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Technical details about Cefixime, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: Cefixime, 97164-56-2, 79350-37-1, Cefixime(e)-form, (e)-cefixime, Cefixime anhydrous, (e)-
Molecular Formula
C16H15N5O7S2
Molecular Weight
453.5  g/mol
InChI Key
OKBVVJOGVLARMR-VINNURBNSA-N
FDA UNII
U7RWT9J78O

A third-generation cephalosporin antibiotic that is stable to hydrolysis by beta-lactamases.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(6R,7R)-7-[[(2E)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
2.1.2 InChI
InChI=1S/C16H15N5O7S2/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27)/b20-9+/t10-,14-/m1/s1
2.1.3 InChI Key
OKBVVJOGVLARMR-VINNURBNSA-N
2.1.4 Canonical SMILES
C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
2.1.5 Isomeric SMILES
C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N/OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
2.2 Other Identifiers
2.2.1 UNII
U7RWT9J78O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Cefixime

2. Cefixime Anhydrous

3. Cefixime Trihydrate

4. Fk 027

5. Fk-027

6. Fk027

7. Fr 17027

8. Fr-17027

9. Fr17027

2.3.2 Depositor-Supplied Synonyms

1. Cefixime

2. 97164-56-2

3. 79350-37-1

4. Cefixime(e)-form

5. (e)-cefixime

6. Cefixime Anhydrous, (e)-

7. U7rwt9j78o

8. Cfix

9. (6r,7r)-7-(((2e)-2-(2-amino-4-thiazolyl)-2-((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid

10. (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

11. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2e)-2-(2-amino-4-thiazolyl)-2-((carboxymethoxy)imino)acetyl)amino)-3-ethenyl-8-oxo-, (6r,7r)-

12. Cefixime Impurity D

13. Unii-u7rwt9j78o

14. (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

15. Cefiximetrihydrate

16. Prestwick2_000462

17. Epitope Id:116227

18. Schembl24946

19. Schembl49534

20. Chembl427069

21. Bdbm88962

22. Chebi:93248

23. Gtpl10898

24. Cid_56642849

25. Hms1569m06

26. (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-((carboxymethoxy)imino)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

27. Zinc4468778

28. Ncgc00185001-01

29. (e)-cefixime (cefixime Ep Impurity D)

30. Q163901

31. J-005196

32. J-501698

33. Brd-k04993501-001-01-9

34. [6r-[6alpha,7beta(e)]]-7-[[(2-amino-4-thiazolyl)[(car

35. (6r,7r)-7-[[(2e)-2-(2-amino-1,3-thiazol-4-yl)-2-(carboxymethoxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

36. (6r,7r)-7-[[(2e)-2-(2-amino-4-thiazolyl)-2-(carboxymethoxyimino)-1-oxoethyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

37. (6r,7r)-7-[[(2e)-2-(2-aminothiazol-4-yl)-2-(carboxymethyloximino)acetyl]amino]-8-keto-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

38. (6r,7r)-7-[[(2e)-2-(2-azanyl-1,3-thiazol-4-yl)-2-(2-hydroxy-2-oxoethyloxyimino)ethanoyl]amino]-3-ethenyl-8-oxidanylidene-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;hydrate

39. (6r,7r)-7-[[(2z)-2-(2-amino-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene -2-carboxylic Acid

40. (6r,7r,e)-7-(2-(2-aminothiazol-4-yl)-2-(carboxymethoxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

2.4 Create Date
2005-11-20
3 Chemical and Physical Properties
Molecular Weight 453.5 g/mol
Molecular Formula C16H15N5O7S2
XLogP3-0.7
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count12
Rotatable Bond Count8
Exact Mass453.04129018 g/mol
Monoisotopic Mass453.04129018 g/mol
Topological Polar Surface Area238 Ų
Heavy Atom Count30
Formal Charge0
Complexity861
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Anti-Bacterial Agents

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


4.2 FDA Pharmacological Classification
4.2.1 Pharmacological Classes
Cephalosporins [CS]; Cephalosporin Antibacterial [EPC]
4.3 ATC Code

J - Antiinfectives for systemic use

J01 - Antibacterials for systemic use

J01D - Other beta-lactam antibacterials

J01DD - Third-generation cephalosporins

J01DD08 - Cefixime


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