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Pivampicillin Hydrochloride

CAT: 0013-GTR19193087-01Size: 25 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19193087-01Size:25 mg
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Description
Piampicillin Hydrochloride is the hydrochloride salt of piampicillin, an orally active ampicillin prodrug. It exhibits antimicrobial activity and is used in research for studying antibiotic efficacy in both in vitro susceptibility assays and in vivo infection models.
CAS Number
26309-95-5
Field of Research
Infectious Disease & Virology, Pharmacology & Drug Discovery
Smiles
Cl.[H][C@]12SC (C) (C) [C@@H] (N1C (=O) [C@H]2NC (=O) [C@H] (N) c1ccccc1) C (=O) OCOC (=O) C (C) (C) C
Molecular Formula
C22H30ClN3O6S
Molecular Weight
500.01
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

Pivampicillin Hydrochloride

Pivampicillin Hydrochloride is the hydrochloride salt form of a semisynthetic, orally active pivalate ester of ampicillin with antibacterial activity. Upon absorption, pivampicillin is hydrolyzed into its active form ampicillin by esterases. Ampicillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall, eventually causing cell lysis.

CAS Number26309-95-5
PubChem CID33477
IUPAC Name2,2-dimethylpropanoyloxymethyl (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;hydrochloride
Molecular FormulaC22H30ClN3O6S
Molecular Weight500.0
Topological Polar Surface Area153
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Heavy Atom Count33
Formal Charge0
Complexity774
SMILES
CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)C(C)(C)C)C.Cl
InChI
InChI=1S/C22H29N3O6S.ClH/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);1H/t13-,14-,15+,18-;/m1./s1
InChIKey
DQECFVGMGBQCPA-GLCLSGQWSA-N
Chemical Structure
2D Structure
2D structure of Pivampicillin Hydrochloride
CAS: 26309-95-5
CID: 33477
Formula: C22H30ClN3O6S
MW: 500.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight500.0
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass499.1543846
Monoisotopic Mass499.1543846
Topological Polar Surface Area153 Ų
Heavy Atom Count33
Formal Charge0
Complexity774
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count2
Compound Is CanonicalizedYes

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