Home > Name List By other > (2S,5R,6R)-3, 3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0] heptane-2-carboxylic acid Japan

CAS No 61-33-6 , (2S,5R,6R)-3,
3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]
heptane-2-carboxylic acid Search by region : Japan

  • Name: (2S,5R,6R)-3,
    3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]
    heptane-2-carboxylic acid
  • Synonyms: Benzylpenicillin; Pfizerpen;(2S,5R,6R)-3,
    3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]
    heptane-2-carboxylic acid; Dropcillin; Benzopenicillin; Abbocillin; Gelacillin; Pencillin G; Benzylpenicillin G;
  • CAS Registry Number:
  • Flash Point: 355°C
  • Boiling Point: 663.3°C at 760 mmHg
  • Density: 1.42g/cm3
  • Refractive index: 1.655
  • Safety Statements: Poison by ingestion, intravenous, intracerebral, intraspinal, subcutaneous, and possibly other routes. Human (child) systemic effects by parenteral route: changes in cochlear (inner ear) structure or function, convulsions, and dyspnea. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx. See other penicillin entries.
  • Hazard Symbols: Xn
  • Flash Point: 355°C
  • EINECS: 200-506-3
  • Molecular Weight: 334.39012
  • InchiKey: JGSARLDLIJGVTE-MBNYWOFBSA-N
  • InChI: InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10
    (19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,
    12+,14-/m1/s1
  • Risk Statements: R42/43
  • Molecular Formula: C16H18N2O4S
  • Molecular Structure:CAS No:61-33-6 (2S,5R,6R)-3,<br />3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]<br />heptane-2-carboxylic acid

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References of (2S,5R,6R)-3,
3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]
heptane-2-carboxylic acid
Title: Penicillin G
CAS Registry Number: 61-33-6
CAS Name: (2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms: benzylpenicillin; benzylpenicillinic acid; penicillin II
Molecular Formula: C16H18N2O4S
Molecular Weight: 334.39
Percent Composition: C 57.47%, H 5.43%, N 8.38%, O 19.14%, S 9.59%
Literature References: Discovery of antibiotic substance produced by Penicillium sp: A. Fleming, Br. J. Exp. Pathol. 10, 226 (1929). Preliminary isoln: P. W. Clutterbuck et al., Biochem. J. 26, 1907 (1932); and chemotherapeutic properties: E. Chain et al., Lancet 2, 226 (1940); E. P. Abraham et al., ibid. 2, 177 (1941). Review of early studies: E. Chain, Annu. Rev. Biochem. 17, 657-704 (1948); H. T. Clarke et al., The Chemistry of Penicillin (Princeton Univ. Press, 1949) 1094 pp. Crystal structure: D. C. Hodgkin, Adv. Sci. 6, 85 (1949). Fermentation process: A. L. Demain, N. L. Somerson, US 3024169 (1962 to Merck & Co.). Total synthesis: J. C. Sheehan, K. R. Henery-Logan, J. Am. Chem. Soc. 81, 5838 (1959); R. A. Firestone et al., J. Org. Chem. 39, 437 (1974). Review of clinical pharmacokinetics of penicillins: M. Barza, L. Weinstein, Clin. Pharmacokinet. 1, 297 (1976). Comprehensive description of the potassium salt: J. Kirschbaum, Anal. Profiles Drug Subs. 15, 427-507 (1987).
Properties: Amorphous white powder. [a]D +282° (ethanol). Sparingly sol in water. Sol in methanol, ethanol, ether, ethyl acetate, benzene, chloroform, acetone. Insol in petr ether.
Optical Rotation: [a]D +282° (ethanol)
 
Derivative Type: Sodium salt
CAS Registry Number: 69-57-8
Trademarks: Crystapen (Britannia); Penilevel (ERN)
Molecular Formula: C16H17N2NaO4S
Molecular Weight: 356.37
Percent Composition: C 53.92%, H 4.81%, N 7.86%, Na 6.45%, O 17.96%, S 9.00%
Properties: Crystals from methanol + ethyl acetate. [a]D24.8 +301° (c = 2.0 in water). uv max (water): 252, 257.5, 264 nm (EM about 300, 240, 180). Freely sol in water, isotonic saline, glucose solns. Sol in methanol; less sol in ethanol. Practically insol in acetone, chloroform, ether, ethyl acetate, fixed oils, liq paraffin.
Optical Rotation: [a]D24.8 +301° (c = 2.0 in water)
Absorption maximum: uv max (water): 252, 257.5, 264 nm (EM about 300, 240, 180)
 
Derivative Type: Potassium salt
CAS Registry Number: 113-98-4
Trademarks: Cristapen (Glaxo Wellcome); Falapen (Frosst); Megacillin (tabl.) (Frosst); Pentids (BMS); Pfizerpen (Roerig)
Molecular Formula: C16H17KN2O4S
Molecular Weight: 372.48
Percent Composition: C 51.59%, H 4.60%, K 10.50%, N 7.52%, O 17.18%, S 8.61%
Properties: Crystals from aq butanol, mp 214-217° (dec). Moderately hygroscopic. [a]D22 +285° (c = 0.748 in water). Freely sol in water, isotonic saline, glucose solns; sparingly sol in ethanol. Practically insol in chloroform, ether, fixed oils, liq paraffin. pH of 6% aq soln 5.0 to 7.5.
Melting point: mp 214-217° (dec)
Optical Rotation: [a]D22 +285° (c = 0.748 in water)
 
Derivative Type: Mixture with clemizole
CAS Registry Number: 6011-39-8
Synonyms: Clemizole-penicillin
Trademarks: Neopenyl (Grñenthal)
Molecular Formula: C19H20ClN3.C16H18N2O4S
Molecular Weight: 660.23
Percent Composition: C 63.67%, H 5.80%, Cl 5.37%, N 10.61%, O 9.69%, S 4.86%
Literature References: Repository form of penicillin. Prepn: H. Mückter et al., Arzneim.-Forsch. 4, 487 (1954).
Properties: White powder, mp 144-145°. [a]D24 +144.5° (c = 10 in DMF). Sol in methanol, ethanol, DMF; slightly sol in water, acetone, dioxane.
Melting point: mp 144-145°
Optical Rotation: [a]D24 +144.5° (c = 10 in DMF)
 
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.