US3105007A - Composition for the alleviation of pain in tumor growth - Google Patents

Composition for the alleviation of pain in tumor growth Download PDF

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US3105007A
US3105007A US823834A US82383459A US3105007A US 3105007 A US3105007 A US 3105007A US 823834 A US823834 A US 823834A US 82383459 A US82383459 A US 82383459A US 3105007 A US3105007 A US 3105007A
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solution
sodium
polyvinylpyrrolidone
pain
formaldehyde sulfoxylate
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Laurence G Bodkin
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    • 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
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K33/00—Medicinal preparations containing inorganic active ingredients
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/32—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers, poly(meth)acrylates, or polyvinyl pyrrolidone

Definitions

  • the present invention relates to a composition for the alleviation of pain in tumor growth and it is particularly useful in relieving pain and stress at the site of carcinomas and in some instances regression of tumor growth has been noted.
  • Another object is to provide a novel composition for the relief of pain in carcinoma without the use of analgesics, narcotics or combinations thereof, to which the body may become accustomed and which might have undesirable side effects and further lose their efficacy as the body becomes accustomed thereto.
  • a further object is to provide a novel composition which may be readily utilized by parenteral administration or by injection directly into the tumor mass and which will be selective in its pain relieving effects to the site of the carcinoma without otherwise causing a general anesthesia and which will have substantially no toxic effects.
  • the above objects of the present invention may be most satisfactorily accomplished by means of a stabilized aqueous solution of polyvinylpyrrolidone and sodium formaldehyde sulfoxylate in relatively dilute aqueous solution with a pH of about 8.0 to 10.0.
  • the polyvinylpyrrolidone molecular weight is too small, it will not etfectively adsorb or take up the sodium formaldehyde sulfoxylate and furthermore it will readily by-pass both the abnormal tumor cells as Well as the normal cell structures without being particularly eifective. Furthermore, a polyvinylpyrrolidone of lower molecular weight will not adsorb as efliciently and will be readily excreted by the kidneys.
  • the rate of release of the sodium formaldehyde sulfoxylate is too slow and there is a very high rate of adsorption with a very slow rate of release, which greatly reduces the efiicacy and furthermore there is a tendency for retention in the reticulo-endothelial system and other phagocyte cells 'in the body.
  • the preferred molecular weight apparently is above 10,000 and below 50,000 molecular weight, and the preferred molecular weight averages around 15,000 to 35,000, with optimums of about 20,000 to 30,000.
  • the combination does not appear to have any toxic or general anesthetic eifect, nor does it cause malfunction of the other body organs.
  • the sodium bicarbonate enhances the efiicacy of the polyvinylpyrrolidonesodium formaldehyde sulfoxylate combination and hastens the release of the sodium formaldehyde sulfoxylate at the site.
  • the reducing power of formaldehyde is greatly enhanced in the presence of sodium bicarbonate.
  • Parenteral water or physiological saline solution is used to make the above up to 40,000 parts by weight.
  • All of the above constituents are desirable first dissolved in about twice to 10 times their weight of water so that they will be in solution in about between 2,000 to 8,000 cubic centimeters of water, and then the solutions are mixed together, using the polyvinylpyrrolidone solution as a base, followed by the addition of the sodium chloride solution and then the sodium bicarbonate solution with agitation with After these three solutions are mixed together, the pH will be about 7.5.
  • the solution may be filtered through a porcelain candle or through charcoal.
  • the final solution contain about 2 /2 parts of sodium formaldehyde sulfoxylate for every 40 parts of the aqueous solution and about 1.4 parts of polyvinylpyrrolidone for every 40 parts of the final solution and the sodium chloride should be about 2 to 4 times the amount of the sodium bicarbonate to achieve the most effective pain alleviation.
  • not more than 500 cc. can be administered intravenously in any six hour period. 7
  • a dosage of about 500 cc. may be used at any one time over a period of four to eight hours.
  • the manner of action of the preparation is not too clear, but it does appear that it causes a necrosis and regression of the tumor or carcinoma in addition to relief .of pain.
  • the formaldehyde, as well as the sulfoxylate part of the compound, tends to insolubilize and precipitate proteins in the tumor tissue.
  • Each of these solutions may be filtered through charcoal or through porcelain candles and then the second and third and fourth solutions are mixed together with air agitation and with sufiicient additional distilled water to make up to 20,000 cc. and the pH is checked at 7.5.
  • the formaldehyde portion of the sodium formaldehyde sulfoxylate as well as the keto group of the polyvinylpyrrolidone appear to have an alleviating effect and it is this combination, in conjunction with the specific molecular weight of the polyvinylpyrrolidone, that is most elfective in the presence of the cancerous cell.
  • a solution for parenteral administration having a pH of from 8.0 to 10.0 consisting essentially of Active ingredients: Parts by weight Polyvinylpyrrolidone having a molecular weigh of from about 10,000 to about 50,000 2,400 Sodium formaldehyde sulfoxylate 1,400 Sodium bicarbonate 90 pH of from 8.0 to 10.0 consisting essentially of Active ingredients: Parts by Weight Polyvinylpyrrolidone having a molecular weight of from about 10,000
  • An isotonic solution for intravenous infusion consisting essentially of 3 grams of polwinylpyrrolidone having a molecular weight of from about 10,000 to about 50,000, 6 grams of sodium formaldehyde sulfoxylate and 0.225 grams of sodium bicarbonate in each cc. of solution, said isotonic solution having a pH of about 8.0 to 10.0.
  • An isotonic solution for intravenous infusion con sisting essentially of 3 grams of polyvinylpyrrolidone having a molecular Weight of from about 10,000 to about 50,000, 6 grams of sodium formaldehyde sulfoxylate and 0.225 gram of sodium bicarbonate in each 100 cc. of physiological saline solution, said isotonic solution having a pH of about 8.0 to 10.0.
  • Bodkin,.L. G. Control of Pain From Rectal Carcinoma Without Sedation, Am. J. Surg., vol. 86, pp. 395- 400 (1953).
  • Wilson et al. Textbook of Organic, Medicinal, and Pharmaceutical Chemistry, 2nd Ed, Lip-pincott and 00., 1954, entries: Sodium Formaldehydesulfoxylate, pp. 114-115, 487-488; P-olyvinylpyrrolidone, p. 742; and Formaldehyde, pp. 1 12-114.
  • Bodkin, L. G. Necrosis in Rectal Carcinoma Following Intravenous Chemotherapy, Am. J. Surg., vol. 88, pp. 367-377, February 1954.
  • Hueper Polyvinyl Pyrrolidone, a Cancerigenic Agent for Rats, Proceedings of the American Association for Cancer Researc vol. 2:2, April 1956, p. 120.
  • Huoper Experimental Carcinogenic Studies in Macromolecular Chemicals, I, Neoplastic Reactions in Rats and Mice After Parenteral Introduction of Polyvinylpyrrolidones, Cancer, vol. 10 pp. 8-18, 1957.
  • Hueper Carcinogenic Studies on Water-Soluble and Insoluble Macromolecules, A.M.A. Arch. Path, vol. 67, pp. 589-617 (1959).

Description

United States Patent 3,105,007 QOMEOSIIIGN FOR TEE ALLEVIATKON OF PAIN El TUMOR GROWTH Laurence G. Bodkin, 558 E. 23rd St, Brooklyn, NH. No Drawing. Filed lane 30, 1959, Ser. No. 823,834 4 Qlaims. ((11. 167-58) The present invention relates to a composition for the alleviation of pain in tumor growth and it is particularly useful in relieving pain and stress at the site of carcinomas and in some instances regression of tumor growth has been noted.
It is among the primary objects of the present invention to provide a composition which will have the elfect of relieving pain at the site of tumor growth Without the use of narcotics and without causing general anesthesia or somnifacient effects.
Another object is to provide a novel composition for the relief of pain in carcinoma without the use of analgesics, narcotics or combinations thereof, to which the body may become accustomed and which might have undesirable side effects and further lose their efficacy as the body becomes accustomed thereto.
A further object is to provide a novel composition which may be readily utilized by parenteral administration or by injection directly into the tumor mass and which will be selective in its pain relieving effects to the site of the carcinoma without otherwise causing a general anesthesia and which will have substantially no toxic effects.
Still further objects and advantages will appear in the more detailed description set forth below, it being undr. stood, however, that this more detailed description is given by way of illustration and explanation only and not by way of limitation, since various changes therein may be made by those skilled in the art without departing from the scope and spirit of the present invention.
The above objects of the present invention may be most satisfactorily accomplished by means of a stabilized aqueous solution of polyvinylpyrrolidone and sodium formaldehyde sulfoxylate in relatively dilute aqueous solution with a pH of about 8.0 to 10.0.
It has been found most important to control the molecular weight of the polyvinylpyrrolidone, which apparently acts as a carrier to adsorb or take up the sodium formaldehyde sulfoxylate and carry it through the body to the site of the tumor or carcinoma without producing toxic effects in the host.
It has been found that if the molecular weight of the polyvinylpyrolidone is controlled, it will lodge and be retained within the tumor or carcinogenic growth and not be subject to retention by normal cell growth.
At the same time if the polyvinylpyrrolidone molecular weight is too small, it will not etfectively adsorb or take up the sodium formaldehyde sulfoxylate and furthermore it will readily by-pass both the abnormal tumor cells as Well as the normal cell structures without being particularly eifective. Furthermore, a polyvinylpyrrolidone of lower molecular weight will not adsorb as efliciently and will be readily excreted by the kidneys.
On the other hand if the polyvinylpyrrolidone molecular weight is too large, the rate of release of the sodium formaldehyde sulfoxylate is too slow and there is a very high rate of adsorption with a very slow rate of release, which greatly reduces the efiicacy and furthermore there is a tendency for retention in the reticulo-endothelial system and other phagocyte cells 'in the body.
The preferred molecular weight apparently is above 10,000 and below 50,000 molecular weight, and the preferred molecular weight averages around 15,000 to 35,000, with optimums of about 20,000 to 30,000.
It has been found that when the molecular weight is so regulated the polyvinylpyrrolidone will effectively adsorb and take up a relatively large amount of the sodium formaldehyde sulfoxylate, which then is fairly quickly released at the site of the stoppage, which release will be controlled at the tumor or cancerous cell growth site without the normal cell life being particularly affected.
Furthermore, this molecular weight is apparently quite effectively retained by the cancerous cell growth and will not lodge or accumulate in the kidney, and when released by the cancerous cell will readily pass out of the system.
The combination does not appear to have any toxic or general anesthetic eifect, nor does it cause malfunction of the other body organs.
It may be readily administered by injection over a long period of time in small amounts, or it may be given in fairly massive doses at spaced intervals.
In making up the solution, it has been found that more rapid action and efficacy is achieved with the addition of sodium bicarbonate. The sodium bicarbonate enhances the efiicacy of the polyvinylpyrrolidonesodium formaldehyde sulfoxylate combination and hastens the release of the sodium formaldehyde sulfoxylate at the site. The reducing power of formaldehyde is greatly enhanced in the presence of sodium bicarbonate.
To give the preferred composition for about each 40,000 parts by weight, the following proportions have been found to be most satisfactory:
All of the above parts are by weight.
Parenteral water or physiological saline solution is used to make the above up to 40,000 parts by weight.
The latter will result in there being present about 340 parts by weight of sodium chloride. Percentage Wise, by volume, there will be about 3.5% of polyvinylpyrrolidone, 6% of sodium formaldehyde sulfoxylate and 0.225% of sodium bicarbonate in parenteral water or physiological saline solution.
Generally there will be 3.5 grams of polyvinylpyrrolidone and 6 grams of sodium formaldehyde sulfoxylate and 0.225 grams of sodium bicarobnate in each cc. of parenteral water or physiological saline solution.
All of the above constituents are desirable first dissolved in about twice to 10 times their weight of water so that they will be in solution in about between 2,000 to 8,000 cubic centimeters of water, and then the solutions are mixed together, using the polyvinylpyrrolidone solution as a base, followed by the addition of the sodium chloride solution and then the sodium bicarbonate solution with agitation with After these three solutions are mixed together, the pH will be about 7.5.
Finally, the sodium formaldehyde sulfoxylate is added and the solution is brought up to 40,000 parts by weight, with the pH being checked at 8.0 to 10.0.
At each stage, or before and after the addition of the sodium formaldehyde sulfoxylate, the solution may be filtered through a porcelain candle or through charcoal.
It will be noted that the final solution contain about 2 /2 parts of sodium formaldehyde sulfoxylate for every 40 parts of the aqueous solution and about 1.4 parts of polyvinylpyrrolidone for every 40 parts of the final solution and the sodium chloride should be about 2 to 4 times the amount of the sodium bicarbonate to achieve the most effective pain alleviation.
In respect to the dosage, desirably not more than 500 cc. can be administered intravenously in any six hour period. 7
Althoughthe exact combination between the polyvinylpyrrolidone and the sodium formaldehyde sulfoxylate is not certain, apparently an addition or adsorption product is formed at least in part.
Desirably a dosage of about 500 cc. may be used at any one time over a period of four to eight hours. The manner of action of the preparation is not too clear, but it does appear that it causes a necrosis and regression of the tumor or carcinoma in addition to relief .of pain. The formaldehyde, as well as the sulfoxylate part of the compound, tends to insolubilize and precipitate proteins in the tumor tissue.
To give a detailed procedure for preparing the final solution of the present preparation, 2400 grams of sodium formaldehyde sulfoxylate are dissolved in suflicient distilled water to make 8,000 cc. of the first solution.
Then 1,400 grams of polyvinylpyrrolidone of molecular weight 20,000 are dissolved in sufiicient distilled water to make 8,000 cc. of the second solution.
Then 340 grams of sodium chloride are dissolved in sufiicient distilled Water to make 4,000 cc. of the third solution.
Finally, 90 grams of sodium bicarbonate are dissolved in suflicient water to make 2,000 cc. of the fourth solution.
Each of these solutions may be filtered through charcoal or through porcelain candles and then the second and third and fourth solutions are mixed together with air agitation and with sufiicient additional distilled water to make up to 20,000 cc. and the pH is checked at 7.5.
Then the sodium form-aldehyde sulfoxylate solution or the first solution is added and suflicient distilled Water is added to make up to 40,000 cc.
When administered intranvenously, there apparently is quick alleviation of the pain and a necrosis and regression in the tumor mass, which appears to lose its attachment and afiinity for adjacent normal tissue.
The formaldehyde portion of the sodium formaldehyde sulfoxylate as well as the keto group of the polyvinylpyrrolidone, appear to have an alleviating effect and it is this combination, in conjunction with the specific molecular weight of the polyvinylpyrrolidone, that is most elfective in the presence of the cancerous cell.
As many changes could be made in the above composition for the alleviation of pain in tumor growth, and many widely different embodiments of this invention could be made Without departure from the scope of the claims, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.
Having now particularly described and ascertained the nature of the invention, and in what manner the same is to be performed, what is claimed is:
1. A solution for parenteral administration having a pH of from 8.0 to 10.0 consisting essentially of Active ingredients: Parts by weight Polyvinylpyrrolidone having a molecular weigh of from about 10,000 to about 50,000 2,400 Sodium formaldehyde sulfoxylate 1,400 Sodium bicarbonate 90 pH of from 8.0 to 10.0 consisting essentially of Active ingredients: Parts by Weight Polyvinylpyrrolidone having a molecular weight of from about 10,000
to about 50,000 1,000 to 5,000 Sodium formaldehyde sulfoxylate 1,000 to 4,000 Sodium bicarbonate 50 to 150 made up to 40,000 parts saline solution.
3. An isotonic solution for intravenous infusion consisting essentially of 3 grams of polwinylpyrrolidone having a molecular weight of from about 10,000 to about 50,000, 6 grams of sodium formaldehyde sulfoxylate and 0.225 grams of sodium bicarbonate in each cc. of solution, said isotonic solution having a pH of about 8.0 to 10.0.
4. An isotonic solution for intravenous infusion con sisting essentially of 3 grams of polyvinylpyrrolidone having a molecular Weight of from about 10,000 to about 50,000, 6 grams of sodium formaldehyde sulfoxylate and 0.225 gram of sodium bicarbonate in each 100 cc. of physiological saline solution, said isotonic solution having a pH of about 8.0 to 10.0.
by weight with physiological References Cited in the file of this patent UNITED STATES PATENTS 2,669,537 Thompson Feb. 16, 1954 2,675,341 Shelanski et 'al Apr. 13, 1954 2,693,417 Orth Nov. 2, 1954 2,738,299 Frost et al. Mar. 13, 1956 2,832,722 Singher Apr. 29, 1958 2,897,120 Cronin et al. July 28, 1959 2,951,766 White Sept. '6, 1960 2,961,374 Lieb et a1 Nov. 22, 1960 3,004,891 Armstrong Oct. 17, 1961 OTHER REFERENCES U.S. Dispensatory, 25th Ed., part I, pp. 1253-1255, 1265-69, part II, pp. 1811-1815, 1863, I. B. Lippincott Co., PhiL, Pa. (19 55). j
Krantz et al.: The Effect of Sodium Formaldehyde Sulphoxylate on Rat Sarcoma, Am. J. Cancer, vol. 25, pp. 789-790, 1935.
Ravdin: J.A.M.A., vol. 150, 1952, p. 10.
Bodkin,.L. G.: Control of Pain From Rectal Carcinoma Without Sedation, Am. J. Surg., vol. 86, pp. 395- 400 (1953).
Wilson et al.: Textbook of Organic, Medicinal, and Pharmaceutical Chemistry, 2nd Ed, Lip-pincott and 00., 1954, entries: Sodium Formaldehydesulfoxylate, pp. 114-115, 487-488; P-olyvinylpyrrolidone, p. 742; and Formaldehyde, pp. 1 12-114.
Bodkin, L. G.: Necrosis in Rectal Carcinoma Following Intravenous Chemotherapy, Am. J. Surg., vol. 88, pp. 367-377, February 1954.
Hansen et al.: Polyvinyl Pyrrolidone, February 1954. (Reprint from Am. Dyestuff Reporter Feb. 1, 1954.)
Hueper: Polyvinyl Pyrrolidone, a Cancerigenic Agent for Rats, Proceedings of the American Association for Cancer Researc vol. 2:2, April 1956, p. 120.
Stern et al.: Effect of Polyvinyl Pyrrolidone (PVP) on Incidence of Spontaneous Mouse Mammary Cancer," Proc. Amer. Assoc. for Cancer Research, p. 150, April 1956.
Weikel et al.: Pharmacology of the Reticulo-Endothelial System, I, Blockade (PVP) as Measured With Radio-Chromic Phosphate in the Rabbit, J. Pharmacology and Exptl Therapeutics, vol. 118, No. 2, pp. 148-152, October 1956.
Soine et al.: Rogers Inorganic Pharmaceutical Chemistry, 6th Ed., Kimpton and Co., London, England (1957), entries: Sodium Bicarbonate, pp. 201-208; Sodium Bisulfite, pp. 210-222.
Huoper: Experimental Carcinogenic Studies in Macromolecular Chemicals, I, Neoplastic Reactions in Rats and Mice After Parenteral Introduction of Polyvinylpyrrolidones, Cancer, vol. 10 pp. 8-18, 1957.
Hueper: Carcinogenic Studies on Water-Soluble and Insoluble Macromolecules, A.M.A. Arch. Path, vol. 67, pp. 589-617 (1959).
by Polyvinylpyrrolidone

Claims (1)

1. A SOLUTION FOR PARENTERAL ADMINISTRATION HAVING A PH OF FROM 8.0 TO 10.0 CONSISTING ESSENTIALLY OF ACTIVE INGRDINENTS: POLYVINYLPYRROLIDONE HAVING A MOLECULAR WEIGH OF FROM ABOUT 10,00 TO ABOUT 50,00 2,400 SODIUM FORMALDEHYDE SULFOXYLATE 1,400 SODIUM BICARBONATE 90 MADE UP TO 40.00 PARTS BY WEIGHT WITH PHYSIOLOGICA; SALINE SOLUTION.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542915A (en) * 1965-10-22 1970-11-24 Laurence G Bodkin X-ray detection of cancer with water-soluble salts of iron and bismuth
US3725541A (en) * 1967-06-23 1973-04-03 A Queuille Treatment of diarrhea using an insoluble homopolymer of vinylpyrrolidone
US4213963A (en) * 1978-12-14 1980-07-22 Janssen Pharmaceutica N.V. Fluspirilene-containing compositions
EP0044446A2 (en) * 1980-07-12 1982-01-27 Bayer Ag Anti-tumor agent

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2669537A (en) * 1952-12-27 1954-02-16 Armour & Co Adrenocorticotrophin-gelatin preparation
US2675341A (en) * 1949-12-28 1954-04-13 Gen Aniline & Film Corp Protein hydrolysate detoxified by polyvinyl pyrrolidone
US2693417A (en) * 1952-03-25 1954-11-02 Jr George Otto Orth Method of preserving fish specimens
US2738299A (en) * 1953-05-11 1956-03-13 Abbott Lab Stable nutritive amino acid compositions
US2832722A (en) * 1953-07-15 1958-04-29 Ortho Pharma Corp Radiopaque formulation comprising pvp as bodying agent
US2897120A (en) * 1954-05-04 1959-07-28 Upjohn Co Low viscosity cmc pharmaceutical vehicle
US2951766A (en) * 1957-07-15 1960-09-06 Le Roy A White Antiseptic plastic
US2961374A (en) * 1950-10-14 1960-11-22 Lieb Hans Injectable pharmaceutical preparation, and a method of making same
US3004891A (en) * 1959-09-17 1961-10-17 Pfizer & Co C Stable, aqueous solutions of sodium phosphite, sodium formaldehyde sulfoxylate, and dihydrostreptomycin sulfate

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2675341A (en) * 1949-12-28 1954-04-13 Gen Aniline & Film Corp Protein hydrolysate detoxified by polyvinyl pyrrolidone
US2961374A (en) * 1950-10-14 1960-11-22 Lieb Hans Injectable pharmaceutical preparation, and a method of making same
US2693417A (en) * 1952-03-25 1954-11-02 Jr George Otto Orth Method of preserving fish specimens
US2669537A (en) * 1952-12-27 1954-02-16 Armour & Co Adrenocorticotrophin-gelatin preparation
US2738299A (en) * 1953-05-11 1956-03-13 Abbott Lab Stable nutritive amino acid compositions
US2832722A (en) * 1953-07-15 1958-04-29 Ortho Pharma Corp Radiopaque formulation comprising pvp as bodying agent
US2897120A (en) * 1954-05-04 1959-07-28 Upjohn Co Low viscosity cmc pharmaceutical vehicle
US2951766A (en) * 1957-07-15 1960-09-06 Le Roy A White Antiseptic plastic
US3004891A (en) * 1959-09-17 1961-10-17 Pfizer & Co C Stable, aqueous solutions of sodium phosphite, sodium formaldehyde sulfoxylate, and dihydrostreptomycin sulfate

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3542915A (en) * 1965-10-22 1970-11-24 Laurence G Bodkin X-ray detection of cancer with water-soluble salts of iron and bismuth
US3725541A (en) * 1967-06-23 1973-04-03 A Queuille Treatment of diarrhea using an insoluble homopolymer of vinylpyrrolidone
US4213963A (en) * 1978-12-14 1980-07-22 Janssen Pharmaceutica N.V. Fluspirilene-containing compositions
EP0044446A2 (en) * 1980-07-12 1982-01-27 Bayer Ag Anti-tumor agent
EP0044446A3 (en) * 1980-07-12 1982-02-03 Bayer Ag Anti-tumor agent

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