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

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Names

[ CAS No. ]:
3485-14-1

[ 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

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)

Related Compounds

  • N-{2-hydroxy-2-[4-(1H-pyrazol-1-yl)phenyl]ethyl}-4,5,6,7-tetrahydro-1,2-benzoxazole-3-carboxamide
  • 2-bromo-N-{2-hydroxy-2-[4-(1H-pyrazol-1-yl)phenyl]ethyl}benzene-1-sulfonamide
  • N-{[4-(morpholin-4-yl)thian-4-yl]methyl}-4-phenyloxane-4-carboxamide
  • 2-(3-Amino-1,1-dioxothian-3-yl)acetic acid;hydrochloride
  • 2-(4-Fluorophenyl)-1-[4-(thian-4-yl)-1,4-diazepan-1-yl]ethan-1-one
  • 2-(2-Chlorophenyl)-1-[4-(thian-4-yl)-1,4-diazepan-1-yl]ethan-1-one
  • 6-{5-Benzyl-octahydropyrrolo[3,4-c]pyrrol-2-yl}-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine
  • 5-[5-(Pyrimidin-2-yl)-octahydropyrrolo[3,4-c]pyrrole-2-carbonyl]-2,1,3-benzothiadiazole
  • 5-Fluoro-2-[(1-{[1,3]thiazolo[4,5-c]pyridin-2-yl}piperidin-4-yl)oxy]pyrimidine
  • 4-[(5-Fluoropyrimidin-2-yl)oxy]-[1,3'-bipiperidine]-2'-one
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