Cas no 4696-76-8 (Bekanamycin)
Bekanamycin Chemical and Physical Properties
Names and Identifiers
-
- Bekanamycin
- (2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4-diol
- Kanamycin B
- aminodeoxykanamycin
- kananmycin B
- kanendomycin
- kdm
- nebramycinfactor5
- nebramycinv
- NK-1006
- Nebramycin V
- 2'-Amino-2'-deoxykanamycin
- nebramycin factor 5
- Bekanamycin [INN]
- NK 1006
- Bekanamycine
- Bekanamycinum
- Becanamicina
- 15JT14C3GI
- Bekanamycin (INN)
- Bekanamycinum [INN-Latin]
- Bekanamycine [INN-French]
- Becanamicina [INN-Spanish]
- (1R,2S,3S,4R,6S)-4,6-diamino-3-[(3-amino-3-deoxy-alpha-D-glucopyranosyl)oxy]-2-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside
- O-
- Spectrum3_000619
- TOBRAMYCIN IMPURITY A [EP IMPURITY]
- KANAMYCIN B [MI]
- NCGC00178790-01
- DTXCID903185
- (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2S,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-2-hydroxy-cyclohexoxy]tetrahydropyran-3,4-diol
- Q3637540
- DB13673
- KBio2_004160
- NCGC00096063-01
- (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-(((1R,2S,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol
- SDCCGMLS-0066707.P001
- DTXSID8023185
- Tox21_113194
- GTPL12182
- NS00011539
- O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1->4)-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1->6))-2-deoxy-D-streptamine
- KBio3_001658
- CHEBI:28098
- Spectrum_001112
- SPBio_000640
- AKOS030526149
- .ALPHA.-D-GLUCOPYRANOSIDE, (1R,2S,3S,4R,6S)-4,6-DIAMINO-3-((3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-2-HYDROXYCYCLOHEXYL 2,6-DIAMINO-2,6-DIDEOXY-
- HY-B1174
- BDBM50368267
- Kanamycin B, Antibiotic for Culture Media Use Only
- Antibiotic derived from Streptomyces kanamyceticus. Kanamycin B
- Kanamycin B; Bekanamycin
- BRN 0061646
- CAS-4696-76-8
- CS-4772
- W-106082
- KBio2_006728
- D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-4)-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1-6))-2-deoxy-
- D07497
- 4696-76-8
- Spectrum4_001831
- ACon0_001346
- CHEMBL176
- BSPBio_002158
- KBioSS_001592
- (1R,2S,3S,4R,6S)-4,6-DIAMINO-3-((3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL)OXY)-2-HYDROXYCYCLOHEXYL 2,6-DIAMINO-2,6-DIDEOXY-.ALPHA.-D-GLUCOPYRANOSIDE
- Spectrum2_000640
- BEKANAMYCIN [WHO-DD]
- SCHEMBL158426
- C00825
- KBioGR_002528
- 9CS
- AB00053732_02
- SBI-0052603.P002
- A924196
- UNII-15JT14C3GI
- EINECS 225-170-5
- Antibiotic derived from Streptomyces kanamyceticus
- KBio2_001592
- (1R,2S,3S,4R,6S)-4,6-diamino-3-(3-amino-3-deoxy-alpha-D-glucopyranosyloxy)-2-hydroxycyclohexyl 2,6-diamino-2,6-dideoxy-alpha-D-glucopyranoside
- MEGxm0_000486
- Spectrum5_000621
- BRD-K73425385-065-04-8
- BRD-K73425385-001-01-9
- SKKLOUVUUNMCJE-FQSMHNGLSA-N
-
- MDL: MFCD01683541
- Inchi: 1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1
- InChI Key: SKKLOUVUUNMCJE-FQSMHNGLSA-N
- SMILES: O([C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CN)O1)O)O)N)[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)N)O)N)N
- BRN: 0061646
Computed Properties
- Exact Mass: 483.25400
- Monoisotopic Mass: 483.254
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 11
- Hydrogen Bond Acceptor Count: 15
- Heavy Atom Count: 33
- Rotatable Bond Count: 6
- Complexity: 639
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count : 15
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Topological Polar Surface Area: 288
- XLogP3: -7.2
Experimental Properties
- Color/Form: No data available
- Density: 1.3771 (rough estimate)
- Melting Point: 177-183°C
- Boiling Point: 807.7°C at 760 mmHg
- Flash Point: 442.3±34.3 °C
- Refractive Index: 1.7600 (estimate)
- PSA: 288.40000
- LogP: -3.82350
- Specific Rotation: D18 +130° (c = 0.5 in water); D21 +114° (c = 0.98 in water)
Bekanamycin Security Information
- Signal Word:Warning
- Hazard Statement: H315; H319; H335
- Warning Statement: P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501
- Safety Instruction: H303May be harmful if swallowed+H313Skin contact may be harmful+H333Inhalation may be harmful to the body
- Toxicity:LD50 i.v. in mice: 136 mg/kg (Wakazawa)
- Storage Condition:Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month
Bekanamycin Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| SHANG HAI XIAN DING Biotechnology Co., Ltd. | B-ZY320-25mg |
Bekanamycin |
4696-76-8 | 98+% | 25mg |
¥315.0 | 2022-09-28 | |
| MedChemExpress | HY-B1174-10mM*1mLinWater |
Bekanamycin |
4696-76-8 | ≥98.0% | 10mM*1mLinWater |
¥550 | 2022-03-28 | |
| MedChemExpress | HY-B1174-100mg |
Bekanamycin |
4696-76-8 | ≥98.0% | 100mg |
¥267 | 2025-04-16 | |
| ChemScence | CS-4772-100mg |
Bekanamycin |
4696-76-8 | ≥98.0% | 100mg |
$60.0 | 2021-09-02 | |
| SHANG HAI TAO SHU Biotechnology Co., Ltd. | T8118-100 mg |
Bekanamycin |
4696-76-8 | 99.97% | 100MG |
¥480.00 | 2022-04-26 | |
| abcr | AB531135-250 mg |
Kanamycin B; . |
4696-76-8 | 250MG |
€87.50 | 2022-03-23 | ||
| abcr | AB531135-1 g |
Kanamycin B, 95%; . |
4696-76-8 | 95% | 1g |
€345.30 | 2023-06-14 | |
| WU HAN AN JIE KAI Biomedical Technology Co., Ltd. | ajce48402-100mg |
Bekanamycin (Kanamycin B) |
4696-76-8 | 98% | 100mg |
¥445.00 | 2023-09-08 | |
| SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd. | B860725-100mg |
Bekanamycin |
4696-76-8 | >98% | 100mg |
¥499.00 | 2022-09-02 | |
| SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd. | B860725-500mg |
Bekanamycin |
4696-76-8 | >98% | 500mg |
¥1,799.00 | 2022-09-02 |
Bekanamycin Suppliers
Bekanamycin Related Literature
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Anjali Patwardhan,J. A. Cowan Dalton Trans. 2011 40 1795
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C.-W. T. Chang,J. Y. Takemoto Med. Chem. Commun. 2014 5 1048
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Marie-Paule Mingeot-Leclercq,Jean-Luc Décout Med. Chem. Commun. 2016 7 586
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Xin Zhang,Chetan B. Sangani,Li-Xin Jia,Pi-Xian Gong,Fang Wang,Jun-Fang Wang,Hai-Liang Zhu RSC Adv. 2014 4 54217
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Jeonghyo Lee,Alina Borovika,Yaroslav Khomutnyk,Pavel Nagorny Chem. Commun. 2017 53 8976
Additional information on Bekanamycin
Recent Advances in Bekanamycin (CAS: 4696-76-8) Research: A Comprehensive Review
Bekanamycin (CAS: 4696-76-8), a well-known aminoglycoside antibiotic, has garnered renewed interest in recent years due to its potential applications in combating antibiotic-resistant bacterial infections. This research briefing synthesizes the latest findings on Bekanamycin, focusing on its molecular mechanisms, therapeutic efficacy, and emerging applications in modern medicine. The compound, originally isolated from Streptomyces kanamyceticus, has been extensively studied for its bactericidal properties, particularly against Gram-negative pathogens.
Recent studies have elucidated the structural basis of Bekanamycin's interaction with the bacterial 30S ribosomal subunit, providing crucial insights into its mechanism of action. High-resolution cryo-EM studies published in 2023 revealed novel binding conformations that explain its superior efficacy compared to related aminoglycosides. These structural findings have significant implications for the development of next-generation antibiotics targeting resistant strains of Pseudomonas aeruginosa and Acinetobacter baumannii.
Pharmacokinetic research has made substantial progress in optimizing Bekanamycin delivery systems. A 2024 study demonstrated the effectiveness of nanoparticle-encapsulated Bekanamycin in overcoming the drug's traditional limitations, including poor oral bioavailability and nephrotoxicity. The novel formulation showed a 3.5-fold increase in tissue penetration while reducing renal accumulation by 60% in preclinical models, addressing one of the major clinical challenges associated with aminoglycoside therapy.
Emerging applications of Bekanamycin extend beyond its antimicrobial properties. Recent investigations have uncovered its potential as an anticancer adjuvant, particularly in combination therapies for solid tumors. The drug's ability to modulate cellular stress responses and enhance chemosensitivity was highlighted in a 2023 Nature Communications paper, where Bekanamycin significantly improved the efficacy of standard chemotherapy regimens in pancreatic cancer models without additional toxicity.
Resistance mechanisms to Bekanamycin have been the subject of intense scrutiny. Whole-genome sequencing of clinical isolates has identified novel resistance determinants, including previously unrecognized aminoglycoside-modifying enzymes. These findings, published in Antimicrobial Agents and Chemotherapy, are informing the development of resistance-breaking analogs and combination therapies to preserve Bekanamycin's clinical utility.
The synthesis of Bekanamycin derivatives has seen remarkable innovation, with several research groups reporting semi-synthetic variants with improved therapeutic indices. A recent Journal of Medicinal Chemistry publication detailed a series of 6'-modified Bekanamycin analogs exhibiting enhanced activity against resistant strains while maintaining favorable safety profiles. These developments suggest promising avenues for next-generation aminoglycoside development.
Clinical trial data from Phase II studies of inhaled Bekanamycin for chronic Pseudomonas infections in cystic fibrosis patients showed encouraging results, with a 72% reduction in exacerbation rates compared to placebo. The 2024 Lancet Respiratory Medicine publication highlighted the drug's potential to address unmet needs in this patient population, with regulatory submissions anticipated in 2025.
In conclusion, recent research on Bekanamycin (4696-76-8) demonstrates its evolving role in modern therapeutics, from its established antimicrobial applications to emerging uses in oncology and beyond. The convergence of structural biology, formulation science, and clinical research is revitalizing interest in this classic antibiotic, positioning it as a valuable tool in addressing contemporary medical challenges.
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