Mecillinam

Names

[ Name ]:
Mecillinam

[Synonym ]:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[[(1E)-(hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-, (2,2-dimethyl-1-oxopropoxy)methyl ester, (5R,6R)-
[(2,2-Dimethylpropanoyl)oxy]methyl (5R,6R)-6-[(E)-(1-azepanylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Amdinocillin
Mecillinam
EINECS 251-277-1
MFCD00056869

Biological Activity

[Description]:

Mecillinam (Amdinocillin), the β-lactam antibiotic, has a broad spectrum of activity against gram-negative organisms[1].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[In Vivo]

Mecillinam (Amdinocillin, 400 mg per kg) is effective for the treatment of catheterassociated infections at high dosages (400 mg per kg of body weight/d)[1]. Animal Model: Mecillinam (Amdinocillin, 400 mg per kg) is effective for the treatment of catheterassociated infections at high dosages (400 mg per kg of body weight/d)[1]. Dosage: 50, 100, 200, and 400 mg per kg. Administration: Intravenously each day in four divided doses over a 72-h period. Result: High dose of 400 mg/kg exhibited significant activity.

[References]

[1]. M E Olson, et al. Amdinocillin Treatment of Catheter-Associated Bacteriuria in Rabbits. J Infect Dis. 1989 Jun;159(6):1065-72.

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
581.0±60.0 °C at 760 mmHg

[ Melting Point ]:
156°C

[ Molecular Formula ]:
C₁₅H₂₃N₃O₃S

[ Molecular Weight ]:
439.569

[ Flash Point ]:
305.2±32.9 °C

[ Exact Mass ]:
439.214081

[ PSA ]:
98.51000

[ LogP ]:
2.97

[ Vapour Pressure ]:
0.0±1.6 mmHg at 25°C

[ Index of Refraction ]:
1.604

[ Storage condition ]:
Store at?0-5°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: XI0185000

CHEMICAL NAME :: 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((hexahydro-1H-azepin-1-yl)methylene) amino)-3,3-dimethyl-7-oxo-, (+)-

CAS REGISTRY NUMBER :: 32887-01-7

LAST UPDATED :: 199512

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C15-H23-N3-O3-S

MOLECULAR WEIGHT :: 325.47

WISWESSER LINE NOTATION :: T45 ANV ESTJ F1 F1 GVQ CNU1- AT7NTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia

REFERENCE :: EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia

REFERENCE :: EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >1500 mg/kg

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

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 16,191,1980

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >20 gm/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3500 mg/kg

TOXIC EFFECTS :: Blood - other changes

REFERENCE :: EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1200 mg/kg

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

REFERENCE :: MDACAP Medicamentos de Actualidad. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1965- Volume(issue)/page/year: 16,191,1980 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 130 gm/kg/26W-I

TOXIC EFFECTS :: Blood - normocytic anemia Liver - changes in liver weight Related to Chronic Data - changes in testicular weight

REFERENCE :: EKFMA7 Eksperimental'naya i Klinicheskaya Farmakoterapiya. (Izdatel'stvo Zinantne, Riga, USSR) No.1- 1970- Volume(issue)/page/year: 9,91,1980

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
XI0185000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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