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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H20N6O7S4
Molecular Weight 584.669
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFODIZIME

SMILES

[H][C@]12SCC(CSC3=NC(C)=C(CC(O)=O)S3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C(O)=O

InChI

InChIKey=XDZKBRJLTGRPSS-BGZQYGJUSA-N
InChI=1S/C20H20N6O7S4/c1-7-10(3-11(27)28)37-20(22-7)36-5-8-4-34-17-13(16(30)26(17)14(8)18(31)32)24-15(29)12(25-33-2)9-6-35-19(21)23-9/h6,13,17H,3-5H2,1-2H3,(H2,21,23)(H,24,29)(H,27,28)(H,31,32)/b25-12-/t13-,17-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H20N6O7S4
Molecular Weight 584.669
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://en.wikipedia.org/wiki/Cefodizime https://www.jstage.jst.go.jp/article/antibiotics1968/37/8/37_8_892/_pdf

Cefodizime is a third-generation cephalosporin with a broad spectrum of antibacterial activity. Administered intravenously or intramuscularly 1 to 4 g of cefodizime daily for an average of 7 to 10 days produces a clinical cure in 80 to 100% of patients (adults, elderly or children) with upper or lower respiratory tract infections or urinary tract infections. In comparative trials cefodizime was as effective as other third generation cephalosporins. A single dose of cefodizime (1 or 2 g) is also useful in treating lower urinary tract infections. Urogenital gonorrhoea, whether caused by beta-lactamase producing or non-beta-lactamase producing Neisseria gonorrhoeae, is very effectively treated by single dose therapy with intramuscular cefodizime. Preliminary data from a small number of patients indicates that cefodizime may also be useful in the treatment of otitis media, sinusitis and gynaecological infections, and for the prophylaxis or treatment of surgical infections. The clinical efficacy of cefodizime compared to other third generation cephalosporins is superior to that predicted from in vitro results. This superior activity of cefodizime may be related to the relatively long elimination half-life of the drug or its ability to modify some functions of the immune system--a potentially important finding awaiting further investigation. Cefodizime is well tolerated and has a tolerability profile similar to other members of its class with systemic adverse events being primarily gastrointestinal or dermatological. Cefodizime may be more convenient to administer than some other agents of its class as it may be given once or twice daily. While there are no trials comparing cefodizime to other third generation cephalosporins in immunosuppressed populations, preliminary information indicates cefodizime may be useful in this group. Cefodizime targets penicillin-binding proteins (PBPs) 1A/B, 2, and 3 resulting in the eventual death of the bacterial cell. In vivo experimental models of infection showed that bacterial clearance by this drug is at least as effective compared with other 3rd generation cephalosporins. It has a similar adverse effect profile to other 3rd generation cephalosporins which is mainly being limited to gastrointestinal or dermatological side effects. It is not currently approved by the FDA for use in the United States.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08149
Gene ID: NA
Gene Symbol: penA
Target Organism: Neisseria gonorrhoeae
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
Curative
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cefodizime. A review of its antibacterial activity, pharmacokinetic properties and therapeutic use.
1992 Nov
Patents

Sample Use Guides

In Vivo Use Guide
intravenously or intramuscularly, cefodizime 1 to 4 g daily for an average of 7 to 10 days
Route of Administration: Other
In Vitro Use Guide
MIC90 is 0.125 mg/l for Streptococcus pneumoniae, Streptococcus pyogenes and other streptococci; and 0.05 mg/l for Haemophilus spp., Neisseria meningitidis, Neisseria gonorrhoeae and Moraxella catarrhalis; while beta-lactamase positive strains of M. catarrhalis require 1 mg/l
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:12:15 GMT 2023
Edited
by admin
on Fri Dec 15 17:12:15 GMT 2023
Record UNII
Z31298J4HQ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFODIZIME
INN   MI   WHO-DD  
INN  
Official Name English
THR 221 FREE ACID
Code English
S-77-1221-B FREE ACID
Code English
(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-3-(((5-(CARBOXYMETHYL)-4-METHYL-2-THIAZOLYL)THIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID 7(SUP 2)-(Z)-(O-METHYLOXIME)
Common Name English
cefodizime [INN]
Common Name English
S 77 1221 B FREE ACID
Code English
HR 221 FREE ACID
Code English
CEFODIZIME SODIUM [JAN]
Common Name English
Cefodizime [WHO-DD]
Common Name English
HR-221 FREE ACID
Code English
THR-221 FREE ACID
Code English
CEFODIZIME [MI]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01DD09
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
NCI_THESAURUS C357
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
WHO-ATC J01DD09
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
Code System Code Type Description
MERCK INDEX
m3199
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
541
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PRIMARY
SMS_ID
100000081823
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PRIMARY
INN
4967
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PRIMARY
RXCUI
20485
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PRIMARY RxNorm
NCI_THESAURUS
C98224
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PRIMARY
FDA UNII
Z31298J4HQ
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
PRIMARY
ChEMBL
CHEMBL2303613
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
PRIMARY
WIKIPEDIA
Cefodizime
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
PRIMARY
MESH
C033356
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PRIMARY
EPA CompTox
DTXSID2022757
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PRIMARY
DRUG BANK
DB13470
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PRIMARY
PUBCHEM
5361871
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PRIMARY
CAS
69739-16-8
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
PRIMARY
CHEBI
63214
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
PRIMARY
EVMPD
SUB07401MIG
Created by admin on Fri Dec 15 17:12:15 GMT 2023 , Edited by admin on Fri Dec 15 17:12:15 GMT 2023
PRIMARY
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