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Chemistry

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Also known as: 65243-33-6, Cefetamet pivoxyl, Globocef, Cefyl, Cefetamet pivaloyloxymethyl ester, F6xa85n260
Molecular Formula
C20H25N5O7S2
Molecular Weight
511.6  g/mol
InChI Key
DASYMCLQENWCJG-XUKDPADISA-N
FDA UNII
F6XA85N260

Cefyl
Cefetamet Pivoxil is the pivalate ester prodrug form of cefetamet, a semi-synthetic, beta-lactamase-stable, third-generation cephalosporin with antibacterial activity. After oral administration of cefetamet pivoxil, the ester bond is cleaved, releasing active cefetamet.
1 2D Structure

Cefyl

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
2.1.2 InChI
InChI=1S/C20H25N5O7S2/c1-9-6-33-16-12(23-14(26)11(24-30-5)10-7-34-19(21)22-10)15(27)25(16)13(9)17(28)31-8-32-18(29)20(2,3)4/h7,12,16H,6,8H2,1-5H3,(H2,21,22)(H,23,26)/b24-11-/t12-,16-/m1/s1
2.1.3 InChI Key
DASYMCLQENWCJG-XUKDPADISA-N
2.1.4 Canonical SMILES
CC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)OCOC(=O)C(C)(C)C
2.1.5 Isomeric SMILES
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)OCOC(=O)C(C)(C)C
2.2 Other Identifiers
2.2.1 UNII
F6XA85N260
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 7-(2 (2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-desacetoxyceph-3-em-4-carboxylic Acid Pivaloyloxymethyl Ester

2. Cefetamet Pivaloyloxymethyl Ester

3. Cefetamet Pivoxyl

4. Ro 15-8075

5. Ro-15-8075

2.3.2 Depositor-Supplied Synonyms

1. 65243-33-6

2. Cefetamet Pivoxyl

3. Globocef

4. Cefyl

5. Cefetamet Pivaloyloxymethyl Ester

6. F6xa85n260

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

8. 5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid,7-[[(2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-methyl-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r,7r)-

9. Unii-f6xa85n260

10. Cefatamet Pivoxil

11. Ncgc00181788-01

12. Schembl74256

13. Cefatamet Pivoxil [mi]

14. Chembl4303443

15. Dasymclqenwcjg-xukdpadisa-

16. Dtxsid40110016

17. Chebi:135812

18. Cefetamet Pivoxil [who-dd]

19. Zinc34027229

20. Cefditoren Impurity 3, Cefetamet Pivoxil

21. Ro-15-8075

22. 7-(2 (2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-desacetoxyceph-3-em-4-carboxylic Acid Pivaloyloxymethyl Ester

23. 243c336

24. (7r)-7beta-[(2-aminothiazol-4-yl)(methoxyimino)acetylamino]-3-methylcepham-3-ene-4-carboxylic Acid Pivaloyloxymethyl Ester

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

26. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-methyl-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r-(6alpha,7beta(z)))-

27. 5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic Acid, 7-(((2z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-methyl-8-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl Ester, (6r,7r)-

2.4 Create Date
2005-08-08
3 Chemical and Physical Properties
Molecular Weight 511.6 g/mol
Molecular Formula C20H25N5O7S2
XLogP33.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count12
Rotatable Bond Count10
Exact Mass511.11954050 g/mol
Monoisotopic Mass511.11954050 g/mol
Topological Polar Surface Area216 Ų
Heavy Atom Count34
Formal Charge0
Complexity933
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.)


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