(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

• ChemBase ID: 298
• Molecular Formular: C16H19N3O4S
• Molecular Mass: 349.40476
• Monoisotopic Mass: 349.1096271
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)[C@H](N)c1ccccc1
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C16H19N3O4S/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)/t9-,10-,11+,14-/m1/s1
• InChIKey: AVKUERGKIZMTKX-NJBDSQKTSA-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
• IUPAC Traditional name: ampicillin
• Brand Name: AB-PC; Ab-Pc Sol; Acillin; Adobacillin; Alpen; Amblosin; Amcill; Amfipen; Amfipen V; Amipenix S; Ampen; Ampi; Ampi-Bol; Ampi-Co; Ampi-Tab; Ampichel; Ampicil; Ampicillin A; Ampicin; Ampifarm; Ampikel; Ampimed; Ampipenin; Ampipenin, Nt3; Ampiscel; Ampisyn; Ampivax; Ampivet; Amplacilina; Amplin; Amplipenyl; Amplisom; Amplital; Ampy-Penyl; Austrapen; BRL; Binotal; Bonapicillin; Britacil; Campicillin; Cimex; Copharcilin; D-Cillin; Delcillin; Deripen; Divercillin; Doktacillin; Duphacillin; Geocillin; Grampenil; Guicitrina; Guicitrine; Lifeampil; Morepen; Norobrittin; Novo-Ampicillin; Nuvapen; Olin Kid; Omnipen; Omnipen-N; Orbicilina; Pen A; Pen Ampil; Pen a Oral; Penbristol; Penbritin; Penbritin Paediatric; Penbritin Syrup; Penbritin-S; Penbrock; Penicline; Penimic; Pensyn; Pentrex; Pentrexl; Pentrexyl; Pfizerpen A; Pfizerpen-A; Polycillin; Polycillin-N; Ponecil; Princillin; Principen; Principen '125'; Principen '250'; Principen '500'; Qidamp; Racenacillin; Ro-Ampen; Rosampline; Roscillin; Semicillin; Semicillin R; Servicillin; Sk-Ampicillin; Spectrobid; Sumipanto; Supen; Synpenin; Texcillin; Tokiocillin; Tolomol; Totacillin; Totacillin-N; Totalciclina; Totapen; Trifacilina; Ultrabion; Ultrabron; Vampen; Viccillin; Viccillin S; Wypicil
• Synonyms: Ampicilline [INN-French]; Ampicillinum [INN-Latin]; Ampicilline; Ampicillina [Dcit]; Ampicillin [Usan:Ban:Inn:Jan]; Ampicillin Trihydrate; Ampicillin Sodium; Ampicillin Base; Ampicillin Anhydrous; Ampicillin Anhydrate; Ampicillin Acid; Ampicilina [INN-Spanish]; Anhydrous Ampicillin; Bayer 5427; D-Ampicillin; Aminobenzylpenicillin; Ampicillin; Ampicillin; Amplital; Penicline; (2S,5R,6R)-6-[[(2RS)-2-Amino-2-(phenyl-d5)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; AY 6108-d5; Albipen-d5; Amfipen-d5; Amplital-d5; Penicline-d5; Ampicillin-d5(Mixture of Diastereomers); (2S,5R,6R)-6-[[(2R)-2-Amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; AY 6108; Albipen; Amfipen; D-(-)-α-Aminobenzylpenicillin; AMPICILLIN ANHYDROUS; 氨苄青霉素; 氨苄西林

Database IDs

• CAS Number: 69-53-4
• EC Number: 200-709-7
• MDL Number: MFCD00005175
• Beilstein Number: 1090925
• PubChem SID: 46505346; 160963761; 24891442
• PubChem CID: 6249
• CHEBI ID: 28971
• ATC CODE: QJ51CA01; S01AA19; J01CA01
• CHEMBL: 174
• Chemspider ID: 6013
• DrugBank ID: DB00415
• KEGG ID: D00204
• Unique Ingredient Identifier: 7C782967RD
• Wikipedia Title: Ampicillin
• Medline Plus: a685002

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 0.88
• LOG S: -2.76
• Solubility (Water): 6.05e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M NH4OH: soluble50 mg/mL; 1 M NH4OH: soluble50 mg/mL, clear, colorless; 1.01E+004 mg/L; DMSO; Water
• Apperance: Off-White to Pale Yellow Solid; White Solid
• Melting Point: 196-198°C (dec.); 199-202°C (dec.); 208 °C decomposes; 208 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +295±5°, c = 0.2% in H2O
• Hydrophobicity(logP): 0.4

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere; 2-8°C; Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• RTECS: XH8350000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 36/37/38-42/43
• Safety Statements: 22-26-36/37
• 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

Pharmacology Properties

• Admin Routes: Oral, intravenous
• Bioavailability: 40% (oral)
• Excretion: 75 to 85% renal
• Half Life: approx 1 hour
• Metabolism: 12 to 50%
• Protein Bound: 15 to 25%
• Pregnancy Category: A (Au), B (U.S.)

Product Information

• Purity: ≥98.0% (NT); 96.0-100.5% (anhydrous basis)
• Suitability: suitable for 1694 per US EPA
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C16H19N3O4S

DETAILS

MP Biomedicals - 02190146

Crystalline

DrugBank - DB00415

• Drug Groups: approved
• Description: Semi-synthetic derivative of penicillin that functions as an orally active broad-spectrum antibiotic. [PubChem]
• Indication: For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
• Pharmacology: Ampicillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name "penicillin" can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Ampicillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ampicillin results from the inhibition of cell wall synthesis and is mediated through Ampicillin binding to penicillin binding proteins (PBPs). Ampicillin is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
• Affected Organisms: Enteric bacteria and other eubacteria
• Elimination: Ampicillin is excreted largely unchanged in the urine.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - A9393

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
A β-lactam antibiotic with an amino group attached to the penicillin structure. 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 is used to select bacteria cells with specific resistance during general microbiology studies. It is used to study antibiotic resistance and penetration limitations, the synergy between multiple antibiotics, certain bloodstream infections, and has been used to develop PCR assays to detect resistance genes in cerebrospinal fluid 1,2,3,4.

Sigma Aldrich - 10047

Biochem/physiol Actions
A β-lactam antibiotic with an amino group attached to the penicillin structure. 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.
Inhibits cell wall synthesis in Escherichia coli1; In the purification of penicillin acylase2; Enhances luminol chemiluminescence.3

Toronto Research Chemicals - A634300

Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.

Toronto Research Chemicals - A634302

Labelled Ampicillin. Orally active, semi-synthetic antibiotic; structurally related to penicillin. Antibacterial.

REFERENCES

• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)
• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)
• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)
• Ivashkiv, E., et al.: Anal. Profiles Drug Subs., 2, 1 (1973)
• Campoli-Richards, D.M., et al.: Drugs, 33, 577 (1973)
• Sill, M. L., et al.: Antimicrob. Agents Chemother., 52, 1551 (1973)