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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H10I4NO4.Na.5H2O
Molecular Weight 888.9282
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVOTHYROXINE SODIUM

SMILES

O.O.O.O.O.[Na+].N[C@@H](CC1=CC(I)=C(OC2=CC(I)=C(O)C(I)=C2)C(I)=C1)C([O-])=O

InChI

InChIKey=JMHCCAYJTTWMCX-QWPJCUCISA-M
InChI=1S/C15H11I4NO4.Na.5H2O/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);;5*1H2/q;+1;;;;;/p-1/t12-;;;;;;/m0....../s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C15H11I4NO4
Molecular Weight 776.87
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
MOL RATIO 5 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Levothyroxine (T4) is a synthetically prepared levo isomer of thyroxine, the major hormone secreted from the thyroid gland. Thyroxine is released from thyroglobulin by proteolysis and secreted into the blood. Thyroxine is peripherally deiodinated to form triiodothyronine (T3) which exerts a broad spectrum of stimulatory effects on cell metabolism. Thyroid hormone increases the metabolic rate of cells of all tissues in the body. In the fetus and newborn, thyroid hormone is important for the growth and development of all tissues including bones and the brain. In adults, thyroid hormone helps to maintain brain function, food metabolism, and body temperature, among other effects. The symptoms of thyroid deficiency relieved by levothyroxine include slow speech, lack of energy, weight gain, hair loss, dry thick skin and unusual sensitivity to cold. Levothyroxine acts like the endogenous thyroid hormone thyroxine (T4, a tetra-iodinated tyrosine derivative). In the liver and kidney, T4 is converted to T3, the active metabolite. In order to increase solubility, the thyroid hormones attach to thyroid hormone binding proteins, thyroxin-binding globulin, and thyroxin-binding prealbumin (transthyretin). Transport and binding to thyroid hormone receptors in the cytoplasm and nucleus then takes place. Thus by acting as a replacement for natural thyroxine, symptoms of thyroxine deficiency are relieved. Levothyroxine is used for use alone or in combination with antithyroid agents to treat hypothyroidism, goiter, chronic lymphocytic thyroiditis, myxedema coma, and stupor.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.136 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Synthroid
Primary
Synthroid

Cmax

ValueDoseCo-administeredAnalytePopulation
76.64 ng/mL
600 μg single, oral
LEVOTHYROXINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1764.14 ng × h/mL
600 μg single, oral
LEVOTHYROXINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.2 day
unknown, unknown
LEVOTHYROXINE serum
Homo sapiens
7.5 h
unknown, unknown
LEVOTHYROXINE serum
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.04%
unknown, unknown
LEVOTHYROXINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
Usual Adult Dose for Hypothyroidism Average full replacement dose: 1.7 mcg/kg/day (e.g., 100 to 125 mcg/day for a 70 kg adult) orally Older patients may require less than 1 mcg/kg/day
Route of Administration: Oral
In Vitro Use Guide
Addition of Levothyroxine at concentrations of 100-200 nM rescued rat cerebellar granule neurons (CGNs) from cell death in K5 in a dose-dependent manner. 200 nM T4 was also effective in maintaining the neurites of CGNs in K5.
Substance Class Chemical
Record UNII
9J765S329G
Record Status Validated (UNII)
Record Version