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

Modify Date: 2024-01-10 12:15:39

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- Structure
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)- structure
Common Name 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(1-aminocyclohexyl)carbonyl]amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
CAS Number 3485-14-1 Molecular Weight 341.42600
Density 1.4g/cm3 Boiling Point 649.6ºC at 760mmHg
Molecular Formula C15H23N3O4S Melting Point 182-183° (anhydrate) (Hou, Poole); mp 156-158° (dec) (Alburn et al.)
MSDS N/A Flash Point N/A

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


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

 Names

Name cyclacillin
Synonym More Synonyms

  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
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)

 Synonyms

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