WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H206444
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.
Hodoodo Cat#: H206444
Name: Ezutromid
CAS#: 945531-77-1
Chemical Formula: C19H15NO3S
Exact Mass: 337.08
Molecular Weight: 337.390
Elemental Analysis: C, 67.64; H, 4.48; N, 4.15; O, 14.23; S, 9.50
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
More Info:
| 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/ |
| 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 |
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.
| 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. |
