Micronomicin sulfate

Names

[ Name ]:
Micronomicin sulfate

[Synonym ]:
α-D-erythro-Hexopyranoside, (1R,2S,3S,4R,6S)-4,6-diamino-3-[[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy]-2-hydroxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-, sulfate (1:1) (salt)
α-D-erythro-Hexopyranoside, (1R,2S,3S,4R,6S)-4,6-diamino-3-[[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy]-2-hydroxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-, sulfat e (1:1) (salt)
(1R,2S,3S,4R,6S)-4,6-Diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-α-D-erythro-hexopyranoside sulfate ( 1:1)
(1R,2S,3S,4R,6S)-4,6-Diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-α-D-erythro-hexopyranoside sulfate (1:1)
Micronomycin sulfate
micronomicin sulfate
Sagamacin

Biological Activity

[Description]:

Micronomicin sulfate (Gentamicin C2b sulfate) is an aminoglycoside antibiotic isolated from Micromonospora. Micronomicin sulfate is a broad-spectrum antibiotic close to the gentamicin-type antibiotics, exhibits a high activity against Pseudomonas, Proteus, Klebsiella pneumoniae, Serratia, etc (MIC=0.001-8.3 μg/ml)[1][2].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

MIC: 0.001-8.3 μg/ml (Pseudomonas, Proteus, Klebsiella pneumoniae, Serratia)[2]

[In Vitro]

Micronomicin has a potent antibacterial activity, it is active against Staphylococcus aureus FDA 209 P, Staphylococcus aureus with the minimal inhibitory values of 0.01 μg/ml. It is also against Escherichia coli St.M. 589, Baker 2, F 14-BK, and R5/W677 with the minimal inhibitory values of 0.75 μg/ml, 0.3 μg/ml, 0.03 μg/ml and 0.03 μg/ml. And it is active against Pseudomonas aeruginosa strains and lebsiella pneumoniae strains (MICs = 0.03-17.5 μg/ml)[1].

[In Vivo]

Micronomicin sulfate is highly active against various bacterial infections in mice, and has an intravenous acute LD50 in mice of 93 mg/kg[1]. Micronomicin sulfate (intravenous injection; 4-100 mg/kg; 30 days) is injected for subacute toxicity study. The wistar rats dies at the dose level of 100 mg/kg (10 out of 30 animals): renal disorders and ataxia. The renal histological disorders occurrs mainly at the dose levels of 25 mg/kg and over[3]. Animal Model: Wistar rats[3] Dosage: 4, 10, 25, 63 mg/kg and 100 mg/kg Administration: Intravenous injection; 30 days Result: Led to death of rat at 100 mg/kg.

[References]

[1]. R Okachi,et al. A New Antibiotic XK-62-2 (Sagamicin). I. Isolation, Physicochemical and Antibacterial Properties. J Antibiot (Tokyo)

[2]. P J Daniels, The Gentamicin Antibiotics. 6. Gentamicin C2b, an Aminoglycoside Antibiotic Produced by Micromonospora Purpurea Mutant JI-33. J Antibiot (Tokyo)

[3]. T Hara, et al. Safety Evaluation of Micronomicin V. Subacute Toxicity in Rats After Intravenous Injection. Jpn J Antibiot. 1983 Nov;36(11):3208-25.

Chemical & Physical Properties

[ Density]:
1.32g/cm3

[ Boiling Point ]:
667.2ºC at 760mmHg

[ Molecular Formula ]:
C₂₀H₄₁N₅O_7.xH₂O₄S

[ Molecular Weight ]:
561.647

[ Flash Point ]:
357.3ºC

[ Exact Mass ]:
561.268005

[ PSA ]:
282.71000

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WK2196000

CHEMICAL NAME :: Streptamine, O-2-amino-2,3,4,6-tetradeoxy-6-(methylamino)-alpha-D- erythro-hexopyranosyl- (1-4)-O-(3-deoxy-4-C-methyl-3-(methylamino)-beta-L-ar abinopyranosyl-(1-6)) -2-deoxy-, sulfate, D-

CAS REGISTRY NUMBER :: 66803-19-8

LAST UPDATED :: 199806

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C21-H43-N5-O6.H2-O4-S

MOLECULAR WEIGHT :: 559.77

WISWESSER LINE NOTATION :: T6OTJ CZ F1M1 BO- BL6TJ AZ CQ EZ DO- BT6OTJ CQ DM1 EQ E1

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1323,1995

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1223 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-18,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 104 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,3204,1983

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 625 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - dyspnea Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,3204,1983

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 15600 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,1323,1995

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 350 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-18,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 245 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-18,1982

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 459 mg/kg

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

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,APP-18,1982

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 459 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,3204,1983

Safety Information

[ Hazard Codes ]:
Xi