DE2301633A1 - Wasserunloesliche biocide antibiotikasalze - Google Patents
Wasserunloesliche biocide antibiotikasalzeInfo
- Publication number
- DE2301633A1 DE2301633A1 DE2301633A DE2301633A DE2301633A1 DE 2301633 A1 DE2301633 A1 DE 2301633A1 DE 2301633 A DE2301633 A DE 2301633A DE 2301633 A DE2301633 A DE 2301633A DE 2301633 A1 DE2301633 A1 DE 2301633A1
- Authority
- DE
- Germany
- Prior art keywords
- polymyxin
- salt
- water
- biocidal
- insoluble
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 38
- 230000003115 biocidal effect Effects 0.000 title claims description 34
- 239000003139 biocide Substances 0.000 title description 2
- 230000002378 acidificating effect Effects 0.000 claims description 13
- 239000002244 precipitate Substances 0.000 claims description 13
- 239000003242 anti bacterial agent Substances 0.000 claims description 12
- 229940088710 antibiotic agent Drugs 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 11
- 229930182566 Gentamicin Natural products 0.000 claims description 11
- 108010040201 Polymyxins Proteins 0.000 claims description 11
- 229960002518 gentamicin Drugs 0.000 claims description 11
- 229930182555 Penicillin Natural products 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 229930186147 Cephalosporin Natural products 0.000 claims description 7
- 229940124587 cephalosporin Drugs 0.000 claims description 7
- 150000001780 cephalosporins Chemical class 0.000 claims description 7
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 6
- 229940049954 penicillin Drugs 0.000 claims description 6
- 108010093965 Polymyxin B Proteins 0.000 claims description 5
- VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 claims description 5
- 241000192125 Firmicutes Species 0.000 claims description 4
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 claims description 4
- 229960001019 oxacillin Drugs 0.000 claims description 4
- 229960000603 cefalotin Drugs 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 229920000024 polymyxin B Polymers 0.000 claims 2
- 229960005266 polymyxin b Drugs 0.000 claims 2
- 238000001035 drying Methods 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 7
- 208000015181 infectious disease Diseases 0.000 description 6
- 206010052428 Wound Diseases 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 5
- 150000001450 anions Chemical class 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- VDUVBBMAXXHEQP-SLINCCQESA-M oxacillin sodium Chemical compound [Na+].N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C([O-])=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 VDUVBBMAXXHEQP-SLINCCQESA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SBKRTALNRRAOJP-BWSIXKJUSA-N N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-6-methylheptanamide (6S)-N-[(2S)-4-amino-1-[[(2S,3R)-1-[[(2S)-4-amino-1-oxo-1-[[(3S,6S,9S,12S,15R,18R,21S)-6,9,18-tris(2-aminoethyl)-15-benzyl-3-[(1R)-1-hydroxyethyl]-12-(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxobutan-2-yl]-6-methyloctanamide sulfuric acid Polymers OS(O)(=O)=O.CC(C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@@H](CCN)NC1=O)[C@@H](C)O.CC[C@H](C)CCCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)[C@@H](NC(=O)[C@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@@H](CCN)NC1=O)[C@@H](C)O SBKRTALNRRAOJP-BWSIXKJUSA-N 0.000 description 3
- 230000002070 germicidal effect Effects 0.000 description 3
- 230000005923 long-lasting effect Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002960 penicillins Chemical class 0.000 description 3
- 229960003548 polymyxin b sulfate Drugs 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 oxacillin Chemical class 0.000 description 2
- 230000035515 penetration Effects 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 229940083555 sodium cephalothin Drugs 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- RDEIXVOBVLKYNT-VQBXQJRRSA-N (2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(1-aminoethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol;(2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4,6-diamino-3-[(2r,3r,6s)-3-amino-6-(aminomethyl)oxan-2-yl]o Chemical compound OS(O)(=O)=O.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@@H](CN)O2)N)[C@@H](N)C[C@H]1N.O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](CC[C@H](O2)C(C)N)N)[C@@H](N)C[C@H]1N.O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N RDEIXVOBVLKYNT-VQBXQJRRSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229920004934 Dacron® Polymers 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 108010087702 Penicillinase Proteins 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 208000002847 Surgical Wound Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- FUBBGQLTSCSAON-PBFPGSCMSA-N cefaloglycin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)COC(=O)C)C(O)=O)=CC=CC=C1 FUBBGQLTSCSAON-PBFPGSCMSA-N 0.000 description 1
- 229950004030 cefaloglycin Drugs 0.000 description 1
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- GPXLMGHLHQJAGZ-JTDSTZFVSA-N nafcillin Chemical compound C1=CC=CC2=C(C(=O)N[C@@H]3C(N4[C@H](C(C)(C)S[C@@H]43)C(O)=O)=O)C(OCC)=CC=C21 GPXLMGHLHQJAGZ-JTDSTZFVSA-N 0.000 description 1
- 229960000515 nafcillin Drugs 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 229950009506 penicillinase Drugs 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/222—Cyclohexane rings substituted by at least two nitrogen atoms
- C07H15/226—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings
- C07H15/234—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2
- C07H15/236—Cyclohexane rings substituted by at least two nitrogen atoms with at least two saccharide radicals directly attached to the cyclohexane rings attached to non-adjacent ring carbon atoms of the cyclohexane rings, e.g. kanamycins, tobramycin, nebramycin, gentamicin A2 a saccharide radical being substituted by an alkylamino radical in position 3 and by two substituents different from hydrogen in position 4, e.g. gentamicin complex, sisomicin, verdamycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/50—Cyclic peptides containing at least one abnormal peptide link
- C07K7/54—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring
- C07K7/60—Cyclic peptides containing at least one abnormal peptide link with at least one abnormal peptide link in the ring the cyclisation occurring through the 4-amino group of 2,4-diamino-butanoic acid
- C07K7/62—Polymyxins; Related peptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Biophysics (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Biotechnology (AREA)
- Materials For Medical Uses (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24746672A | 1972-04-25 | 1972-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2301633A1 true DE2301633A1 (de) | 1973-11-08 |
Family
ID=22935052
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2301633A Pending DE2301633A1 (de) | 1972-04-25 | 1973-01-13 | Wasserunloesliche biocide antibiotikasalze |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4920317A (enExample) |
| CA (1) | CA950831A (enExample) |
| CH (1) | CH553815A (enExample) |
| DE (1) | DE2301633A1 (enExample) |
| FR (1) | FR2186230B1 (enExample) |
| GB (1) | GB1400464A (enExample) |
| ZA (1) | ZA723917B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD2633C2 (ro) * | 2001-08-31 | 2005-08-31 | ХЕРАУС КУЛЦЕР ГмбХ и Ко. КГ | Procedeu de aplicare a învelişului antibiotic pe corpuri cu microcavităţi interconexe (variante), corp cu microcavităţi interconexe cu inveliş antibiotic (variante) şi utilizarea acestuia |
| US7030093B2 (en) | 2002-06-21 | 2006-04-18 | Heraeus Kulzer Gmbh & Co. Kg | Antibiotic coating for porous bodies and method for its production as well as its use |
| US7358232B2 (en) | 2001-08-31 | 2008-04-15 | Heraeus Kulzer Gmbh & Co.Kg | Method for the antibiotic coating of bodies with interconnecting microcavities as well as coated bodies and their usage |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0115001B1 (de) * | 1982-12-28 | 1988-06-15 | Bayer Ag | Stabile Aminoglykosid-Penicillin-Injektionsformulierungen |
| AUPN771596A0 (en) * | 1996-01-25 | 1996-02-15 | Mclean, Allan Joseph | Methods of and compositions for potentiating the action of agents active on cell-wall sites of susceptible bacteria |
| SK3999A3 (en) * | 1996-07-16 | 1999-07-12 | Gist Brocades Nv | 'beta'-lactam granules free of organic solvents |
| CA2661576A1 (en) | 2006-09-26 | 2008-04-03 | Taro Pharmaceuticals North America, Inc. | Stabilizing compositions for antibiotics and methods of use |
| US10682360B2 (en) | 2014-01-27 | 2020-06-16 | Susanne GARDNER | Antimicrobial formulations and applications thereof |
| WO2017019943A1 (en) * | 2015-07-29 | 2017-02-02 | Susanne Gardner | Antimicrobial formulations and applications thereof |
-
1972
- 1972-06-02 CA CA143,773,A patent/CA950831A/en not_active Expired
- 1972-06-06 GB GB2631872A patent/GB1400464A/en not_active Expired
- 1972-06-08 ZA ZA723917A patent/ZA723917B/xx unknown
- 1972-08-17 FR FR7229465A patent/FR2186230B1/fr not_active Expired
- 1972-09-11 JP JP47090523A patent/JPS4920317A/ja active Pending
- 1972-10-03 CH CH1439272A patent/CH553815A/fr not_active IP Right Cessation
-
1973
- 1973-01-13 DE DE2301633A patent/DE2301633A1/de active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MD2633C2 (ro) * | 2001-08-31 | 2005-08-31 | ХЕРАУС КУЛЦЕР ГмбХ и Ко. КГ | Procedeu de aplicare a învelişului antibiotic pe corpuri cu microcavităţi interconexe (variante), corp cu microcavităţi interconexe cu inveliş antibiotic (variante) şi utilizarea acestuia |
| US7358232B2 (en) | 2001-08-31 | 2008-04-15 | Heraeus Kulzer Gmbh & Co.Kg | Method for the antibiotic coating of bodies with interconnecting microcavities as well as coated bodies and their usage |
| US7030093B2 (en) | 2002-06-21 | 2006-04-18 | Heraeus Kulzer Gmbh & Co. Kg | Antibiotic coating for porous bodies and method for its production as well as its use |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA723917B (en) | 1973-07-25 |
| FR2186230B1 (enExample) | 1976-07-02 |
| FR2186230A1 (enExample) | 1974-01-11 |
| CH553815A (fr) | 1974-09-13 |
| GB1400464A (en) | 1975-07-16 |
| CA950831A (en) | 1974-07-09 |
| JPS4920317A (enExample) | 1974-02-22 |
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