ENMETAZOBACTAM

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National Institutes of Health Divider Arrow

NCATS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H14N4O5S
Molecular Weight	314.318
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of ENMETAZOBACTAM

Structure Search

SMILES

[H][C@@]12CC(=O)N1[C@@H](C([O-])=O)[C@](C)(CN3C=C[N+](C)=N3)S2(=O)=O

InChI

InChIKey=HFZITXBUTWITPT-YWVKMMECSA-N

InChI=1S/C11H14N4O5S/c1-11(6-14-4-3-13(2)12-14)9(10(17)18)15-7(16)5-8(15)21(11,19)20/h3-4,8-9H,5-6H2,1-2H3/t8-,9+,11+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C11H14N4O5S
Molecular Weight	314.318
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

Substance Class	Chemical Created by `admin` on `Sat Dec 16 11:48:59 UTC 2023` Edited by `admin` on `Sat Dec 16 11:48:59 UTC 2023`
Record UNII	80VUN7L00C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AAI-101

Preferred Name

English

ENMETAZOBACTAM

Official Name

English

OCID-5090

Code

English

(2S,3S,5R)-3-METHYL-3-((3-METHYLTRIAZOL-3-IUM-1-YL)METHYL)-4,4,7-TRIOXO-4^6-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLATE

Systematic Name

English

1H-1,2,3-TRIAZOLIUM, 3-(((2S,3S,5R)-2-CARBOXY-3-METHYL-4,4-DIOXIDO-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPT-3-YL)METHYL)-1-METHYL-, INNER SALT

Systematic Name

English

enmetazobactam [INN]

Common Name

English

Code System Code Type Description

NCI_THESAURUS

C171696

Created by admin on Sat Dec 16 11:48:59 UTC 2023 , Edited by admin on Sat Dec 16 11:48:59 UTC 2023

PRIMARY

PUBCHEM

23653540

Created by admin on Sat Dec 16 11:48:59 UTC 2023 , Edited by admin on Sat Dec 16 11:48:59 UTC 2023

PRIMARY

SMS_ID

300000010200

Created by admin on Sat Dec 16 11:48:59 UTC 2023 , Edited by admin on Sat Dec 16 11:48:59 UTC 2023

PRIMARY

FDA UNII

80VUN7L00C

Created by admin on Sat Dec 16 11:48:59 UTC 2023 , Edited by admin on Sat Dec 16 11:48:59 UTC 2023

PRIMARY

CAS

1001404-83-6

Created by admin on Sat Dec 16 11:48:59 UTC 2023 , Edited by admin on Sat Dec 16 11:48:59 UTC 2023

PRIMARY

INN

10913

Created by admin on Sat Dec 16 11:48:59 UTC 2023 , Edited by admin on Sat Dec 16 11:48:59 UTC 2023

PRIMARY

Related Record Type Details


					3JG9E47DHU

ENMETAZOBACTAM HYDRIODIDE

SALT/SOLVATE -> PARENT

Related Record Type Details


					80VUN7L00C

ACTIVE MOIETY

Comments:

We evaluated the in vitro potency of cefepime combined with AAI101, a novel extended-spectrum .BETA.-lactamase inhibitor, against a population of clinical Escherichia coli and Klebsiella pneumoniae collected from USA hospitals. Of the 223 cefepime non-susceptible isolates, 95% were ceftazidime non-susceptible, 49% ertapenem non-susceptible, 57% piperacillin/tazobactam non-susceptible, 90% were multidrug-resistant (resistant to 3 drug classes), 22% produced carbapenemases, and 67% produced ESBLs. Addition of AAI101 restored the activity of cefepime such that the MIC50 was reduced from >64 mg/L for cefepime to 0.13 mg/L for cefepime/AAI101, supporting its continued development treatment for infections caused by these organisms.