Details of the Drug

General Information of Drug (ID: DMP54C7)

Drug Name
Bacampicillin
Synonyms
Bacampicilina; Bacampicilline; Bacampicillinum; Penglobe; Bacampicillin hydrochloride; Bacampicilina [INN-Spanish]; Bacampicillin (INN); Bacampicillin [INN:BAN]; Bacampicilline [INN-French]; Bacampicillinum [INN-Latin]; Penglobe (TN); Spectrobid (TN); (2S,5R,6R)-6((R)-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ester with ethyl 1-hydroxyethylcarbonate; 1'-Ethoxycarbonyloxyethyl-(6-D-alpha-aminophenylacetamido)penicillanate; 1-Ethoxycarbonyloxyethyl (2S,5R,6R)-6((R)-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carboxylat; 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-{[(2R)-2-amino-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 1-[(ethoxycarbonyl)oxy]ethyl 6beta-[(2R)-2-amino-2-phenylacetamido]-2,2-dimethylpenam-3alpha-carboxylate; 1-ethoxycarbonyloxyethyl (2S,5R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2S)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate; 6-((R)-2-Amino-2-phenylacetamido)penicillansaeure-(1-(ethoxycarbonyloxy)ethylester
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Urinary tract infection GC08 Approved [2]
Sinusitis CA0A.Z Investigative [2]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 465.5
Logarithm of the Partition Coefficient (xlogp) 2.7
Rotatable Bond Count (rotbonds) 10
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 9
ADMET Property
Absorption
The drug is absorbed after oral administration []
Chemical Identifiers
Formula
C21H27N3O7S
IUPAC Name
1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Canonical SMILES
CCOC(=O)OC(C)OC(=O)[C@H]1C(S[C@H]2N1C(=O)[C@H]2NC(=O)[C@@H](C3=CC=CC=C3)N)(C)C
InChI
InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1
InChIKey
PFOLLRNADZZWEX-FFGRCDKISA-N
Cross-matching ID
PubChem CID
441397
ChEBI ID
CHEBI:2968
CAS Number
50972-17-3
DrugBank ID
DB01602
TTD ID
D04CFW
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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 Binder [3]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Bacampicillin (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
SODIUM CITRATE DMHPD2Y Moderate Decreased absorption of Bacampicillin due to altered gastric pH caused by SODIUM CITRATE. Discovery agent [N.A.] [4]
Dexlansoprazole DM1DBV5 Moderate Decreased absorption of Bacampicillin due to altered gastric pH caused by Dexlansoprazole. Gastro-oesophageal reflux disease [DA22] [4]

References

1 FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 050520.
2 Bacampicillin FDA Label
3 Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34.
4 Honig PK, Gillespie BK "Clinical significance of pharmacokinetic drug interactions with over-the-counter (OTC) drugs." Clin Pharmacokinet 35 (1998): 167-71. [PMID: 9784931]