CEFTAROLINE

ID: ALA4594371

Chembl Id: CHEMBL4594371

Cas Number: 189345-04-8

PubChem CID: 9938701

Max Phase: Unknown

Molecular Formula: C22H20N8O5S4

Molecular Weight: 604.72

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Ceftaroline | T 91825 | T-91825 | T-91825|189345-04-8|T 91825|UNII-H36Z0FHR8K|H36Z0FHR8K|PPI 0903M|CHEBI:70729|DTXSID90172341|(6R,7R)-7-{[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)acetyl]amino}-3-{[4-(1-methylpyridinium-4-yl)-1,3-thiazol-2-yl]sulfanyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate|Pyridinium, 4-(2-(((6R,7R)-7-(((2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(ethoxyimino)-1-oxoethyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)thio)-4-thiazolyl)-Show More⌵

Canonical SMILES:  CCO/N=C(\C(=O)N[C@@H]1C(=O)N2C(C(=O)[O-])=C(Sc3nc(-c4cc[n+](C)cc4)cs3)CS[C@H]12)c1nsc(N)n1

Standard InChI:  InChI=1S/C22H20N8O5S4/c1-3-35-27-13(16-26-21(23)39-28-16)17(31)25-14-18(32)30-15(20(33)34)12(9-36-19(14)30)38-22-24-11(8-37-22)10-4-6-29(2)7-5-10/h4-8,14,19H,3,9H2,1-2H3,(H3-,23,25,26,28,31,33,34)/b27-13-/t14-,19-/m1/s1

Standard InChI Key:  RGFBRLNVZCCMSV-BIRGHMBHSA-N

Alternative Forms

1. Parent:

   

   ALA4594371

   CEFTAROLINE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 604.72

Molecular Weight (Monoisotopic): 604.0439

AlogP: -0.04

#Rotatable Bonds: 9

Polar Surface Area: 179.70

Molecular Species: ACID

HBA: 14

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 2.62

CX Basic pKa: 0.36

CX LogP: -2.71

CX LogD: -3.00

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.14

Np Likeness Score: -0.80

References

1. Unpublished dataset, 

2. Shalaby MW, Dokla EME, Serya RAT, Abouzid KAM..  (2020)  Penicillin binding protein 2a: An overview and a medicinal chemistry perspective.,  199  [PMID:32442851] [10.1016/j.ejmech.2020.112312]

3. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(2):

• Scientific Literature
• Active Ingredient of a Prodrug