ML109
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MedKoo CAT#: 555782

CAS#: 1186649-91-1 (free base)

Description: ML-109, also known as CID-25246343 and (S)-(+)-NCGC00161870, is a potent and full thyroid stimulating hormone receptor (TSHR) agonist. ML109 is the first selective and orally available small-molecule TSHR agonist, and the probe will be a useful pharmacological tool to study TSHR biology in thyroidal and extrathyroidal tissues

Chemical Structure

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ML109
CAS# 1186649-91-1 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555782
Name: ML109
CAS#: 1186649-91-1 (free base)
Chemical Formula: C31H29N3O5
Exact Mass: 523.21
Molecular Weight: 523.590
Elemental Analysis: C, 71.11; H, 5.58; N, 8.03; O, 15.28

Price and Availability

Size Price Availability Quantity
10mg USD 150 Ready to ship
25mg USD 250 Ready to ship
50mg USD 450 Ready to ship
100mg USD 750 Ready to ship
200mg USD 1350 Ready to ship
500mg USD 2950 Ready to ship
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Related CAS #: ML109 HCl   1186649-91-1 (free base)    

Synonym: ML-109; ML 109; ML109; CID-25246343; CID 25246343; CID25246343; (S)-(+)-NCGC00161870; NCGC-00161870; NCGC 00161870;

IUPAC/Chemical Name: N-(4-((5-(3-benzyl-5-hydroxy-4-oxo-1,2,3,4-tetrahydroquinazolin-2-yl)-2-methoxybenzyl)oxy)phenyl)acetamide

InChi Key: JRVXFGNCHKHBPA-UHFFFAOYSA-N

InChi Code: InChI=1S/C31H29N3O5/c1-20(35)32-24-12-14-25(15-13-24)39-19-23-17-22(11-16-28(23)38-2)30-33-26-9-6-10-27(36)29(26)31(37)34(30)18-21-7-4-3-5-8-21/h3-17,30,33,36H,18-19H2,1-2H3,(H,32,35)

SMILES Code: CC(NC1=CC=C(OCC2=CC(C(N3CC4=CC=CC=C4)NC5=C(C(O)=CC=C5)C3=O)=CC=C2OC)C=C1)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: Thyroid Stimulating Hormone (TSH) is a heterodimeric glycoprotein hormone that regulates thyroid homeostasis upon interaction with the TSH receptor (TSHR). TSH binds to the TSH receptor, which couples preferentially to the G-alpha (s) (Gs) protein, resulting in activation of adenylate cyclase and increase in cyclic adenosine 3′, 5′ monophosphate (cAMP).

Biological target: ML-109 is a potent and full thyroid stimulating hormone receptor (TSHR) agonist with an EC50 of 40 nM
In vitro activity: The effects of CID-25246343/ML109 or TSH on cAMP accumulation in cells expressing TSHR, TSHR-KFLR in which the large amino-terminal ectodomain to which TSH binds, is deleted, or N5.47A in which Asn at position-5.47 was mutated to Ala. Docking of CID-25246343/ML109 into the homology model of TSHR predicts CID-25246343/ML109 binds within the transmembrane helical bundlen (left panel). Enlargement of the boxed region in the left panel (right panel) shows an interaction of CID-25246343/ML109 with an Asn in TMH5 (N5.47). CID-25246343/ML109 activates TSHR by binding to the transmembrane helical bundle. Reference: National Center for Biotechnology Information (US); 2010. https://pubmed.ncbi.nlm.nih.gov/21735603/
In vivo activity: Vehicle (PEG 300, control) or CID-25246343/ML109 (2.5 mg) was given by esophageal gavage and serum T4 was measured 2 hr later. Vehicle (control) or CID-25246343/ML109 (2.5 mg) was given by esophageal gavage on days 1 and 2. On the morning of the 3rd day, Na125I (20 μCi) was administered by esophageal gavage and the mice were sacrificed 2 hr later. The thyroid glands and small pieces of liver were excised and counted for 125I radioactivity. These in vivo studies (Figure 6) showed that CID25246343/ML109 could increase secretion of T4 and thyroidal iodide uptake in mice after administration by esophageal gavage, suggesting CID-25246343/ML109 is an orally available small molecule that can stimulate thyroid gland function1. Reference: National Center for Biotechnology Information (US); 2010. https://pubmed.ncbi.nlm.nih.gov/21735603/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 83.0 158.50

Preparing Stock Solutions

The following data is based on the product molecular weight 523.59 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Titus S, Huang W, Marugan J, Southall N, Inglese J, Austin C, Zheng W, Englund E, Neumann S, Gershengorn M. Identification of Potent and Selective Thyroid Stimulating Hormone Receptor Agonists. 2009 Sep 1 [updated 2011 Mar 25]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 21735603.
In vitro protocol: 1. Titus S, Huang W, Marugan J, Southall N, Inglese J, Austin C, Zheng W, Englund E, Neumann S, Gershengorn M. Identification of Potent and Selective Thyroid Stimulating Hormone Receptor Agonists. 2009 Sep 1 [updated 2011 Mar 25]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 21735603.
In vivo protocol: 1. Titus S, Huang W, Marugan J, Southall N, Inglese J, Austin C, Zheng W, Englund E, Neumann S, Gershengorn M. Identification of Potent and Selective Thyroid Stimulating Hormone Receptor Agonists. 2009 Sep 1 [updated 2011 Mar 25]. In: Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010–. PMID: 21735603.

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Titus S, Huang W, Marugan J, et al. Identification of Potent and Selective Thyroid Stimulating Hormone Receptor Agonists. In: Probe Reports from the NIH Molecular Libraries Program. Bethesda (MD): National Center for Biotechnology Information (US); 2010.