MedKoo Cat#: 558080 | Name: Dibekacin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dibekacin is an antibiotic.

Chemical Structure

Dibekacin
CAS#34493-98-6 (free base)

Theoretical Analysis

MedKoo Cat#: 558080

Name: Dibekacin

CAS#: 34493-98-6 (free base)

Chemical Formula: C18H37N5O8

Exact Mass:

Molecular Weight: 451.52

Elemental Analysis: C, 47.88; H, 8.26; N, 15.51; O, 28.35

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
3',4'-Dideoxykanamycin B; BRN 1441606; Debecacin;
IUPAC/Chemical Name
D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-erythro-hexopyranosyl)-(1-4)-2-deoxy-
InChi Key
JJCQSGDBDPYCEO-HGMONVNRSA-N
InChi Code
InChI=1S/C18H37N5O8/c19-4-6-1-2-7(20)17(28-6)30-15-8(21)3-9(22)16(14(15)27)31-18-13(26)11(23)12(25)10(5-24)29-18/h6-18,24-27H,1-5,19-23H2/t6-,7+,8-,9+,10+,11-,12+,13+,14-,15+,16-,17+,18-/m0/s1
SMILES Code
O[C@H]1[C@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@H](CN)CC[C@H]3N)[C@@H](N)C[C@H]2N)O[C@H](CO)[C@@H](O)[C@@H]1N
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 451.52 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Umemura E, Sakamoto Y, Takahashi Y, Miyake T. Synthesis and antibacterial activity of 1-N-[(S)-ω-amino-2-hydroxyalkyl] derivatives of dibekacin, 5-deoxydibekacin, 3'-deoxykanamycin A and gentamicin B. J Antibiot (Tokyo). 2015 Jun;68(6):421-3. doi: 10.1038/ja.2015.6. Epub 2015 Feb 25. PubMed PMID: 25712399. 2: Lopitaux R, Hermet R, Sirot J, Cluzel M. [Dibekacin in the treatment of urinary infections in the elderly]. Pathol Biol (Paris). 1984 Jun;32(5 Pt 2):563-6. French. PubMed PMID: 6462747. 3: Kitasato I, Niizato T, Watanabe T, Inouye S. Reduction of dibekacin-induced nephrotoxicity in the rat by the formation of N-alkylsulfonate derivatives. Drugs Exp Clin Res. 1989;15(6-7):239-47. PubMed PMID: 2591296. 4: Sasaki K, Kobayashi Y, Kurihara T, Yamashita Y, Takahashi Y, Miyake T, Akamatsu Y. Synthesis and antibacterial activity of 4″ or 6″-alkanoylamino derivatives of arbekacin. J Antibiot (Tokyo). 2015 Dec;68(12):741-7. doi: 10.1038/ja.2015.61. Epub 2015 May 20. PubMed PMID: 25990952. 5: Noone P. Sisomicin, netilmicin and dibekacin. A review of their antibacterial activity and therapeutic use. Drugs. 1984 Jun;27(6):548-78. Review. PubMed PMID: 6376062. 6: Tada T, Miyoshi-Akiyama T, Dahal RK, Mishra SK, Shimada K, Ohara H, Kirikae T, Pokhrel BM. Identification of a novel 6'-N-aminoglycoside acetyltransferase, AAC(6')-Iak, from a multidrug-resistant clinical isolate of Stenotrophomonas maltophilia. Antimicrob Agents Chemother. 2014 Oct;58(10):6324-7. doi: 10.1128/AAC.03354-14. Epub 2014 Aug 4. PubMed PMID: 25092711; PubMed Central PMCID: PMC4187913. 7: Takeshima Y. [Genetic Diagnosis and Molecular Therapies for Duchenne Muscular Dystrophy]. Rinsho Byori. 2015 Oct;63(10):1194-201. Review. Japanese. PubMed PMID: 26897856. 8: Bopp S, Marre R, Schulz E, Sack K. [Animal experiments on the nephrotoxicity, pharmacokinetics and therapeutic efficacy of dibekacin]. Arzneimittelforschung. 1981;31(3):473-7. German. PubMed PMID: 7194672. 9: Duriez D, Dewilde A, Marzin D, Wattré P. Quantitative determination of dibekacin using radioimmunoassay, substrate-labelled fluorescent immunoassay and rate nephelometric inhibition immunoassay for tobramycin. Ann Inst Pasteur Microbiol (1985). 1985 May-Jun;136A(3):381-8. PubMed PMID: 3901881. 10: Funatsu Y, Hasegawa N, Fujiwara H, Namkoong H, Asami T, Tasaka S, Kimizuka Y, Kamata H, Ishii M, Iketani O, Ogata H, Iwata S, Betsuyaku T. Pharmacokinetics of arbekacin in bronchial epithelial lining fluid of healthy volunteers. J Infect Chemother. 2014 Oct;20(10):607-11. doi: 10.1016/j.jiac.2014.05.007. Epub 2014 Jun 25. PubMed PMID: 24973909. 11: Hwang JH, Lee JH, Hwang JH, Chung KM, Lee EJ, Yoon YJ, Moon MK, Kim JS, Won KS, Lee CS. Comparison of Arbekacin and Vancomycin in Treatment of Chronic Suppurative Otitis Media by Methicillin Resistant Staphylococcus aureus. J Korean Med Sci. 2015 Jun;30(6):688-93. doi: 10.3346/jkms.2015.30.6.688. Epub 2015 May 13. PubMed PMID: 26028918; PubMed Central PMCID: PMC4444466. 12: Komiya I, Murata S, Umemura K, Tomono N, Kikai S, Fujita M. Acute toxicity and pharmacokinetics of dibekacin mice. J Pharmacobiodyn. 1981 May;4(5):356-61. PubMed PMID: 7288553. 13: Inouye S, Niizato T, Komiya I, Yuda Y, Yamada Y. Mode of protective action of fosfomycin against dibekacin-induced nephrotoxicity in the dehydrated rats. J Pharmacobiodyn. 1982 Dec;5(12):941-50. PubMed PMID: 7169607. 14: Sato K. External ocular infections due to methicillin-resistant Staphylococcus aureus and medical history. Can J Ophthalmol. 2015 Oct;50(5):e97-9. doi: 10.1016/j.jcjo.2015.05.006. Epub 2015 Jul 23. PubMed PMID: 26455994. 15: Navarro AS, Lanao JM, Dominguez-Gil Hurlé A. In-vitro interaction between dibekacin and penicillins. J Antimicrob Chemother. 1986 Jan;17(1):83-9. PubMed PMID: 3949639. 16: Sader HS, Rhomberg PR, Farrell DJ, Jones RN. Arbekacin activity against contemporary clinical bacteria isolated from patients hospitalized with pneumonia. Antimicrob Agents Chemother. 2015;59(6):3263-70. doi: 10.1128/AAC.04839-14. Epub 2015 Mar 23. PubMed PMID: 25801559; PubMed Central PMCID: PMC4432132. 17: Sawae Y, Okada K, Umemura K. [Pharmacokinetic studies on intravenous drip infusion of dibekacin in elderly subjects without apparent renal failure (author's transl)]. Jpn J Antibiot. 1982 Mar;35(3):770-8. Japanese. PubMed PMID: 7097979. 18: Aonuma S, Ariji F, Oizumi K, Konno K. Electron microscopy of Pseudomonas aeruginosa treated with sulbenicillin and dibekacin. Tohoku J Exp Med. 1987 Jun;152(2):119-28. PubMed PMID: 3114912. 19: Harada Y, Chong Y, Shimono N, Miyake N, Uchida Y, Kadowaki M, Akashi K, Shimoda S. Nosocomial spread of meticillin-resistant Staphylococcus aureus with β-lactam-inducible arbekacin resistance. J Med Microbiol. 2014 May;63(Pt 5):710-4. doi: 10.1099/jmm.0.065276-0. Epub 2014 Feb 3. PubMed PMID: 24493159. 20: Komiya I, Murata S, Umemura K, Tomono N, Kikai S, Fujita M. Pharmacokinetics of dibekacin in rabbits and dogs. J Pharmacobiodyn. 1981 May;4(5):362-73. PubMed PMID: 7288554.