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,^[1]^[2] and first patented in 1970.^[3] It has been sold under a wide variety of trade names globally, including Orbicin,^[4] Dibekacin Meiji,^[5] Panimycin,^[6] and Tokocin.^[7] Clinical trials have found it to be effective against E. coli, Klebsiella, Enterobacter, Serratia, and Pseudomonas aeruginosa.^[4]^[8]

It has been used in combination with sulbenicillin.^[9]

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.

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Dibekacin

References