Ezutromid
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MedKoo CAT#: 206444

CAS#: 945531-77-1

Description: Ezutromid, also known as BMN-195 and SMTC-1100, is a first orally bioavailable utrophin's translation modulator. Duchenne muscular dystrophy (DMD) is a lethal, progressive muscle wasting disease caused by a loss of sarcolemmal bound dystrophin, which results in the death of the muscle fibers leading to the gradual depletion of skeletal muscle.


Chemical Structure

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Ezutromid
CAS# 945531-77-1

Theoretical Analysis

MedKoo Cat#: 206444
Name: Ezutromid
CAS#: 945531-77-1
Chemical Formula: C19H15NO3S
Exact Mass: 337.07726
Molecular Weight: 337.39
Elemental Analysis: C, 67.64; H, 4.48; N, 4.15; O, 14.23; S, 9.50

Price and Availability

Size Price Availability Quantity
25.0mg USD 150.0 2 weeks
100.0mg USD 450.0 2 weeks
200.0mg USD 750.0 2 weeks
500.0mg USD 1450.0 2 weeks
1.0g USD 2450.0 2 weeks
5.0g USD 4950.0 2 weeks
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Synonym: BMN-195; BMN 195; BMN195; SMTC-1100; SMTC1100; SMTC 1100; VOX-C1100; Ezutromid

IUPAC/Chemical Name: 5-(ethylsulfonyl)-2-(naphthalen-2-yl)benzo[d]oxazole

InChi Key: KSGCNXAZROJSNW-UHFFFAOYSA-N

InChi Code: InChI=1S/C19H15NO3S/c1-2-24(21,22)16-9-10-18-17(12-16)20-19(23-18)15-8-7-13-5-3-4-6-14(13)11-15/h3-12H,2H2,1H3

SMILES Code: O=S(C1=CC=C(OC(C2=CC=C3C=CC=CC3=C2)=N4)C4=C1)(CC)=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, not in water

Shelf Life: >2 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

Product Data:

Biological target: Ezutromid (SMT C1100) is a first-in-class, orally active benzoxazole utrophin modulator with an EC50 of 0.91 μM.
In vitro activity: SMT C1100 shows a maximal increase of four to five-fold compared to vehicle with an EC50 of 0.4 µM (Fig. 1A). In vitro dosing of human myoblasts with SMT C1100 leads to a 25% increase in utrophin mRNA (Fig. 1B) when compared to vehicle-only dosing after three days of treatment. Treatment of human DMD cells with SMT C1100 lead to a 2-fold increase in utrophin protein levels at an optimal concentration of 0.3 µM after 3 days of treatment (Fig. 1C). Reference: PLoS One. 2011 May 6;6(5):e19189. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089598/
In vivo activity: To confirm the in vivo activity of SMT C1100, the dystrophin-deficient mdx mouse was used to monitor any changes in the dystrophic phenotype after chronic dosing for several weeks. Fig. 3A demonstrates a two-fold increase in utrophin mRNA as determined by quantitative PCR from mdx mice dosed daily with SMT C1100 for 28 days compared to vehicle only. This data confirms SMT C1100 drives increased utrophin transcriptional expression in vivo and, more importantly, demonstrates increased utrophin staining at the required site of action - the sarcolemma - and independently from muscle work load. Reference: PLoS One. 2011 May 6;6(5):e19189. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089598/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 6.5 19.27
DMSO:PBS (pH 7.2) (1:2) 0.3 0.89
DMF 2.0 5.93

Preparing Stock Solutions

The following data is based on the product molecular weight 337.39 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. Tinsley JM, Fairclough RJ, Storer R, Wilkes FJ, Potter AC, Squire SE, Powell DS, Cozzoli A, Capogrosso RF, Lambert A, Wilson FX, Wren SP, De Luca A, Davies KE. Daily treatment with SMTC1100, a novel small molecule utrophin upregulator, dramatically reduces the dystrophic symptoms in the mdx mouse. PLoS One. 2011 May 6;6(5):e19189. doi: 10.1371/journal.pone.0019189. PMID: 21573153; PMCID: PMC3089598.
In vitro protocol: 1. Tinsley JM, Fairclough RJ, Storer R, Wilkes FJ, Potter AC, Squire SE, Powell DS, Cozzoli A, Capogrosso RF, Lambert A, Wilson FX, Wren SP, De Luca A, Davies KE. Daily treatment with SMTC1100, a novel small molecule utrophin upregulator, dramatically reduces the dystrophic symptoms in the mdx mouse. PLoS One. 2011 May 6;6(5):e19189. doi: 10.1371/journal.pone.0019189. PMID: 21573153; PMCID: PMC3089598.
In vivo protocol: 1. Tinsley JM, Fairclough RJ, Storer R, Wilkes FJ, Potter AC, Squire SE, Powell DS, Cozzoli A, Capogrosso RF, Lambert A, Wilson FX, Wren SP, De Luca A, Davies KE. Daily treatment with SMTC1100, a novel small molecule utrophin upregulator, dramatically reduces the dystrophic symptoms in the mdx mouse. PLoS One. 2011 May 6;6(5):e19189. doi: 10.1371/journal.pone.0019189. PMID: 21573153; PMCID: PMC3089598.

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