DE1211357B - Verfahren zum Stabilisieren von Catechinaminen - Google Patents
Verfahren zum Stabilisieren von CatechinaminenInfo
- Publication number
- DE1211357B DE1211357B DER32552A DER0032552A DE1211357B DE 1211357 B DE1211357 B DE 1211357B DE R32552 A DER32552 A DE R32552A DE R0032552 A DER0032552 A DE R0032552A DE 1211357 B DE1211357 B DE 1211357B
- Authority
- DE
- Germany
- Prior art keywords
- adrenaline
- solutions
- boric acid
- solution
- sodium bisulfite
- 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.)
- Pending
Links
- 150000003943 catecholamines Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 5
- 230000000087 stabilizing effect Effects 0.000 title description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 claims description 64
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 22
- 239000004327 boric acid Substances 0.000 claims description 22
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 21
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 21
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims description 16
- 239000005725 8-Hydroxyquinoline Substances 0.000 claims description 14
- 229960003540 oxyquinoline Drugs 0.000 claims description 14
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- 235000010265 sodium sulphite Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 208000010412 Glaucoma Diseases 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000006641 stabilisation Effects 0.000 description 3
- 238000011105 stabilization Methods 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GEFQWZLICWMTKF-CDUCUWFYSA-N (-)-alpha-Methylnoradrenaline Chemical compound C[C@H](N)[C@H](O)C1=CC=C(O)C(O)=C1 GEFQWZLICWMTKF-CDUCUWFYSA-N 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- RPHLQSHHTJORHI-UHFFFAOYSA-N Adrenochrome Chemical compound O=C1C(=O)C=C2N(C)CC(O)C2=C1 RPHLQSHHTJORHI-UHFFFAOYSA-N 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229950009305 nordefrin Drugs 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen 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
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- 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
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
-
- 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
- A61K47/02—Inorganic compounds
-
- 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
- A61K9/0048—Eye, e.g. artificial tears
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Inorganic Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US106237A US3149035A (en) | 1961-04-28 | 1961-04-28 | Stabilization of epinephrine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1211357B true DE1211357B (de) | 1966-02-24 |
Family
ID=22310285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DER32552A Pending DE1211357B (de) | 1961-04-28 | 1962-04-26 | Verfahren zum Stabilisieren von Catechinaminen |
Country Status (6)
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3526698A (en) * | 1968-04-11 | 1970-09-01 | Merck & Co Inc | Stabilization of levo-3-(3,4-dihydroxyphenyl)-2-methylalanine with sodium bisulfite and sorbitol |
| US3966905A (en) * | 1973-05-29 | 1976-06-29 | Barnes-Hind Pharmaceuticals, Inc. | Stabilized catechol amine solutions |
| US4220636A (en) * | 1978-11-07 | 1980-09-02 | Deutsche Gesellschaft fuer Unwelt-Schutz e. V. | Stabilized suppositories containing ergo-alkaloids |
| US4623664A (en) | 1985-10-31 | 1986-11-18 | University Of Iowa Research Foundation | Oil suspended phenylephrine |
| US4689223A (en) * | 1986-04-24 | 1987-08-25 | T & R Chemicals, Inc. | Method of treating the symptoms of the common cold |
| JPS635091A (ja) * | 1986-06-26 | 1988-01-11 | Senjiyu Seiyaku Kk | 着色防止方法 |
| ES2432241T3 (es) * | 2009-06-04 | 2013-12-02 | Alk Ag | Composición estabilizada que comprende al menos un compuesto adrenérgico |
| US8628805B2 (en) * | 2009-06-04 | 2014-01-14 | Alk Ag | Stabilized composition comprising at least one adrenergic compound |
| US20120101167A1 (en) | 2010-10-25 | 2012-04-26 | Langham Maurice E | Treatment of ocular and cerebral ischemia |
| WO2014057365A1 (en) | 2012-10-08 | 2014-04-17 | Wockhardt Limited | Stable injectable pharmaceutical composition of epinephrine or salts thereof |
| EP3687475A4 (en) | 2017-09-26 | 2021-07-28 | YS Pharmtech | STABILIZATION OF EPINEPHRINE FORMULATIONS |
| AU2018348277A1 (en) | 2017-10-10 | 2020-05-28 | Merck Patent Gmbh | Stabilized injectable pharmaceutical compositions of L-epinephrine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2382546A (en) * | 1941-11-03 | 1945-08-14 | Curtis David | Anesthetic solutions |
| US2391552A (en) * | 1942-02-25 | 1945-12-25 | Curtis David | Stabilized aromatic compounds |
| US2493471A (en) * | 1945-06-04 | 1950-01-03 | Parke Davis & Co | Stabilized organic compounds and methods of obtaining the same |
| US2783132A (en) * | 1953-08-12 | 1957-02-26 | Pennsylvania Salt Mfg Co | Stabilization of hydrogen peroxide |
| US2948680A (en) * | 1957-03-15 | 1960-08-09 | Standard Oil Co | Lubricant compositions |
-
0
- NL NL277824D patent/NL277824A/xx unknown
- BE BE617022D patent/BE617022A/xx unknown
-
1961
- 1961-04-28 US US106237A patent/US3149035A/en not_active Expired - Lifetime
-
1962
- 1962-04-19 GB GB15363/62A patent/GB930452A/en not_active Expired
- 1962-04-25 CH CH499062A patent/CH431817A/de unknown
- 1962-04-26 DE DER32552A patent/DE1211357B/de active Pending
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| US3149035A (en) | 1964-09-15 |
| NL277824A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) | |
| CH431817A (de) | 1967-03-15 |
| GB930452A (en) | 1963-07-03 |
| BE617022A (c_deeref_Disk_and_Scratch_Disk_Pools_and_Their_Defaults.html) |
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