AU2003295442B2 - Contrast media formulations having improved biological tolerance - Google Patents
Contrast media formulations having improved biological tolerance Download PDFInfo
- Publication number
- AU2003295442B2 AU2003295442B2 AU2003295442A AU2003295442A AU2003295442B2 AU 2003295442 B2 AU2003295442 B2 AU 2003295442B2 AU 2003295442 A AU2003295442 A AU 2003295442A AU 2003295442 A AU2003295442 A AU 2003295442A AU 2003295442 B2 AU2003295442 B2 AU 2003295442B2
- Authority
- AU
- Australia
- Prior art keywords
- formulation
- tris
- iosimenol
- citric acid
- rcm
- 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.)
- Ceased
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 41
- 238000009472 formulation Methods 0.000 title claims abstract description 38
- 239000002872 contrast media Substances 0.000 title claims abstract description 10
- 229940039231 contrast media Drugs 0.000 title abstract description 7
- 150000001412 amines Chemical class 0.000 claims abstract description 28
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 69
- 239000007983 Tris buffer Substances 0.000 claims description 64
- DLPPIGPJCKKVBA-UHFFFAOYSA-N Iosimenol Chemical compound OCC(O)CNC(=O)C1=C(I)C(C(=O)N)=C(I)C(N(CC(O)CO)C(=O)CC(=O)N(CC(O)CO)C=2C(=C(C(=O)NCC(O)CO)C(I)=C(C(N)=O)C=2I)I)=C1I DLPPIGPJCKKVBA-UHFFFAOYSA-N 0.000 claims description 35
- 229950004246 iosimenol Drugs 0.000 claims description 34
- 239000000872 buffer Substances 0.000 claims description 30
- 239000000243 solution Substances 0.000 claims description 16
- 150000001735 carboxylic acids Chemical class 0.000 claims description 11
- 239000003189 dimeric nonionic contrast media Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 229960004359 iodixanol Drugs 0.000 claims description 5
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 claims description 5
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 4
- XUHXFSYUBXNTHU-UHFFFAOYSA-N Iotrolan Chemical compound IC=1C(C(=O)NC(CO)C(O)CO)=C(I)C(C(=O)NC(CO)C(O)CO)=C(I)C=1N(C)C(=O)CC(=O)N(C)C1=C(I)C(C(=O)NC(CO)C(O)CO)=C(I)C(C(=O)NC(CO)C(O)CO)=C1I XUHXFSYUBXNTHU-UHFFFAOYSA-N 0.000 claims description 3
- 239000002738 chelating agent Substances 0.000 claims description 3
- 229960003182 iotrolan Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001954 sterilising effect Effects 0.000 claims description 3
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical group CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 2
- 239000003690 nonionic contrast media Substances 0.000 claims 2
- UHFJDMPHJXNQEI-UHFFFAOYSA-N 1-hydroxy-1$l^{3},2-iodoxane Chemical compound OI1CCCCO1 UHFJDMPHJXNQEI-UHFFFAOYSA-N 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 17
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 12
- 230000009885 systemic effect Effects 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- -1 citric acid Chemical class 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 150000003858 primary carboxamides Chemical class 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000007979 citrate buffer Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000002059 diagnostic imaging Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229960002603 iopromide Drugs 0.000 description 2
- DGAIEPBNLOQYER-UHFFFAOYSA-N iopromide Chemical compound COCC(=O)NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I DGAIEPBNLOQYER-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 210000004789 organ system Anatomy 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000002798 spectrophotometry method Methods 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 101000807541 Homo sapiens Ubiquitin carboxyl-terminal hydrolase 24 Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- 102100037176 Ubiquitin carboxyl-terminal hydrolase 24 Human genes 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001687 destabilization Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229940029407 ioxaglate Drugs 0.000 description 1
- TYYBFXNZMFNZJT-UHFFFAOYSA-N ioxaglic acid Chemical compound CNC(=O)C1=C(I)C(N(C)C(C)=O)=C(I)C(C(=O)NCC(=O)NC=2C(=C(C(=O)NCCO)C(I)=C(C(O)=O)C=2I)I)=C1I TYYBFXNZMFNZJT-UHFFFAOYSA-N 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicinal Preparation (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43287902P | 2002-12-12 | 2002-12-12 | |
| US60/432,879 | 2002-12-12 | ||
| US10/701,586 US7250153B2 (en) | 2002-12-12 | 2003-11-05 | Contrast media formulations having improved biological tolerance |
| US10/701,586 | 2003-11-05 | ||
| PCT/US2003/035762 WO2004054637A2 (en) | 2002-12-12 | 2003-11-07 | Contrast media formulations having improved biological tolerance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2003295442A1 AU2003295442A1 (en) | 2004-07-09 |
| AU2003295442B2 true AU2003295442B2 (en) | 2008-11-06 |
Family
ID=34107426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2003295442A Ceased AU2003295442B2 (en) | 2002-12-12 | 2003-11-07 | Contrast media formulations having improved biological tolerance |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7250153B2 (enExample) |
| EP (1) | EP1575621B1 (enExample) |
| JP (1) | JP2006509841A (enExample) |
| KR (1) | KR101067159B1 (enExample) |
| CN (1) | CN1738651A (enExample) |
| AT (1) | ATE447416T1 (enExample) |
| AU (1) | AU2003295442B2 (enExample) |
| CA (1) | CA2509035C (enExample) |
| CY (1) | CY1110105T1 (enExample) |
| DE (1) | DE60329939D1 (enExample) |
| DK (1) | DK1575621T3 (enExample) |
| ES (1) | ES2333863T3 (enExample) |
| IL (1) | IL169119A (enExample) |
| NO (1) | NO332350B1 (enExample) |
| NZ (1) | NZ541139A (enExample) |
| PT (1) | PT1575621E (enExample) |
| SI (1) | SI1575621T1 (enExample) |
| WO (1) | WO2004054637A2 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070015517A (ko) * | 2004-03-11 | 2007-02-05 | 말린크로트, 인코포레이티드 | 요오드화된 단량체 및 이량체의 혼합물을 포함하는 ｘ-선조영제 제형 |
| FR2899581B1 (fr) * | 2006-04-07 | 2008-06-27 | Guerbet Sa | Procede d'atomisation du ioxilan |
| WO2009091758A1 (en) | 2008-01-14 | 2009-07-23 | Mallinckrodt Inc. | Process for the preparation of iosimenol |
| RU2012138280A (ru) * | 2010-03-23 | 2014-04-27 | ДжиИ Хелткер АС | Получение стабилизированной диагностической композиции для рентгеновского исследования |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4396597A (en) * | 1978-07-04 | 1983-08-02 | Nyegaard & Co. A/S | Process for the preparation of a sterile injectable physiologically acceptable solution of an X-ray contrast agent and solutions of the X-ray contrast agent and a buffer |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5698739A (en) * | 1989-07-05 | 1997-12-16 | Schering Aktiengesellschaft | Carboxamide non-ionic contrast media |
| KR19990022943A (ko) * | 1995-06-16 | 1999-03-25 | 밀로스 소박 | 비이온성 조영제로서의 포르밀 유도체 |
| DE19648650C2 (de) | 1996-01-29 | 1998-07-02 | Schering Ag | Puffersysteme und deren Verwendung zur Stabilisierung pharmazeutischer Zubereitung |
-
2003
- 2003-11-05 US US10/701,586 patent/US7250153B2/en not_active Expired - Lifetime
- 2003-11-07 EP EP03786628A patent/EP1575621B1/en not_active Expired - Lifetime
- 2003-11-07 WO PCT/US2003/035762 patent/WO2004054637A2/en not_active Ceased
- 2003-11-07 DE DE60329939T patent/DE60329939D1/de not_active Expired - Lifetime
- 2003-11-07 NZ NZ541139A patent/NZ541139A/en not_active IP Right Cessation
- 2003-11-07 SI SI200331689T patent/SI1575621T1/sl unknown
- 2003-11-07 KR KR1020057010571A patent/KR101067159B1/ko not_active Expired - Fee Related
- 2003-11-07 AU AU2003295442A patent/AU2003295442B2/en not_active Ceased
- 2003-11-07 CA CA2509035A patent/CA2509035C/en not_active Expired - Lifetime
- 2003-11-07 ES ES03786628T patent/ES2333863T3/es not_active Expired - Lifetime
- 2003-11-07 CN CNA2003801090166A patent/CN1738651A/zh active Pending
- 2003-11-07 PT PT03786628T patent/PT1575621E/pt unknown
- 2003-11-07 AT AT03786628T patent/ATE447416T1/de active
- 2003-11-07 DK DK03786628T patent/DK1575621T3/da active
- 2003-11-07 JP JP2005508300A patent/JP2006509841A/ja not_active Abandoned
-
2005
- 2005-06-09 IL IL169119A patent/IL169119A/en active IP Right Grant
- 2005-07-08 NO NO20053343A patent/NO332350B1/no not_active IP Right Cessation
-
2010
- 2010-02-01 CY CY20101100092T patent/CY1110105T1/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4396597A (en) * | 1978-07-04 | 1983-08-02 | Nyegaard & Co. A/S | Process for the preparation of a sterile injectable physiologically acceptable solution of an X-ray contrast agent and solutions of the X-ray contrast agent and a buffer |
Also Published As
| Publication number | Publication date |
|---|---|
| SI1575621T1 (sl) | 2010-01-29 |
| CY1110105T1 (el) | 2015-01-14 |
| US20050025711A1 (en) | 2005-02-03 |
| NO20053343D0 (no) | 2005-07-08 |
| AU2003295442A1 (en) | 2004-07-09 |
| NO20053343L (no) | 2005-09-08 |
| WO2004054637A3 (en) | 2004-09-16 |
| CA2509035C (en) | 2011-07-19 |
| WO2004054637A2 (en) | 2004-07-01 |
| US7250153B2 (en) | 2007-07-31 |
| IL169119A0 (en) | 2007-07-04 |
| PT1575621E (pt) | 2009-11-13 |
| CN1738651A (zh) | 2006-02-22 |
| CA2509035A1 (en) | 2004-07-01 |
| EP1575621B1 (en) | 2009-11-04 |
| EP1575621A4 (en) | 2008-11-26 |
| KR20050088312A (ko) | 2005-09-05 |
| ATE447416T1 (de) | 2009-11-15 |
| DE60329939D1 (de) | 2009-12-17 |
| KR101067159B1 (ko) | 2011-09-22 |
| ES2333863T3 (es) | 2010-03-02 |
| NO332350B1 (no) | 2012-09-03 |
| EP1575621A2 (en) | 2005-09-21 |
| JP2006509841A (ja) | 2006-03-23 |
| DK1575621T3 (da) | 2009-12-14 |
| IL169119A (en) | 2010-06-16 |
| NZ541139A (en) | 2008-07-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0675738B1 (en) | Aqueous injectable formulations useful for radio-diagnosis comprising iodinated aromatic compounds used as x-ray contrast media | |
| HU227951B1 (en) | Oil in water emulsions containing propofol and disodium edetate | |
| CN107810000B (zh) | 来氟米林的可注射药物组合物 | |
| TWI277414B (en) | Esmolol formulation | |
| EP1725268B1 (en) | X-ray contrast formulation comprising a mixture of iodinated monomer and dimer | |
| AU2003295442B2 (en) | Contrast media formulations having improved biological tolerance | |
| CN112823787B (zh) | 一种含有美洛昔康的注射液及其制备方法 | |
| AU675553B2 (en) | Intramuscular and subcutaneous injection solution for anianimals | |
| EP1792894B1 (en) | Contrast agents | |
| HU220867B1 (en) | Pharmaceutical compositions as a solution, containing bis-triazole derivatives and process for producing them | |
| KR100362080B1 (ko) | 고리 올리고당과 그들의 유도체를 이용한 조영제의 새로운포접 착체 | |
| US7662859B2 (en) | Contrast agents | |
| GB2465663A (en) | X-ray contrast agent compositions comprising an iodinated X-ray contrast agent and ethylenediamine-N,N-disuccinic acid | |
| WO2024151603A1 (en) | Hydromorphone formulations for multi-dose products | |
| KR20150014526A (ko) | 고농도의 조영제를 포함하여 높은 조영 증강 효과를 나타내는 조영제 조성물 | |
| HK1100816A (en) | Glycyrrhizin-containing suppository compositions for rectal infusion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK5 | Application lapsed section 142(2)(e) - patent request and compl. specification not accepted | ||
| NA | Applications received for extensions of time, section 223 |
Free format text: AN APPLICATION TO EXTEND THE TIME FROM 14 APR 2008 TO 14 NOV 2008 IN WHICH TO GAIN ACCEPTANCE HAS BEEN FILED . |
|
| NB | Applications allowed - extensions of time section 223(2) |
Free format text: THE TIME IN WHICH TO GAIN ACCEPTANCE HAS BEEN EXTENDED TO 14 NOV 2008. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |