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66803-19-8

66803-19-8 structure
66803-19-8 structure
  • Name: Micronomicin sulfate
  • Chemical Name: (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(methylaminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol,sulfuric acid
  • CAS Number: 66803-19-8
  • Molecular Formula: C20H41N5O7.xH2O4S
  • Molecular Weight: 561.647
  • Catalog: API Antibiotics Aminoglycoside
  • Create Date: 2018-02-16 08:00:00
  • Modify Date: 2024-01-09 15:28:37
  • 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].

Name (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(methylaminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol,sulfuric acid
Synonyms 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
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
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.

Density 1.32g/cm3
Boiling Point 667.2ºC at 760mmHg
Molecular Formula C20H41N5O7.xH2O4S
Molecular Weight 561.647
Flash Point 357.3ºC
Exact Mass 561.268005
PSA 282.71000

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
Hazard Codes Xi