1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

• ChemBase ID: 1379
• Molecular Formular: C21H27N3O7S
• Molecular Mass: 465.51998
• Monoisotopic Mass: 465.15697122
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)OC(OC(=O)OCC)C)C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: CCOC(=O)OC(OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)[C@@H](c1ccccc1)N)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

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• IUPAC Traditional name: bacampicilline; bacampicillin
• Brand Name: Penglobe; Spectrobid
• Synonyms: Bacampicillin Hydrochloride; Bacampicillin

Database IDs

• CAS Number: 50972-17-3; 37661-08-8
• PubChem SID: 160964839; 46507859
• PubChem CID: 39849; 441397
• CHEBI ID: 2968
• ATC CODE: J01CA06
• CHEMBL: 1583
• Chemspider ID: 390135
• DrugBank ID: DB01602
• Unique Ingredient Identifier: 8GM2J22278
• Wikipedia Title: Bacampicillin

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.7201185
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.4384752
• LogD (pH = 7.4): 1.1510522
• Log P: 1.4712881
• Molar Refractivity: 113.7604 cm^3
• Polarizability: 45.85553 Å^3
• Polar Surface Area: 137.26 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.17
• LOG S: -3.58
• Solubility (Water): 1.23e-01 g/l

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Metabolism: Rapidly hydrolyzed to ampicillin

DETAILS

DrugBank - DB01602

• Drug Groups: approved
• Description: Bacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.
• Indication: For infections at the following sites: upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: Gram-positive: streptococci (including S. faecalis and S. pneumoniae) and nonpenicillinase-producing staphylococci; Gram-negative: H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis, Salmonellae and Shigellae.
• Pharmacology: Bacampicillin is a prodrug of ampicillin and is microbiologically inactive.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Absorbed following oral administration.
• External Links: Drugs.com