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Chemistry

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Also known as: Cefetamet pivoxil hydrochloride, 111696-23-2, 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(2e)-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;hydrochloride, Ncgc00181788-01, Dsstox_cid_28516, Dsstox_rid_82788

Molecular Formula

C₂₀H₂₆ClN₅O₇S₂

Molecular Weight

548.0 g/mol

InChI Key

XAAOHMIKXULDKJ-LZRHLYMTSA-N

Cefetamet Pivoxil Hydrochloride is the hydrochloride salt form of cefetamet pivoxil, a pivalate ester prodrug form of a cefetamet. After oral administration of cefetamet pivoxil hydrochloride, the ester bond is cleaved, releasing active cefetamet.

1 2D Structure

Cefetamet Pivoxil Hydrochloride

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2E)-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;hydrochloride

2.1.2 InChI

InChI=1S/C20H25N5O7S2.ClH/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);1H/b24-11+;/t12-,16-;/m1./s1

2.1.3 InChI Key

XAAOHMIKXULDKJ-LZRHLYMTSA-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.Cl

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.Cl

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. Cefetamet Pivoxil Hydrochloride

2. 111696-23-2

3. 2,2-dimethylpropanoyloxymethyl (6r,7r)-7-[[(2e)-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;hydrochloride

4. Ncgc00181788-01

5. Dsstox_cid_28516

6. Dsstox_rid_82788

7. Dsstox_gsid_48590

8. Chembl2355376

9. Dtxsid1048590

10. Tox21_112919

11. Akos032949665

12. Cas-111696-23-2

13. Q27114287

14. Toluene-4-sulfonicacid(s)-1-chlorocarbonyl-ethylester

15. (pivaloyloxy)methyl (6r,7r)-7-((z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Hydrochloride

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

2.3 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₂₆ClN₅O₇S₂
Molecular Weight	548.0 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	10
Exact Mass	547.0962182 g/mol
Monoisotopic Mass	547.0962182 g/mol
Topological Polar Surface Area	216 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	933
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2