Details of the Drug

General Information of Drug (ID: DMM76GL)

Drug Name

Ceftobiprole

Synonyms

BAL 9141; BAL 9141-000; BAL-9141; Ro 63-9141; Ro-63-9141; Ro-63-9141/000; (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-ylidene)-2-nitrosoacetyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)-pyrrolidin-3-yl]pyrrolidin-3-ylidene]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Indication

Disease Entry	ICD 11	Status	REF
Community-acquired pneumonia	CA40.Z	Phase 3	[1]
Skin and skin-structure infection	1F28-1G0Z	Phase 3	[2]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 3

Molecular Weight (mw)

534.6

Logarithm of the Partition Coefficient (xlogp)

-2.4

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H22N8O6S2
IUPAC Name: (6R,7R)-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-[(E)-[2-oxo-1-[(3R)-pyrrolidin-3-yl]pyrrolidin-3-ylidene]methyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Canonical SMILES: C1CNC[C@@H]1N2CC/C(=C\\C3=C(N4[C@@H]([C@@H](C4=O)NC(=O)/C(=N\\O)/C5=NSC(=N5)N)SC3)C(=O)O)/C2=O
InChI: InChI=1S/C20H22N8O6S2/c21-20-24-14(26-36-20)11(25-34)15(29)23-12-17(31)28-13(19(32)33)9(7-35-18(12)28)5-8-2-4-27(16(8)30)10-1-3-22-6-10/h5,10,12,18,22,34H,1-4,6-7H2,(H,23,29)(H,32,33)(H2,21,24,26)/b8-5+,25-11-/t10-,12-,18-/m1/s1
InChIKey: VOAZJEPQLGBXGO-SDAWRPRTSA-N

Cross-matching ID

PubChem CID: 135413542
ChEBI ID: CHEBI:140407
CAS Number: 209467-52-7
DrugBank ID: DB04918
TTD ID: D0CI9T

Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Bacterial Penicillin binding protein (Bact PBP)	TTJP4SM	NOUNIPROTAC	Modulator	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	ClinicalTrials.gov (NCT03439124) Ceftobiprole in the Treatment of Pediatric Patients With Pneumonia. U.S. National Institutes of Health.
2	ClinicalTrials.gov (NCT03137173) Ceftobiprole in the Treatment of Patients With Acute Bacterial Skin and Skin Structure Infections. U.S. National Institutes of Health.
3	Binding of ceftobiprole and comparators to the penicillin-binding proteins of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and ... Antimicrob Agents Chemother. 2007 Jul;51(7):2621-4.