Dibekacin

Dibekacin
Clinical data
Trade names	Panimycin, Tokocin
Other names	3',4'-Dideoxykanamycin B
AHFS/Drugs.com	International Drug Names
ATC code	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 InfoCard	100.047.316
Chemical and physical data
Formula	C18H37N5O8
Molar mass	451.521 g·mol−1
3D 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, and first patented in 1970. It has been sold under a wide variety of trade names globally, including Orbicin, Dibekacin Meiji, Panimycin, and Tokocin. Clinical trials have found it to be effective against E. coli, Klebsiella, Enterobacter, Serratia, and Pseudomonas aeruginosa.

It has been used in combination with sulbenicillin.

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). Tokyo: 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): 3379–3384. PMID 7155844.
↑ US patent 3753973, Umezawa S, Umezawa H, Tsuchiya T, "The preparation of 3'-4'-dideoxykanamycin B active against resistant bacteria", published 1973-08-21, issued 1973-08-21, assigned to Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai
1 2 Schassan HH, Witt U (1979). "[Dibekacin--a novel aminoglycoside antibioticl. Antimicrobial activity and parallel resistance in vitro]". Arzneimittel-Forschung. 29 (2): 174–178. PMID 582126.
↑ "DIBEKACIN - Inxight Drugs". Inxight Drugs. National Center for Advancing Translational Sciences. Retrieved 2026-08-09.
↑ "Panimycin Injection 50mg". Kusuri-no-Shiori(Drug Information Sheet). Japan Drug Information Institute Development Center. Retrieved 2026-08-09.
↑ PubChem. "Dibekacin (Compound)". PubChem. National Center for Biotechnology Information. Retrieved 2026-08-09.
↑ Paradelis AG, Douboyas J, Stathopoulos G, Grigoriadou-Edipides A, Triantaphylidis C, Papapanagiotou J (September 1978). "In vitro comparison of kanamycin, kanendomycin, gentamicin, amikacin, sisomicin, and dibekacin against 200 strains of Pseudomonas aeruginosa". Antimicrobial Agents and Chemotherapy. 14 (3): 514–515. doi:10.1128/aac.14.3.514. PMC 352495. PMID 101135.
↑ Aonuma S, Ariji F, Oizumi K, Konno K (June 1987). "Electron microscopy of Pseudomonas aeruginosa treated with sulbenicillin and dibekacin". The Tohoku Journal of Experimental Medicine. 152 (2): 119–128. doi:10.1620/tjem.152.119. PMID 3114912.

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[1] 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). Tokyo: 485–487. doi:10.7164/antibiotics.24.485. PMID 4998037.

[Umezawa_1982-2] 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): 3379–3384. PMID 7155844.

[3] US patent 3753973, Umezawa S, Umezawa H, Tsuchiya T, "The preparation of 3'-4'-dideoxykanamycin B active against resistant bacteria", published 1973-08-21, issued 1973-08-21, assigned to Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai

[Schassan_1979-4] 1 2 Schassan HH, Witt U (1979). "[Dibekacin--a novel aminoglycoside antibioticl. Antimicrobial activity and parallel resistance in vitro]". Arzneimittel-Forschung. 29 (2): 174–178. PMID 582126.

[5] "DIBEKACIN - Inxight Drugs". Inxight Drugs. National Center for Advancing Translational Sciences. Retrieved 2026-08-09.

[6] "Panimycin Injection 50mg". Kusuri-no-Shiori(Drug Information Sheet). Japan Drug Information Institute Development Center. Retrieved 2026-08-09.

[7] PubChem. "Dibekacin (Compound)". PubChem. National Center for Biotechnology Information. Retrieved 2026-08-09.

[8] Paradelis AG, Douboyas J, Stathopoulos G, Grigoriadou-Edipides A, Triantaphylidis C, Papapanagiotou J (September 1978). "In vitro comparison of kanamycin, kanendomycin, gentamicin, amikacin, sisomicin, and dibekacin against 200 strains of Pseudomonas aeruginosa". Antimicrobial Agents and Chemotherapy. 14 (3): 514–515. doi:10.1128/aac.14.3.514. PMC 352495. PMID 101135.

[Aonuma_1987-9] Aonuma S, Ariji F, Oizumi K, Konno K (June 1987). "Electron microscopy of Pseudomonas aeruginosa treated with sulbenicillin and dibekacin". The Tohoku Journal of Experimental Medicine. 152 (2): 119–128. doi:10.1620/tjem.152.119. PMID 3114912.