRIAZOL-4-YLTHIO)METHYL)THIO)-, MONOHYDROCHLORIDE, MONOHYDRATE, (6R-(6.ALPHA.,7.BETA.(Z)))-

Common Name

English

CEFMATILEN MONOHYDROCHLORIDE MONOHYDRATE

Common Name

English

CEFMATILEN HYDROCHLORIDE HYDRATE [JAN]

Common Name

English

(-)-CEFMATILEN MONOHYDROCHLORIDE MONOHYDRATE

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2Z)-(2-AMINO-4-THIAZOLYL)(HYDROXYIMINO)ACETYL)AMINO)-8-OXO-3-(((1H-1,2,3-TRIAZOL-4-YLTHIO)METHYL)THIO)-, MONOHYDROCHLORIDE, MONOHYDRATE, (6R,7R)-

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2Z)-2-(2-AMINO-4-THIAZOLYL)-2-(HYDROXYIMINO)ACETYL)AMINO)-8-OXO-3-(((1H-1,2,3-TRIAZOL-5-YLTHIO)METHYL)THIO)-, HYDROCHLORIDE, HYDRATE (1:1:1), (6R,7R)-

Common Name

English

Code System Code Type Description

CAS

154776-45-1

Created by admin on Mon Mar 31 21:29:40 GMT 2025 , Edited by admin on Mon Mar 31 21:29:40 GMT 2025

PRIMARY

FDA UNII

PA4O9CKP1M

Created by admin on Mon Mar 31 21:29:40 GMT 2025 , Edited by admin on Mon Mar 31 21:29:40 GMT 2025

PRIMARY

PUBCHEM

9690121

Created by admin on Mon Mar 31 21:29:40 GMT 2025 , Edited by admin on Mon Mar 31 21:29:40 GMT 2025

PRIMARY

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ACTIVE MOIETY

Details

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Approved Use

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound