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Details

Stereochemistry RACEMIC
Molecular Formula C15H11I4NO4
Molecular Weight 776.87
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THYROXINE, DL-

SMILES

NC(CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C(O)=O

InChI

InChIKey=XUIIKFGFIJCVMT-UHFFFAOYSA-N
InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C15H11I4NO4
Molecular Weight 776.87
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

There is no information related to the pharmacological application of DL-thyroxine, but is known, that this is a mixture of two: L (levothyroxine) and D (dextrothyroxine) forms, and it was shown, that levothyroxine possessed greater antioxidative effect, than the DL.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Circannual pattern of hypothalamic-pituitary-thyroid (HPT) function and mood during extended antarctic residence.
2001-05
Variable effects of goitrogens in inducing precocious metamorphosis in sea lampreys (Petromyzon marinus).
2001-04-15
Iodine deficiency as a cause of brain damage.
2001-04
Combined tall cell carcinoma and Hürthle cell carcinoma (collision tumor) of the thyroid.
2001-04
Sulfate and chloride transport in Caco-2 cells: differential regulation by thyroxine and the possible role of DRA gene.
2001-04
The pituitary-thyroid axis in healthy men living under subarctic climatological conditions.
2001-04
Effect of thyroxine administration on the IGF/IGF binding protein system in neonatal and adult thyroidectomized rats.
2001-04
Habituation of thermal sensations, skin temperatures, and norepinephrine in men exposed to cold air.
2001-04
Effect of different drugs on the level of DNA-hydrolyzing polyclonal IgG antibodies in sera of patients with Hashimoto's thyroiditis and nontoxic nodal goiter.
2001-03-21
Intractable diarrhea in hyperthyroidism: management with beta-adrenergic blockade.
2001-03-16
Serum thyrotropin in primary hypothyroidism: a reliable and accurate predictor of optimal daily levothyroxine dose.
2001-03-16
Prepro-orexin mRNA levels in the rat hypothalamus, and orexin receptors mRNA levels in the rat hypothalamus and adrenal gland are not influenced by the thyroid status.
2001-03-16
Maternal thyroid deficiency: is it responsible for a low IQ in the offspring?
2001-03-13
Thyroid hormone promotes serine phosphorylation of p53 by mitogen-activated protein kinase.
2001-03-06
[Comparison of the effectiveness of two different dosages of levothyroxine-iodide combinations for the therapy of euthyroid diffuse goiter].
2001-03-02
Transthyretin stability as a key factor in amyloidogenesis: X-ray analysis at atomic resolution.
2001-03-02
Thyroid stimulating hormone secretion is a dynamic process.
2001-03
Transient hypothyroxinaemia in preterm infants.
2001-03
Effects of L-thyroxine on incorporation of (32)P into phospholipids of freshwater eels.
2001-03
Characterization of hepatic low-K(m) outer-ring deiodination in red drum (Sciaenops ocellatus).
2001-03
Hyponatremia due to hypothyroidism: a pure renal mechanism.
2001-03
Maternal isodisomy for chromosome 2p causing severe congenital hypothyroidism.
2001-03
Selenium decreases thyroglobulin concentrations but does not affect the increased thyroxine-to-triiodothyronine ratio in children with congenital hypothyroidism.
2001-03
Effect of levothyroxine on cardiac function and structure in subclinical hypothyroidism: a double blind, placebo-controlled study.
2001-03
Usefulness of thyrotropin (TSH)-releasing hormone test and nocturnal surge of TSH for diagnosis of isolated deficit of TSH secretion.
2001-03
A randomized trial comparing levothyroxine with radioactive iodine in the treatment of sporadic nontoxic goiter.
2001-03
Evaluation and treatment of sporadic nontoxic goiter--some answers and more questions.
2001-03
Thyroglobulin messenger ribonucleic acid levels in the peripheral blood of children with benign and malignant thyroid disease.
2001-03
Evaluation of the male pubertal assay's ability to detect thyroid inhibitors and dopaminergic agents.
2001-03
[Hyperthyroidism in early childhood and a very rare variant of glutaric aciduria: coincidence or causal relation?].
2001-02-28
Relationships between plasma levels of organochlorines, retinol and thyroid hormones from polar bears (Ursus maritimus) at Svalbard.
2001-02-23
[Clinical thinking and decision making in practice. The internist as a consultant for a patient with unexplained anemia in the cardiology department].
2001-02-17
Thyroid function after bone marrow transplantation: possible association between immune-mediated thyrotoxicosis and hypothyroidism.
2001-02-15
Measurement of serum concentrations of free thyroxine, total thyroxine, and total triiodothyronine in cats with hyperthyroidism and cats with nonthyroidal disease.
2001-02-15
[A young man with adynamia, subepicardial ischemia and sleep apnea].
2001-02-09
What is the optimal treatment for hypothyroidism?
2001-02-05
Side-effects of iodized oil administration in patients with simple goiter.
2001-02
Changes in serum thyroid hormone levels in newborn calves as a diagnostic index of endemic goiter.
2001-02
Daily migraine with visual aura associated with an occipital arteriovenous malformation.
2001-02
Effects of melatonin in perimenopausal and menopausal women: a randomized and placebo controlled study.
2001-02
Routine measurement of serum calcitonin is useful for early detection of medullary thyroid carcinoma in patients with nodular thyroid diseases.
2001-01
Direct effect of thyroxine on pig sphincter of Oddi contractility.
2001-01
Intellectual outcome of patients with congenital hypothyroidism detected by neonatal screening.
2001-01
Thyrotoxic periodic paralysis in a patient abusing thyroxine for weight reduction.
2001-01
[Diagnosis of hyperthyroidism].
2001-01
Relationship of etiology to treatment in congenital hypothyroidism.
2001-01
Impairment in cognitive and exercise performance during prolonged antarctic residence: effect of thyroxine supplementation in the polar triiodothyronine syndrome.
2001-01
Occult parathyroid carcinoma in a patient with papillary thyroid carcinoma and Hashimoto's thyroiditis.
2001-01
Effect of acute elevation of IGF-I on circulating GH, TSH, insulin, IGF-II and IGFBP-3 levels in non-endocrine short stature (NESS).
2001-01
Hypothalamus-hypophysis-thyroid axis, triiodothyronine and antithyroid antibodies in patients with primary and secondary Sjögren's syndrome.
2001
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Changes in catalase, superoxide dismutase (SOD) and caspase activity, genomic DNA, and nitric oxide (NO) generation were investigated biochemically using Rana japonica tadpole tails undergoing regression during thyroid hormone enhancement. DNA fragmentation and ladder formation with concomitant shortening of tadpole tail were induced by DL-thyroxine (T4) in culture medium. Catalase activity was also decreased by T4 treatment. T4 was also found to increase NO synthase (NOS) activity in cultured tadpole tail with concomitant increase in the concentration of NO2- plus NO3- (NOx) in the culture medium. Additional treatment with N-monomethyl-L-arginine (NMMA), a potent inhibitor of NOS, suppressed the enhancing effects of T4 on tail shortening and catalase activity reduction. These results suggested that T4 enhances NO generation, thereby strongly inhibiting catalase activity, resulting in an increase in hydrogen peroxide, and that the oxidative stress elicited by excess hydrogen peroxide might activate cysteine-dependent aspartate-directed protease-3 (caspase-3-like protease), which is thought to cause DNA fragmentation, leading to apoptosis.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:26 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:26 GMT 2025
Record UNII
QR0BV3BRIA
Record Status Validated (UNII)
Record Version
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Name Type Language
THYROXINE, DL-
Common Name English
DL-THYROXINE
MI  
Preferred Name English
DL-THYROXINE [MI]
Common Name English
(±)-3-(4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL)ALANINE
Systematic Name English
O-(4-HYDROXY-3,5-DIIODOPHENYL)-3,5-DIIODO-DL-TYROSINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1553
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
Code System Code Type Description
EPA CompTox
DTXSID0023662
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY
NCI_THESAURUS
C90975
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY
MERCK INDEX
m10840
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY Merck Index
FDA UNII
QR0BV3BRIA
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY
SMS_ID
300000056910
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY
ECHA (EC/EINECS)
206-088-9
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY
PUBCHEM
853
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY
CAS
300-30-1
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY
CHEBI
30660
Created by admin on Mon Mar 31 17:45:26 GMT 2025 , Edited by admin on Mon Mar 31 17:45:26 GMT 2025
PRIMARY