DIIODOTYROSINE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2005222 | https://www.ncbi.nlm.nih.gov/pubmed/1149735

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

Targets

Primary Target	Pharmacology	Condition	Potency
Thyroid peroxidase 9 Target ID: P07202\|\|\|Q8TCI9 Gene ID: 7173.0 Gene Symbol: TPO Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1149735	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Infection 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2005222	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Sepsis 71 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2005222	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Enzymatic deiodination of diiodotyrosine; possible mediation by reduced flavin nucleotide.	1969 Apr	4387948
Inhibition of deiodination of diiodotyrosine in vivo; relation to catecholamine biosynthesis.	1969 Mar 15	5781529
Free diiodotyrosine effects on protein iodination and thyroid hormone synthesis catalyzed by thyroid peroxidase.	1975 Feb 21	1149735
Diiodotyrosine (DIT): a new marker of leukocyte phagocytic activity in sepsis and severe infections.	1989	2780722
Elevated serum diiodotyrosine (DIT) in severe infections and sepsis: DIT, a possible new marker of leukocyte activity.	1991 Apr	2005222

Patents

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 GMT 2023` Edited by `admin` on `Fri Dec 15 16:27:54 GMT 2023`
Record UNII	6L57Q44ZWW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIIODOTYROSINE

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

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