GB1033378A - Stable injectable protamine-active solutions - Google Patents
Stable injectable protamine-active solutionsInfo
- Publication number
- GB1033378A GB1033378A GB1970162A GB1970162A GB1033378A GB 1033378 A GB1033378 A GB 1033378A GB 1970162 A GB1970162 A GB 1970162A GB 1970162 A GB1970162 A GB 1970162A GB 1033378 A GB1033378 A GB 1033378A
- Authority
- GB
- United Kingdom
- Prior art keywords
- protamine
- formaldehyde
- complex
- sulphoxylate
- bisulphite
- 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
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 9
- 108010007568 Protamines Proteins 0.000 abstract 7
- 102000007327 Protamines Human genes 0.000 abstract 7
- 229940048914 protamine Drugs 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 241000972773 Aulopiformes Species 0.000 abstract 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 abstract 2
- 241000252203 Clupea harengus Species 0.000 abstract 2
- 108010040512 Clupeine Proteins 0.000 abstract 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 229910002651 NO3 Inorganic materials 0.000 abstract 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 abstract 2
- 229910019142 PO4 Inorganic materials 0.000 abstract 2
- 108010070346 Salmine Proteins 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- HRKQOINLCJTGBK-UHFFFAOYSA-N dihydroxidosulfur Chemical compound OSO HRKQOINLCJTGBK-UHFFFAOYSA-N 0.000 abstract 2
- QJQZEJFUIOWFMS-UHFFFAOYSA-N formaldehyde;sulfanediol Chemical compound O=C.OSO QJQZEJFUIOWFMS-UHFFFAOYSA-N 0.000 abstract 2
- DXRFSTNITSDOKK-UHFFFAOYSA-N formaldehyde;sulfurous acid Chemical compound O=C.OS(O)=O DXRFSTNITSDOKK-UHFFFAOYSA-N 0.000 abstract 2
- 235000019514 herring Nutrition 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract 2
- 239000010452 phosphate Substances 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 235000019515 salmon Nutrition 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- 239000011734 sodium Substances 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 2
- 229940095064 tartrate Drugs 0.000 abstract 2
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000012670 alkaline solution Substances 0.000 abstract 1
- 239000000729 antidote Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229960002897 heparin Drugs 0.000 abstract 1
- 229920000669 heparin Polymers 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 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
- A61K9/0012—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
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
Protamine-active compounds are prepared by heating together, in aqueous alkaline solution, protamine or an acid addition salt thereof and a formaldehyde-bisulphite or formaldehyde-sulphoxylate complex. The reactants are preferably heated above 40 DEG C., advantageously at 90-100 DEG C., and at a pH of 9.5 to 13. The product can be precipitated from solution by addition of a water-miscible organic solvent, e.g. an alcohol such as ethanol. The formaldehyde complex is preferably that obtained with an alkali metal (e.g. Na or K) bisulphite or sulphoxylate. Suitable salts of protamine include the hydrochloride, hydrobromide, phosphate, nitrate, citrate, tartrate and sulphate. In examples, the protamine used is salmine (from salmon) and clupeine (from herring).ALSO:Aqueous protamine-active injectable solutions of improved stability and useful as antidote for excess heparin administration comprise protamine and/or a physiologically acceptable acid addition salt thereof in simple admixture, or in chemical combination, with a formaldehyde-bisulphite and/or formaldehyde-sulphoxylate complex. The protamine combines with the formaldehyde complex when the substances are heated in aqueous solution at alkaline pH. Protamine salts specified are the hydrochloride, hydrobromide, phosphate, nitrate, citrate, tartrate and sulphate. The formaldehyde complex is preferably a complex with an alkali metal, e.g. sodium or potassium, bisulphite or sulphoxylate. The protamine used in the examples is salmine (derived from salmon sperm) and clupeine (derived from herring).
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1970162A GB1033378A (en) | 1962-05-22 | 1962-05-22 | Stable injectable protamine-active solutions |
| ES287913A ES287913A1 (en) | 1962-05-22 | 1963-05-11 | A procedure for the preparation of aqueous solutions (Machine-translation by Google Translate, not legally binding) |
| BR149255/63A BR6349255D0 (en) | 1962-05-22 | 1963-05-20 | PROCESS FOR THE PREPARATION OF PHARMACEUTICAL COMPOSITIONS CONTAINING PROTAMINE |
| FR935612A FR2613M (en) | 1962-05-22 | 1963-05-21 | Composition with protamine activity. |
| AT414763A AT249872B (en) | 1962-05-22 | 1963-05-22 | Process for the preparation of aqueous, protamine-active, injectable solutions with improved stability |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1970162A GB1033378A (en) | 1962-05-22 | 1962-05-22 | Stable injectable protamine-active solutions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1033378A true GB1033378A (en) | 1966-06-22 |
Family
ID=10133758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1970162A Expired GB1033378A (en) | 1962-05-22 | 1962-05-22 | Stable injectable protamine-active solutions |
Country Status (2)
| Country | Link |
|---|---|
| ES (1) | ES287913A1 (en) |
| GB (1) | GB1033378A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1356809A4 (en) * | 2000-12-28 | 2008-05-14 | Takeda Pharmaceutical | SUSTAINED RELEASE PREPARATIONS |
-
1962
- 1962-05-22 GB GB1970162A patent/GB1033378A/en not_active Expired
-
1963
- 1963-05-11 ES ES287913A patent/ES287913A1/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1356809A4 (en) * | 2000-12-28 | 2008-05-14 | Takeda Pharmaceutical | SUSTAINED RELEASE PREPARATIONS |
| US8637077B2 (en) | 2000-12-28 | 2014-01-28 | Takeda Pharmaceutical Company Limited | Sustained-release preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| ES287913A1 (en) | 1963-11-16 |
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