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Details

Stereochemistry RACEMIC
Molecular Formula C12H18IN
Molecular Weight 299.1836
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IOFETAMINE I-123

SMILES

CC(C)NC(C)CC1=CC=C([123I])C=C1

InChI

InChIKey=ISEHJSHTIVKELA-DCWJVSPSSA-N
InChI=1S/C12H18IN/c1-9(2)14-10(3)8-11-4-6-12(13)7-5-11/h4-7,9-10,14H,8H2,1-3H3/i13-4

HIDE SMILES / InChI
Iofetamine hydrochloride I-123 is a radiopharmaceutical for cerebral perfusion imaging. lofetamine is the N-isopropyl derivative of amphetamine with iodine 123(1123) at the para position to serve as the tracer. This configuration was systematically derived by Winchell et al. to provide sufficient brain uptake and retention for brain imaging, which typically requires an acquisition time of 25-40 minutes. After experimental intraarterial injection the drug has a high extraction ratio (> 90 percent) in the brain. Iofetamine hydrochloride I-123 permits cerebral blood perfusion imaging with single photon emission computed tomography (SPECT). Iofetamine is an amphetamine analog that is rapidly taken up by the lungs, then redistributed principally to the liver and brain. The precise mechanism of localization has not been determined, but is believed to result from nonspecific receptor binding. Brain uptake peaks at 30 minutes postinjection and remains relatively constant through 60 minutes. The drug is metabolized and excreted in the urine, with negligible activity remaining at 48 hours. When compared with CT in stroke patients, visualization may be performed sooner after symptom onset and a larger zone of involvement may be evident with iofetamine. Localization of seizure foci and diagnosis of Alzheimer's disease may also be possible. As CT has revolutionized noninvasive imaging of brain anatomy, SPECT with iofetamine permits routine cerebral blood flow imaging. Iofetamine hydrochloride I-123 under the brand name Spectamine was approved for use in the United States as a diagnostic aid in determining the localization of and in the evaluation of non-lacunar stroke and complex partial seizures, as well as in the early diagnosis of Alzheimer's disease in 1987. However it was discontinued in USA.

CNS Activity

Curator's Comment: A lipophilic substance, Iofetamine hydrochloride I-123 crosses the blood-brain barrier and binds to nonspecific high-capacity binding sites.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
SPECTAMINE

Approved Use

Evaluation of stroke. Localization of seizure foci and diagnosis of Alzheimer's disease.

Launch Date

5.6721598E11
Diagnostic
SPECTAMINE

Approved Use

Evaluation of stroke. Localization of seizure foci and diagnosis of Alzheimer's disease.

Launch Date

5.6721598E11
PubMed

PubMed

TitleDatePubMed
Cerebral perfusion imaging in Alzheimer's disease. Use of single photon emission computed tomography and iofetamine hydrochloride I 123.
1987 Feb

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Pharmacological actions of iofetamine appear to be minimal at doses employed for diagnostic imaging. Typically 111 MBq (3 mCi) is administered, containing iofetamine 0.45 mg, a dose that has not been associated with significant pharmacological effect in animals. Doses above 0.6 mg/kg have caused transient changes in electroencephalogram (EEG) activity and blood flow. https://www.ncbi.nlm.nih.gov/pubmed/2655294
Iofetamine hydrochloride I-123 (5 mCi) was injected into an antecubital vein while the subject was seated with eyes open in a quiet softly lit room. After ten minutes, patients were placed supine using a head holder to minimize motion. Single photon emission computed tomography was performed with a rotating gamma camera (GE 400 AC), equipped with a long-bore collimator.
Route of Administration: Intravenous
Name Type Language
IOFETAMINE I-123
Common Name English
IOFETAMINE I 123
MI  
Common Name English
IOFETAMINE I 123 [MI]
Common Name English
IOFETAMINE, I-123
Common Name English
Iofetamine (123 i) [WHO-DD]
Common Name English
IOFETAMINE (123I)
INN  
INN  
Official Name English
IOFETAMINE (123 I)
WHO-DD  
Common Name English
IOFETAMINE ((SUP 123)I)
Common Name English
N-ISOPROPYL-P-IODOAMPHETAMINE ((SUP 123)I)
Common Name English
(±)-P-IODO-(SUP 123)I-N-ISOPROPYL-.ALPHA.-METHYLPHENETHYLAMINE
Common Name English
((SUP 123)I)(±)-N-ISOPROPYL-P-IODOAMPHETAMINE
Common Name English
123I-M123
Code English
iofetamine (¹²³I) [INN]
Common Name English
BENZENEETHANAMINE, 4-(IODO-(SUP 123)I)-.ALPHA.-METHYL-N-(1-METHYLETHYL)-, (±)-
Common Name English
Classification Tree Code System Code
WHO-ATC V09AB01
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
WHO-VATC QV09AB01
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
Code System Code Type Description
DRUG BANK
DB09480
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
DRUG CENTRAL
1459
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
NCI_THESAURUS
C174677
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
EVMPD
SUB08220MIG
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
CAS
75873-14-2
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
SUPERSEDED
CAS
75917-92-9
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
WIKIPEDIA
Iofetamine (123I)
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
INN
5526
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201308
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
FDA UNII
LV23B78IJC
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
MERCK INDEX
m6362
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY Merck Index
SMS_ID
100000083653
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
PUBCHEM
156375
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID50997294
Created by admin on Fri Dec 15 16:21:33 UTC 2023 , Edited by admin on Fri Dec 15 16:21:33 UTC 2023
PRIMARY