D-Streptamine,O-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-O-[b-D-ribofuranosyl-(1®5)]-2-deoxy

Modify Date: 2025-08-21 14:11:21

D-Streptamine,O-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-O-[b-D-ribofuranosyl-(1®5)]-2-deoxy structure	Common Name	D-Streptamine,O-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-O-[b-D-ribofuranosyl-(1®5)]-2-deoxy
	CAS Number	25546-65-0	Molecular Weight	552.55100
	Density	N/A	Boiling Point	N/A
	Molecular Formula	C₁₇H₃₆N₄O₁₄S	Melting Point	192-195°; mp 175-180° (dec)
	MSDS	N/A	Flash Point	N/A

Use of D-Streptamine,O-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-O-[b-D-ribofuranosyl-(1®5)]-2-deoxy

Ribostamycin (Vistamycin) is a broad-spectrum aminoglycoside antibiotic. Ribostamycin is effective against Gram-Negative and Gram-Positive bacterial infection. Ribostamycin also inhibits the chaperone activity of PDI[1][2].

Name	ribostamycin
Synonym	More Synonyms

Description	Ribostamycin (Vistamycin) is a broad-spectrum aminoglycoside antibiotic. Ribostamycin is effective against Gram-Negative and Gram-Positive bacterial infection. Ribostamycin also inhibits the chaperone activity of PDI[1][2].
Related Catalog	Research Areas >> Infection Signaling Pathways >> Anti-infection >> Bacterial
In Vitro	Ribostamycin 抑制 Borrelia burgdorferi 活性，MIC90 为 32 mg/L[2]。 Ribostamycin (1-100 μM, 0-15 min) 可抑制 PDI 的分子伴侣活性[3]。 Ribostamycin 抑制大肠杆菌 (Escherichia coli) 活性，MIC 为 0.9-7.2 μM[4]。 Cell Viability Assay[4] Cell Line: Escherichia coli strains Concentration: 0-64 μg/mL Incubation Time: 14 h Result: Inhibited Escherichia coli strains with a MIC of 0.9-7.2 μM.
In Vivo	Ribostamycin (40 mg/kg，肌肉注射，每天，持续 14 天) 对大鼠几乎没有肾毒性 (通过尿液分析评估)[5]。
References	[1]. Zheng T, et al. Linear self-assembly formation between gold nanoparticles and aminoglycoside antibiotics. Colloids Surf B Biointerfaces. 2018 Apr 1;164:185-191. [2]. Hunfeld KP, et al. In vitro activity of mezlocillin, meropenem, aztreonam, vancomycin, teicoplanin, ribostamycin and fusidic acid against Borrelia burgdorferi. Int J Antimicrob Agents. 2001 Mar;17(3):203-8. [3]. Horibe T, et al. Ribostamycin inhibits the chaperone activity of protein disulfide isomerase. Biochem Biophys Res Commun. 2001 Dec 21;289(5):967-72. [4]. Kong J, et al. Exploration of Antibiotic Activity of Aminoglycosides, in Particular Ribostamycin Alone and in Combination With Ethylenediaminetetraacetic Acid Against Pathogenic Bacteria. Front Microbiol. 2020 Jul 29;11:1718. [5]. Kitasato I, et al. Comparative nephrotoxicity of ribostamycin and gentamicin in rats evaluated by urinalysis. Drugs Exp Clin Res. 1989;15(6-7):273-89.

Melting Point	192-195°; mp 175-180° (dec)
Molecular Formula	C₁₇H₃₆N₄O₁₄S
Molecular Weight	552.55100
Exact Mass	552.19500
PSA	345.36000
Index of Refraction	1.662
InChIKey	NSKGQURZWSPSBC-VVPCINPTSA-N
SMILES	NCC1OC(OC2C(N)CC(N)C(O)C2OC2OC(CO)C(O)C2O)C(N)C(O)C1O

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WK2299000

CHEMICAL NAME :: D-Streptamine, O-2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1-4 )- O-(beta-D-ribofuranosyl-(1-5))-2-deoxy-

CAS REGISTRY NUMBER :: 25546-65-0

LAST UPDATED :: 199612

DATA ITEMS CITED :: 20

MOLECULAR FORMULA :: C17-H34-N4-O10

MOLECULAR WEIGHT :: 454.55

WISWESSER LINE NOTATION :: T6OTJ B1Z CQ DQ EZ FO- BL6TJ AZ DQ EZ CO- BT5OTJ CQ DQ E1Q

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 :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 4400 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >8 gm/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 535 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1850 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 32,949,1984

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 7 gm/kg

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

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 1,141,1980

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2830 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3350 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 300 mg/kg

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

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

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1600 mg/kg

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

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 1,141,1980

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

ROUTE OF EXPOSURE :: Intracerebral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 66800 ug/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2489,1970 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 52 gm/kg/30D-I

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 78 gm/kg/26W-I

TOXIC EFFECTS :: Related to Chronic Data - death

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 26 gm/kg/30D-I

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5200 mg/kg/30D-I

TOXIC EFFECTS :: Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2464,1970 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 9 gm/kg

SEX/DURATION :: female 10-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2502,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 3 gm/kg

SEX/DURATION :: female 10-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2502,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 1500 mg/kg

SEX/DURATION :: female 8-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2502,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 3 gm/kg

SEX/DURATION :: female 8-13 day(s) after conception

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

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 4,2502,1970

Hazard Codes	T
Risk Phrases	61-20/21/22
Safety Phrases	53-22-36/37/39-45
WGK Germany	3
RTECS	WK2300000

Name: Antibacterial activity against Escherichia coli expressing ANT(2'')-I
Source: ChEMBL
Target: Escherichia coli
External Id: CHEMBL3784625

Name: Antimicrobial activity against amikacin-susceptible Nocardia farcinica IFM 10152 harb...
Source: ChEMBL
Target: Nocardia farcinica
External Id: CHEMBL1264326

Name: Antibacterial activity against Pseudomonas aeruginosa expressing ANT(4')-II
Source: ChEMBL
Target: Pseudomonas aeruginosa
External Id: CHEMBL3784624

Name: Antimicrobial activity against amikacin-susceptible Nocardia farcinica IFM 10152 harb...
Source: ChEMBL
Target: Nocardia farcinica
External Id: CHEMBL1264325

Name: Antibacterial activity against Staphylococcus aureus expressing ANT(4')-I
Source: ChEMBL
Target: Staphylococcus aureus
External Id: CHEMBL3784623

Name: Antimicrobial activity against amikacin-resistant Nocardia farcinica IFM 10580 after ...
Source: ChEMBL
Target: Nocardia farcinica
External Id: CHEMBL1264324

Name: Antibacterial activity against Acinetobacter baumannii expressing AAC(3)-I, APH(3')-V...
Source: ChEMBL
Target: Acinetobacter baumannii
External Id: CHEMBL3784622

Name: Antibacterial activity against Escherichia coli expressing A-site methyltransferase A...
Source: ChEMBL
Target: Escherichia coli
External Id: CHEMBL3782988

Name: Antibacterial activity against Escherichia coli expressing AAC(3)-IV
Source: ChEMBL
Target: Escherichia coli
External Id: CHEMBL3782987

Name: Antibacterial activity against Staphylococcus aureus expressing AAC(6')/APH(2'')
Source: ChEMBL
Target: Staphylococcus aureus
External Id: CHEMBL3784627

Total 69, Current Page 1 of 7

Ribastamin

Antibiotic SF 733

Ribostamicina

Ribostamycinum

(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol

Vistamycin

Xylostatin

Hetangmycin

Dekamycin IV

Ribostamycine

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D-Streptamine,O-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-O-[b-D-ribofuranosyl-(1®5)]-2-deoxy

Use of D-Streptamine,O-2,6-diamino-2,6-dideoxy-a-D-glucopyranosyl-(1®4)-O-[b-D-ribofuranosyl-(1®5)]-2-deoxy

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Safety Information

Bioassay

Synonyms

The content on this webpage is sourced from various professional data sources. If you have any questions or concerns regarding the content, please feel free to contact service1@chemsrc.com.