US2751324A - Antibiotic compositions comprising oxytetracycline and carbomycin - Google Patents
Antibiotic compositions comprising oxytetracycline and carbomycin Download PDFInfo
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- US2751324A US2751324A US299758A US29975852A US2751324A US 2751324 A US2751324 A US 2751324A US 299758 A US299758 A US 299758A US 29975852 A US29975852 A US 29975852A US 2751324 A US2751324 A US 2751324A
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- Prior art keywords
- oxytetracycline
- carbomycin
- antibiotic
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- composition
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- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 40
- FQVHOULQCKDUCY-OGHXVOSASA-N [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(1s,3r,7r,8s,9s,10r,12r,14e,16s)-7-acetyloxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimeth Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@H]1[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/[C@@H]2O[C@H]2C[C@@H](C)OC(=O)C[C@H]([C@@H]1OC)OC(C)=O)[C@H]1C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O1 FQVHOULQCKDUCY-OGHXVOSASA-N 0.000 title claims description 29
- 229930188120 Carbomycin Natural products 0.000 title claims description 27
- 229950005779 carbomycin Drugs 0.000 title claims description 27
- 239000004100 Oxytetracycline Substances 0.000 title claims description 26
- 229960000625 oxytetracycline Drugs 0.000 title claims description 26
- 235000019366 oxytetracycline Nutrition 0.000 title claims description 26
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 title claims description 26
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 title claims description 26
- 230000003115 biocidal effect Effects 0.000 title claims description 21
- 244000005700 microbiome Species 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 5
- 229940088710 antibiotic agent Drugs 0.000 description 5
- 229960004368 oxytetracycline hydrochloride Drugs 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KIPLYOUQVMMOHB-MXWBXKMOSA-L [Ca++].CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O.CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O Chemical compound [Ca++].CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O.CN(C)[C@H]1[C@@H]2[C@@H](O)[C@H]3C(=C([O-])[C@]2(O)C(=O)C(C(N)=O)=C1O)C(=O)c1c(O)cccc1[C@@]3(C)O KIPLYOUQVMMOHB-MXWBXKMOSA-L 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940063650 terramycin Drugs 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000002195 synergetic effect Effects 0.000 description 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000000721 bacterilogical effect Effects 0.000 description 2
- 235000010633 broth Nutrition 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 108010093965 Polymyxin B Proteins 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 1
- 229960004475 chlortetracycline Drugs 0.000 description 1
- 235000019365 chlortetracycline Nutrition 0.000 description 1
- CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- -1 known Chemical compound 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229920000024 polymyxin B Polymers 0.000 description 1
- 229960005266 polymyxin b Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/65—Tetracyclines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
Definitions
- Oxytetracycline is a highly effective compound, especi ally useful in the treatment of infectious diseases.
- Carbomycin has been shown to be effective against a variety of different microorganisms. This compound is described in detail and claimed by the name of antibiotic P. A. 97 in the copending patent application of Fred W. Tanner, Jr., et al., filed on February 7, 1952, under Serial No. 270,298. It has now been found that compositions containing a oxytetracycline antibiotic and a carbomycin antibiotic act in a synergistic manner against certain microorganisms which cause serious infections in vivo. In particular, these compositions are quite effective against Micrococci and streptococci, especially Micrccoccus pyogenes and Streptomyces faecalis.
- compositions containing from approximately 5 to approximately 95 parts by weight of an oxytetracycline antibiotic, together with from about 95 to about 5 parts by weight of a carbomycin antibiotic exert the synergistic activity described above. It may be found that a particular organism is more susceptible to a certain formulation of these compositions than to others. For instance, one organism may be quite susceptible to a composition containing parts of carbomycin with 90 parts of oxytetracycline, whereas another may be considerably more susceptible to a composition containing equal amounts of each of the component antibiotics. A minimum of bacteriological testing is required to determine the most useful of these compositions for combating any particular organism.
- compositions containing equal parts by weight of carbomycin and oxytetracycline, and a 10% carbomycin: oxytetracycline formulation also proved effective at the same level. The utility of the new products for disinfecting purposes and other in vitro applications is thus demonstrated.
- Example 111 The effectiveness of compositions of carbomycin with oxytetracycline was tested in vitro against a strain of Micrococcus pyogenes var. aureus (Y-l) which had been found to be quite resistant to a variety of antibiotics. When oxytetracycline was tested alone against this microorganism, it was found that 50 micrograms were required per milliliter of medium to inhibit the organism. 2.5 micrograms of carbomycin hydrochloride per milliliter were required to inhibit this organism. However, a total of only 1.5 micrograms of a composition containing 75 by weight of carbomycin hydrochloride and 25% by weight of oxytetracycline hydrochloride per milliliter of medium was necessary to inhibit this resistant organism.
- compositions containing 90% of the carbomycin salt and 10% of oxytetracycline hydrochloride were tested, it was found that a total concentration of the composition containing 1.50 micrograms/milliliter was also effective in inhibiting the growth of the resistant organism. It is apparent that low levels of oxytetracycline very definitely increase the activity of carbomycin against this organism, despite the fact that oxytetracycline of itself has a relatively low level of activity on this particular organism.
- the novel compositions thus exhibit definite and unexpected synergism.
- a bacteriologically active composition which comprises an oxytetracycline antibiotic and a carbomycin antibiotic.
- a bacteriologically active composition which comprises a major proportion of an oxytetracycline antibiotic, together with a minor proportion of a carbomycin antibiotic.
- composition according to claim 2 wherein each of the two antibiotic constituents is in the form of a salt.
- a bacteriologcially active composition which com- 4 prises between 5 and 95 parts by weight of oxytetracycline hydrochloride, together with between 95 and 5 parts by weight of carbomycin hydrochloride.
- Tanner et al. Some Properties of Magnamycin. Antibiotics and Chemotherapy, September 1952, p. 441.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
ANTIBIOTIC COMPOSITIONS COMPRISING OXY- TETRACYCLINE AND CARBOMYCIN Arthur R. English, Mineola, N. Y., assiguor to Chas. Pfizer & Co., Inc., Brooklyn, N. Y., a corporation of Delaware No Drawing. Application July 18, 1952, Serial No. 299,758
4 Claims. (Cl. 167-65) This application is concerned with certain antibiotic compositions. In particular, it is concerned with compositions of oxytetracycline (also known by the registered trademark Terramycin) and carbomycin.
Oxytetracycline is a highly effective compound, especi ally useful in the treatment of infectious diseases. Carbomycin has been shown to be effective against a variety of different microorganisms. This compound is described in detail and claimed by the name of antibiotic P. A. 97 in the copending patent application of Fred W. Tanner, Jr., et al., filed on February 7, 1952, under Serial No. 270,298. It has now been found that compositions containing a oxytetracycline antibiotic and a carbomycin antibiotic act in a synergistic manner against certain microorganisms which cause serious infections in vivo. In particular, these compositions are quite effective against Micrococci and streptococci, especially Micrccoccus pyogenes and Streptomyces faecalis.
In this application, where reference is made to an oxytetracycline antibiotic, the term is meant to include not only amphoteric oxytetracycline, but salts of oxytetracycline with acids, such as hydrochloric or sulfuric acids, and with metals such as sodium, as well as other known, biologically active forms of the antibiotic. Not only may pure amphoteric oxytetracycline and salts thereof be used, but also crude products recovered from fermentation broths, concentrates thereof, and the like. bomycin is a basic compound which forms salts such as the sulfate or the hydrochloride; and the phrase a carbomycin antibiotic as used herein denotes not only the base per se, but its various salts and other biologically active derivatives.
Compositions containing from approximately 5 to approximately 95 parts by weight of an oxytetracycline antibiotic, together with from about 95 to about 5 parts by weight of a carbomycin antibiotic, exert the synergistic activity described above. It may be found that a particular organism is more susceptible to a certain formulation of these compositions than to others. For instance, one organism may be quite susceptible to a composition containing parts of carbomycin with 90 parts of oxytetracycline, whereas another may be considerably more susceptible to a composition containing equal amounts of each of the component antibiotics. A minimum of bacteriological testing is required to determine the most useful of these compositions for combating any particular organism.
The compositions of this invention may be used in a variety of forms and manners, depending upon the particular microorganisms involved. Thus, the materials may be employed as disinfectants in vitro, or applied in vivo locally in forms of solutions, suspensions, powders, ointments and so forth. The compositions may also be injected intramuscularly for veterinary use in suitable media for such injections. For instance, a solution in saline or water may be employed. The oral administration of suitable preparations of the compositions of this invention may also be used for the treatment of certain nited States Patent O 2,751,324 Ce Patented June 19, 1956 2 diseases. The oral preparations may take the form of capsules, tablets, elixirs, or other dry or liquid prepara- Example I A composition was prepared containing 10% of pure, crystalline carbomycin and 90% crystalline oxytetracycline hydrochloride. milliliters of double strength standard bacteriological nutrient broth was placed in each of a number of test tubes. A portion of the antibiotic composition was added to each tube. This was followed by a 0.5-rnilliliter portion of a standard inoculum of Micrococcus pyogenes var. aureus. Finally. the volume of the mixture was diluted to 4 milliliters with sterile water. The tubes were incubated at 37 C. overnight and then were observed for evidence of growth of the microorganism as indicated by turbidity. From a series of such tests, all conducted under sterile conditions and to which varying amounts of the antibiotic composition Were added, there was determined the minimum concentration of the composition required to inhibit growth of the microorganism in question. It was found that with the particular composition tested a total of 0.30 microgram of the composition per milliliter of the mixture was effective. However, when either carbomycin or oxytetracycline hydrochloride was used alone, 0.50 microgram of the antibiotic per milliliter of medium was necessary to achieve the same inhibition. When a mixture containing 25% of carbomycin and of oxytetracycline was used, it was found that a total of 0.30 microgram of this composition was effective in inhibiting the growth of the organism. Compositions containing equal parts by weight of carbomycin and oxytetracycline, and a 10% carbomycin: oxytetracycline formulation also proved effective at the same level. The utility of the new products for disinfecting purposes and other in vitro applications is thus demonstrated.
by weight by weight of A sample of 2 Example 11 The effectiveness of compositions containing various proportions of amphoteric oxytetracycline and carbomycin base was tested in the same manner as in Example I against Streptococcus faecalis A121. Neither carbomycin nor oxytetracycline proved effective in inhibiting this organism at a level of 0.50 mcg./ml., whereas compositions of carbomycin with oxytetracycline ranging from 9 parts of oxytetracycline with 1 part of carbomycin to 1 oxytetracycline for 9 parts carbomycin, proved effective at levels of 0.30 microgram of the individual compositions per milliliter.
Example 111 The effectiveness of compositions of carbomycin with oxytetracycline was tested in vitro against a strain of Micrococcus pyogenes var. aureus (Y-l) which had been found to be quite resistant to a variety of antibiotics. When oxytetracycline was tested alone against this microorganism, it was found that 50 micrograms were required per milliliter of medium to inhibit the organism. 2.5 micrograms of carbomycin hydrochloride per milliliter were required to inhibit this organism. However, a total of only 1.5 micrograms of a composition containing 75 by weight of carbomycin hydrochloride and 25% by weight of oxytetracycline hydrochloride per milliliter of medium was necessary to inhibit this resistant organism. When a composition containing 90% of the carbomycin salt and 10% of oxytetracycline hydrochloride was tested, it was found that a total concentration of the composition containing 1.50 micrograms/milliliter was also effective in inhibiting the growth of the resistant organism. It is apparent that low levels of oxytetracycline very definitely increase the activity of carbomycin against this organism, despite the fact that oxytetracycline of itself has a relatively low level of activity on this particular organism. The novel compositions thus exhibit definite and unexpected synergism.
What is claimed is:
l. A bacteriologically active composition which comprises an oxytetracycline antibiotic and a carbomycin antibiotic.
2. A bacteriologically active composition which comprises a major proportion of an oxytetracycline antibiotic, together with a minor proportion of a carbomycin antibiotic.
3. A composition according to claim 2, wherein each of the two antibiotic constituents is in the form of a salt. 4. A bacteriologcially active composition which com- 4 prises between 5 and 95 parts by weight of oxytetracycline hydrochloride, together with between 95 and 5 parts by weight of carbomycin hydrochloride.
References Cited in the file of this patent Neter et al.: Synergistic eiiects of polymyxin B and terramycin on bacteria encountered in urinary tract infactions. J. Urol., 67(5):773775. 1952. Through Biol. Abstr., November 1952, p. 2807.
Tanner et al.: Some Properties of Magnamycin. Antibiotics and Chemotherapy, September 1952, p. 441.
Welch et al.: Bacterial Spectrum of Erythromycin, Carbomycin, Chloramphenicol, Aureomycin and Terramycin. Antibiotics and Chemotherapy, December 1952, pp. 693 to 696.
Hobby et al.: The tnberculostatic activity of terramycin." Am. Rev. Tubere., vol. 63, pp. 434 to 440, April 1951. Through Squibb Abstract Bulletin, vol. 24, No. 17, April 25, 1951, p. A-362.
Armstrong: Effect of Combinations of Antibiotics. J. Lab. and Clin. Med., vol. 37, April 1951, pp. 584 to
Claims (1)
1. A BACTERIOLOGICALLY ACTIVE COMPOSITION WHICH COMPRISES AN OXYTETRACYCLINE ANTIBIOTIC AND A CARBOMYCIN ANTIBIOTIC.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US299758A US2751324A (en) | 1952-07-18 | 1952-07-18 | Antibiotic compositions comprising oxytetracycline and carbomycin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US299758A US2751324A (en) | 1952-07-18 | 1952-07-18 | Antibiotic compositions comprising oxytetracycline and carbomycin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2751324A true US2751324A (en) | 1956-06-19 |
Family
ID=23156162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US299758A Expired - Lifetime US2751324A (en) | 1952-07-18 | 1952-07-18 | Antibiotic compositions comprising oxytetracycline and carbomycin |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2751324A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899362A (en) * | 1959-08-11 | Hemostatic sponges and method of | ||
| US2945784A (en) * | 1956-03-29 | 1960-07-19 | Lepetit Spa | Streptomycin and dihydrostreptomycin salts |
-
1952
- 1952-07-18 US US299758A patent/US2751324A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2899362A (en) * | 1959-08-11 | Hemostatic sponges and method of | ||
| US2945784A (en) * | 1956-03-29 | 1960-07-19 | Lepetit Spa | Streptomycin and dihydrostreptomycin salts |
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