US3164521A - Antimycotic compositions comprising chloromethyl 5-nitro-2-furyl ketone - Google Patents
Antimycotic compositions comprising chloromethyl 5-nitro-2-furyl ketone Download PDFInfo
- Publication number
- US3164521A US3164521A US218517A US21851762A US3164521A US 3164521 A US3164521 A US 3164521A US 218517 A US218517 A US 218517A US 21851762 A US21851762 A US 21851762A US 3164521 A US3164521 A US 3164521A
- Authority
- US
- United States
- Prior art keywords
- chloromethyl
- nitro
- furyl ketone
- antimycotic
- acid
- 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
- 230000001857 anti-mycotic effect Effects 0.000 title claims description 9
- 239000002543 antimycotic Substances 0.000 title claims description 9
- DQJAAEADFORVGZ-UHFFFAOYSA-N 2-chloro-1-(5-nitrofuran-2-yl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CCl)O1 DQJAAEADFORVGZ-UHFFFAOYSA-N 0.000 title claims description 7
- 239000000203 mixture Substances 0.000 title description 8
- -1 POLYOXYETHYLENE Polymers 0.000 claims description 6
- 239000006216 vaginal suppository Substances 0.000 claims description 6
- 229940120293 vaginal suppository Drugs 0.000 claims description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 208000010484 vulvovaginitis Diseases 0.000 description 8
- 239000000829 suppository Substances 0.000 description 7
- 241000233866 Fungi Species 0.000 description 3
- 206010046914 Vaginal infection Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 241000222178 Candida tropicalis Species 0.000 description 1
- 241000235048 Meyerozyma guilliermondii Species 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 208000012868 Overgrowth Diseases 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241000235645 Pichia kudriavzevii Species 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 241000222126 [Candida] glabrata Species 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940095731 candida albicans Drugs 0.000 description 1
- 210000003756 cervix mucus Anatomy 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 229940126702 topical medication Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/345—Nitrofurans
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/15—Suppositories
Definitions
- Mycotic vulvovaginitis is characterized by pruritus which is oftentimes mild but may become persistent and unrelenting causing great discomfiture and embarrassment. Etiologically this condition may arise from the use of broad spectrum antibiotics which sometimes change the vaginal flora permitting the emergence and overgrowth of fungi. Pregnancy is oftentimes a predisposing factor to vulvovaginal infection by certain fungi. Among the fungi most often causative of this condition, Candida albicans is predominant.
- Candida guilliermondi Candida tropicalis
- Candida krusei Candida parakrusei
- Torulopsis glabrata Other species, such as Candida guilliermondi, Candida tropicalis, Candida krusei, Candida parakrusei and Torulopsis glabrata, are frequently involved. Eradication of these microorganisms is necessary to secure relief. This is most conveniently and effectively accomplished by topical medication.
- chloromethyl 'S-nitro-Z-furyl ketone is surprisingly highly active against those organisms involved in mycotic vulvovaginitis and that its great efiiciency in this respect may be made available through in corporation in acceptable pharmaceutical vehicles to provide topical compositions which are readily and conveniently applicable to the'infeoted site.
- suppository as the most convenient form for administering chloromethyl-S-nitro-Z-furyl ketone.
- a suppository base those materials known to the apothecary art for such purpose may be used. We prefenhowever, to use a base which is hydrophilic and readily adrnixable with vaginal secretions thereby permitting optimal release of the active agent.
- Suitable hydrophilic. base materials consist of the solid polyethylene glycols, the solid polypropylene glycols, and the polyoxyethylene esters of palmitic, stearic and myristic acid.
- An exemplary composition of our invention is:
- compositions comprising chloromethyl-S-nitro-Z-furyl ketone, for instance, in suppository form as exemplified above, for the control of vulvovaginitis, we have found it advantageous to add a small amount of an acid, such as hydrochloric, to pose a slightly acid medium. It is generally believed that vaginal infections are, in part, traceable to and complicated by a shift in normal vaginal pH toward the alkaline side. Maintenance of pH on the acid side is, therefore, beneficial when vaginal infection is being treated to present,
- hydrochloric acid which we deem to be an advantageous additament to our antimycotic compositions is very small.
- the (addition of as little as 0.028 part by weight of concentrated hydrochloric acid is sufficient to accomplish the desired purpose.
- Such addition is conveniently accomplished in accordance with the preparation of the exampled composition by introducing the acid into the melt prior to pouring into the suppository mold.
- An antimycotic vaginal suppository comprising a baseof polyoxyethylene wax and about 0.05% by weight thereof of chloromethyl 5-nitro-2furyl ketone.
- An acid antimycotic vaginal suppository comprising (1) a base of polyoxyethylene wax; (2) about 0.05% by weight thereof of chloromethyl 5-nitro-2-furyl ketone; and
- An acid antimycotic vaginal suppository comprising 13.80 parts by weight of polyoxyethylene palmitate containing 20 oxyethylene units per mol; 86.122 parts by weight of a polyethylene glycol Wax having an average molecular weight of 1000; 0.05 part by weight of chloromethyl S-nitro-Z-furyl ketone and 0.028 part by Weight of concentrated hydrochloric acid.
- the method of combatting mycotic vulvovaginitis which comprises the intravaginal administration to an infected host of an acid antimycotic suppository containing chloromethyl 5-nitro-2-furyl ketone as the active antifungal agent and concentrated hydrochloric acid as the acid posing agent.
Description
United States Patent 6 s5 ANTIMYCOTIC COMPOSITIONS COMPRISING CHLOROIVETHY L S-NITRO-Z-FURYL KET ONE Joseph Edward Gray and Russell Youker Mosher, Norwich, N.Y., assignors to The Norwich Pharmacal Company, a corporation of New York N0 Drawing. Filed Aug. 22, 1962, Set. No. 218,517
' 5 Claims. (Cl. 167-64) ketone useful for combatting mycotic vulvovaginitis Still more particularly, this invention is concerned with a vaginal suppository efiective in the control of mycotic vulvovaginitis.
Mycotic vulvovaginitis is characterized by pruritus which is oftentimes mild but may become persistent and unrelenting causing great discomfiture and embarrassment. Etiologically this condition may arise from the use of broad spectrum antibiotics which sometimes change the vaginal flora permitting the emergence and overgrowth of fungi. Pregnancy is oftentimes a predisposing factor to vulvovaginal infection by certain fungi. Among the fungi most often causative of this condition, Candida albicans is predominant.
Other species, such as Candida guilliermondi, Candida tropicalis, Candida krusei, Candida parakrusei and Torulopsis glabrata, are frequently involved. Eradication of these microorganisms is necessary to secure relief. This is most conveniently and effectively accomplished by topical medication.
Numerous topical medicaments have been employed in the treatment of vulvovaginitis. That their use has not been wholly successful is underlined by the continued search for agents which are specifically and highly effective against the causative microorganisms and which maintain this degree of effectiveness in repetitive usage.
We have discovered that chloromethyl 'S-nitro-Z-furyl ketone is surprisingly highly active against those organisms involved in mycotic vulvovaginitis and that its great efiiciency in this respect may be made available through in corporation in acceptable pharmaceutical vehicles to provide topical compositions which are readily and conveniently applicable to the'infeoted site.
In accordance with our invention, we prefer the suppository as the most convenient form for administering chloromethyl-S-nitro-Z-furyl ketone. As a suppository base those materials known to the apothecary art for such purpose may be used. We prefenhowever, to use a base which is hydrophilic and readily adrnixable with vaginal secretions thereby permitting optimal release of the active agent.
Suitable hydrophilic. base materials consist of the solid polyethylene glycols, the solid polypropylene glycols, and the polyoxyethylene esters of palmitic, stearic and myristic acid. An exemplary composition of our invention is:
Parts by Ingredient: weight '(A) Polyoxyethylene palmitate containing 20 oxyethylene units per mol 13.80
(B) Polyethylene glycol of average molecular weight 1000 86.15 (C) Chloromethyl 5nitro-2-furyl ketone 0.05
In the use of our compositions comprising chloromethyl-S-nitro-Z-furyl ketone, for instance, in suppository form as exemplified above, for the control of vulvovaginitis, we have found it advantageous to add a small amount of an acid, such as hydrochloric, to pose a slightly acid medium. It is generally believed that vaginal infections are, in part, traceable to and complicated by a shift in normal vaginal pH toward the alkaline side. Maintenance of pH on the acid side is, therefore, beneficial when vaginal infection is being treated to present,
insofar as possible, a physiologic pH locale so that unwanted and infectious producing agents resident therein may be dealt with in most expeditious fashion.
The amount of hydrochloric acid which we deem to be an advantageous additament to our antimycotic compositions is very small. In the hereinabove exemplified suppository form the (addition of as little as 0.028 part by weight of concentrated hydrochloric acid is sufficient to accomplish the desired purpose. Such addition is conveniently accomplished in accordance with the preparation of the exampled composition by introducing the acid into the melt prior to pouring into the suppository mold. Concornitantly, we have noted that .the addition of small amounts of such an acid, while producing an acid vaginal suppository considered to be desirable in the treatment of vaginitis for reasons hereinbefore alluded to, also evokes a salutary effect upon the appearance and general shelf-life of our suppository composition.
What is claimed is:
1. An antimycotic vaginal suppository comprising a baseof polyoxyethylene wax and about 0.05% by weight thereof of chloromethyl 5-nitro-2furyl ketone.
2. An acid antimycotic vaginal suppository comprising (1) a base of polyoxyethylene wax; (2) about 0.05% by weight thereof of chloromethyl 5-nitro-2-furyl ketone; and
.(3) about 0.028% by weight thereof of concentrated hydrochloric acid.
3. An acid antimycotic vaginal suppository comprising 13.80 parts by weight of polyoxyethylene palmitate containing 20 oxyethylene units per mol; 86.122 parts by weight of a polyethylene glycol Wax having an average molecular weight of 1000; 0.05 part by weight of chloromethyl S-nitro-Z-furyl ketone and 0.028 part by Weight of concentrated hydrochloric acid.
4. The method of combatting mycotic vulvovaginitis which comprises the intravaginal administration to an infected host of an antimycotic suppository containing as active agent chloromethyl 5-nitro-2- furyl ketone.
5. The method of combatting mycotic vulvovaginitis which comprises the intravaginal administration to an infected host of an acid antimycotic suppository containing chloromethyl 5-nitro-2-furyl ketone as the active antifungal agent and concentrated hydrochloric acid as the acid posing agent.
References Citedin the file of this patent UNITED STATES PATENTS Stillman et al May 18, 1943 Hayes et al Mar. 21, 1961 OTHER REFERENCES
Claims (1)
1. AN ANTIMYCOTIC VAGINAL SUPPOSITORY COMPRISING A BASE OF POLYOXYETHYLENE WAX AND ABOUT 0.05% BY WEIGHT THEREOF OF CHLOROMETHYL 5-NITRO-2-FURYL KETONE.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US218517A US3164521A (en) | 1962-08-22 | 1962-08-22 | Antimycotic compositions comprising chloromethyl 5-nitro-2-furyl ketone |
ES0290954A ES290954A1 (en) | 1962-08-22 | 1963-08-20 | Antimycotic compositions comprising chloromethyl 5-nitro-2-furyl ketone |
FR945274A FR2945M (en) | 1962-08-22 | 1963-08-21 | New drug has antimycotic properties. |
BR152191/63A BR6352191D0 (en) | 1962-08-22 | 1963-08-22 | PROCESS TO PREPARE CHLOROMETHIL 5-NITRO-2 FURIL-KETONE |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US218517A US3164521A (en) | 1962-08-22 | 1962-08-22 | Antimycotic compositions comprising chloromethyl 5-nitro-2-furyl ketone |
Publications (1)
Publication Number | Publication Date |
---|---|
US3164521A true US3164521A (en) | 1965-01-05 |
Family
ID=22815446
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US218517A Expired - Lifetime US3164521A (en) | 1962-08-22 | 1962-08-22 | Antimycotic compositions comprising chloromethyl 5-nitro-2-furyl ketone |
Country Status (4)
Country | Link |
---|---|
US (1) | US3164521A (en) |
BR (1) | BR6352191D0 (en) |
ES (1) | ES290954A1 (en) |
FR (1) | FR2945M (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3723477A (en) * | 1970-05-15 | 1973-03-27 | Morton Norwich Products Inc | 4-fluoro-3-methylphenyl 5-nitro-2-furyl ketone |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2319481A (en) * | 1941-05-31 | 1943-05-18 | Norwich Pharma Co | Antiseptic |
US2976300A (en) * | 1959-02-20 | 1961-03-21 | Norwich Pharma Co | Method of preparing methyl 5-nitro-2-furyl ketone |
-
1962
- 1962-08-22 US US218517A patent/US3164521A/en not_active Expired - Lifetime
-
1963
- 1963-08-20 ES ES0290954A patent/ES290954A1/en not_active Expired
- 1963-08-21 FR FR945274A patent/FR2945M/en active Active
- 1963-08-22 BR BR152191/63A patent/BR6352191D0/en unknown
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2319481A (en) * | 1941-05-31 | 1943-05-18 | Norwich Pharma Co | Antiseptic |
US2976300A (en) * | 1959-02-20 | 1961-03-21 | Norwich Pharma Co | Method of preparing methyl 5-nitro-2-furyl ketone |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3723477A (en) * | 1970-05-15 | 1973-03-27 | Morton Norwich Products Inc | 4-fluoro-3-methylphenyl 5-nitro-2-furyl ketone |
Also Published As
Publication number | Publication date |
---|---|
BR6352191D0 (en) | 1973-07-03 |
ES290954A1 (en) | 1964-01-16 |
FR2945M (en) | 1964-11-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4803066A (en) | Antibacterial and/or antifungal compositions for topical application | |
WO2021147236A9 (en) | Use of substituted aminopropionate compound in treatment of sars-cov-2 infections | |
US4797392A (en) | Use of anorectal compositions | |
US3755561A (en) | Bactericidal contact lens solution | |
GB1252207A (en) | ||
NZ198559A (en) | Pharmaceutical compositions containing betamethasone dipropionate and clotrimazole | |
JP2017078088A5 (en) | ||
JP2002524503A5 (en) | ||
US3164521A (en) | Antimycotic compositions comprising chloromethyl 5-nitro-2-furyl ketone | |
US2730483A (en) | Therapeutic compositions comprising neomycin, gramicidin and quaternary ammonium salt of thonzylamine | |
Barr et al. | A study of the inhibitory concentrations of glycerin-sorbitol and propylene glycol-sorbitol combinations on the growth of microorganisms | |
DE2425281A1 (en) | PHARMACEUTICAL COMPOSITION | |
RU2700066C1 (en) | Composition for protecting building materials from biodeterioration | |
JPH0475237B2 (en) | ||
CN111787802A (en) | Antibacterial spermicidal lubricant | |
JPH01305035A (en) | Veterinary synergistic drug and production thereof | |
US3347743A (en) | Method of treating bovine masititis | |
US2480556A (en) | Bactericidal compositions | |
GB1599159A (en) | Pharmaceutical compositions containing chlorhexidine | |
FR2421173A1 (en) | 2- (4-ETHYLPIPERAZINO) -4-PHENYLQUINOLEINE AND ITS SALTS, USEFUL IN PARTICULAR AS ANTIDEPRESSANTS, AND THEIR PREPARATION PROCESS | |
RU2674765C2 (en) | Antifungal composition of eutectic type (options) | |
Beggs | Combined activity of ketoconazole and sulphamethoxazole against Candida albicans | |
US3072525A (en) | Fungicidal composition comprising a salicylate and a pyrazole | |
RU2706115C1 (en) | Antifungal and antimicrobial agent of complex action | |
US2585048A (en) | Carboxylated methyl cellulose with quaternary ammonium compound as topical remedy |