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

CAS No 3485-14-1 , (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,
3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

  • Name: (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,
    3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • Synonyms: Cyclapen;ciclacillin; Syngacillin; CYCLACILLIN; Ultracillin;(2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,
    3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; Bastcillin; Citosarin; Vastcillin; Calthor; Ciclacillum;
  • CAS Registry Number:
  • Flash Point: 346.7°C
  • Boiling Point: 649.6°Cat760mmHg
  • Density: 1.4g/cm3
  • Refractive index: 1.631
  • Safety Statements: Moderately toxic by ingestion and other routes. Human systemic effects by ingestion: dermatitis and diarrhea. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of SOx and NOx.
  • Flash Point: 346.7°C
  • EINECS: 222-470-8
  • Molecular Weight: 341.42582
  • InchiKey: HGBLNBBNRORJKI-WCABBAIRSA-N
  • InChI: InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)
    15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,
    11-/m1/s1
  • Molecular Formula: C15H23N3O4S
  • Molecular Structure:CAS No:3485-14-1 (2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)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-[(1-aminocyclohexanecarbonyl)amino]-3,
3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Title: Cyclacillin
CAS Registry Number: 3485-14-1
CAS Name: (2S,5R,6R)-6-[[(1-Aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Synonyms: 6-(1-aminocyclohexanecarboxamido)penicillanic acid; (1-aminocyclohexyl)penicillin; ciclacillin
Manufacturers' Codes: Wy-4508
Trademarks: Calthor (Ayerst); Citosarin (Toyo Jozo); Cyclapen (Wyeth); Syngacillin (Wyeth); Ultracillin (Grñenthal); Vastcillin (Takeda); Vatracin (Tobishi); Vipicil (Wyeth); Wyvital (Wyeth)
Molecular Formula: C15H23N3O4S
Molecular Weight: 341.43
Percent Composition: C 52.77%, H 6.79%, N 12.31%, O 18.74%, S 9.39%
Literature References: Semi-synthetic antibiotic related to penicillin. Prepn: Alburn et al., US 3194802; C. A. Robinson, J. J. Nescio, DE 1800698; eidem, US 3478018 (1965, 1969, 1969, all to Am. Home Prods.). Activity studies: Rosenman et al., Antimicrob. Agents Chemother. 1967, 590; Hopper et al., ibid. 597; Yurchenco et al., ibid. 602; Chemotherapy 15, 209 (1970). Metabolic studies: Poole, J. Pharm. Sci. 59, 1255 (1970); Tucker et al., Toxicol. Appl. Pharmacol. 19, 361 (1971). Physicochemical data: Alburn et al., Antimicrob. Agents Chemother. 1967, 586; Hou, Poole, J. Pharm. Sci. 58, 1510 (1969); Poole, Bahal, ibid. 59, 1265 (1970).
Properties: Crystals, mp 182-183° (anhydrate) (Hou, Poole); also reported as mp 156-158° (dec) (Alburn et al.). [a]D25 +268° (water). pK1, pK2 in water: 2.68, 7.50; in 50% dioxane: 4.16, 7.04. Stable in acid. Soly at 38°: about 29 mg/ml.
Melting point: mp 182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)
pKa: pK1, pK2 in water: 2.68, 7.50; in 50% dioxane: 4.16, 7.04
Optical Rotation: [a]D25 +268° (water)
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Penicillins.