(Z)-Carumonam

Names

[ Name ]:
(Z)-Carumonam

[Synonym ]:
Ro 17-2301/006
Amasulin (TN)
(3S,4S)-cis-3-[2-(2-Amino-4-thiazolyl)-2-(Z)-carboxymethoxyiminoacetamido]-4-carbamoyloxymethyl-2-azetidinone-1-sulfonic Acid
(Z)-[[[(2-Amino-4-thiazolyl)[[(2S,3S)-2-(hydroxymethyl)-4-oxo-1-sulfo-3-azetidinyl]carbamoyl]methylene]-amino]oxy]acetic Acid Carbamate (Ester)
Acetic acid, 2-[[[(1Z)-2-[[(2S,3S)-2-[[(aminocarbonyl)oxy]methyl]-4-oxo-1-sulfo-3-azetidinyl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]-
Carumonam
CRMN
MFCD00875847
Mobactam
[2S-[2a,3a(Z)]]-[[[2-[[2-[[(Aminocarbonyl)oxy]methyl]-4-oxo-1-sulfo-3-azetidinyl]amino]-1-(2-amino-4-thiazolyl)-2-oxoethylidene]amino]oxy]aceticAcid
({[(1Z)-1-(2-Amino-1,3-thiazol-4-yl)-2-({(2S,3S)-2-[(carbamoyloxy)methyl]-4-oxo-1-sulfoazetidin-3-yl}amino)-2-oxoethylidene]amino}oxy)acetic acid
({(Z)-[1-(2-Amino-1,3-thiazol-4-yl)-2-({(2S,3S)-2-[(carbamoyloxy)methyl]-4-oxo-1-sulfo-3-azetidinyl}amino)-2-oxoethylidene]amino}oxy)acetic acid
disodium,2-[(Z)-[1-(2-amino-1,3-thiazol-4-yl)-2-[[(2S,3S)-2-(carbamoyloxymethyl)-4-oxo-1-sulfonatoazetidin-3-yl]amino]-2-oxoethylidene]amino]oxyacetate
Carumonam disodium salt
Acetic acid, (((Z)-(2-(((2S,3S)-2-(((aminocarbonyl)oxy)methyl)-4-oxo-1-sulfo-3-azetidinyl)amino)-1-(2-amino-4-thiazolyl)-2-oxoethylidene)amino)oxy)-
Amasulin

Biological Activity

[Description]:

Carumonam disodium is a potent antibiotic. Carumonam disodium shows antibacterial activity. Carumonam disodium induces seizure[1][2].

[Related Catalog]:

Research Areas >> Infection

Research Areas >> Neurological Disease

Signaling Pathways >> Anti-infection >> Bacterial

[In Vitro]

Carumonam disodium (0-100 µg/mL) 表现出抗菌活性，对 Escherichia coli (cefazolin sensitive), Escherichia coli (cefazolin resistant), Klebsiella pneumoniae (cefazolin sensitive), Klebsiella pneumoniae (cefazolin resistant), Klebsiella oxytoca, Enterobacter cloacae, Serratia marcescens (gentamicin sensitive), Serratia marcescens (gentamicin resistant), Proteus vulgaris, Proteus mirabilis, Proteus morganii, Proteus rettgeri, Proteus inconstans 的 MIC90 值分别为 0.2, 3.13, 0.2, 0.39, 0.2, 6.25, 0.2, 3.13, 0.05, 0.025, 0.78, 0.013, 0.025 µg/mL[1]。

[In Vivo]

Carumonam disodium (1.31-6.89 mmol/kg; i.p.) 诱导 DBA/2、Swiss 和 C57 小鼠癫痫发作[2]。 Animal Model: 16-24g, 42-48 days DBA/2; 18-28, 42-48 days Swiss and C57 mice[2] Dosage: 1.31-6.89 mmol/kg Administration: I.p. Result: Induced seizure in DBA/2, Swiss and C57 mice.

[References]

[1]. Imada A, et al. In vitro and in vivo antibacterial activities of carumonam (AMA-1080), a new N-sulfonated monocyclic beta-lactam antibiotic. Antimicrob Agents Chemother. 1985 May;27(5):821-7.

[2]. De Sarro A, et al. Comparative epileptogenic properties of two monobactam derivatives in C57, Swiss and DBA/2 mice. J Antimicrob Chemother. 1996 Sep;38(3):475-84.

Chemical & Physical Properties

[ Density]:
2.1±0.1 g/cm3

[ Melting Point ]:
250ºC (dec.)(lit.)

[ Molecular Formula ]:
C₁₂H₁₄N₆O₁₀S₂

[ Molecular Weight ]:
466.404

[ Exact Mass ]:
466.021271

[ PSA ]:
295.73000

[ LogP ]:
-2.26

[ Index of Refraction ]:
1.820

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AF2450000

CHEMICAL NAME :: Acetic acid, (((2-((2-(((aminocarbonyl)oxy)methyl)-4-oxo-1-sulfo-3 -azotidinyl)amino)-1- (2- amino-4-thiazolyl)-2-oxoethylidene)amino)oxy)-, disodium salt, (2S-(2-alpha,3-alpha(Z)))-

CAS REGISTRY NUMBER :: 86832-68-0

LAST UPDATED :: 199707

DATA ITEMS CITED :: 14

MOLECULAR FORMULA :: C12-H14-N6-O10-S2.2Na

MOLECULAR WEIGHT :: 512.42

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 :: Gastrointestinal - hypermotility, diarrhea

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 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 :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 10 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea Skin and Appendages - hair

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4650 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8870 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 :: 8870 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Nutritional and Gross Metabolic - body temperature decrease

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7740 mg/kg

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

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 35 gm/kg/5W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in bladder weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Metabolism (Intermediary) - other proteins

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 35 gm/kg/5W-I

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight Blood - normocytic anemia

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 10500 mg/kg/5W-I

TOXIC EFFECTS :: Liver - other changes Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Primate - monkey

DOSE/DURATION :: 35 gm/kg/5W-I

TOXIC EFFECTS :: Liver - changes in liver weight Liver - other changes Kidney, Ureter, Bladder - changes in bladder weight

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

DOSE :: 13 gm/kg

SEX/DURATION :: female 6-18 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Reproductive - Fertility - abortion

MUTATION DATA

TYPE OF TEST :: DNA repair

TEST SYSTEM :: Bacteria - Bacillus subtilis

DOSE/DURATION :: 250 ug/disc

REFERENCE :: YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 14,3887,1986

Safety Information

[ Hazard Codes ]:
Xi

[ Risk Phrases ]:
36/37/38

[ Safety Phrases ]:
S26-S36