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USP

Levothyroxine

United States Pharmacopeia (USP) Reference Standard

Synonym(s):

L-Thyroxine, 3,3′,5,5″-Tetraiodo-L-thyronine, 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine, T4

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About This Item

Linear Formula:
HOC6H2(I)2OC6H2(I)2CH2CH(NH2)CO2H
CAS Number:
Molecular Weight:
776.87
Beilstein:
2228515
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

levothyroxine

manufacturer/tradename

USP

mp

223 °C (dec.) (lit.)

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

N[C@@H](Cc1cc(I)c(Oc2cc(I)c(O)c(I)c2)c(I)c1)C(O)=O

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)/t12-/m0/s1

InChI key

XUIIKFGFIJCVMT-LBPRGKRZSA-N

Gene Information

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General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

Levothyroxine USP reference standard for use in specified quality tests and assays.

Also used to prepare standard stock, and system suitability solutions for impurity analysis according to given below monographs of the United States Pharmacopeia (USP):
  • Levothyroxine Sodium
  • Levothyroxine Sodium Tablets

Biochem/physiol Actions

L-Thyroxine (T4) and triiodo-L-thyronine (T3) are iodine-containing hormones produced from thyroglobulin in the thyroid follicular cells. The stimulation of metabolic rate and regulation of growth and development by these hormones appear to be due to their effects on DNA transcription and, thus, protein synthesis.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

STOT RE 1

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Levothyroxine Sodium
United States Pharmacopeia, 45(2) (2020)
Steffen Mayerl et al.
The Journal of clinical investigation, 124(5), 1987-1999 (2014-04-03)
Allan-Herndon-Dudley syndrome (AHDS), a severe form of psychomotor retardation with abnormal thyroid hormone (TH) parameters, is linked to mutations in the TH-specific monocarboxylate transporter MCT8. In mice, deletion of Mct8 (Mct8 KO) faithfully replicates AHDS-associated endocrine abnormalities; however, unlike patients
B Velkeniers et al.
Human reproduction update, 19(3), 251-258 (2013-01-19)
BACKGROUND Previous meta-analyses of observational data indicate that pregnant women with subclinical hypothyroidism have an increased risk of adverse pregnancy outcome. Potential benefits of levothyroxine (LT4) supplementation remain unclear, and no systematic review or meta-analysis of trial findings is available
Shannon E Scratch et al.
Pediatrics, 133(4), e955-e963 (2014-04-02)
Preterm infants commonly have transient hypothyroxinemia of prematurity after birth, which has been associated with deficits in general intellectual functioning, memory, attention, and academic achievement. However, research has predominantly focused on thyroxine levels in the first 2 weeks of life
Yoshiyuki Watanabe et al.
Genome research, 25(3), 328-337 (2015-02-06)
Integration of DNA viruses into the human genome plays an important role in various types of tumors, including hepatitis B virus (HBV)-related hepatocellular carcinoma. However, the molecular details and clinical impact of HBV integration on either human or HBV epigenomes

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