(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid trihydrate

• ChemBase ID: 105414
• Molecular Formular: C16H25N3O7S
• Molecular Mass: 403.4506
• Monoisotopic Mass: 403.14132116
• SMILES: O=C(O)[C@@H]1N2C(=O)[C@@H](NC(=O)[C@@H](c3ccccc3)N)[C@H]2SC1(C)C.O.O.O
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C.O.O.O
• InChI: InChI=1S/C16H19N3O4S.3H2O/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8;;;/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23);3*1H2/t9-,10-,11+,14-;;;/m1.../s1
• InChIKey: RXDALBZNGVATNY-CWLIKTDRSA-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-carboxylic acid trihydrate
• IUPAC Traditional name: ampicillin trihydrate
• Synonyms: D-(-)-α-Aminobenzylpenicillin; Aminobenzylpenicillin trihydrate; alpha-Aminobenzylpenicillin trihydrate; AMPICILLIN TRIHYDRATE; Ampicillin; Ampicillin trihydrate; (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 trihydrate; 氨苄青霉素; 氨苄西林 三水合物; 氨苄西林; 氨苄西林 三水合物

Database IDs

• CAS Number: 7177-48-2
• EC Number: 200-709-7
• MDL Number: MFCD00072036
• Beilstein Number: 5399534
• PubChem SID: 24890564; 24869717; 162092119; 24891059
• PubChem CID: 23565

CALCULATED PROPERTIES

• Acid pKa: 3.2380536
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.0056438
• LogD (pH = 7.4): -2.2605202
• Log P: -2.0066502
• Molar Refractivity: 87.5235 cm^3
• Polarizability: 34.874416 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 198-200 °C (dec.)(lit.); 198-200°C; 200-202 °C (dec.)
• Optical Rotation: [α]20/D +250±10°, c = 0.5% in H2O

Safety Information

• Storage Condition: 2-8°C
• RTECS: XH8425000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43; R:22
• Safety Statements: 22-26-36/37; S:36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H315-H317-H319-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥96.0% (NT); 96.0-100.5% anhydrous basis (HPLC)
• Grade: VETRANAL™, analytical standard
• Salt Data: 3 H2O
• Suitability: meets USP testing specifications
• Ignition Residue: ≤0.05%
• Empirical Formula (Hill Notation): C16H19N3O4S · 3H2O

DETAILS

MP Biomedicals - 02190147

Trihydrate Crystalline

Sigma Aldrich - A6140

Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Ampicillin Trihydrate is commonly used to select for ampicillin resistance in mutated and transformed cells.

Sigma Aldrich - 31591

Application
Commission Regulation (EU) No 37/2010 of 22 December 2009 on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin
Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 10045

Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Application
Ampicillin Trihydrate is commonly used to select for ampicillin resistance in mutated and transformed cells. It is used in intracellular targeting of antibiotics on biodegradable polymeric carriers 1. Nanoparticle-bound ampicillin has been shown to be more effective than free ampicillin against Listeria monocytogenes in mouse peritoneal macrophages2. Ampicillin has been shown to cause Clostridium difficile-Associated ileocecitis in the hamster model3.

Sigma Aldrich - A1593

Application
Used to select for ampicillin resistance in mutated and transformed cells.
Biochem/physiol Actions
A β-lactam antibiotic with an amino group side chain attached to the penicillin structure. Penicillin derivative that inhibits bacterial cell-wall synthesis (peptidoglycan cross-linking) by inactivating transpeptidases on the inner surface of the bacterial cell membrane. Bactericidal only to growing Escherichia coli . Mode of resistance: Cleavage of β-lactam ring of ampicillin by β-lactamase. Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.