(2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 873
• Molecular Formular: C15H23N3O4S
• Molecular Mass: 341.42582
• Monoisotopic Mass: 341.14092723
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)C1(N)CCCCC1
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)NC(=O)C1(N)CCCCC1
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Brand Name: Bastcillin; Calthor; Citosarin; Cyclapen; Cyclapen-W; Orfilina; Syngacillin; Ultracillin; Vastcillin; Vipicil; Wyvital
• Synonyms: Ciclacilline [INN-French]; Ciclacillinum [INN-Latin]; Ciclacilina [INN-Spanish]; Aminocyclohexylpenicillin; Ciclacillin; Ciclacillum; Cyclacillin

Database IDs

• CAS Number: 3485-14-1
• PubChem SID: 46508073; 160964336
• PubChem CID: 19003

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3042057
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.9151417
• LogD (pH = 7.4): -1.9473974
• Log P: -1.9145718
• Molar Refractivity: 84.2196 cm^3
• Polarizability: 33.79713 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.56
• LOG S: -2.26
• Solubility (Water): 1.90e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.4

DETAILS

DrugBank - DB01000

• Drug Groups: approved
• Description: A cyclohexylamido analog of penicillanic acid. [PubChem]
• Indication: For the treatment of bacterial infections caused by susceptible organisms.
• Pharmacology: Cyclacillin, a penicillin, is a cyclohexylamido analog of penicillanic acid. Cyclacillin is more resistant to beta-lactamase hydrolysis than ampicillin, is much better absorbed when given by mouth and, as a result, the levels reached in the blood and in the urine are considerably higher than those obtained with the same dose of ampicillin. Cyclacillin has been replaced by newer penicillin treatments.
• Toxicity: Symptoms of overdose include severe diarrhea, nausea and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Moderately absorbed.