[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate

• ChemBase ID: 1381
• Molecular Formular: C22H29N3O6S
• Molecular Mass: 463.54716
• Monoisotopic Mass: 463.17770666
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)OCOC(=O)C(C)(C)C)C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: O=C([C@@H](c1ccccc1)N)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)OCOC(=O)C(C)(C)C)(C)C
• InChI: InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1
• InChIKey: ZEMIJUDPLILVNQ-ZXFNITATSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• Brand Name: Pondocillin
• Synonyms: Ampicillin pivaloyloxymethyl ester; Pivaloylampicillin; Pivaloyloxymethyl ampicillinate; Pivampicilina [inn-spanish]; Pivampicilline [inn-french]; Pivampicillinum [inn-latin]; Pivampicillin

Database IDs

• CAS Number: 33817-20-8
• PubChem SID: 160964841; 46505340
• PubChem CID: 33478

CALCULATED PROPERTIES

JChem

• Acid pKa: 11.707929
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.15542963
• LogD (pH = 7.4): 1.7449553
• Log P: 2.0651925
• Molar Refractivity: 116.2483 cm^3
• Polarizability: 46.953476 Å^3
• Polar Surface Area: 128.03 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.43
• LOG S: -4.12
• Solubility (Water): 3.54e-02 g/l

DETAILS

DrugBank - DB01604

• Drug Groups: approved
• Description: Pivalate ester analog of ampicillin.
• Indication: or the treatment of respiratory tract infections (including acute bronchitis, acute exacerbations of chronic bronchitis and pneumonia); ear, nose and throat infections; gynecological infections; urinary tract infections (including acute uncomplicated gonococcal urethritis) when caused by non penicillinase-producing susceptible strains of the following organisms: gram-positive organisms, e.g., streptococci, pneumococci and staphylococci; gram-negative organisms, e.g., H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis.
• Pharmacology: Pivampicillin is the pivaloyloxymethyl ester of (the semi-synthetic penicillin) ampicillin. It is an inactive pro-drug, which is converted during its absorption from the gastrointestinal tract to the microbiologically active ampicillin, together with formaldehyde and pivalic acid, by non-specific esterases present in most body tissues. Amounts in excess of 99% of the pivampicillin absorbed are converted to ampicillin within 15 minutes of absorption.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Absorbed following oral administration.
• Half Life: Approximately 1 hour.
• References: Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. [Pubmed] ; Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. Pubmed
• Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. Pubmed