CEFCLIDIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H26N8O6S2
Molecular Weight	550.611
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(C[N+]34CCC(CC3)(CC4)C(N)=O)=C(N2C1=O)C([O-])=O)C5=NSC(N)=N5

InChI

InChIKey=JUVHVMCKLDZLGN-TVNFHGJBSA-N

InChI=1S/C21H26N8O6S2/c1-35-26-11(14-25-20(23)37-27-14)15(30)24-12-16(31)28-13(18(32)33)10(9-36-17(12)28)8-29-5-2-21(3-6-29,4-7-29)19(22)34/h12,17H,2-9H2,1H3,(H5-,22,23,24,25,27,30,32,33,34)/b26-11-/t12-,17-,21?,29?/m1/s1

HIDE SMILES / InChI

Molecular Formula	C21H26N8O6S2
Molecular Weight	550.611
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1399855 | https://www.ncbi.nlm.nih.gov/pubmed/1493980 | https://www.ncbi.nlm.nih.gov/pubmed/7942366

Cefclidin is a fourth-generation cephalosporin antibiotic effective against a clinical strain of Citrobacter freundii. The affinity of cefclidin for the β-lactamase isolated from these mutants was lower than that of ceftazidime, and the kinetic parameters of enzymatic hydrolysis showed that cefclidin was hydrolyzed more slowly at a low concentration than was ceftazidime. It is suggested that the high activity of cefclidin against strains derepressed for β-lactamase plays a major role in the absence of emergence of resistant mutants.

Originator

Approval Year

PubMed

Title	Date	PubMed
Cefclidin (E1040), a novel cephalosporin: lack of selection of beta-lactamase overproducing mutants in an in vitro pharmacokinetic model system.	1992-08	1399855

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:56:59 GMT 2025` Edited by `admin` on `Wed Apr 02 08:56:59 GMT 2025`
Record UNII	78963CJ0OG
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFCLIDIN

Official Name

English

CEFCLIDIN [MI]

Preferred Name

English

CEFCLIDIN [JAN]

Common Name

English

cefclidin [INN]

Common Name

English

(+)-1-(((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)METHYL)-4-CARBAMOYLQUINUCLIDINIUM HYDROXIDE, INNER SALT, 7(SUP 2)-(Z)-(O-METHYLOXIME)

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357