ES2432241T3 - Composición estabilizada que comprende al menos un compuesto adrenérgico - Google Patents
Composición estabilizada que comprende al menos un compuesto adrenérgico Download PDFInfo
- Publication number
- ES2432241T3 ES2432241T3 ES10734927T ES10734927T ES2432241T3 ES 2432241 T3 ES2432241 T3 ES 2432241T3 ES 10734927 T ES10734927 T ES 10734927T ES 10734927 T ES10734927 T ES 10734927T ES 2432241 T3 ES2432241 T3 ES 2432241T3
- Authority
- ES
- Spain
- Prior art keywords
- compound
- antioxidant
- range
- adrenergic compound
- metabisulfite
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 108
- 230000001800 adrenalinergic effect Effects 0.000 title claims abstract description 98
- 239000000203 mixture Substances 0.000 title claims abstract description 47
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 80
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 76
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 claims abstract description 69
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 claims abstract description 63
- 229930182837 (R)-adrenaline Natural products 0.000 claims abstract description 58
- 229960005139 epinephrine Drugs 0.000 claims abstract description 58
- 239000007788 liquid Substances 0.000 claims abstract description 43
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 41
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 41
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims abstract description 35
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- -1 sulfite compound Chemical class 0.000 claims abstract description 30
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 claims description 18
- 229940001584 sodium metabisulfite Drugs 0.000 claims description 17
- 235000010262 sodium metabisulphite Nutrition 0.000 claims description 17
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 12
- 229940090047 auto-injector Drugs 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 208000003455 anaphylaxis Diseases 0.000 claims description 8
- 206010002198 Anaphylactic reaction Diseases 0.000 claims description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 6
- 230000036783 anaphylactic response Effects 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 230000006641 stabilisation Effects 0.000 claims description 6
- 238000011105 stabilization Methods 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 5
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 100
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- 239000000243 solution Substances 0.000 description 31
- 238000009472 formulation Methods 0.000 description 13
- 239000012535 impurity Substances 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 9
- 230000035882 stress Effects 0.000 description 9
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- 150000003943 catecholamines Chemical class 0.000 description 8
- 230000008859 change Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010586 diagram Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 5
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- RPHLQSHHTJORHI-UHFFFAOYSA-N Adrenochrome Chemical compound O=C1C(=O)C=C2N(C)CC(O)C2=C1 RPHLQSHHTJORHI-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
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- YLXIPWWIOISBDD-NDAAPVSOSA-N (2r,3r)-2,3-dihydroxybutanedioic acid;4-[(1r)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.CNC[C@H](O)C1=CC=C(O)C(O)=C1 YLXIPWWIOISBDD-NDAAPVSOSA-N 0.000 description 3
- TYYGQMPOZGEFQL-UHFFFAOYSA-N 1-(3,4-dihydroxyphenyl)-2-(methylazaniumyl)ethanesulfonate Chemical compound CNCC(S(O)(=O)=O)C1=CC=C(O)C(O)=C1 TYYGQMPOZGEFQL-UHFFFAOYSA-N 0.000 description 3
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- 206010002199 Anaphylactic shock Diseases 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
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- 150000001340 alkali metals Chemical class 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
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- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960004308 acetylcysteine Drugs 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 229960002433 cysteine Drugs 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009931 harmful effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
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- 230000036962 time dependent Effects 0.000 description 2
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
- IOVGROKTTNBUGK-SJKOYZFVSA-N (1S,2R)-ritodrine Chemical compound N([C@H](C)[C@@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJKOYZFVSA-N 0.000 description 1
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- LEBVLXFERQHONN-UHFFFAOYSA-N 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide Chemical compound CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C LEBVLXFERQHONN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- SPCZYEWHGDYTOP-UHFFFAOYSA-N CS(=O)(=O)O.OC=1C=C(C=CC1O)CN Chemical compound CS(=O)(=O)O.OC=1C=C(C=CC1O)CN SPCZYEWHGDYTOP-UHFFFAOYSA-N 0.000 description 1
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- 206010007522 Cardiac asthma Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-DUZGATOHSA-N D-araboascorbic acid Natural products OC[C@@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-DUZGATOHSA-N 0.000 description 1
- JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- 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
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010028735 Nasal congestion Diseases 0.000 description 1
- 208000004327 Paroxysmal Dyspnea Diseases 0.000 description 1
- 206010049771 Shock haemorrhagic Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
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- 239000000048 adrenergic agonist Substances 0.000 description 1
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- 239000000443 aerosol Substances 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
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- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 229960003150 bupivacaine Drugs 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 239000005556 hormone Substances 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical compound OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
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- 159000000001 potassium salts Chemical class 0.000 description 1
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
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- YNJORDSKPXMABC-UHFFFAOYSA-M sodium;2-hydroxypropane-2-sulfonate Chemical compound [Na+].CC(C)(O)S([O-])(=O)=O YNJORDSKPXMABC-UHFFFAOYSA-M 0.000 description 1
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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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Dermatology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| US8628805B2 (en) * | 2009-06-04 | 2014-01-14 | Alk Ag | Stabilized composition comprising at least one adrenergic compound |
| CN102525893B (zh) * | 2012-01-04 | 2013-11-20 | 上海禾丰制药有限公司 | 盐酸去氧肾上腺素注射液及其制剂工艺 |
| CN102525894A (zh) * | 2012-01-04 | 2012-07-04 | 上海禾丰制药有限公司 | 盐酸异丙肾上腺素注射液及其制剂工艺 |
| AU2013328393A1 (en) * | 2012-10-08 | 2015-04-09 | Wockhardt Limited | Stable injectable pharmaceutical composition of epinephrine or salts thereof |
| TWI780236B (zh) * | 2013-02-04 | 2022-10-11 | 法商賽諾菲公司 | 胰島素類似物及/或胰島素衍生物之穩定化醫藥調配物 |
| US20150231334A1 (en) * | 2013-12-18 | 2015-08-20 | Windgap Medical, Inc. | Drug mixing and delivery system and method |
| US12239822B2 (en) | 2013-03-15 | 2025-03-04 | Windgap Medical, Inc. | Portable drug mixing and delivery device and associated methods |
| KR20160070077A (ko) | 2013-10-03 | 2016-06-17 | 임프리미스 파마슈티컬스 인코포레이티드 | 안구내 투여를 위한 에피네프린-기반 안과용 조성물 및 이의 제조 방법 |
| CN103520096B (zh) * | 2013-10-25 | 2015-02-25 | 成都晶博生物科技有限责任公司 | 一种硫酸特布他林注射液的生产工艺 |
| KR20160104724A (ko) | 2014-01-09 | 2016-09-05 | 사노피 | 인슐린 유사체 및/또는 인슐린 유도체의 안정화된 약제학적 제형 |
| UY35988A (es) | 2014-02-27 | 2015-09-30 | Sint Sa | Proceso para la producción de una solución inyectable de noradrenalina de baja concentración |
| PL2990031T3 (pl) * | 2014-08-28 | 2020-05-18 | Sun Pharmaceutical Industries Ltd | Pozajelitowa postać norepinefryny |
| HK1244450A1 (zh) * | 2014-12-18 | 2018-08-10 | 温德加普医疗股份有限公司 | 用於溶解或增溶治疗剂的方法和组合物 |
| US9119876B1 (en) * | 2015-03-13 | 2015-09-01 | Par Pharmaceutical, Inc. | Epinephrine formulations |
| US20170189352A1 (en) | 2015-03-13 | 2017-07-06 | Par Pharmaceutical, Inc. | Epinephrine formulations |
| US11517525B2 (en) * | 2015-09-18 | 2022-12-06 | Hikma Pharmaceuticals Usa Inc. | Epinephrine spray formulations |
| US10039710B2 (en) * | 2015-09-18 | 2018-08-07 | Insys Development Company, Inc. | Epinephrine spray formulations |
| JP2019524896A (ja) | 2016-08-25 | 2019-09-05 | ハーロウ・ヘルス・インコーポレイテッドＨａｒｒｏｗ Ｈｅａｌｔｈ， Ｉｎｃ． | 眼内投与のためのエピネフリンベースの眼科組成物及びその製造方法 |
| RU2635759C1 (ru) * | 2016-09-13 | 2017-11-15 | Интеллег Сосьете Анониме | Фармацевтическая композиция для парентерального введения и способ ее получения |
| US10835503B2 (en) * | 2017-01-13 | 2020-11-17 | Teva Pharmaceuticals Usa, Inc. | Pre-filled syringe |
| US20250177328A1 (en) | 2017-01-30 | 2025-06-05 | Nevakar Injectables Inc. | Norepinephrine compositions and methods therefor |
| WO2018140894A1 (en) | 2017-01-30 | 2018-08-02 | Nevakar, Inc | Norepinephrine compositions and methods therefor |
| EP3612173B1 (en) * | 2017-04-17 | 2023-10-11 | Hikma Pharmaceuticals USA Inc. | Epinephrine spray formulations |
| EP3687475A4 (en) * | 2017-09-26 | 2021-07-28 | YS Pharmtech | STABILIZATION OF EPINEPHRIN FORMULATIONS |
| RU2020114880A (ru) | 2017-10-10 | 2021-11-12 | Мерк Патент Гмбх | Стабилизированные инъекционные фармацевтические композиции l- эпинефрина |
| WO2019182745A1 (en) | 2018-03-19 | 2019-09-26 | Bryn Pharma, LLC | Epinephrine spray formulations |
| CA3093725C (en) | 2018-03-23 | 2021-08-24 | Nevakar Inc. | Epinephrine compositions and containers |
| US10952962B1 (en) | 2018-04-11 | 2021-03-23 | QuVa Pharma, Inc. | Ready to use liquid formulation |
| WO2019200076A1 (en) | 2018-04-11 | 2019-10-17 | QuVa Pharma, Inc. | Ready to use liquid reck formulation |
| US10478406B2 (en) | 2019-03-18 | 2019-11-19 | HARC Therapeutics AG | High-pH solid-state epinephrine formulation |
| CN116474219A (zh) * | 2019-06-28 | 2023-07-25 | 四川普锐特药业有限公司 | 保持给药均一度的药物流体分配器及右美托咪定鼻喷器 |
| AU2020325831B2 (en) | 2019-08-08 | 2025-09-25 | Sun Pharmaceutical Industries Limited | Infusion dosage form of norepinephrine |
| USD1004518S1 (en) | 2019-09-09 | 2023-11-14 | Brunswick Corporation | Railing for a marine vessel |
| US12097170B2 (en) | 2020-03-06 | 2024-09-24 | Baxter International Inc. | Packaged, sealed container system for stable storage of an oxygen sensitive pharmaceutical formulation |
| USD984953S1 (en) | 2021-05-03 | 2023-05-02 | Brunswick Corporation | Safely railing having buoy holder |
| AU2021203856B2 (en) * | 2021-06-10 | 2023-03-09 | Animal Ethics Pty Ltd | Topical anaesthetic composition having improved vasoconstrictor stability |
| AU2023332633A1 (en) * | 2022-08-27 | 2025-04-03 | Biophore India Pharmaceuticals Pvt. Ltd | Trientine liquid dosage forms |
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| GB425678A (en) | 1933-06-15 | 1935-03-15 | Novocol Chemical Mfg Co Inc | Improvements relating to anesthetics for hypodermic injection |
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| DD150694A1 (de) | 1980-04-16 | 1981-09-16 | Gisela Raether | Verfahren zur stabilisierung von pharmazeutischen praeparaten mit oxidationsempfindlichen bestandteilen |
| US4734438A (en) | 1983-04-26 | 1988-03-29 | Macri Frank J | Norepinephrine potentiated compositions and method of use |
| AU5680994A (en) | 1992-12-10 | 1994-07-04 | Abbott Laboratories | Stabilized catecholamine solutions |
| JP3535537B2 (ja) * | 1993-04-15 | 2004-06-07 | 日本製薬株式会社 | 静脈注射剤 |
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| CA2424021A1 (en) | 2000-09-29 | 2002-04-04 | Board Of Trustees Operating Michigan State University | Catecholamine compositions and uses thereof |
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| US20060129122A1 (en) * | 2004-12-06 | 2006-06-15 | Wyrick Ronald E | Method and apparatus for delivering epinephrine |
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