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Details

Stereochemistry ACHIRAL
Molecular Formula C11H11IN2O
Molecular Weight 314.1223
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IODOANTIPYRINE

SMILES

CN1N(C(=O)C(I)=C1C)C2=CC=CC=C2

InChI

InChIKey=ZZOBLCHCPLOXCE-UHFFFAOYSA-N
InChI=1S/C11H11IN2O/c1-8-10(12)11(15)14(13(8)2)9-6-4-3-5-7-9/h3-7H,1-2H3

HIDE SMILES / InChI

Molecular Formula C11H11IN2O
Molecular Weight 314.1223
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/8091756

Iodoantipyrine belongs to the group of nonsteroid anti-inflammatory compounds. It has being shown to treat and prevent tick-borne encephalitis in mice. Iodoantipyrine has also be shown to be useful as a cerebral blood flow marker. ¹²³I-4-Iodoantipyrine (4-IAP) has been suggested as a radiopharmaceutical for direct imaging of regional cerebral perfusion.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
27 h
18 MBq single, intravenous
dose: 18 MBq
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IODOANTIPYRINE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
9 h
18 MBq single, intravenous
dose: 18 MBq
route of administration: Intravenous
experiment type: SINGLE
co-administered:
IODOANTIPYRINE plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
0.03 g 3 times / day multiple, oral
Studied dose
Dose: 0.03 g, 3 times / day
Route: oral
Route: multiple
Dose: 0.03 g, 3 times / day
Sources:
unhealthy, 33 years
Health Status: unhealthy
Age Group: 33 years
Sex: F
Sources:
Other AEs: Goitre...
0.03 g 6 times / day multiple, oral
Studied dose
Dose: 0.03 g, 6 times / day
Route: oral
Route: multiple
Dose: 0.03 g, 6 times / day
Sources:
unhealthy, 48 years
Health Status: unhealthy
Age Group: 48 years
Sex: F
Sources:
Other AEs: Goitre...
AEs

AEs

AESignificanceDosePopulation
Goitre
0.03 g 3 times / day multiple, oral
Studied dose
Dose: 0.03 g, 3 times / day
Route: oral
Route: multiple
Dose: 0.03 g, 3 times / day
Sources:
unhealthy, 33 years
Health Status: unhealthy
Age Group: 33 years
Sex: F
Sources:
Goitre
0.03 g 6 times / day multiple, oral
Studied dose
Dose: 0.03 g, 6 times / day
Route: oral
Route: multiple
Dose: 0.03 g, 6 times / day
Sources:
unhealthy, 48 years
Health Status: unhealthy
Age Group: 48 years
Sex: F
Sources:
PubMed

PubMed

TitleDatePubMed
[Use of interferon inducers for pharmacological correction of cytokine disturbances in patients with recurrent genital herpes].
2010-08
[Use of the interferon inductor iodantipirine in the prevention and treatment of some viral infections].
2010-07-09
Animal models and biomarkers of neuropathy in diabetic rodents.
2010-06
The effects of isoflurane pretreatment on cerebral blood flow, capillary permeability, and oxygen consumption in focal cerebral ischemia in rats.
2010-05-01
Mapping selective neuronal loss and microglial activation in the salvaged neocortical penumbra in the rat.
2010-01-01
Fenofibrate improves cerebral blood flow after middle cerebral artery occlusion in mice.
2010-01
Quantitative imaging of coronary blood flow.
2010
Effects of fentanyl pretreatment on regional cerebral blood flow in focal cerebral ischemia in rats.
2010
Increase in tumour permeability following TGF-beta type I receptor-inhibitor treatment observed by dynamic contrast-enhanced MRI.
2009-12-01
Why amphibians are more sensitive than mammals to xenobiotics.
2009-11-04
Sex differences in functional brain activation during noxious visceral stimulation in rats.
2009-09
Quantitative estimation of tissue blood flow rate.
2009
Changes in regional brain perfusion during functional brain activation: comparison of [(64)Cu]-PTSM with [(14)C]-Iodoantipyrine.
2008-10-09
Changes of cerebral blood flow during the secondary expansion of a cortical contusion assessed by 14C-iodoantipyrine autoradiography in mice using a non-invasive protocol.
2008-07
Soluble epoxide hydrolase gene deletion is protective against experimental cerebral ischemia.
2008-07
The effect of isovolemic hemodilution with oxycyte, a perfluorocarbon emulsion, on cerebral blood flow in rats.
2008-04-23
Flattened cortical maps of cerebral function in the rat: a region-of-interest approach to data sampling, analysis and display.
2008-03-28
A flow sensitive alternating inversion recovery (FAIR)-MRI protocol to measure hemispheric cerebral blood flow in a mouse stroke model.
2008-03
Wide therapeutic time window for Rho-kinase inhibition therapy in ischemic brain damage in a rat cerebral thrombosis model.
2008-02-08
Reorganization of functional brain maps after exercise training: Importance of cerebellar-thalamic-cortical pathway.
2007-12-12
[Epileptogenic and non-epileptogenic zones: blood flow studies of temporo-limbic seizures].
2007-12
Soluble epoxide hydrolase: a novel therapeutic target in stroke.
2007-12
Direct comparison study between FDG-PET and IMP-SPECT for diagnosing Alzheimer's disease using 3D-SSP analysis in the same patients.
2007-07
Cortical contusion induces trans-hemispheric reorganization of blood flow maps.
2007-04-13
Persistent cerebrovascular effects of MDMA and acute responses to the drug.
2006-07
Multiple retinal hemorrhage following anterior chamber paracentesis in uveitic glaucoma.
2006-06
Optimal window for ictal blood flow mapping. Insight from the study of discrete temporo-limbic seizures in rats.
2006-05
Effects of estrogen on platelet reactivity after transient forebrain ischemia in rats.
2005-10
Time course and mapping of cerebral perfusion during amygdala secondarily generalized seizures.
2005-08
The endothelin B (ETB) receptor agonist IRL 1620 is highly vasoconstrictive in two syngeneic rat tumour lines: potential for selective tumour blood flow modification.
2005-07-11
Restoration of cerebral vasoreactivity by an L-type calcium channel blocker following fluid percussion brain injury.
2005-07
Role of nitric oxide in cerebral blood flow changes during kainate seizures in mice: genetic and pharmacological approaches.
2005-03
Relationship between flow-metabolism uncoupling and evolving axonal injury after experimental traumatic brain injury.
2004-09
Regional heterogeneity of cerebral blood flow response to graded pressure-controlled hemorrhage.
2004-03
Evolution of diaschisis in a focal stroke model.
2004-03
Extension of cerebral hypoperfusion and ischaemic pathology beyond MCA territory after intraluminal filament occlusion in C57Bl/6J mice.
2004-01-30
Activation of cerebral cortex during acoustic challenge or acute foot-shock in freely moving, nontethered rats.
2004-01-02
Effects of chronic isovolaemic haemodilution on regional cerebral blood flow in conscious rats.
2004-01
Inhibition of [18F]FP-TZTP binding by loading doses of muscarinic agonists P-TZTP or FP-TZTP in vivo is not due to agonist-induced reduction in cerebral blood flow.
2003-11
Functional brain mapping in freely moving rats during treadmill walking.
2003-08
Effects of tin-protoporphyrin IX on blood flow in a rat tumor model.
2003-05
Direct comparison of local cerebral blood flow rates measured by MRI arterial spin-tagging and quantitative autoradiography in a rat model of experimental cerebral ischemia.
2003-02
Cerebral hypoperfusion and delayed hippocampal response after induction of adult kaolin hydrocephalus.
2003-01
Cortical spreading depression causes a long-lasting decrease in cerebral blood flow and induces tolerance to permanent focal ischemia in rat brain.
2003-01
Progesterone administration during reperfusion, but not preischemia alone, reduces injury in ovariectomized rats.
2002-10
Dynamic variations of local cerebral blood flow in maximal electroshock seizures in the rat.
2002-10
Early effects of acid-base management during hypothermia on cerebral infarct volume, edema, and cerebral blood flow in acute focal cerebral ischemia in rats.
2002-10
The vascular response of tumor and normal tissues in the rat to the vascular targeting agent, combretastatin A-4-phosphate, at clinically relevant doses.
2002-10
Effect of mild hypothermia on energy state recovery following transient forebrain ischemia in the gerbil.
2002-07
Neuroprotection and P450 2C11 upregulation after experimental transient ischemic attack.
2002-06
Patents

Sample Use Guides

In Vivo Use Guide
Mice - for treating and preventing experimental tick-borne encephalitis - orally in a dose of 50 mg/kg
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:30:38 GMT 2025
Edited
by admin
on Mon Mar 31 18:30:38 GMT 2025
Record UNII
V30V6H1QX4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IODOANTIPYRINE
Common Name English
IODOPHENAZONE
WHO-DD  
Preferred Name English
ANTIPYRINE IODIDE
Common Name English
IODOPYRINE
Common Name English
ANTIPYRINE, 4-IODO-
Common Name English
3H-PYRAZOL-3-ONE, 1,2-DIHYDRO-4-IODO-1,5-DIMETHYL-2-PHENYL-
Systematic Name English
4-IODOANTIPYRINE
Common Name English
Iodophenazone [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
Code System Code Type Description
SMS_ID
100000077380
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
CAS
129-81-7
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
MESH
C008135
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
EVMPD
SUB14251MIG
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID7046047
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
FDA UNII
V30V6H1QX4
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
NCI_THESAURUS
C77360
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
PUBCHEM
8522
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
204-966-6
Created by admin on Mon Mar 31 18:30:38 GMT 2025 , Edited by admin on Mon Mar 31 18:30:38 GMT 2025
PRIMARY