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Chemistry

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Also known as: 92339-11-2, Visipaque, Indixanol, Iodixanolum, 2-5410-3a, Hw8w27htxx

Molecular Formula

C₃₅H₄₄I₆N₆O₁₅

Molecular Weight

1550.2 g/mol

InChI Key

NBQNWMBBSKPBAY-UHFFFAOYSA-N

FDA UNII

HW8W27HTXX

Iodixanol is a dimeric iso-osmolar, non-ionic, hydrophilic iodinated radiocontrast agent used in diagnostic imaging. Upon intravascular administration and during computed tomography (CT) imaging, iodixanol blocks x-rays and appears opaque on x-ray images. This allows body structures that absorb iodine to be visualized. The degree of opacity produced by iodixanol is directly proportional to the total amount of the iodinated contrast agent in the path of the x-rays. The visualization of body structures is dependent upon the distribution and elimination of iodixanol. Compared to other iodinated contrast agents, iodixanol appears to exhibit less nephrotoxicity.

Iodixanol is a Radiographic Contrast Agent. The mechanism of action of iodixanol is as a X-Ray Contrast Activity.

1 2D Structure

Iodixanol

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-[acetyl-[3-[N-acetyl-3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

2.1.2 InChI

InChI=1S/C35H44I6N6O15/c1-13(52)46(30-26(38)20(32(59)42-3-15(54)9-48)24(36)21(27(30)39)33(60)43-4-16(55)10-49)7-19(58)8-47(14(2)53)31-28(40)22(34(61)44-5-17(56)11-50)25(37)23(29(31)41)35(62)45-6-18(57)12-51/h15-19,48-51,54-58H,3-12H2,1-2H3,(H,42,59)(H,43,60)(H,44,61)(H,45,62)

2.1.3 InChI Key

NBQNWMBBSKPBAY-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(=O)N(CC(CN(C1=C(C(=C(C(=C1I)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O)I)C(=O)C)O)C2=C(C(=C(C(=C2I)C(=O)NCC(CO)O)I)C(=O)NCC(CO)O)I

2.2 Other Identifiers

2.2.1 UNII

HW8W27HTXX

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Contrast Media 2-5410-3

2. Iodixanol-320

3. Visipaque

4. Visipaque Unique Softpac

2.3.2 Depositor-Supplied Synonyms

1. 92339-11-2

2. Visipaque

3. Indixanol

4. Iodixanolum

5. 2-5410-3a

6. Hw8w27htxx

7. Nsc-760069

8. 5,5'-((2-hydroxytrimethylene)bis(acetylimino))bis(n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)

9. Chebi:31705

10. 5-[acetyl-[3-[n-acetyl-3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

11. 2-541o-3a

12. Dsstox_cid_25523

13. Dsstox_rid_80929

14. Dsstox_gsid_45523

15. 1,3-benzenedicarboxamide, 5,5'-((2-hydroxy-1,3-propanediyl)bis(acetylimino))bis(n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-

16. 5-[acetyl-[3-[n-acetyl-3,5-bis[[(2s)-2,3-dihydroxypropyl]carbamoyl]-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-1-n,3-n-bis[(2s)-2,3-dihydroxypropyl]-2,4,6-triiodobenzene-1,3-dicarboxamide

17. Optiprep; Visipaque; Visipaque 270;2-5410-3a

18. Visipaque 270

19. Visipaque 320

20. Iodixanolum [latin]

21. Optiprep

22. 1,3-benzenedicarboxamide, 5,5'-[(2-hydroxy-1,3-propanediyl)bis(acetylimino)]bis[n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-

23. 5,5'-((2-hydroxypropane-1,3-diyl)bis(acetylazanediyl))bis(n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)

24. Ccris 7567

25. Sr-01000872678

26. Unii-hw8w27htxx

27. Hsdb 8076

28. Iodixanol [usan:usp:inn:ban]

29. Visipaque (tn)

30. Ncgc00016958-01

31. Cas-92339-11-2

32. Visipaque;iodixanolum

33. Iodixanol [inn]

34. Iodixanol [jan]

35. Iodixanol [mi]

36. Iodixanol [usan]

37. Prestwick0_000848

38. Prestwick1_000848

39. Prestwick2_000848

40. Prestwick3_000848

41. Iodixanol [vandf]

42. Iodixanol [mart.]

43. Ec 618-837-0

44. Iodixanol [usp-rs]

45. Iodixanol [who-dd]

46. Iodixanol (jan/usp/inn)

47. Schembl21546

48. Bspbio_000835

49. Spbio_002756

50. Bpbio1_000919

51. Iodixanol [orange Book]

52. Chembl1200507

53. Dtxsid2045523

54. Iodixanol [ep Monograph]

55. Iodixanol [usp Impurity]

56. Iodixanol [usp Monograph]

57. Hms1570j17

58. Hms2097j17

59. Hms3714j17

60. Pharmakon1600-01503835

61. Bcp11111

62. Hy-b1426

63. Tox21_110711

64. Nsc760069

65. S5218

66. Akos015895607

67. Tox21_110711_1

68. Ac-7610

69. Ccg-213207

70. Db01249

71. Nsc 760069

72. Ncgc00179408-01

73. Ncgc00179408-03

74. 5-(acetyl-(3-(acetyl-(3,5-bis(2,3-dihydroxypropylcarbamoyl)-2,4,6-triiodophenyl)amino)-2- Hydroxypropyl)amino)-n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide; 5,5'-((2-hydroxytrimethylene)bis(acetylimino))bis(n,n'-bis(2,3-dihydroxypropyl)-2,4,6- Triiodoisophthalamide);

75. Ab00513936

76. Cs-0013137

77. Ft-0627254

78. Ft-0645028

79. D01474

80. Ab00513936_02

81. 339i112

82. A844203

83. Q2419291

84. Sr-01000872678-1

85. Sr-01000872678-2

86. Brd-a08660406-001-01-8

87. Optiprep(tm) Density Gradient Medium, Used For Cell And Subcellular Organelle Isolation

88. 5,5'-(2-hydroxypropane-1,3-diyl)bis(acetylazanediyl)bis(n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide)

89. 5,5'-[(2-hydroxypropane-1,3-diyl)bis(acetylimino)]bis[n,n'-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide]

90. 5,5-[(2-hydroxy-1,3-propanediyl)bis(acetylimino)]bis[n,n-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

91. 5-[[3-[[3,5-bis[2,3-bis(oxidanyl)propylcarbamoyl]-2,4,6-tris(iodanyl)phenyl]-ethanoyl-amino]-2-oxidanyl-propyl]-ethanoyl-amino]-n1,n3-bis[2,3-bis(oxidanyl)propyl]-2,4,6-tris(iodanyl)benzene-1,3-dicarboxamide

92. 5-[acetyl-[3-[n-acetyl-3,5-bis[(2,3-dihydroxypropylamino)-oxomethyl]-2,4,6-triiodoanilino]-2-hydroxypropyl]amino]-n1,n3-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

93. 5-{n-[3-(n-{3,5-bis[(2,3-dihydroxypropyl)carbamoyl]-2,4,6-triiodophenyl}acetamido)-2-hydroxypropyl]acetamido}-1-n,3-n-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₃₅H₄₄I₆N₆O₁₅
Molecular Weight	1550.2 g/mol
XLogP3	-3.4
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	22
Exact Mass	1549.7133 g/mol
Monoisotopic Mass	1549.7133 g/mol
Topological Polar Surface Area	339 Å²
Heavy Atom Count	62
Formal Charge	0
Complexity	1330
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	4
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Visipaque 270
Active Ingredient	Iodixanol
Dosage Form	Injectable
Route	Injection
Strength	55%
Market Status	Prescription
Company	Ge Healthcare

2 of 4
Drug Name	Visipaque 320
Active Ingredient	Iodixanol
Dosage Form	Injectable
Route	Injection
Strength	65.2%
Market Status	Prescription
Company	Ge Healthcare

3 of 4
Drug Name	Visipaque 270
Active Ingredient	Iodixanol
Dosage Form	Injectable
Route	Injection
Strength	55%
Market Status	Prescription
Company	Ge Healthcare

4 of 4
Drug Name	Visipaque 320
Active Ingredient	Iodixanol
Dosage Form	Injectable
Route	Injection
Strength	65.2%
Market Status	Prescription
Company	Ge Healthcare

4.2 Therapeutic Uses

Iodixanol is indicated for contrast enhanced computerized tomography imaging of the head and body, excretory urography, and peripheral venography. /Included in US product label/

US Natl Inst Health; DailyMed. Current Medication Information for VISIPAQUE (iodixanol) injection, solution (May 2009). Available from, as of July 11, 2012: https://dailymed.nlm.nih.gov/dailymed/lookup.cfm?setid=2d964c13-88ad-43be-88d4-a3a7ea4d5b5e

Iodixanol is indicated for angiocardiography (left ventriculography and selective coronary arteriography), peripheral arteriography, visceral arteriography, and cerebral arteriography. /Included in US product label/

Iodixanol is indicated for intra-arterial digital subtraction angiography. /Included in US product label/

Iodixanol is indicated for contrast enhanced computerized tomography imaging of the head and body, and excretory urography. /Included in US product label/

For more Therapeutic Uses (Complete) data for Iodixanol (6 total), please visit the HSDB record page.

4.3 Drug Warning

The following selected adverse events were reported in ?0.5% of the 1244 patients in controlled clinical trials who received iodixanol injection: General Disorders: back pain, fatigue, malaise; Cardiovascular Disorders: arrhythmias, cardiac failure, conduction abnormalities, hypotension, myocardial infarction; Nervous System: cerebral vascular disorder, convulsions, hypoesthesia, stupor, confusion; Gastrointestinal System Disorders: dyspepsia; Hypersensitivity Disorders: pharyngeal edema; Respiratory System Disorders: asthma, bronchitis, dyspnea, pulmonary edema, rhinitis; Renal System Disorders: abnormal renal function, acute renal failure, hematuria; Peripheral Vascular Disorders: flushing, peripheral ischemia; Skin and Appendage Disorders: hematoma, increased sweating; Special Senses, Other Disorders: tinnitus; Vision Disorders: abnormal vision.

Additional adverse events reported in other clinical studies and in foreign postmarketing surveillance and foreign clinical trials with the use of iodixanol injection are: anaphylactic reactions, anaphylactoid reactions, hypoglycemia, amnesia, cardiac arrest, hypertension, dyskinesia, hemorrhage not otherwise specified, polymyalgia rheumatica, pulmonary embolism, respiratory depression, and cortical blindness.

... Selected commonly reported adverse events in pediatrics include: vomiting, nausea, fever, rash, and pruritus. Less frequently reported events are apnea, disseminated intravascular coagulation, atrioventricular block and bundle branch block, arrhythmia, cardiac failure, renal failure and taste perversion.

In patients with normal blood-brain barriers and renal failure, iodinated contrast agents have been associated with blood-brain barrier disruption and accumulation of contrast in the brain.

For more Drug Warnings (Complete) data for Iodixanol (28 total), please visit the HSDB record page.

4.4 Drug Indication

Iodixanol is a contrast agent during coronary angiography.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Iodixanol is a contrast agent commonly used during coronary angiography, particularly in individuals with renal dysfunction, as it is believed to be less toxic to the kidneys than most other intravascular contrast agents. It is an imaging contrast agent with the same osmolality as blood (290mOsm/kg H20).

5.2 MeSH Pharmacological Classification

Contrast Media

Substances used to allow enhanced visualization of tissues. (See all compounds classified as Contrast Media.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

IODIXANOL

5.3.2 FDA UNII

HW8W27HTXX

5.3.3 Pharmacological Classes

X-Ray Contrast Activity [MoA]; Radiographic Contrast Agent [EPC]

5.4 ATC Code

V08AB09

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

V - Various

V08 - Contrast media

V08A - X-ray contrast media, iodinated

V08AB - Watersoluble, nephrotropic, low osmolar x-ray contrast media

V08AB09 - Iodixanol

5.5 Absorption, Distribution and Excretion

Route of Elimination

In adults, approximately 97% of the injected dose of iodixanol is excreted unchanged in urine within 24 hours, with less than 2% excreted in feces within five days post-injection.

Volume of Distribution

0.26 L/kg

Absorption and excretion of iodixanol 320 mg I/ml were investigated in rats after intragastric administration of 2.5 g I/kg b.w. Animals were observed for up to 96 hours after treatment, and blood, urine and feces taken at several time-points throughout the experiment. Concentrations of iodixanol in serum and urine were measured by means of reversed-phase high-performance liquid chromatography. Fecal concentrations of iodixanol, based on iodine measurements, were determined by X-ray fluorescence spectrometry. Serial radiographs were obtained and histopathological examination was performed on selected tissues. The results indicate that less than 1% of the intragastric dose of iodixanol is absorbed from the intestine into the blood stream. No adverse clinical signs were observed, and there were no treatment-related histomorphological findings.

PMID:8610524 Dunkel JA et al; Acta Radiol Suppl 399: 253-7 (1995)

In 40 healthy, young male volunteers receiving a single intravenous administration of iodixanol injection in doses of 0.3 to 1.2 gI/kg body weight, ... renal clearance was 110 mL/min (+/-14), equivalent to glomerular filtration (108 mL/min). These values were independent of the dose administered.

... In a study of 16 adult patients who were scheduled for renal transplant, the elimination of iodixanol 320 mgI/mL was studied. The patients' baseline mean creatinine levels were 6.3 mg/dL (+/-1.5) and mean creatinine clearances were 13.61 mL/min (+/- 4.67). ... In these patients, levels of iodixanol were detected 5 days after dosing. Contrast enhancement time in kidneys increased from 6 hours to at least 24 hours. ...

Plasma and urine levels suggest that body clearance of iodixanol is primarily due to renal clearance. In adults, approximately 97% of the injected dose of iodixanol is excreted unchanged in urine within 24 hours, with less than 2% excreted in feces within five days post-injection.

For more Absorption, Distribution and Excretion (Complete) data for Iodixanol (14 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

Excreted unchanged

Iodixanol metabolites have not been demonstrated.

5.7 Biological Half-Life

2.1 hours. In patients with significantly impaired renal function (mean creatinine clearance rate, 9.91 [± 3.58] mL per minute), the plasma half-life is increased to 23 hours.

Forty pediatric patients < or = 12 years old, with renal function that is normal for their age, received multiple intra-arterial administrations of iodixanol injection in doses of 0.32 to 3.2 gI/kg body weight. The elimination half-lives for these patients are ...: 0.185 hr -1 (newborn to 2 months old), 0.256 hr -1 (2 to <6 months old), 0.299 hr -1 (6 months to<1 year), 0.322 hr -1 (1 to<2 years), and 0.307 hr -1 (2 to < or = 12 years old). The adult mean terminal elimination rate constant is 0.336 hr-1. ...

In 40 healthy, young male volunteers receiving a single intravenous administration of iodixanol injection in doses of 0.3 to 1.2 gI/kg body weight, the elimination half-life was 2.1 hr (+/- 0.1) ...

... Iodixanol was rapidly excreted, mainly via the kidneys, with a plasma half-life in rats and monkeys of 25 and 76 mins, respectively. ...

PMID:8610532 Heglund IF et al; Acta Radiol Suppl 399: 69-82 (1995)

... In a study of 16 adult patients who were scheduled for renal transplant, the elimination of iodixanol 320 mgI/mL was studied. ... In these patients, the plasma half-life was increased to 23 hours (normal t1/2 = 2 hours). ...

5.8 Mechanism of Action

Organic iodine compounds attenuate x-rays as they pass through the body, thereby allowing the body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. After intravascular administration, iodixanol makes opaque those internal structures in its path of flow, allowing their visualization until significant hemodilution and elimination occur.

Intravascular injection of iodixanol opacifies those vessels in the path of flow of the contrast agent, permitting radiographic visualization of the internal structures until significant dilution and elimination occurs.

API SUPPLIERS

01

Sichuan Renan Pharmaceutical

China

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CPHI Middle east

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02

Jiangsu Hengrui Medicine

China

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CPHI Middle east

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03

Zhejiang Starry Pharmaceutical Co....

China

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04

IMAX DIAGNOSTIC IMAGING HOLDING LI...

Ireland

India

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09

Divis Laboratories

India

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10

BrightGene Bio-Medical Technology ...

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USDMF

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Imax Diagnostic Imaging Holding Ltd

Ireland

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02

Jiangsu Hengrui Pharmaceuticals Co L...

China

Medlab Asia & Asia Health

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03

Sichuan Renan Pharmaceutical Co Ltd

China

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04

Zhejiang Starry Pharmaceutical Co Lt...

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CEP/COS

01

GE HEALTHCARE AS Oslo NO

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02

JIANGSU YUTIAN PHARMACEUTICAL CO., ...

China

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03

ZHEJIANG STARRY PHARMACEUTICAL CO.,...

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Blue Jet Healthcare

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Biophore India Pharmaceuticals Pvt. Ltd

India

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Iodixanol

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Dosage Form : Injection

Dosage Strength : 150MG/ML

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02

Biophore India Pharmaceuticals Pvt. Ltd

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Biophore India Pharmaceuticals Pvt. Ltd

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Dosage Form : Injection

Dosage Strength : 320MG/ML

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04

Jiangsu Hengrui Medicine Co., Ltd.

China

Medlab Asia & Asia Health

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Jiangsu Hengrui Medicine Co., Ltd.

China

Medlab Asia & Asia Health

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06

Jodas Expoim Pvt. Ltd

India

Medlab Asia & Asia Health

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07

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Yangtze River Pharmaceutical Group

China

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Iodixanol (10 kg) API needed in Egypt [ENA19537]

A company that focuses on development & manufacturing of high quality injectable finished formulations is looking for suppliers of Iodixanol (10 kg) API for commercial purposes. The suppliers must support this enquiry with GMP & CoA.

20 May 2024

Iodixanol (50 kg) API needed in India [ENA18058]

A WHO-GMP accredited company that focuses on contract manufacturing services, P2P (product to procurement) manufacturing and branded ethical formulation is looking for suppliers of Iodixanol (50 kg) API for commercial purposes. The suppliers must support this enquiry with open part DMF & CoA.

18 Sep 2023

Various APIs needed in India [ENA13556]

A CDMO that specializes in manufacturing of beta lactam & non beta lactam liquid ampoules, liquid vials, dry powder, eye/ ear drops, mouth inhalation with nasal spray is looking for suppliers of Various APIs for development purpose. The required quantity is 100 g for each. The suppliers must support this enquiry with CoA. 1. Iodixanol API 2. Meglumine Diatrizoate API

07 May 2022

Various APIs needed in Vietnam [ENA13284]

A leading biopharmaceutical company that specializes in research, develop, manufacture and market a wide range of therapeutic injection products is looking for suppliers of Various APIs for commercial purpose. The suppliers must support this enquiry with GMP & CoA. 1. Injectable Grade Sodium Lactate (50 kg) API 2. Injectable Grade Succinyl Gelatin (180 kg) API 3. Injectable Grade Iobitridol (2 MT) API 4. Injectable Grade Iodixanol (2 MT) API 5. Injectable Grade Iohexol (2 MT) API

12 Apr 2022

Iodixanol API needed in Egypt [ENA12162]

A company operating in the pharmaceutical field for the development, manufacturing, marketing, distributing and exporting of a comprehensive array of branded and generic drugs is looking for suppliers of Iodixanol API for both development & commercial purpose. The suppliers must support this enquiry with GMP & CoA.

20 Dec 2021

Various APIs needed in Kazakhstan [ENA11475]

A leading pharmaceutical company that deals in the production & manufacturing of infusion and injection solutions is looking for suppliers of Various APIs for commercial purpose. The required quantity is MOQ for each. The suppliers must support this enquiry with DMF, GMP & CoA. 1. Ph.Eur. Grade Dextran 40 API 2. Ph.Eur. Grade Iodixanol API 3. Ph.Eur. Grade Iopromide API 4. Ph.Eur. Grade Mannitol API 5. Ph.Eur. Grade Metronidazole API 6. USP/ Ph.Eur. Grade Linezolid API

23 Sep 2021

Iodixanol (MOQ) API needed in Vietnam [ENA06813]

A manufacturing company that deals in over 300 products including probiotic suspension, solution for nebuliser, ophthalmic, injection, oral solution, aerosol and dual-chamber is looking for suppliers of Iodixanol (MOQ) API. The suppliers must support this enquiry with CoA & GMP.

11 Mar 2020

IP/BP/USP Grade Iodixanol (200 kg, 400 kg) API needed in India [ENA06355]

A pharmaceutical manufacturing company is looking for suppliers of IP/BP/USP Grade Iodixanol (200 kg, 400 kg) API. The supplier must support this enquiry with CoA.

22 Jan 2020

Iodixanol (1 MT) API needed in China [ENA05040]

A pharmaceutical company mainly engaged in integrating scientific research and development and production of biomedical raw materials and intermediates is looking for suppliers of Iodixanol (1 MT) API.

30 Aug 2019

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R0-CEP 2020-410 - Rev 00

Valid

Chemical

2022-06-22

2215

01

R0-CEP 2021-497 - Rev 00