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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H9I2NO3
Molecular Weight 432.9816
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIIODOTYROSINE

SMILES

N[C@@H](CC1=CC(I)=C(O)C(I)=C1)C(O)=O

InChI

InChIKey=NYPYHUZRZVSYKL-ZETCQYMHSA-N
InChI=1S/C9H9I2NO3/c10-5-1-4(2-6(11)8(5)13)3-7(12)9(14)15/h1-2,7,13H,3,12H2,(H,14,15)/t7-/m0/s1

HIDE SMILES / InChI
Molecular Formula C9H9I2NO3
Molecular Weight 432.9816
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Diiodotyrosine (DIT) is a regulatory ligand for thyroid peroxidase, enzyme, which is involved in the production of thyroxine (T4) and triiodothyronine (T3), the thyroid hormones. Diiodotyrosine was proposed to be a new marker of leukocyte phagocytic activity in sepsis and severe infections.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Thyroid peroxidase
9
Target ID: P07202|||Q8TCI9
Gene ID: 7173.0
Gene Symbol: TPO
Target Organism: Homo sapiens (Human)
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
Diagnostic
Natural Metabolite
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Enzymatic deiodination of diiodotyrosine; possible mediation by reduced flavin nucleotide.
1969 Apr
Patents

Patents

US2435947
1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Inhibition of thyroglobulin iodination catalyzed by thyroid peroxidase was observed when free diiodotyrosine concentration was higher than 5 muM. This inhibition was competitive, suggesting that free diiodotyrosine interacts with the substrate site(s) of thyroid peroxidase. Free diiodotyrosine also competively inhibited iodide peroxidation to I2. 2. Free diiodotyrosine, when incubated with thyroid peroxidase in the absence of iodide was recovered unmodified; in the presence of iodide an exchange reaction was observed between the iodine atoms present in the diiodotyrosine molecule and iodide present in the medium. Using 14C-labelled diiodotyrosine, 14C-labelled non-iodinated products were also observed, showing that deiodination occurred as a minor degradation pathway.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:27:54 UTC 2023
Edited
by admin
on Fri Dec 15 16:27:54 UTC 2023
Record UNII
6L57Q44ZWW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIIODOTYROSINE
MART.  
Systematic Name English
NSC-4143
Code English
DIIODOTYROSINE [EP IMPURITY]
Common Name English
LIOTHYRONINE SODIUM IMPURITY B [EP IMPURITY]
Common Name English
3,5-DIIODOTYROSINE, L-
Common Name English
3,5-DIIODOTYROSINE L-FORM [MI]
Common Name English
(2S)-2-AMINO-3-(4-HYDROXY-3,5-DIIODOPHENYL)PROPANOIC ACID
Systematic Name English
L-DIIODOTYROSINE
Common Name English
L-TYROSINE, 3,5-DIIODO-
Systematic Name English
3,5-DIIODOTYROSINE L-FORM
MI  
Common Name English
TYROSINE, 3,5-DIIODO-, L-
Systematic Name English
DIIODOTYROSINE, L-
Common Name English
DIIODOTYROSINE [MART.]
Common Name English
3,5-DIIODO-L-TYROSINE
Systematic Name English
Classification Tree Code System Code
WHO-VATC QH03BX01
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
WHO-ATC H03BX01
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
DSLD 3527 (Number of products:4)
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
Code System Code Type Description
CAS
300-39-0
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
PUBCHEM
9305
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
CHEBI
57506
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
NSC
4143
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
ECHA (EC/EINECS)
206-092-0
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
FDA UNII
6L57Q44ZWW
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
SMS_ID
100000079224
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
DRUG CENTRAL
3146
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
WIKIPEDIA
DIIODOTYROSINE
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
CHEBI
15768
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
MERCK INDEX
m4480
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY Merck Index
EVMPD
SUB13599MIG
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
EPA CompTox
DTXSID0048680
Created by admin on Fri Dec 15 16:27:54 UTC 2023 , Edited by admin on Fri Dec 15 16:27:54 UTC 2023
PRIMARY
Related Record Type Details
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Structure of LIOTHYRONINE SODIUM
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EP
NIH
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