CAS 135821-54-4

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Chemistry

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Also known as: Ceftizoxime alapivoxil, 135821-54-4, Ceftizoxime alapivoxil [inn], 3mm3320ljn, As-924, Unii-3mm3320ljn

Molecular Formula

C₂₂H₂₈N₆O₈S₂

Molecular Weight

568.6 g/mol

InChI Key

VOPANQNVVCPHQR-IVVGYLHBSA-N

FDA UNII

3MM3320LJN

Ceftizoxime Alapivoxil is the alapivalate ester prodrug form of ceftizoxime, a semi-synthetic, broad-spectrum, beta-lactamase-resistant, third-generation cephalosporin with antibacterial activity. After oral administration of ceftizoxime alapivoxil, the ester bond is cleaved, releasing active ceftizoxime.

1 2D Structure

CAS 135821-54-4

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2,2-dimethylpropanoyloxymethyl (6R,7R)-7-[[(2Z)-2-[2-[[(2S)-2-aminopropanoyl]amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

2.1.2 InChI

InChI=1S/C22H28N6O8S2/c1-10(23)15(29)26-21-24-11(8-38-21)13(27-34-5)16(30)25-14-17(31)28-12(6-7-37-18(14)28)19(32)35-9-36-20(33)22(2,3)4/h6,8,10,14,18H,7,9,23H2,1-5H3,(H,25,30)(H,24,26,29)/b27-13-/t10-,14+,18+/m0/s1

2.1.3 InChI Key

VOPANQNVVCPHQR-IVVGYLHBSA-N

2.1.4 Canonical SMILES

CC(C(=O)NC1=NC(=CS1)C(=NOC)C(=O)NC2C3N(C2=O)C(=CCS3)C(=O)OCOC(=O)C(C)(C)C)N

2.1.5 Isomeric SMILES

C[C@@H](C(=O)NC1=NC(=CS1)/C(=N/OC)/C(=O)N[C@H]2[C@@H]3N(C2=O)C(=CCS3)C(=O)OCOC(=O)C(C)(C)C)N

2.2 Other Identifiers

2.2.1 UNII

3MM3320LJN

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (2-(2-alanylaminothiazol-4-yl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylate

2. As 924

3. As-924

4. Ceftizoxime Alapivoxil

2.3.2 Depositor-Supplied Synonyms

1. Ceftizoxime Alapivoxil

2. 135821-54-4

3. Ceftizoxime Alapivoxil [inn]

4. 3mm3320ljn

5. As-924

6. Unii-3mm3320ljn

7. Chembl2106058

8. Zinc59660352

9. C21592

10. (2-(2-alanylaminothiazol-4-yl)-2-methoxyiminoacetamido)-3-cephem-4-carboxylate

11. (+)-(pivaloyloxy)methyl (6r,7r)-7-(2-(2-(l-alanylamino)thiazol-4-yl)glyoxylamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 7(sup 2)-(z)-(o)-methyloxime)

12. (+)-(pivaloyloxy)methyl (6r,7r)-7-(2-(2-(l-alanylamino)thiazol-4-yl)glyoxylamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 7,2-(z)-(o)-methyloxime)

13. (+)-(pivaloyloxy)methyl (6r,7r)-7-(2-(2-(l-alanylamino)thiazol-4-yl)glyoxylamido)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate 72-(z)-(o)-methyloxime)

14. (7r)-7-[2-[2-[[(2s)-2-aminopropionyl]amino]thiazole-4-yl]-2-(methoxyimino)acetylamino]cepham-3-ene-4-carboxylic Acid (pivaloyloxy)methyl Ester

2.4 Create Date

2006-10-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₈N₆O₈S₂
Molecular Weight	568.6 g/mol
XLogP3	1.1
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	13
Rotatable Bond Count	12
Exact Mass	568.14100422 g/mol
Monoisotopic Mass	568.14100422 g/mol
Topological Polar Surface Area	245 Å²
Heavy Atom Count	38
Formal Charge	0
Complexity	1050
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1