US3401221A - Treatment of urinary tract infection - Google Patents
Treatment of urinary tract infection Download PDFInfo
- Publication number
- US3401221A US3401221A US392023A US39202364A US3401221A US 3401221 A US3401221 A US 3401221A US 392023 A US392023 A US 392023A US 39202364 A US39202364 A US 39202364A US 3401221 A US3401221 A US 3401221A
- Authority
- US
- United States
- Prior art keywords
- nitrofurantoin
- urinary tract
- mesh
- treatment
- tract infection
- 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.)
- Expired - Lifetime
Links
- 208000019206 urinary tract infection Diseases 0.000 title description 4
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 17
- 229960000564 nitrofurantoin Drugs 0.000 description 16
- 239000013078 crystal Substances 0.000 description 13
- 206010047700 Vomiting Diseases 0.000 description 10
- 206010028813 Nausea Diseases 0.000 description 7
- 230000008693 nausea Effects 0.000 description 5
- 239000002775 capsule Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 230000002485 urinary effect Effects 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 210000001635 urinary tract Anatomy 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 238000009505 enteric coating Methods 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
Classifications
-
- 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
Definitions
- This invention relates to the therapy of urinary tract infection. More particularly it is concerned with improvements in the treatment of urinary tract infection with nitrofurantoin.
- nitrofurantoin has come to 0ccupy a leading role in the treatment of infections of the urinary tract. Its widespread use in this respect has been attended with a minimum of side effects. Nonetheless, in common with other widely used therapeutic agents, its use has provoked side effects whose alleviation would be welcomed by the medical practitioner.
- the most vexing side effect occasioned through the use of nitrofurantoin is that of nauesea and emesis which occurs in a relatively minor proportion of those to whom it is administered.
- Various attempts to mitigate this problem through reduced dosage regimens, controlled diet or enteric coating of tablets containing it have not been wholly satisfactory thus depriving a relatively minor but nevertheless significant number of its benefits.
- Nitrofurantoin crystals that vomited 50-60 mesh (300-250,:1.) 0 80-120 mesh (180-120 r) 6.3 140-200 mesh (10075,u) 15.6 200-400 mesh (-40,:t) 37.5
- nitrofurantoin contemplated in this invention may be readily secured by saturating an appropriate solvent such as nitromethane therewith, advan tageously at elevated temperature, and allowing crystallization to take place spontaneously preferably on cooling slowly, or, if it is desired to hasten the process, a seed crystal may be introduced, until a sufiicient crop is secured. The deposited crop is filtered, dried, ground if necessary, and screened to obtain the desired crystal size range.
- nitrofurantoin crystal size of this invention is preferably composed into capsules using suitable dispersants and excipients such as milk sugar and dextrose to insure even distribution and dispersion.
- suitable dispersants and excipients such as milk sugar and dextrose to insure even distribution and dispersion.
- Other acceptable pharmaceutical dosage forms such as a thixotropic suspension which will preserve the integrity of the crystal size may be employed.
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
United States Patent ABSTRACT OF THE DISCLOSURE Crystalline nitrofurantoin of a surface area from 120 cm. gm. to 1000 cm. /gm. will maintain efficacy in treat ing urinary tract infections while substantially reducing the nausea and emesis associated with that drug.
3,401,221 Patented Sept. 10, 1968 of passing through a 50 US. mesh screen but not through a 400 US. mesh screen, are especially adapted to reduction of nausea and emesis upon oral administration without impairment of efiicacy. When nitrofurantoin of the crystal dimensions stated above is administered to a host, effective urinary tract concentration is secured without manifestation of nausea and emesis. The results attained pursuant to a 100 mg. peroral dose in capsule form of the nitroufurantoin crystal of this invention are set forth in the following Table I.
It is readily apparent from the foregoing table that the 50-400 mesh size of nitrofurantoin, a convenient manner of designating crystal size, presents effective urinary concentration of drug and that within that range the 80- 200 mesh size is preferred for optimal performance.
A further delineation of the reduced nausea-emesis propensity present within the crystal size range of nitro- TABLE I Average Average Average Average Average maximum time of maximum time max. N itroiurantoin, 100 mg. capsule total percent maximum urinary urinary percent excreted in percent cone. cone. excreted a 2-hour excretion, attained, attained,
period hours mg./l. hours 50-60 mesh (120-144 cmJ/gm.) 19. 6 8.3 4. 9 83 5. 5 80-120 mesh (195-290 omfi/gm.) 29. 8 12. 9 4. 6 124 5. 0 140-200 mesh (340-485 cmJ/gm.) 32. 3 16. 6 3.8 159 4. 1 200400 mesh (485-970 emJ/gm.) 35. 4 17. 8 3. 6 156 3. 4 Commercial 100 mg. Nitroiurantoiu tablet (ca. 4,000 cmJ/gm.) 36. 1 20. 0 3. 6 151 3. 0
This invention relates to the therapy of urinary tract infection. More particularly it is concerned with improvements in the treatment of urinary tract infection with nitrofurantoin.
In little over a decade nitrofurantoin has come to 0ccupy a leading role in the treatment of infections of the urinary tract. Its widespread use in this respect has been attended with a minimum of side effects. Nonetheless, in common with other widely used therapeutic agents, its use has provoked side effects whose alleviation would be welcomed by the medical practitioner. The most vexing side effect occasioned through the use of nitrofurantoin is that of nauesea and emesis which occurs in a relatively minor proportion of those to whom it is administered. Various attempts to mitigate this problem through reduced dosage regimens, controlled diet or enteric coating of tablets containing it have not been wholly satisfactory thus depriving a relatively minor but nevertheless significant number of its benefits.
It is an object of this invention to provide nitrofurantoin in a form designed to substantially negate the elicitation of nausea and emesis sometimes attendant to its use without impairment of its efficacy.
It is a further object of this invention to provide nitrofurantoin of a crystal size which is readily secured and which is readily formulated in suitable dosage form,
It is a still further object of this invention to provide crystalline nitrofurantoin in a particular crystal size which is substantially devoid of the nausea-emesis drawback sometimes encountered upon its use.
In accordance with the aforestated objects it has been discovered that crystals of nitrofurantoin having a surface area ranging from about 120 cm. /gm. to about 1000 cm. /gm., being substantially in cubic form and capable furantoin of this invention is evoked through the administration of a 10 mg./kg. dose thereof to dogs, a very emetic sensitive species, The results of such administration is shown in Table II below:
TABLE II Percent of dogs Nitrofurantoin crystals: that vomited 50-60 mesh (300-250,:1.) 0 80-120 mesh (180-120 r) 6.3 140-200 mesh (10075,u) 15.6 200-400 mesh (-40,:t) 37.5
It is readily apparent from the foregoing table that the larger size nitrofurantoin is least provocative of emesis again pointing to the -200 mesh size as the preferred embodiment of this invention to secure maximal urinary concentration and minimal nausea and emesis.
The crystal size of nitrofurantoin contemplated in this invention may be readily secured by saturating an appropriate solvent such as nitromethane therewith, advan tageously at elevated temperature, and allowing crystallization to take place spontaneously preferably on cooling slowly, or, if it is desired to hasten the process, a seed crystal may be introduced, until a sufiicient crop is secured. The deposited crop is filtered, dried, ground if necessary, and screened to obtain the desired crystal size range.
For convenient administration the nitrofurantoin crystal size of this invention is preferably composed into capsules using suitable dispersants and excipients such as milk sugar and dextrose to insure even distribution and dispersion. Other acceptable pharmaceutical dosage forms such as a thixotropic suspension which will preserve the integrity of the crystal size may be employed.
What is claimed is:
1.- Crystalline nitrofurantoin having essentially a surface area ranging from 195 cnL gm. to 485 cm. /gm.
2. A pharmaceutical preparation in unit capsule dosage form containing 100 mg. of crystalline nitrofurantoin having essentially a surface area ranging from 195 cm. /gm. to 485 cmfi/gm.
4 References Cited Wilson and Jones: American Drug Index for 1962, pp. 334, 335 and 518 (1962).
5 ALBERT T. MEYERS, Primary Examiner.
I. D. GOLDBERG, Assistant Examiner.
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US392023A US3401221A (en) | 1964-08-25 | 1964-08-25 | Treatment of urinary tract infection |
| NL6506369A NL6506369A (en) | 1964-08-25 | 1965-05-19 | |
| DE19651492055 DE1492055B1 (en) | 1964-08-25 | 1965-05-25 | New form of preparation of N- (5-nitrofurfurylidene) -1-aminohydantoin |
| ES0313664A ES313664A1 (en) | 1964-08-25 | 1965-06-01 | Procedure for the preparation of nitrofurantoina cristalina. (Machine-translation by Google Translate, not legally binding) |
| IL23668A IL23668A (en) | 1964-08-25 | 1965-06-03 | Crystalline nitrofuranthoin and processes for its preparation |
| SE07949/65A SE326186B (en) | 1964-08-25 | 1965-06-16 | |
| DK316165AA DK116132B (en) | 1964-08-25 | 1965-06-22 | Process for the preparation of substantially cubic nitrofurantoin crystals for oral administration. |
| NO159004A NO118491B (en) | 1964-08-25 | 1965-07-19 | |
| JP40043717A JPS4924651B1 (en) | 1964-08-25 | 1965-07-21 | |
| FR27293A FR4844M (en) | 1964-08-25 | 1965-08-05 | |
| GB34070/65A GB1040980A (en) | 1964-08-25 | 1965-08-09 | Improvements in or relating to the preparation of nitrofurantoin |
| FI1983/65A FI42961B (en) | 1964-08-25 | 1965-08-18 | |
| AT774865A AT261117B (en) | 1964-08-25 | 1965-08-24 | Process for the production of a highly effective, well-tolerated preparation form of N (5 nitrofurfurylidene) 1 amino hydantoin |
| BE668774D BE668774A (en) | 1964-08-25 | 1965-08-25 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US392023A US3401221A (en) | 1964-08-25 | 1964-08-25 | Treatment of urinary tract infection |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3401221A true US3401221A (en) | 1968-09-10 |
Family
ID=23548942
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US392023A Expired - Lifetime US3401221A (en) | 1964-08-25 | 1964-08-25 | Treatment of urinary tract infection |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3401221A (en) |
| JP (1) | JPS4924651B1 (en) |
| AT (1) | AT261117B (en) |
| BE (1) | BE668774A (en) |
| DE (1) | DE1492055B1 (en) |
| DK (1) | DK116132B (en) |
| ES (1) | ES313664A1 (en) |
| FI (1) | FI42961B (en) |
| FR (1) | FR4844M (en) |
| GB (1) | GB1040980A (en) |
| IL (1) | IL23668A (en) |
| NL (1) | NL6506369A (en) |
| NO (1) | NO118491B (en) |
| SE (1) | SE326186B (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772473A (en) * | 1986-06-16 | 1988-09-20 | Norwich Eaton Pharmaceuticals, Inc. | Nitrofurantoin dosage form |
| US4798725A (en) * | 1986-06-16 | 1989-01-17 | Norwich Eaton Pharmaceuticals, Inc. | Sustained release capsule |
| EP0410517A1 (en) * | 1989-07-25 | 1991-01-30 | Norwich Eaton Pharmaceuticals, Inc. | Liquid suspensions of nitrofurantoin |
| US5332832A (en) * | 1989-07-26 | 1994-07-26 | Procter & Gamble Pharmaceuticals, Inc. | Nitrofurantoin crystals |
| US20060002997A1 (en) * | 2002-08-23 | 2006-01-05 | Puneet Shamar | Nitrofurantoin controlled release dosage form |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2348334C2 (en) * | 1973-09-26 | 1982-11-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | New form of preparation of N-4- [2- (5-chloro-2-methoxybenzamido) ethyl] -phenyl-sulfonyl-N'-cyclohexylurea |
| DE3033919A1 (en) * | 1980-09-09 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | SOLID PHARMACEUTICAL PREPARATIONS CONTAINING NIFEDIPINE AND METHOD FOR THE PRODUCTION THEREOF |
-
1964
- 1964-08-25 US US392023A patent/US3401221A/en not_active Expired - Lifetime
-
1965
- 1965-05-19 NL NL6506369A patent/NL6506369A/xx unknown
- 1965-05-25 DE DE19651492055 patent/DE1492055B1/en active Pending
- 1965-06-01 ES ES0313664A patent/ES313664A1/en not_active Expired
- 1965-06-03 IL IL23668A patent/IL23668A/en unknown
- 1965-06-16 SE SE07949/65A patent/SE326186B/xx unknown
- 1965-06-22 DK DK316165AA patent/DK116132B/en unknown
- 1965-07-19 NO NO159004A patent/NO118491B/no unknown
- 1965-07-21 JP JP40043717A patent/JPS4924651B1/ja active Pending
- 1965-08-05 FR FR27293A patent/FR4844M/fr not_active Expired
- 1965-08-09 GB GB34070/65A patent/GB1040980A/en not_active Expired
- 1965-08-18 FI FI1983/65A patent/FI42961B/fi active
- 1965-08-24 AT AT774865A patent/AT261117B/en active
- 1965-08-25 BE BE668774D patent/BE668774A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4772473A (en) * | 1986-06-16 | 1988-09-20 | Norwich Eaton Pharmaceuticals, Inc. | Nitrofurantoin dosage form |
| US4798725A (en) * | 1986-06-16 | 1989-01-17 | Norwich Eaton Pharmaceuticals, Inc. | Sustained release capsule |
| EP0410517A1 (en) * | 1989-07-25 | 1991-01-30 | Norwich Eaton Pharmaceuticals, Inc. | Liquid suspensions of nitrofurantoin |
| US5178880A (en) * | 1989-07-25 | 1993-01-12 | Norwich Eaton Pharmaceuticals, Inc. | Liquid suspensions of nitrofurantoin |
| US5332832A (en) * | 1989-07-26 | 1994-07-26 | Procter & Gamble Pharmaceuticals, Inc. | Nitrofurantoin crystals |
| US20060002997A1 (en) * | 2002-08-23 | 2006-01-05 | Puneet Shamar | Nitrofurantoin controlled release dosage form |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6506369A (en) | 1966-02-28 |
| GB1040980A (en) | 1966-09-01 |
| BE668774A (en) | 1965-12-16 |
| IL23668A (en) | 1969-07-30 |
| AT261117B (en) | 1968-04-10 |
| DE1492055B1 (en) | 1971-05-13 |
| ES313664A1 (en) | 1965-09-01 |
| JPS4924651B1 (en) | 1974-06-25 |
| FR4844M (en) | 1967-02-20 |
| NO118491B (en) | 1970-01-05 |
| FI42961B (en) | 1970-09-02 |
| DK116132B (en) | 1969-12-15 |
| SE326186B (en) | 1970-07-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: NORWICH EATON PUERTO RICO, INC. CARRETERA NO. 2, Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:EATON LABORATORIES, INC. A CORP. OF DE;REEL/FRAME:004022/0627 Effective date: 19820609 |
|
| AS | Assignment |
Owner name: EATON LABORATORIES, INC. Free format text: CHANGE OF NAME;ASSIGNOR:NORWICH EATON PUERTO RICO;REEL/FRAME:004065/0147 Effective date: 19820806 Owner name: EATON LABORATORIES, INC., STATELESS Free format text: CHANGE OF NAME;ASSIGNOR:NORWICH EATON PUERTO RICO;REEL/FRAME:004065/0147 Effective date: 19820806 |