Cyclacillin

Molecular Structure of Cyclacillin (CAS NO. 3485-14-1):

EINECS: 222-470-8
IUPAC Name: (2S,5R,6R)-6-[(1-Aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid  
Molecular Formula: C₁₅H₂₃N₃O₄S
Molecular Weight: 341.425820 g/mol
XLogP3: 1.3
H-Bond Donor: 3
H-Bond Acceptor: 5
Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C
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
InChIKey: HGBLNBBNRORJKI-WCABBAIRSA-N
Index of Refraction: 1.631
Molar Refractivity: 86.37 cm³
Molar Volume: 242.3 cm³
Surface Tension: 68.8 dyne/cm
Density: 1.4 g/cm³
Flash Point: 346.7 °C
Enthalpy of Vaporization: 104.45 kJ/mol
Boiling Point: 649.6 °C at 760 mmHg
Vapour Pressure: 1.5E-18 mmHg at 25 °C
Water Solubility: 530.8 mg/L at 25 °C
BRN of Cyclacillin (CAS NO. 3485-14-1): 0938663

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 SO_x and NO_x.

  Cyclacillin with cas registry number of 3485-14-1 is an aminopenicillin antibiotic, also known as (1-Aminocyclohexyl)penicillin ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((1-aminocyclohexyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))- ; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(1-aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo- (8CI) ; AC 98 ; AC-PC ; Bastcillin ; 6-(1-Aminocyclohexanecarboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ; 6-(1-Aminocyclohexanecarboxamido)penicillanic acid ; 6-(1-Aminocyclohexylcarboxamido)penicillanic acid ; Aminocyclohexyl penicillin ; Aminocyclohexylpenicillin ; Calthor ; Ciclacilina ; Ciclacilina [INN-Spanish] ; Ciclacillin ; Ciclacilline ; Ciclacilline [INN-French] ; Ciclacillinum ; Ciclacillinum [INN-Latin] ; Ciclacillum ; Citosarin ; Cyclapen ; Cyclacillin [USAN] ; Cyclapen-W ; NSC 88789 ; Noblicil ; Orfilina ; Peamezin ; Penicillin, (aminocyclohexyl)- ; Syngacillin ; UNII-72ZJ154X86 ; Ultracillin ; Vastcillin ; Vipicil ; Wy 4508 ; Wypicil ; Wyvital . Cyclacillin is associated with significantly fewer and milder adverse effects than ampicillin at least in children. Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States.