Azoramide
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MedKoo CAT#: 329524

CAS#: 932986-18-0

Description: Azoramide is a small-molecule modulator of the unfolded protein response with antidiabetic activity. Azoramide mproves ER protein-folding ability and activates ER chaperone capacity to protect cells against ER stress in multiple systems. Azoramide also exhibited potent antidiabetic efficacy in two independent mouse models of obesity by improving insulin sensitivity and pancreatic β cell function. Azoramide can be potential drug candidate for type 2 diabetes. Azoramide is a novel anti-diabetic agent which protects cells against endoplasmic reticulum (ER) stress.

Chemical Structure

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Azoramide
CAS# 932986-18-0
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329524
Name: Azoramide
CAS#: 932986-18-0
Chemical Formula: C15H17ClN2OS
Exact Mass: 308.08
Molecular Weight: 308.824
Elemental Analysis: C, 58.34; H, 5.55; Cl, 11.48; N, 9.07; O, 5.18; S, 10.38

Price and Availability

Size Price Availability Quantity
25mg USD 120 Ready to ship
50mg USD 190 Ready to ship
100mg USD 350 Ready to ship
200mg USD 630 Ready to ship
500mg USD 1350 Ready to ship
1g USD 2250 Ready to ship
2g USD 4050 2 Weeks
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Synonym: Azoramide

IUPAC/Chemical Name: N-[2-[2-(4-chlorophenyl)-4-thiazolyl]ethyl]-butanamide

InChi Key: VYBFWKKCWTXCQX-UHFFFAOYSA-N

InChi Code: InChI=1S/C15H17ClN2OS/c1-2-3-14(19)17-9-8-13-10-20-15(18-13)11-4-6-12(16)7-5-11/h4-7,10H,2-3,8-9H2,1H3,(H,17,19)

SMILES Code: CCCC(NCCC1=CSC(C2=CC=C(Cl)C=C2)=N1)=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: >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: Azoramide is a dual-function endoplasmic reticulum (ER) modulator.
In vitro activity: CCK-8 assay showed that 3 and 10 μM azoramide significantly enhanced cell viability (27 and 39%, respectively) (Fig. 2e). Therefore, 10 μM was used as a working concentration of azoramide for neuroprotection. Western blotting demonstrated that 10 μM azoramide dramatically inhibited the release of cytochrome c from mitochondria and decreased the cleaved level of caspase 3 and the ratio of Bax/Bcl2 in PLA2G6 mutant neurons (Fig. 2g, h). Azoramide significantly enhanced expression of CREB in PLA2G6 mutant neurons (Fig. 2g, h). Reference: Cell Death Dis. 2020 Feb; 11(2): 130. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7028918/
In vivo activity: Briefly, 14-day-old C57BL/6 mice were injected with recombinant BMP2 three times a day for 5 days into the periosteal tissue overlying the right parietal bone with vehicle injected to the left parietal bone as a negative control. Meanwhile, azoramide and DMSO control were administered via intraperitoneal injection once a day for 14 consecutive days (Fig. 1a). The azoramide treatment group, induced by BMP2, showed remarkable reductions in new bone formations compared with the control group (Fig. 1b); the volume of newly formed bone was approximately 68% smaller in the groups injected with azoramide (Fig. 1b, c). These data indicated that azoramide treatment could impair the BMP2-induced formation of new bone. Histological analysis of the local new bone tissues in responses to azoramide showed an obvious decrease in the number of osteoblasts and a significant increase in the number of adipocytes in the newly formed bone marrow spaces after azoramide treatment (Fig. 1d, e). Taken together, the results suggested that azoramide inhibited the bone forming ability of mesenchymal progenitor cells under BMP2 induction. More likely, it preferentially induces MSCs towards adipocytes rather than osteoblasts. Reference: Stem Cell Res Ther. 2018; 9: 57. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5845182/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 37.0 119.81
DMF 20.0 64.76
Ethanol 40.5 131.14
Ethanol:PBS (pH 7.2) (1:1) 0.5 1.62

Preparing Stock Solutions

The following data is based on the product molecular weight 308.82 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. Ke M, Chong CM, Zeng H, Huang M, Huang Z, Zhang K, Cen X, Lu JH, Yao X, Qin D, Su H. Azoramide protects iPSC-derived dopaminergic neurons with PLA2G6 D331Y mutation through restoring ER function and CREB signaling. Cell Death Dis. 2020 Feb 18;11(2):130. doi: 10.1038/s41419-020-2312-8. PMID: 32071291; PMCID: PMC7028918. 2. Walenna NF, Kurihara Y, Chou B, Ishii K, Soejima T, Hiromatsu K. Chlamydia pneumoniae infection-induced endoplasmic reticulum stress causes fatty acid-binding protein 4 secretion in murine adipocytes. J Biol Chem. 2020 Feb 28;295(9):2713-2723. doi: 10.1074/jbc.RA119.010683. Epub 2020 Jan 28. PMID: 31992597; PMCID: PMC7049972. 3. Ruan B, Zhu Z, Yan Z, Yang W, Zhai D, Wang L, Ye Z, Lu H, Xiang A, Liang J, Jiang Y, Xu C, Wang Z, Wei M, Lei X, Cao X, Lu Z. Azoramide, a novel regulator, favors adipogenesis against osteogenesis through inhibiting the GLP-1 receptor-PKA-β-catenin pathway. Stem Cell Res Ther. 2018 Mar 9;9(1):57. doi: 10.1186/s13287-018-0771-y. PMID: 29523188; PMCID: PMC5845182. 4. Fu S, Yalcin A, Lee GY, Li P, Fan J, Arruda AP, Pers BM, Yilmaz M, Eguchi K, Hotamisligil GS. Phenotypic assays identify azoramide as a small-molecule modulator of the unfolded protein response with antidiabetic activity. Sci Transl Med. 2015 Jun 17;7(292):292ra98. doi: 10.1126/scitranslmed.aaa9134. PMID: 26084805; PMCID: PMC5063051.
In vitro protocol: 1. Ke M, Chong CM, Zeng H, Huang M, Huang Z, Zhang K, Cen X, Lu JH, Yao X, Qin D, Su H. Azoramide protects iPSC-derived dopaminergic neurons with PLA2G6 D331Y mutation through restoring ER function and CREB signaling. Cell Death Dis. 2020 Feb 18;11(2):130. doi: 10.1038/s41419-020-2312-8. PMID: 32071291; PMCID: PMC7028918. 2. Walenna NF, Kurihara Y, Chou B, Ishii K, Soejima T, Hiromatsu K. Chlamydia pneumoniae infection-induced endoplasmic reticulum stress causes fatty acid-binding protein 4 secretion in murine adipocytes. J Biol Chem. 2020 Feb 28;295(9):2713-2723. doi: 10.1074/jbc.RA119.010683. Epub 2020 Jan 28. PMID: 31992597; PMCID: PMC7049972.
In vivo protocol: 1. Ruan B, Zhu Z, Yan Z, Yang W, Zhai D, Wang L, Ye Z, Lu H, Xiang A, Liang J, Jiang Y, Xu C, Wang Z, Wei M, Lei X, Cao X, Lu Z. Azoramide, a novel regulator, favors adipogenesis against osteogenesis through inhibiting the GLP-1 receptor-PKA-β-catenin pathway. Stem Cell Res Ther. 2018 Mar 9;9(1):57. doi: 10.1186/s13287-018-0771-y. PMID: 29523188; PMCID: PMC5845182. 2. Fu S, Yalcin A, Lee GY, Li P, Fan J, Arruda AP, Pers BM, Yilmaz M, Eguchi K, Hotamisligil GS. Phenotypic assays identify azoramide as a small-molecule modulator of the unfolded protein response with antidiabetic activity. Sci Transl Med. 2015 Jun 17;7(292):292ra98. doi: 10.1126/scitranslmed.aaa9134. PMID: 26084805; PMCID: PMC5063051.

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1: Miao W, Shi J, Huang J, Lin Y, Cui C, Zhu Y, Zheng B, Li M, Jiang Q, Chen M. Azoramide ameliorated tachypacing-induced injury of atrial myocytes differentiated from human induced pluripotent stem cell by regulating endoplasmic reticulum stress. Stem Cell Res. 2022 Apr;60:102686. doi: 10.1016/j.scr.2022.102686. Epub 2022 Jan 24. PMID: 35101669.


2: Bagci R, Sahinturk V, Sahin E. Azoramide ameliorates fructose-induced nonalcoholic fatty liver disease in mice. Tissue Cell. 2019 Aug;59:62-69. doi: 10.1016/j.tice.2019.07.001. Epub 2019 Jul 2. PMID: 31383290.


3: Okatan EN, Olgar Y, Tuncay E, Turan B. Azoramide improves mitochondrial dysfunction in palmitate-induced insulin resistant H9c2 cells. Mol Cell Biochem. 2019 Nov;461(1-2):65-72. doi: 10.1007/s11010-019-03590-z. Epub 2019 Jul 20. PMID: 31327095.


4: Ke M, Chong CM, Zeng H, Huang M, Huang Z, Zhang K, Cen X, Lu JH, Yao X, Qin D, Su H. Azoramide protects iPSC-derived dopaminergic neurons with PLA2G6 D331Y mutation through restoring ER function and CREB signaling. Cell Death Dis. 2020 Feb 18;11(2):130. doi: 10.1038/s41419-020-2312-8. PMID: 32071291; PMCID: PMC7028918.


5: Ruan B, Zhu Z, Yan Z, Yang W, Zhai D, Wang L, Ye Z, Lu H, Xiang A, Liang J, Jiang Y, Xu C, Wang Z, Wei M, Lei X, Cao X, Lu Z. Azoramide, a novel regulator, favors adipogenesis against osteogenesis through inhibiting the GLP-1 receptor- PKA-β-catenin pathway. Stem Cell Res Ther. 2018 Mar 9;9(1):57. doi: 10.1186/s13287-018-0771-y. PMID: 29523188; PMCID: PMC5845182.


6: Guillen C. Azoramide: a new drug for the treatment of type 2 diabetes? Ann Transl Med. 2016 Oct;4(Suppl 1):S45. doi: 10.21037/atm.2016.10.18. PMID: 27868013; PMCID: PMC5104614.


7: Fu S, Yalcin A, Lee GY, Li P, Fan J, Arruda AP, Pers BM, Yilmaz M, Eguchi K, Hotamisligil GS. Phenotypic assays identify azoramide as a small-molecule modulator of the unfolded protein response with antidiabetic activity. Sci Transl Med. 2015 Jun 17;7(292):292ra98. doi: 10.1126/scitranslmed.aaa9134. PMID: 26084805; PMCID: PMC5063051.


8: Lin G, Tepe B, McGrane G, Tipon RC, Croft G, Panwala L, Hope A, Liang AJH, Zuo Z, Byeon SK, Wang L, Pandey A, Bellen HJ. Exploring therapeutic strategies for infantile neuronal axonal dystrophy (INAD/PARK14). Elife. 2023 Jan 16;12:e82555. doi: 10.7554/eLife.82555. PMID: 36645408; PMCID: PMC9889087.


9: Walenna NF, Kurihara Y, Chou B, Ishii K, Soejima T, Hiromatsu K. Chlamydia pneumoniae infection-induced endoplasmic reticulum stress causes fatty acid- binding protein 4 secretion in murine adipocytes. J Biol Chem. 2020 Feb 28;295(9):2713-2723. doi: 10.1074/jbc.RA119.010683. Epub 2020 Jan 28. PMID: 31992597; PMCID: PMC7049972.


10: Kurihara Y, Walenna NF, Ishii K, Soejima T, Chou B, Yoshimura M, Ozuru R, Shimizu A, Itoh R, Furuhashi M, Hotamisligil GS, Hiromatsu K. Chlamydia pneumoniae Lung Infection in Mice Induces Fatty Acid-Binding Protein 4-Dependent White Adipose Tissue Pathology. J Immunol. 2023 Apr 15;210(8):1086-1097. doi: 10.4049/jimmunol.2200601. PMID: 36883861.