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Chemistry

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Also known as: 104145-95-1, Cefditoren [inn], 81qs09v3yw, Chebi:59343, Cefditoren (inn), (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular Formula
C19H18N6O5S3
Molecular Weight
506.6  g/mol
InChI Key
KMIPKYQIOVAHOP-YLGJWRNMSA-N
FDA UNII
81QS09V3YW

Cefditoren
Cefditoren is a semisynthetic, broad-spectrum, beta-lactamase-resistant, third-generation cephalosporin with antibacterial activity. Cefditoren binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
Cefditoren is a Cephalosporin Antibacterial.
1 2D Structure

Cefditoren

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(Z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C19H18N6O5S3/c1-8-11(33-7-21-8)4-3-9-5-31-17-13(16(27)25(17)14(9)18(28)29)23-15(26)12(24-30-2)10-6-32-19(20)22-10/h3-4,6-7,13,17H,5H2,1-2H3,(H2,20,22)(H,23,26)(H,28,29)/b4-3-,24-12-/t13-,17-/m1/s1
2.1.3 InChI Key
KMIPKYQIOVAHOP-YLGJWRNMSA-N
2.1.4 Canonical SMILES
CC1=C(SC=N1)C=CC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)O
2.1.5 Isomeric SMILES
CC1=C(SC=N1)/C=C\C2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
81QS09V3YW
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cefditoren, Sodium Salt, (6r-(3(z),6alpha,7beta(z)))-isomer

2. Me 1206

3. Me-1206

2.3.2 Depositor-Supplied Synonyms

1. 104145-95-1

2. Cefditoren [inn]

3. 81qs09v3yw

4. Chebi:59343

5. Cefditoren (inn)

6. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

7. Cefditoren [usan:inn]

8. Unii-81qs09v3yw

9. Cdtr

10. Cefditoren [mi]

11. Cefditoren [vandf]

12. Cefditoren [who-dd]

13. Chembl1743

14. Schembl37473

15. Dtxsid501328012

16. Db01066

17. (6r-(3(z),6alpha,7beta(z)))-7-((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

18. C-2467

19. C21546

20. D07639

21. Cefditorene, Antibiotic For Culture Media Use Only

22. (+)-(6r,7r)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-3-((z)-2-(4-methyl-5-thiazolyl)vinyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7(sup 2)-(z)-(o-methyloxime)

23. (6r,7r)-7-[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

24. (6r,7r)-7-{[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

25. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino-3-(2-(4-methyl-5-thiazolyl)ethenyl)-8-oxo-, (6r-(3(z),6alpha,7beta(z)))-

26. 7beta-(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido-3-[(z)-2-(4-methyl-1,3-thiazol-5-yl)ethenyl]-3,4-didehydrocepham-4-carboxylic Acid

2.4 Create Date
2006-10-25
3 Chemical and Physical Properties
Molecular Weight 506.6 g/mol
Molecular Formula C19H18N6O5S3
XLogP30.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count12
Rotatable Bond Count7
Exact Mass506.05008122 g/mol
Monoisotopic Mass506.05008122 g/mol
Topological Polar Surface Area242 Ų
Heavy Atom Count33
Formal Charge0
Complexity928
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the treatment of mild to moderate infections in adults and adolescents (12 years of age or older) which are caused by susceptible strains of microorganisms in acute bacterial exacerbation of chronic bronchitis, community-acquired pneumonia, pharyngitis/tonsillitis, and uncomplicated skin and skin-structure infections.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Cefditoren pivoxil is a prodrug which is hydrolyzed by esterases during absorption, and the drug is distributed in the circulating blood as active cefditoren. Cefditoren is a cephalosporin with antibacterial activity against gram-positive and gram-negative pathogens. Cefditoren is effective against Staphylococcus aureus (methicillin-susceptible strains, including b-lactamase-producing strains), penicillin-susceptible strains of Staphylococcus aureus and Streptococcus pneumoniae, Streptococcus pyogenes, Haemophilus influenzae (including b-lactamase-producing strains), Haemophilus parainfluenzae (including b-lactamase-producing strains), Moraxella catarrhalis (including b-lactamase-producing strains), Streptococcus agalactiae, Streptococcus Groups C and G, and Streptococcus, viridans group (penicillin-susceptible and -intermediate strains).


5.2 MeSH Pharmacological Classification

Anti-Bacterial Agents

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CEFDITOREN
5.3.2 FDA UNII
81QS09V3YW
5.3.3 Pharmacological Classes
Chemical Structure [CS] - Cephalosporins
5.4 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DD - Third-generation cephalosporins

J01DD16 - Cefditoren


5.5 Absorption, Distribution and Excretion

Absorption

Following oral administration, cefditoren pivoxil is absorbed from the gastrointestinal tract and hydrolyzed to cefditoren by esterases. Under fasting conditions, the estimated absolute bioavailability of cefditoren pivoxil is approximately 14%. The absolute bioavailability of cefditoren pivoxil administered with a low fat meal (693 cal, 14 g fat, 122 g carb, 23 g protein) is 16.1 ± 3.0%.


Route of Elimination

Pivalate is mainly eliminated (>99%) through renal excretion, nearly exclusively as pivaloylcarnitine.


Volume of Distribution

9.3 1.6 L


Clearance

renal cl=4-5 L/h [oral administration]


5.6 Metabolism/Metabolites

Hydrolysis of cefditoren pivoxil to its active component, cefditoren, results in the formation of pivalate. Cefditoren is not appreciably metabolized.


5.7 Biological Half-Life

Mean terminal elimination half-life is 1.6 ± 0.4 hours in young healthy adults.


5.8 Mechanism of Action

The bactericidal activity of cefditoren results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefditoren is stable in the presence of a variety of b-lactamases, including penicillinases and some cephalosporinases.


API Reference Price

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11-Jan-2021
23-Nov-2024
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ABOUT THIS PAGE

Cefditoren Manufacturers

A Cefditoren manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Cefditoren, including repackagers and relabelers. The FDA regulates Cefditoren manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Cefditoren API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Cefditoren manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Cefditoren Suppliers

A Cefditoren supplier is an individual or a company that provides Cefditoren active pharmaceutical ingredient (API) or Cefditoren finished formulations upon request. The Cefditoren suppliers may include Cefditoren API manufacturers, exporters, distributors and traders.

click here to find a list of Cefditoren suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Cefditoren GMP

Cefditoren Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Cefditoren GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Cefditoren GMP manufacturer or Cefditoren GMP API supplier for your needs.

Cefditoren CoA

A Cefditoren CoA (Certificate of Analysis) is a formal document that attests to Cefditoren's compliance with Cefditoren specifications and serves as a tool for batch-level quality control.

Cefditoren CoA mostly includes findings from lab analyses of a specific batch. For each Cefditoren CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Cefditoren may be tested according to a variety of international standards, such as European Pharmacopoeia (Cefditoren EP), Cefditoren JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Cefditoren USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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