kanamycin
Trade name: Kantrex
Approved
Feb 13, 1973
Kanamycin A is aminoglycoside anti-bacterial agent. Active against many strains of Gram-negative bacteria and Gram-positive Staphylococcus aureus and epidermis. Some strains of Mycobacterium bacterium are sensitive. Most active in alkaline solution. It binds to bacterial ribosomes and reduces mRNA translation hence reduces protein biosynthesis. However, it also exhibits some toxic effects towards mammalian cells. — NCATS
Clinical trial activity
10 trials · 20 clinical orgs · 14 marketing orgs
Earliest trial started Mar 1, 2003 (NCT00042289)
Timeline
1970s
- Feb 13, 1973
Bristol-Myers — Earliest FDA Approval
- Feb 13, 1973
Apothecon — Marketing Organization
- Feb 13, 1973
Bristol-Myers — NDA Organization
1980s
- Nov 5, 1981
West-Ward Pharmaceutical — Marketing Organization
- Nov 5, 1981
Hikma — Marketing Organization
- May 9, 1985
Watson Pharmaceuticals — Marketing Organization
1990s
- Jul 31, 1992
Flaga Group — Marketing Organization
2000s
2010s
- Jan 1, 2015
Earliest Phase 2 Sponsor(trial)
Indications
Approved for
Mechanism of action
- Bacterial 70S ribosomeINHIBITOR
Bacterial 70S ribosome inhibitor
16s RRNA
- 30S ribosomal protein S2 (rpsB) ↗
- 50S ribosomal protein L4 (rplD) ↗
- 30S ribosomal protein S15 (rpsO) ↗
- 30S ribosomal protein S16 (rpsP) ↗
- 30S ribosomal protein S17 (rpsQ) ↗
- 30S ribosomal protein S18 (rpsR) ↗
- 30S ribosomal protein S19 (rpsS) ↗
- 30S ribosomal protein S20 (rpsT) ↗
- 30S ribosomal protein S21 (rpsU) ↗
- 30S ribosomal protein S3 (rpsC) ↗
- 30S ribosomal protein S4 (rpsD) ↗
- 30S ribosomal protein S5 (rpsE) ↗
- 30S ribosomal protein S6 (rpsF) ↗
- 30S ribosomal protein S7 (rpsG) ↗
- 30S ribosomal protein S8 (rpsH) ↗
- 30S ribosomal protein S9 (rpsI) ↗
- 50S ribosomal protein L35 (rpmI) ↗
- 50S ribosomal protein L36 2 (ykgO) ↗
- 50S ribosomal protein L36 (rpmJ) ↗
- 50S ribosomal protein L3 (rplC) ↗
- 50S ribosomal protein L5 (rplE) ↗
- 50S ribosomal protein L6 (rplF) ↗
- 50S ribosomal protein L7/L12 (rplL) ↗
- 30S ribosomal protein S1 (rpsA) ↗
- 30S ribosomal protein S10 (rpsJ) ↗
- 30S ribosomal protein S11 (rpsK) ↗
- 30S ribosomal protein S12 (rpsL) ↗
- 30S ribosomal protein S13 (rpsM) ↗
- 30S ribosomal protein S14 (rpsN) ↗
- 50S ribosomal protein L10 (rplJ) ↗
- 50S ribosomal protein L11 (rplK) ↗
- 50S ribosomal protein L13 (rplM) ↗
- 50S ribosomal protein L14 (rplN) ↗
- 50S ribosomal protein L15 (rplO) ↗
- 50S ribosomal protein L16 (rplP) ↗
- 50S ribosomal protein L17 (rplQ) ↗
- 50S ribosomal protein L18 (rplR) ↗
- 50S ribosomal protein L19 (rplS) ↗
- 50S ribosomal protein L1 (rplA) ↗
- 50S ribosomal protein L20 (rplT) ↗
- 50S ribosomal protein L21 (rplU) ↗
- 50S ribosomal protein L22 (rplV) ↗
- 50S ribosomal protein L23 (rplW) ↗
- 50S ribosomal protein L24 (rplX) ↗
- 50S ribosomal protein L25 (rplY) ↗
- 50S ribosomal protein L27 (rpmA) ↗
- 50S ribosomal protein L28 (rpmB) ↗
- 50S ribosomal protein L29 (rpmC) ↗
- 50S ribosomal protein L2 (rplB) ↗
- 50S ribosomal protein L30 (rpmD) ↗
- 50S ribosomal protein L31 type B (ykgM) ↗
- 50S ribosomal protein L31 (rpmE) ↗
- 50S ribosomal protein L32 (rpmF) ↗
- 50S ribosomal protein L33 (rpmG) ↗
- 50S ribosomal protein L34 (rpmH) ↗
Approval history
- approvedFeb 13, 1973
Chemistry & pharmacology
SMILES
NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H](N)C[C@@H]2N)[C@H](O)[C@@H](O)[C@@H]1O- Mol. weight
- 484.5 g/mol
- Lipinski Ro5
- 2 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral
- Availability
- Discontinued
Oral
Yes
Parenteral
Yes
Topical
No
Sources
- ChEMBLCHEMBL1384 ↗
- WikipediaKanamycin A ↗
- NCATSEQK9Q303C5 ↗
- ChEMBLCHEMBL223520 ↗
- ChEMBLCHEMBL2218908 ↗
- ChEMBLCHEMBL1446 ↗
Also known as
- 4,6-diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-α-d-glucoside
- 4,6-diamino-2-hydroxy-1,3-cyclohexane 3,6'diamino-3,6'-dideoxydi-α-d-glucoside
- 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-d-glucopyranoside
- 4,6-diamino-2-hydroxy-1,3-cyclohexylene 3,6'-diamino-3,6'-dideoxydi-d-glucopyranoside
- cantrex
- cantrex
- kanacin
- kanamycin
- kanamycin
- kanamycin
- kanamycin
- kanamycin
- kanamycin
- kanamycin
- kanamycin
- kanamycin a
- kanamycin a
- kanamycin a
- kanamycin a sulfate
- kanamycine
- kanamycine
- kanamycin monosulfate
- kanamycin monosulfate
- kanamycin monosulfate
- kanamycin monosulfate
- kanamycin monosulfate
- kanamycin monosulfate
- kanamycin sulfate
- kanamycin sulfate
- kanamycin sulfate
- kanamycin sulfate
- kannasyn
- kannasyn
- kantrex
- kantrex
- kantrex
- kantrim
- kantrim
- klebcil
- klebcil
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT03593252 | N/A | Sep 1, 2018 | McMaster University |
| NCT02975570 | Phase 3 | Aug 1, 2017 | Boston University, University of Florida, Westat |
| NCT02354014 | Phase 2 | May 3, 2016 | Johnson and Johnson |
| NCT02409290 | Phase 3 | Apr 1, 2016 | IUATLD, Inc, Medical Research Council |
| NCT02454205 | Phase 2/Phase 3 (Phase 3) | Oct 1, 2015 | Stellenbosch University, University of Cape Town, University of Limpopo, Walter Sisulu University |
| NCT02365623 | Phase 2 | Feb 18, 2015 | Janssen Pharmaceutica NV, Johnson and Johnson |
| NCT02128308 | Phase 1 | Nov 1, 2013 | Seoul National University |
| NCT00816426 | Phase 1 | Dec 29, 2008 | Government of Korea, National Institute of Allergy and Infectious Diseases (NIAID), Novartis, University of Ulsan |
| NCT00508690 | Phase 3 | Sep 1, 2007 | Japan Multinational Trial Organization, National Hospital Organization Kyoto Medical Center |
| NCT00042289 | Phase 4 | Mar 1, 2003 | Boston University, National Institute of Allergy and Infectious Diseases (NIAID), National Institutes of Health (NIH) |
Organizations
Research & Development (20)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Boston University | Academic/Hospital | 2 | 1 | 2 | 2003 |
| Johnson and Johnson | For profit | 2 | 2 | 1 | 2015 |
| National Institute of Allergy and Infectious Diseases (NIAID) | Government | 2 | 2 | 2 | 2003 |
| Government of Korea | Government | 1 | 0 | 1 | 2008 |
| IUATLD, Inc | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Janssen Pharmaceutica NV | For profit | 1 | 0 | 1 | 2015 |
| Japan Multinational Trial Organization | Academic/Hospital | 1 | 1 | 1 | 2007 |
| McMaster University | Academic/Hospital | 1 | 1 | 1 | 2018 |
| Medical Research Council | Government | 1 | 0 | 1 | 2016 |
| National Hospital Organization Kyoto Medical Center | Academic/Hospital | 1 | 0 | 1 | 2007 |
| National Institutes of Health (NIH) | Government | 1 | 0 | 1 | 2003 |
| Novartis | For profit | 1 | 0 | 1 | 2008 |
| Seoul National University | Academic/Hospital | 1 | 1 | 1 | 2013 |
| Stellenbosch University | Academic/Hospital | 1 | 0 | 1 | 2015 |
| University of Cape Town | Academic/Hospital | 1 | 1 | 1 | 2015 |
| University of Florida | Academic/Hospital | 1 | 0 | 1 | 2017 |
| University of Limpopo | Academic/Hospital | 1 | 0 | 1 | 2015 |
| University of Ulsan | Academic/Hospital | 1 | 0 | 1 | 2008 |
| Walter Sisulu University | Academic/Hospital | 1 | 0 | 1 | 2015 |
| Westat | For profit | 1 | 0 | 1 | 2017 |
Marketing (14)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Abraxis | For profit | MKTG | — |
| Apothecon | For profit | MKTG | Feb 13, 1973 |
| Athenex, Inc. | For profit | MKTG | — |
| Bristol-Myers | For profit | NDA | Feb 13, 1973 |
| Flaga Group | For profit | MKTG | Jul 31, 1992 |
| Fresenius | For profit | MKTG | Dec 17, 2002 |
| Hikma | For profit | MKTG | Nov 5, 1981 |
| International Medication | For profit | MKTG | — |
| King Pharmaceuticals | For profit | MKTG | — |
| Pharmafair | For profit | MKTG | — |
| SOLOPAK | For profit | MKTG | — |
| Warner Chilcott | For profit | MKTG | — |
| Watson Pharmaceuticals | For profit | MKTG | May 9, 1985 |
| West-Ward Pharmaceutical | For profit | MKTG | Nov 5, 1981 |