Home > Name List By other > (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

CAS No 69-53-4 , (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

  • Name: (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
  • Synonyms: Omnipen; Aminobenzylpenicillin;(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; Ampicillin acid; Amcill; Principen; Pentrexyl; Penbritin; Ampicilline; Polycillin;
  • CAS Registry Number:
  • Transport: OTH
  • Melting Point: 208 ºC (DEC.)
  • Density: 1.45 g/cm3
  • Safety Statements: R36/37/38;R42/43
  • Hazard Symbols: Xn: Harmful;
  • HS Code: 29212900
  • EINECS: 200-709-7
  • Molecular Weight: 349.40476
  • InchiKey: AVKUERGKIZMTKX-NJBDSQKTSA-N
  • 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
  • Risk Statements: S22;S26;S36/37
  • Molecular Formula: C16H19N3O4S
  • Molecular Structure:CAS No:69-53-4 (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,<br />3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

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References of (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
Title: Ampicillin
CAS Registry Number: 69-53-4
CAS Name: (2S,5R,6R)-6-[[(2R)-Aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms: 6-[D(-)-a-aminophenylacetamido]penicillanic acid; D(-)-a-aminobenzylpenicillin
Manufacturers' Codes: AY-6108; BRL-1341; P-50
Trademarks: Albipen (Intervet); Amfipen (Yamanouchi); Ampitab (V oquinol); Amplital (Pharmacia); Omnipen (Wyeth); Pénicline (Sanofi-Aventis)
Molecular Formula: C16H19N3O4S
Molecular Weight: 349.40
Percent Composition: C 55.00%, H 5.48%, N 12.03%, O 18.32%, S 9.18%
Literature References: Orally active, semi-synthetic antibiotic; structurally related to penicillin. Prepn: Doyle et al., US 2985648 (1961); eidem, GB 902703 (1962 to Beecham); Doyle et al., J. Chem. Soc. 1962, 1440. Prepn of the trihydrate: D. A. Johnson, G. A. Hardcastle, US 3157640 (1964 to Bristol-Myers); of the anhydrous crystalline form: N. H. Grant, H. E. Alburn, US 3144445 (1964 to Am. Home Prods.). Alternate syntheses: Dane, Dockner, Ber. 98, 789 (1965); F. Kajfez et al., J. Heterocycl. Chem. 13, 561 (1976). LC determn: M. Margosis, J. Assoc. Off. Anal. Chem. 70, 206 (1987). Series of articles on pharmacology and antibacterial activity: Br. Med. J. 2, 193-206 (1961). Comprehensive description: E. Ivashkiv, Anal. Profiles Drug Subs. 2, 1-61 (1973). Review of pharmacology and clinical efficacy in combination with sulbactam, q.v.: D. M. Campoli-Richards, R. N. Brogden, Drugs 33, 577-609 (1987).
Properties: Crystals, dec 199-202°. [a]D23 +287.9° (c = 1 in water). Sparingly sol in water.
Optical Rotation: [a]D23 +287.9° (c = 1 in water)
 
Derivative Type: Monohydrate
Properties: Crystals from water, dec 202°. [a]D21 +281° (water). Sparingly sol in water at room temp.
Optical Rotation: [a]D21 +281° (water)
 
Derivative Type: Sesquihydrate
Properties: Dec 199-202°. [a]D20 +283.1° (water).
Optical Rotation: [a]D20 +283.1° (water)
 
Derivative Type: Trihydrate
CAS Registry Number: 7177-48-2
Trademarks: Amblosin (Hoechst); Amipenix (Toyo Jozo); Ampilar (Sandoz); Cymbi (Dolorgiet); Doktacillin (AstraZeneca); Penbritin (GSK); Polycillin (BMS); Principen (BMS); Rosampline (Tedis); Totapen (BMS); Vidopen (APS)
 
Derivative Type: Sodium salt
CAS Registry Number: 69-52-3
Trademarks: Ampicin (BMS); Binotal (Grñenthal); Cilleral (BMS); Penbristol (BMS); Pentrex (BMS); Pentrexyl (BMS); Polycillin-N (BMS); Synpenin (Sankyo); Totacillin N (GSK); Viccillin (Meiji)
Molecular Formula: C16H18NaN3O4S
Molecular Weight: 371.39
Percent Composition: C 51.74%, H 4.89%, Na 6.19%, N 11.31%, O 17.23%, S 8.63%
 
Derivative Type: L(+)-Form
Properties: Crystals, dec at about 205°. [a]D20 +209° (c = 0.2 in water). Less active as an antibiotic than D(-)-form.
Optical Rotation: [a]D20 +209° (c = 0.2 in water)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.