Cephalothin

Names

[ CAS No. ]:
153-61-7

[ Name ]:
Cephalothin

[Synonym ]:
Cemastin
Toricelocin
Ceporacin
Cefalothin
Tokiosarl Ampullen
EINECS 205-815-7
3-(Hydroxymethyl)-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxyli
Lospoven
Cephalothin
Cephalotin
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-, (6R,7R)-
Cefalotina
Microtin
Cefalotine
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
(6R-trans)-3-[(Acetyloxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbo
(6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[(thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-, (6R,7R)-
Cepovenin
Coaxin
(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefalotinum
(6R,7R)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cephalothinum
Synclotin
Cefalotin

Biological Activity

[Description]:

Cephalotin (Cephalotin) is a beta-lactam antibiotic, inhibits class C β-lactamase AmpC, with an Ki of 0.32 µM[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Ki: 0.32 μM (β-lactamase AmpC)[1]

[References]

[1]. Morandi S, et al. Structure-based optimization of cephalothin-analogue boronic acids as beta-lactamase inhibitors. Bioorg Med Chem. 2008 Feb 1;16(3):1195-205. Epub 2007 Nov 7.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
757.2±60.0 °C at 760 mmHg

[ Melting Point ]:
160-161ºC

[ Molecular Formula ]:
C₁₆H₁₆N₂O₆S₂

[ Molecular Weight ]:
396.438

[ Flash Point ]:
411.8±32.9 °C

[ Exact Mass ]:
396.044983

[ PSA ]:
166.55000

[ LogP ]:
1.45

[ Vapour Pressure ]:
0.0±2.7 mmHg at 25°C

[ Index of Refraction ]:
1.676

[ Water Solubility ]:
158 MG/L

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XI0388000

CHEMICAL NAME :: 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-(hydroxymethyl)-8-oxo-7-(2-(2- thienyl)acetamido)-, acetate (ester)

CAS REGISTRY NUMBER :: 153-61-7

LAST UPDATED :: 199707

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C16-H16-N2-O6-S2

MOLECULAR WEIGHT :: 396.46

WISWESSER LINE NOTATION :: T46 ANV ES GUTJ G1OV1 HVQ CMV1- BT5SJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4296 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - acute pulmonary edema Kidney, Ureter, Bladder - other changes

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

ROUTE OF EXPOSURE :: Parenteral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 23 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4990 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7 gm/kg

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

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

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 81 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 70 gm/kg/35D-I

TOXIC EFFECTS :: Blood - normocytic anemia Skin and Appendages - dermatitis, other (after systemic exposure) Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 21 gm/kg/21D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - other changes in urine composition Nutritional and Gross Metabolic - changes in sodium

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 31 gm/kg/31D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 8800 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 18 gm/kg

SEX/DURATION :: female 9-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - skin and skin appendages

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 9 gm/kg

SEX/DURATION :: female 9-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

MUTATION DATA

TYPE OF TEST :: Phage inhibition capacity

TEST SYSTEM :: Microorganism - not otherwise specified

DOSE/DURATION :: 25 ug/plate

REFERENCE :: ZMMPAO Zentralblatt fuer Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene, Abteilung 1: Originale, Reihe A: Medizinische Mikrobiologie und Parasitologie. (Stuttgart, Fed. Rep. Ger.) V.217-245, 1971-79. Volume(issue)/page/year: 231,369,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83991 No. of Facilities: 33 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 1452 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83991 No. of Facilities: 290 (estimated) No. of Industries: 1 No. of Occupations: 8 No. of Employees: 21013 (estimated) No. of Female Employees: 19052 (estimated)

Safety Information

[ Hazard Codes ]:
Xi

Precursor & DownStream

Precursor

DownStream

Related Compounds

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