Dibekacin

Chemical compound

J01GB09 (WHO) S01AA29 (WHO)

Identifiers

IUPAC name

(2S,3R,4S,5S,6R)-4-Amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol

CAS Number

34493-98-6

PubChem CID

470999

ChemSpider

413666

UNII

45ZFO9E525

KEGG

D07811

ChEMBL

ChEMBL560976

PDB ligand

84D (PDBe, RCSB PDB)

CompTox Dashboard (EPA)

DTXSID2022915

ECHA InfoCard100.047.316

Chemical and physical dataFormulaC₁₈H₃₇N₅O₈Molar mass451.521 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

C1C[C@H]([C@H](O[C@@H]1CN)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)N)O)N)N)N

InChI

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
Key:JJCQSGDBDPYCEO-XVZSLQNASA-N

Dibekacin (3',4'-dideoxykanamycin B) is an aminoglycoside antibiotic. It is a semisynthetic derivative of kanamycin developed by Hamao Umezawa and collaborators for Meiji Seika.^[1]^[2]

It has been used in combination with sulbenicillin.^[3]

References

^ Umezawa H, Umezawa S, Tsuchiya T, Okazaki Y (July 1971). "3',4'-Dideoxy-Kanamycin B Active Against Kanamycin-Resistant Escherichia coli and Pseudomonas aeruginosa". The Journal of Antibiotics. 24 (7): 485–487. doi:10.7164/antibiotics.24.485. PMID 4998037.
^ Umezawa H (November 1982). "Découverte de la dibékacine et de ses aspects chimiques [Discovery of dibekacin and its chemical aspects]". La Nouvelle Presse Médicale. 11 (46): 3379–84. PMID 7155844.
^ Aonuma S, Ariji F, Oizumi K, Konno K (June 1987). "Electron microscopy of Pseudomonas aeruginosa treated with sulbenicillin and dibekacin". Tohoku J. Exp. Med. 152 (2): 119–28. doi:10.1620/tjem.152.119. PMID 3114912.

Antibacterials that inhibit protein synthesis (J01A, J01B, J01F, J01G, QJ01XQ)

30S

Aminoglycosides
(initiation inhibitors)

-mycin (Streptomyces)	Streptomycin^# Dihydrostreptomycin Neomycin^# Framycetin Paromomycin^# Ribostamycin Kanamycin Amikacin^# Arbekacin Bekanamycin Dibekacin Tobramycin (+loteprednol) Spectinomycin^# Hygromycin B Totomycin Apramycin Nourseothricin
-micin (Micromonospora)	Gentamicin^# Netilmicin Sisomicin Micronomicin Plazomicin^# Isepamicin Verdamicin Astromicin
other	Butirosin

Tetracycline antibiotics
(tRNA binding)

Tetracyclines	Doxycycline^# Chlortetracycline Clomocycline Demeclocycline Eravacycline Lymecycline Meclocycline^‡ Metacycline Minocycline Omadacycline Oxytetracycline Penimepicycline Rolitetracycline Sarecycline Tetracycline^#
Glycylcyclines	Tigecycline

50S

Oxazolidinone
(initiation inhibitors)

Peptidyl transferase

Amphenicols	Chloramphenicol^# Azidamfenicol Thiamphenicol Florfenicol
Pleuromutilins	Azamulin Lefamulin Retapamulin Tiamulin Valnemulin

MLS (transpeptidation/translocation)

Macrolides	Azithromycin^# Boromycin Carbomycin Clarithromycin^# Dirithromycin Erythromycin^# Flurithromycin Gamithromycin Josamycin Kitasamycin Midecamycin Miocamycin Oleandomycin Rokitamycin Roxithromycin Solithromycin Spiramycin Telithromycin Tildipirosin Tilmicosin Troleandomycin Tulathromycin Tylosin Tylvalosin
Ketolides	Telithromycin^‡ Cethromycin Solithromycin^†
Lincosamides	Clindamycin^# Lincomycin Pirlimycin
Streptogramins	Pristinamycin (IA, IIA, IIB) NXL103 (Flopristin, Linopristin) Quinupristin/dalfopristin (Dalfopristin, Quinupristin) Streptogramin A Streptogramin B Virginiamycin (S1)