4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

Names

[ Name ]:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-

[Synonym ]:
6-(1-aminocyclohexanecarboxamido)penicillanic acid
Vastcillin
Ultracillin
Cyclapen
CYCLACILLIN
(2S,5R,6R)-6-[(1-aminocyclohexanecarbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Citosarin
Ciclacillin
Bastcillin
Calthor
Vipicil
Syngacillin

Biological Activity

[Description]:

Cyclacillin (Wy-4508) is an orally active aminopenicillin antibiotic, shows antibacterial activity against a wide range of gram-positive and gram-negative pathogens[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Cyclacillin (0-125 μg/mL) inhibits varies pathogens except Klebsiella an Enterobacter organisms with MIC values range from 0.24 μg/mL to 7.8 μg/mL[1].

[In Vivo]

Cyclacillin (0-287 mg/kg; p.o.; single dose) shows oral activity in mice and rescues mice injected with gram-positive and gram-negative pathogens[1]. Cyclacillin (10 mg/kg; i.v.; single dose) is absorbed by the rat intestinal tissue at relatively low concentrations (less than 1 mg/mL) followed solely Michaelis-Menten kinetics[2].

Chemical & Physical Properties

[ Density]:
1.4g/cm3

[ Boiling Point ]:
649.6ºC at 760mmHg

[ Melting Point ]:
182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)

[ Molecular Formula ]:
C₁₅H₂₃N₃O₄S

[ Molecular Weight ]:
341.42600

[ Exact Mass ]:
341.14100

[ PSA ]:
138.03000

[ LogP ]:
1.30880

[ Index of Refraction ]:
1.631

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: GT8450000

CHEMICAL NAME :: Cyclacillin

CAS REGISTRY NUMBER :: 3485-14-1

LAST UPDATED :: 199612

DATA ITEMS CITED :: 11

MOLECULAR FORMULA :: C15-H23-N3-O4-S

MOLECULAR WEIGHT :: 341.47

WISWESSER LINE NOTATION :: T45 ANV ESTJ F1 F1 GVQ CMV- AL6TJ AZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 210 mg/kg/7D-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: CHTHBK Chemotherapy (Basel). (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.13- 1968- Volume(issue)/page/year: 22,154,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5010 mg/kg

TOXIC EFFECTS :: Liver - other changes

REFERENCE :: CHTHBK Chemotherapy (Basel). (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.13- 1968- Volume(issue)/page/year: 22,154,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5010 mg/kg

TOXIC EFFECTS :: Liver - other changes

REFERENCE :: CHTHBK Chemotherapy (Basel). (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.13- 1968- Volume(issue)/page/year: 22,154,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 6500 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: TAKHAA Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. (Takeda Yakuhin Kogyo K.K., 2-17-85 Jusohon-machi, Yodogawa-ku, Osaka 532, Japan) V.29- 1970- Volume(issue)/page/year: 29,117,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5010 mg/kg

TOXIC EFFECTS :: Liver - other changes

REFERENCE :: CHTHBK Chemotherapy (Basel). (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.13- 1968- Volume(issue)/page/year: 22,154,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3776 mg/kg

TOXIC EFFECTS :: Liver - other changes

REFERENCE :: CHTHBK Chemotherapy (Basel). (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.13- 1968- Volume(issue)/page/year: 22,154,1976

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7500 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: TAKHAA Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. (Takeda Yakuhin Kogyo K.K., 2-17-85 Jusohon-machi, Yodogawa-ku, Osaka 532, Japan) V.29- 1970- Volume(issue)/page/year: 29,117,1970

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 2500 mg/kg

TOXIC EFFECTS :: Liver - other changes

REFERENCE :: CHTHBK Chemotherapy (Basel). (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.13- 1968- Volume(issue)/page/year: 22,154,1976 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 87 gm/kg/26W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis)

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 29,1,1974

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 108 gm/kg/30D-C

TOXIC EFFECTS :: Behavioral - food intake (animal) Kidney, Ureter, Bladder - changes in bladder weight Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: TAKHAA Takeda Kenkyusho Ho. Journal of the Takeda Research Laboratories. (Takeda Yakuhin Kogyo K.K., 2-17-85 Jusohon-machi, Yodogawa-ku, Osaka 532, Japan) V.29- 1970- Volume(issue)/page/year: 29,117,1970 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X9351 No. of Facilities: 25 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 101 (estimated) No. of Female Employees: 51 (estimated)