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Substance Name: Cyclacillin [USAN:USP]
RN: 3485-14-1
UNII: 72ZJ154X86
InChIKey: HGBLNBBNRORJKI-WCABBAIRSA-N

Note

  • A cyclohexylamido analog of PENICILLANIC ACID.

Molecular Formula

  • C15-H23-N3-O4-S

Molecular Weight

  • 341.4297
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibacterial
  • Drug / Therapeutic Agent
  • Human Data
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Names and Synonyms

Name of Substance

  • Ciclacillin [INN]
  • Cyclacillin
  • Cyclacillin [USAN:USP]

MeSH Heading

  • Cyclacillin

Synonyms

  • (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))-
  • 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
  • AC 98
  • AC-PC
  • Aminocyclohexyl penicillin
  • Aminocyclohexylpenicillin
  • Bastcillin
  • BRN 0938663
  • Calthor
  • Ciclacilina
  • Ciclacilina [INN-Spanish]
  • Ciclacillin
  • Ciclacilline
  • Ciclacilline [INN-French]
  • Ciclacillinum
  • Ciclacillinum [INN-Latin]
  • Ciclacillum
  • Citosarin
  • Cyclacillin
  • Cyclapen
  • Cyclapen-W
  • EINECS 222-470-8
  • Noblicil
  • NSC 88789
  • Orfilina
  • Peamezin
  • Penicillin, (aminocyclohexyl)-
  • Syngacillin
  • Ultracillin
  • UNII-72ZJ154X86
  • Vastcillin
  • Vipicil
  • Wy 4508
  • Wy-4508
  • Wypicil
  • Wyvital

Systematic Names

  • 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)
  • Ciclacillin
  • Cyclacillin

Registry Numbers

CAS Registry Number

  • 3485-14-1

FDA UNII

  • 72ZJ154X86

System Generated Number

  • 0003485141

Structure Descriptors

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

Smiles

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)C3(CCCCC3)N)C(=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral 2500mg/kg (2500mg/kg) LIVER: OTHER CHANGES Chemotherapy Vol. 22, Pg. 154, 1976.
human TDLo oral 210mg/kg/7D-I (210mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

GASTROINTESTINAL: OTHER CHANGES

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
Chemotherapy Vol. 22, Pg. 154, 1976.
mouse LD50 intraperitoneal 3776mg/kg (3776mg/kg) LIVER: OTHER CHANGES Chemotherapy Vol. 22, Pg. 154, 1976.
mouse LD50 oral 5010mg/kg (5010mg/kg) LIVER: OTHER CHANGES Chemotherapy Vol. 22, Pg. 154, 1976.
mouse LD50 subcutaneous 7500mg/kg (7500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 29, Pg. 117, 1970.
rat LD50 intraperitoneal 5010mg/kg (5010mg/kg) LIVER: OTHER CHANGES Chemotherapy Vol. 22, Pg. 154, 1976.
rat LD50 oral 5010mg/kg (5010mg/kg) LIVER: OTHER CHANGES Chemotherapy Vol. 22, Pg. 154, 1976.
rat LD50 subcutaneous 6500mg/kg (6500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. Vol. 29, Pg. 117, 1970.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 182-183 deg C   EXP
log P (octanol-water) 1.31 (none)   EXP
Water Solubility 531 mg/L 25 EST
Vapor Pressure 2.84E-14 mm Hg 25 EST
Henry's Law Constant 5.38E-16 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 9.84E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.