2702. Cyclacillin
Nomenclature
CAS number: 3485-14-1
(2S,5R,6R)-6-[[(1-Aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic
acid; 6-(1-aminocyclohexanecarboxamido)penicillanic acid; (1-aminocyclohexyl)penicillin; ciclacillin; Wy-4508; Calthor (Ayerst); Citosarin (Toyo Jozo); Cyclapen (Wyeth); Syngacillin (Wyeth); Ultracillin (Grünenthal); Vastcillin (Takeda); Vatracin (Tobishi); Vipicil (Wyeth); Wyvital (Wyeth). C15H23N3O4S; mol wt 341.43.
C 52.77%, H 6.79%, N 12.31%, O 18.74%, S 9.39%.
Description and 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.). [α]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.Therapeutic Category
Antibacterial.
Keywords
Antibacterial (Antibiotics); β-Lactams; Penicillins