IODIPAMIDE

First approved in 1954

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H14I6N2O6
Molecular Weight	1139.7618
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)C1=C(I)C=C(I)C(NC(=O)CCCCC(=O)NC2=C(I)C=C(I)C(C(O)=O)=C2I)=C1I

InChI

InChIKey=FFINMCNLQNTKLU-UHFFFAOYSA-N

InChI=1S/C20H14I6N2O6/c21-7-5-9(23)17(15(25)13(7)19(31)32)27-11(29)3-1-2-4-12(30)28-18-10(24)6-8(22)14(16(18)26)20(33)34/h5-6H,1-4H2,(H,27,29)(H,28,30)(H,31,32)(H,33,34)

HIDE SMILES / InChI

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/009321s028lbl.pdf
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB04711

Iodipamide is used as a contrast agent for cholecystography and intravenous cholangiography. Following intravenous administration of Cholografin Meglumine, iodipamide is carried to the liver where it is rapidly secreted. The contrast medium appears in the bile within 10 to 15 minutes after injection, thus permitting visualization of the hepatic and common bile ducts, even in cholecystectomized patients. Iodipamide (Cholografin Meglumine) is indicated for intravenous cholangiography and cholecystography as follows: (a) visualization of the gallbladder and biliary ducts in the differential diagnosis of acute abdominal conditions, (b) visualization of the biliary ducts, especially in patients with symptoms after cholecystectomy, and (c) visualization of the gallbladder in patients unable to take oral contrast media or to absorb contrast media from the gastrointestinal tract. The biliary ducts are readily visualized within about 25 minutes after administration, except in patients with impaired liver function. The gallbladder begins to fill within an hour after injection; maximum filling is reached after two to two and one-half hours. Organic iodine compounds block x-rays as they pass through the body, thereby allowing body structures containing iodine to be delineated in contrast to those structures that do not contain iodine. The degree of opacity produced by these iodinated organic compounds is directly proportional to the total amount (concentration and volume) of the iodinated contrast agent in the path of the x-rays. Iodipamide's primary excretion through the hepato-biliary system and concentration in bile allows visualization of the gallbladder and biliary ducts.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cholesteryl ester transfer protein 15 Target ID: CHEMBL1163116 Sources: http://www.ncbi.nlm.nih.gov/pubmed/?term=20116902	Inhibitor 8297
Complement factor B 3 Target ID: CHEMBL5731 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6922882	Inhibitor 8297
Complement C3 3 Target ID: CHEMBL4917 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6922882	Inhibitor 8297
Complement factor B 3 Target ID: CHEMBL5731 Sources: http://www.ncbi.nlm.nih.gov/pubmed/6922882	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hepatobiliary disease 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/009321s028lbl.pdf	Diagnostic		Approved 8429	CHOLOGRAFIN MEGLUMINE Approved Use intravenous cholangiography and cholecystography Launch Date -4.948992E11

Doses

Dose	Population	Adverse events
20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003	Other AEs: Hypotension, Nausea... Other AEs: Hypotension (severe, 1 patient) Nausea (3 patients) Urticaria (2 patients) Wheezing (1 patient) Pruritus (1 patient) Tingling (1 patient) Nasal congestion (1 patient) Coughing (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/182003
60 mL single, intravenous Dose: 60 mL Route: intravenous Route: single Dose: 60 mL Sources: https://pubmed.ncbi.nlm.nih.gov/4406624 https://pubmed.ncbi.nlm.nih.gov/463851	healthy, 66 years n = 1 Health Status: healthy Age Group: 66 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4406624 https://pubmed.ncbi.nlm.nih.gov/463851	Other AEs: Hepatotoxicity... Other AEs: Hepatotoxicity Sources: https://pubmed.ncbi.nlm.nih.gov/4406624 https://pubmed.ncbi.nlm.nih.gov/463851

AEs

AE	Significance	Dose	Population
Coughing	1 patient	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Nasal congestion	1 patient	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Pruritus	1 patient	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Tingling	1 patient	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Wheezing	1 patient	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Urticaria	2 patients	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Nausea	3 patients	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Hypotension	severe, 1 patient	20 mL single, intravenous Dose: 20 mL Route: intravenous Route: single Dose: 20 mL Sources: https://pubmed.ncbi.nlm.nih.gov/182003	unhealthy, 19 - 83 years n = 45 Health Status: unhealthy Age Group: 19 - 83 years Sex: M+F Population Size: 45 Sources: https://pubmed.ncbi.nlm.nih.gov/182003
Hepatotoxicity		60 mL single, intravenous Dose: 60 mL Route: intravenous Route: single Dose: 60 mL Sources: https://pubmed.ncbi.nlm.nih.gov/4406624 https://pubmed.ncbi.nlm.nih.gov/463851	healthy, 66 years n = 1 Health Status: healthy Age Group: 66 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4406624 https://pubmed.ncbi.nlm.nih.gov/463851

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT1 599 OAT3 642 BSEP 402 CYP1A2 1524 CYP2C19 1478 OATP1B1 788 OATP1B3 706

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNjUyNjgifX0%3D	no [Activation >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNjUyNjgifX0%3D	no [Activation >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNjUyNjgifX0%3D	no [Activation >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE2NTI2OCJ9fQ%3D%3D	no [Activation >10 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTE2NTI2OCJ9fQ%3D%3D	no [Activation >10 uM]
BSEP 403	inhibitor 3277 Sources: http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=50238666, https://pubmed.ncbi.nlm.nih.gov/22961681/	unlikely [IC50 >969.9 uM]
OAT3 644	inhibitor 3277 Sources: http://www.asas.or.jp/jsaae_old/zasshi/WC6_PC/paper447.pdf	yes [IC50 111 uM]
OAT1 603	inhibitor 3277 Sources: http://www.asas.or.jp/jsaae_old/zasshi/WC6_PC/paper447.pdf	yes [IC50 5.7 uM]
OATP1B1 803	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNjUyNjgifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 715	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNjUyNjgifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0738	http://www.3bsc.com/index/pro_info.php?id=20094
AA Blocks	AA003QXS	https://www.aablocks.com/goods/Goods/detail?id=AA003QXS
AHH Chemical co.,ltd	API-1710	http://www.ahhchemical.com/product/API-1710.html
AK Scientific, Inc. (AKSCI)	X6858	http://www.aksci.com/item_detail.php?cat=X6858
Alfa Chemistry	AP606177-A	https://reagents.alfa-chemistry.com/product/iodipamide-cas-606-17-7-13940.html
Alfa Chemistry	AP606177-B	https://reagents.alfa-chemistry.com/product/iodipamide-cas-606-17-7-13941.html
Angel Pharmatech	AG-20568	http://www.angelpharmatech.com/606-17-7.html
BOC Sciences	606-17-7	https://www.bocsci.com/iodipamide-cas-606-17-7-item-72876.html
Chem Scene	CS-0013062	http://www.chemscene.com/606-17-7.html
Chemspace	CSSB00000054167	https://chem-space.com/CSSB00000054167
Clearsynth	CS-T-56713	https://www.clearsynth.com/en/CST56713.html
DC Chemicals	DC12160	http://www.dcchemicals.com/product_show-606-17-7.html
Debye Scientific	DB-053672	http://www.debyesci.com/cas_606-17-7.html
Finetech	FT-0627253	http://www.finetechnology-ind.com/prod/detail/pub/606-17-7.html
Hairui	HR122591	http://www.hairuichem.com/en/product/606-17-7.html
LGC Standards	DRE-C14329000	https://www.lgcstandards.com/US/en/p/DRE-C14329000
Lab Network	LN01298648	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01298648
MedChem Express	HY-B1292	https://www.medchemexpress.com/Iodipamide.html
MolPort	MolPort-001-783-518	https://www.molport.com/shop/molecule-link/MolPort-001-783-518
Molcore	MC562909	https://www.molcore.com/product/606-17-7
MuseChem	R009675	https://www.musechem.com/product/R009675.html
Oakwood	245748	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=167598&ExtHyperLink=1
Sigma-Aldrich	I0639_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/i0639?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1343007_USP	https://www.sigmaaldrich.com/catalog/product/usp/1343007?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S530723	http://www.smolecule.com/products/s530723
THE BioTek	bt-271527	https://www.thebiotek.com/product/inhibitors/bt-271527
Vesino Industrial Co Ltd	VA10176	http://www.vsnchem.com/goto/product/23677/
Yuhao Chemical	JZ3909	http://www.chemyuhao.com/606-17-7.html
abcr GmbH	AB137192	http://www.abcr.de/shop/en/AB137192
eNovation Chemicals	D674395	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674395
mcule	MCULE-6605409948	https://mcule.com/MCULE-6605409948/

PubMed

Title	Date	PubMed
Iodipamide kinetics: capacity-limited biliary excretion with simultaneous pseudo-first-order renal excretion.	1977 Dec	925927
Thallium-201 accumulation in a patient with brain abscess.	2002 Jul	12230095
[The effect of diagnostic contrast media on the activity of lactate dehydrogenase in rat blood].	2002 Jul-Aug	12449078
Multi-slice three-dimensional spiral CT cholangiography: a new technique for diagnosis of biliary diseases.	2002 Nov	14607694
Virtual CT cholangiography in patients with choledocholithiasis.	2003 Jul-Aug	14580098
[Impact of spiral CT cholangiography on suspected obstructive jaundice].	2003 May	12839692
Distributing pattern of the bile duct of the caudate lobe on computed tomography with drip infusion cholangiography and its surgical significance.	2004 Jan-Feb	15011825
Accuracy of computed tomographic intravenous cholangiography (CT-IVC) with iotroxate in the detection of choledocholithiasis.	2005 Aug	15627178
Volume rendering of three-dimensional drip infusion CT cholangiography in patients with suspected obstructive biliary disease: a retrospective study.	2005 Dec	16352582
Concordance of second-order portal venous and biliary tract anatomies on MDCT angiography and MDCT cholangiography.	2005 Jan	15615953
Stability of doxorubicin combined with Radioselectan, a contrast agent, for chemoembolization.	2005 Jun	15896243
The value of drip infusion cholangiography using multidetector-row helical CT in patients with choledocholithiasis.	2005 Oct	15968515
Spiral computed tomography-intravenous cholangiography with three-dimensional reconstructions for imaging the biliary tree.	2006 Apr	16635032
Cholecystocolonic fistula diagnosed with CT-intravenous cholangiography.	2006 Oct	16981948
Crystallographic analysis of human serum albumin complexed with 4Z,15E-bilirubin-IXalpha.	2008 Aug 29	18602119
Rapid analysis of iodinated X-ray contrast media in secondary and tertiary treated wastewater by direct injection liquid chromatography-tandem mass spectrometry.	2008 Dec 12	18980771
CT cholangiography in potential liver donors: effect of premedication with intravenous morphine on biliary caliber and visualization.	2008 Jun	18424689
Determining binding sites of drugs on human serum albumin using FIA-QCM.	2008 Sep 15	18436441
[Hyponatremia induced by iodipamide: three cases report].	2009 Jul	19961734
Cystic artery bleeding due to blunt gallbladder injury: computed tomography findings and treatment with transcatheter arterial embolization.	2010 Feb	20182852
Fate of nine recycled water trace organic contaminants and metal(loid)s during managed aquifer recharge into a anaerobic aquifer: Column studies.	2010 Mar	19939429
Intravenous 64-multi-detector row CT-cholangiography of porcine livers: a feasibility study with definition of the temporal window for optimal bile duct delineation.	2010 Sep	20703845

Patents

Sample Use Guides

In Vivo Use Guide

The usual adult dose is 20 mL. For infants and children, the suggested dose is 0.3 to 0.6 mL/kg of body weight; the dosage for infants and children should not exceed 20 mL.

Route of Administration: Intravenous

In Vitro Use Guide

Hepatocytes (2x10^6 per ml) were incubated at 37C, pH 7.4 under O2/CO2 atmosphere (95%/5%) with 4.3 uM, 8.6 uM and 12.9 uM iodipamide to attain approximately 1, 2, and 3 nmol/mg cell protein concentration, respectively, in ~20 min.

Name

Type

Language

IODIPAMIDE

Common Name

English

ADIPIODONE

Official Name

English

IODIPAMIDE [USP-RS]

Common Name

English

IODIPAMIDE [USP MONOGRAPH]

Common Name

English

BENZOIC ACID, 3,3'-((1,6-DIOXO-1,6-HEXANEDIYL)DIIMINO)BIS(2,4,6-TRIIODO-

Common Name

English

adipiodone [INN]

Common Name

English

Adipiodone [WHO-DD]

Common Name

English

ADIPIODONE [JAN]

Common Name

English

3,3'-(ADIPOYLDIIMINO)BIS(2,4,6-TRIIODOBENZOIC ACID)

Systematic Name

English

ADIPIODONE [MART.]

Common Name

English

IODIPAMIDE [MI]

Common Name

English

CHOLOGRAFIN

Brand Name

English

NSC-757423

Code

English

Classification Tree Code System Code

NDF-RT

N0000180185