Liothyronine

HCID 5920CAS 15785-49-6

Grundinformationen

Standard-SMILES
N[C@@H](Cc1cc(I)c(Oc2ccc(O)c(I)c2)c(I)c1)C(=O)O
InChIKey
AUYYCJSJGJYCDS-LBPRGKRZSA-N
Summenformel
C15H12I3NO4
Durchschnittliche Molmasse
650,97 g/mol
Monoisotopische Masse
650,79005186

Überblick

3,3',5-triiodo-L-thyronine is an iodothyronine compound having iodo substituents at the 3-, 3'- and 5-positions. Although some is produced in the thyroid, most of the 3,3',5-triiodo-L-thyronine in the body is generated by mono-deiodination of L-thyroxine in the peripheral tissues. Its metabolic activity is about 3 to 5 times that of L-thyroxine. The sodium salt is used in the treatment of hypothyroidism. It has a role as a thyroid hormone, a mouse metabolite and a human metabolite. It is an iodophenol, an iodothyronine and a 2-halophenol. It is a conjugate acid of a 3,3',5-triiodo-L-thyroninate. It is a tautomer of a 3,3',5-triiodo-L-thyronine zwitterion.

Namen und Bezeichner

Bevorzugter Name
Liothyronine
IUPAC
(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid

Namen und Synonyme

liothyronine3,3',5-Triiodo-L-thyroninetriiodothyronine6893-02-3Liothyronin3,5,3'-triiodothyronineL-LiothyronineTresitopetriothyroneO-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosineLiotironinaTriiodo-L-thyronine
Weitere Namen anzeigen
L-triiodothyronine3,5,3'-Triiodo-L-thyronineLiothyroninumLyothyronineCyronineL-3,3',5-TriioDOThyronine(2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid3,3',5-Triiodothyronine

Datenbank-Bezeichner

CAS
15785-49-6、6893-02-3
PubChem CID
5920
DTXSID
DTXSID8023216
ChEMBL
CHEMBL1544
ChEBI
CHEBI:18258
UNII
06LU7C9H1V
EC Number
229-999-3
Nikkaji
J85.948F

Eigenschaften

Berechnete Struktureigenschaften

XLogP
1,7
Polarare Oberfläche (TPSA)
92,8 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
5
Frei drehbare Bindungen
5
Schwere Atome
23

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
LogPlog Kow = 0.93
Color/FormCRYSTALS
Solubility · 4 Einträge

Very slightly soluble

In water, 3.958 mg/l at 37 °C.

Soluble in dilute alkalies with the formation of a brownish, water-soluble, sodium salt. Insoluble in propylene glycol.

11.4 [ug/mL] (The mean of the results at pH 7.4)

Human DrugsBreast Feeding; Lactation; Milk, Human; Thyroid Hormones
Endocrine DisruptorsPotential endocrine disrupting compound

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Warning

H315 (98.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 174 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Other Safety InformationIMAP assessments - L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-: Environment tier I assessment
FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Special Reports · 2 Einträge

Hays MT; J Clin Endocrinol 63: 527 (1970). Absorption of triiodothyronine in man.

Surks MI, et al; J Clin Invest 52: 805 (1973). Determination of iodothyronine absorption and conversion to L-thyroxine (T4) to L-triiodothyronine (T3) using a rate turnover technique.

Hazard Classes and CategoriesSkin Irrit. 2 (98.9%)

Sicherheit und Schutzausrüstung

Storage Conditions · 1 Eintrag

Commercially available liothyronine sodium tablets should be stored in tight containers at a temperature less than 40 °C, preferably between 15-30 °C. Commercially available liothyronine sodium injection should be stored at 2-8 °C. /Liothyronine sodium/

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Interactions · 5 Einträge

USE OF PROPRANOLOL IN CONJUNCTION WITH REPLACEMENT THERAPY HAS BEEN REPORTED TO DECR RISK OF ARRHYTHMIA & ANGINA...

THYROID COMPOUNDS THAT PRODUCE HYPERMETABOLIC STATE (LIOTHYRONINE...) INCR RATE OF DECAY OF VITAMIN K-DEPENDENT CLOTTING FACTORS, & IN PRESENCE OF ORAL ANTICOAGULANTS /EG, WARFARIN/, NORMAL COMPENSATION BY INCR SYNTHESIS IS PREVENTED.

THERE IS CONSIDERABLE CLINICAL EVIDENCE THAT A PATIENT'S THYROID STATE AFFECTS RESPONSE TO TRICYCLIC ANTIDEPRESSANT DRUGS. ADDITION OF LIOTHYRONINE (25 UG/DAY) MAY PREVENT RELATIVELY LONG LAG TIME THAT OCCURS BEFORE CLINICAL EFFECTIVENESS OF TRICYCLIC ANTIDEPRESSANTS IS OBSERVED.

CHOLESTYRAMINE MAY CAUSE CLINICALLY SIGNIFICANT DECR IN ABSORPTION OF THYROID HORMONE WHEN THESE DRUGS ARE GIVEN SIMULTANEOUSLY. /THYROID HORMONE/

For more Interactions (Complete) data for LIOTHYRONINE (16 total), please visit the HSDB record page.

Exposure Routes95% in 4 hours
Milk ConcentrationsAlthough only minimal amounts of thyroid hormones are distributed into milk. ... /Thyroid agents/
Toxicity Summary · 1 Eintrag

The hormones, T<sub>4</sub> and T<sub>3</sub>, are tyrosine-based hormones produced by the thyroid gland. Iodine is an important component in their synthesis. The major form of thyroid hormone in the blood is thyroxine (T<sub>4</sub>). This is converted to the more active liothyronine form by deiodinases in peripheral tissues. Liothyronine acts on the body to increase the basal metabolic rate, affect protein synthesis and increase the body's sensitivity to catecholamines (such as adrenaline). The thyroid hormones are essential to proper development and differentiation of all cells of the human body. To various extents T<sub>4</sub> and T<sub>3</sub> regulate protein, fat and carbohydrate metabolism. Their most pronounced effect is on how human cells use energetic compounds. The thyroid hormone derivatives bind to the thyroid hormone receptors initially to initiate their downstream effects.

Human Toxicity Excerpts · 3 Einträge

UNTOWARD EFFECTS OF OVERDOSES OF THYROID HORMONES INCL TACHYCARDIA...ANGINA PECTORIS, HYPERTENSION...HYPERKINESIS...GI DISTURBANCES, & HYPOADRENOCORTICISM. ...MAY CAUSE ALLERGIC REACTIONS. /THYROID HORMONES/

FRANKLY TOXIC DOSES INDUCE UNPLEASANT BUT TRANSIENT SYMPTOMS THAT RESEMBLE THYROTOXICOSIS (THYROID STORM). SIGNS & SYMPTOMS INCL PALPITATIONS, RAPID & IRREGULAR PULSE, HEADACHE, TREMORS, NERVOUSNESS, INSOMNIA, DELIRIUM, DIAPHORESIS, HYPERPYREXIA, VOMITING (SOMETIMES UNCONTROLLABLE), COLLAPSE & COMA. /THYROID/

LOW TOXICITY @ NORMAL DOSAGE.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

Regulatorische Informationen

FDA Requirements · 1 Eintrag

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Chemie und Industrie

Pharmakologische Informationen

ATC CodeH03AA03
Bionecessity · 2 Einträge

STATE OF DEFICIENCY: WHEN THERE IS A DEFICIENCY OF IODINE IN RAT THYROID... THE RATIO OF THYROXINE TO TRIIODOTHYRONINE DECREASES FROM 4:1 TO 1:3.

STATE OF DEFICIENCY: IN ABSENCE OF...TRIIODOTHYRONINE, GROWTH IS DEFICIENT, PARTICULARLY AT YOUNGER AGES.

Protein Binding · 1 Eintrag

Liothyronine presents a very large binding to plasma proteins and around 99.7% of the administered dose can be found bound. Liothyronine is found to be bound to thyroxine-binding globulin, thyroxine-binding prealbumin and albumin. It is important to consider that only the little unbound portion of liothyronine is metabolically active.

Pharmacodynamics · 1 Eintrag

In hormonal replacement, liothyronine is more potent and present a faster action when compared to levothyroxine but the time of action is significantly shorter. The type of treatment needs to be well evaluated as the fast correction of thyroid hormones in certain diseases presents additional risks such as heart failure. The onset of activity is observed a few hours after administration and the maximum effect is observed after 2-3 days. Treatment with liothyronine has been shown to produce normal plasma levels of T3 hormone but to have no effect on the T4 plasma concentration.

Mechanism of Action · 3 Einträge

Liothyronine replaces endogenous thyroid hormone and then exerts its physiologic effects by controlling DNA transcription and protein synthesis. This effect on DNA is obtained by the binding of liothyronine to the thyroid receptors attached to DNA. Exogenous liothyronine exerts all the normal effects of the endogenous thyroid T3 hormone. Hence, it increases energy expenditure, accelerates the rate of cellular oxidation stimulating growth, maturation, and metabolism of the body tissues, aids in myelination of nerves and development of synaptic processes in the nervous system and enhances carbohydrate and protein metabolism.

LIOTHYRONINE IS ONLY LOOSELY BOUND TO PLASMA PROTEINS & HENCE DOES NOT ELEVATE PLASMA BOUND IODINE SIGNIFICANTLY...PBI MAY ACTUALLY BE LOWERED, BECAUSE OF HOMEOSTATIC DECR IN THYROXINE RELEASE FROM THYROID GLAND.

TRIIODOTHYRONINE INCR METABOLIC RATE & OXYGEN CONSUMPTION OF ANIMAL TISSUES.

Biological Half-LifeThe half-life of liothyronine is reported to be between 1 and 2 days.

Verwendung und Herstellung

Uses · 2 Einträge

THERAP CAT: Thyroid hormone; THERAP CAT (VET): Thyroid hormone.

Used as replacement or supplemental therapy in patients with hypothyroidism of any etiology, except transient hypothyrodism during the recovery phase of subacute thyroiditis.

Methods of Manufacturing · 1 Eintrag

Formation from diiodothyronine: Roche et al., Biochem Biophys Acta 11, 215 (1953). Isoln from thyroid gland and synthesis: Gross, Pitt-Rivers, Biochem J 53, 645 (1953); Roche et al., Bull Soc Chim France 4, 462 (1957); Plati, Wenner, U.S. pat 2,784,222 (1957 to Hoffmann-La Roche); Pitt-Rivers, Gross, U.S. pat 2,823,164 (1958 to Nat Res Dev Corp); Razdan, Wetherill, U.S. pat 2,993,928 (1961 to Glaxo).

Formulations/Preparations · 4 Einträge

LIOTHYRONINE SODIUM, USP (CYTOMEL), IS...DESIGNATION FOR SALT OF L-TRIIODOTHYRONINE. ...ALSO IS MARKETED AS TABLETS CONTAINING 5, 25, & 50 UG. KITS FOR PREPN OF POWDER FOR INJECTION ARE AVAILABLE FROM MFR. /LIOTHYRONINE SODIUM/

ORAL TABLETS 5, 25, & 50 MCG; INJECTION: POWDER (FOR SOLN) 114 UG/ML. NOT COMMERCIALLY AVAILABLE; MFR WILL SUPPLY KIT UPON REQUEST.,.

/SODIUM SALT LIOTHYRONINE IS/ COMMONLY USED FORM. /LIOTHYRONINE SODIUM/.

...TRIIODOTHYRONINE REPRESENTS RELATIVELY MINOR FRACTION (ABOUT 5%) /OF ORGANIC IODINE/.

General Manufacturing Information · 2 Einträge

IN DOGS & MAN IT HAS APPROX 2,500 TIMES THE ORAL POTENCY OF OFFICIAL THYROID PREPN.

Possesses 5 times the activity of L-thyroxine.

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