CEFTOBIPROLE MEDOCARIL


Synonyms	BAL-5788 BAL-5788-001 BAL5788 BAL5788-001 Ceftobiprole medocaril Ceftobiprole medocaril sodium Ceftobiprole medocaril sodium salt RO 65-5788 RO-65-5788 RO-655788
Status
Molecule Category	Mixture
ATC	J01DI01
UNII	N99027V28J


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	HFTSMHTWUFCYMJ-FDNJTQOMSA-N
Smiles	Cc1oc(=O)oc1COC(=O)N1CC[C@@H](N2CC/C(=C\C3=C(C(=O)O)N4C(=O)[C@@H](NC(=O)/C(=N/O)c5nsc(N)n5)[C@H]4SC3)C2=O)C1
InChI	InChI=1S/C26H26N8O11S2/c1-10-14(45-26(41)44-10)8-43-25(40)32-4-3-13(7-32)33-5-2-11(20(33)36)6-12-9-46-22-16(21(37)34(22)17(12)23(38)39)28-19(35)15(30-42)18-29-24(27)47-31-18/h6,13,16,22,42H,2-5,7-9H2,1H3,(H,28,35)(H,38,39)(H2,27,29,31)/b11-6+,30-15+/t13-,16-,22-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C26H26N8O11S2
Molecular Weight	690.67
AlogP	-0.54
Hydrogen Bond Acceptor	16.0
Hydrogen Bond Donor	4.0
Number of Rotational Bond	8.0
Polar Surface Area	264.3
Molecular species	ACID
Aromatic Rings	2.0
Heavy Atoms	47.0

Bioactivity

Mechanism of Action	Action	Reference
Bacterial penicillin-binding protein inhibitor	INHIBITOR	Other

Assay Description	Organism	Bioactivity
Inhibition of methicillin-susceptible Staphylococcus aureus ATCC 29213 PBP 1	Staphylococcus aureus	0.1 ug.mL-1
Inhibition of methicillin-susceptible Staphylococcus aureus ATCC 29213 PBP 2	Staphylococcus aureus	0.5 ug.mL-1
Inhibition of methicillin-susceptible Staphylococcus aureus ATCC 29213 PBP 3	Staphylococcus aureus	0.05 ug.mL-1
Inhibition of methicillin-susceptible Staphylococcus aureus ATCC 29213 PBP 4	Staphylococcus aureus	1.0 ug.mL-1
Inhibition of methicillin-resistant Staphylococcus aureus OC 3726 PBP 2a	Staphylococcus aureus	0.9 ug.mL-1

Cross References

Resources	Reference
ChEMBL	CHEMBL1652606
FDA SRS	N99027V28J
PubChem	135413543
ZINC	ZINC000072123798
ChEMBL	CHEMBL4297101
FDA SRS	N99027V28J
PubChem	135413543
SureChEMBL	SCHEMBL3069914

CONTENTS


PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains. Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).