MedKoo Biosciences

O304
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 555641

CAS#: 1261289-04-6

Description: O-304 is a pan-activator of AMP-activated protein kinase (AMPK). It increases levels of phosphorylated AMPK (pAMPK) without reducing cellular ATP. O304 improves glucose homeostasis and microvascular perfusion in mice and type 2 diabetes patients.

Chemical Structure

O304

CAS# 1261289-04-6

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 555641
Name: O304
CAS#: 1261289-04-6
Chemical Formula: C16H11Cl2N3O2S
Exact Mass: 378.99
Molecular Weight: 380.243
Elemental Analysis: C, 50.54; H, 2.92; Cl, 18.65; N, 11.05; O, 8.42; S, 8.43

Price and Availability

Size	Price	Availability
100mg	USD 950
200mg	USD 1450
500mg	USD 2950	2 Weeks
1g	USD 4250	2 Weeks
2g	USD 6950	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: O-304; O 304; O304;

IUPAC/Chemical Name: 4-chloro-N-[2-[(4-chlorophenyl)methyl]-2,3-dihydro-3-oxo-1,2,4-thiadiazol-5-yl]-benzamide

InChi Key: WEDWLYRQKUTOAX-UHFFFAOYSA-N

InChi Code: InChI=1S/C16H11Cl2N3O2S/c17-12-5-1-10(2-6-12)9-21-16(23)20-15(24-21)19-14(22)11-3-7-13(18)8-4-11/h1-8H,9H2,(H,19,20,22,23)

SMILES Code: O=C(NC(SN1CC2=CC=C(Cl)C=C2)=NC1=O)C3=CC=C(Cl)C=C3

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

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	O-304 is a first-in-class, orally available pan-AMPK activator.
In vitro activity:	Firstly, HKC-8 cells, a renal proximal tubular cell line, were pretreated with O304, followed by administration of D-gal. Western blot analyses showed that the expressional levels of p-AMPK, AMPK, CPT1A and ACOX1 were significantly inhibited by D-gal, but restored after O304 treatment (Figures 7A–F). Besides, the results of quantitative real-time PCR showed that O304 reversed the downregulation of PPARα and ACOX1 induced by D-Gal (Figures 7G,H). In addition, Nile red staining also showed that the accumulation of fat induced by D-Gal was also inhibited by O304 treatment. (Figure 7I). All these results confirmed that O304 could promote fatty acid metabolism in vitro. Reference: Front Pharmacol. 2022 Mar 2;13:836496. https://pubmed.ncbi.nlm.nih.gov/35308246/
In vivo activity:	Moreover, like exercise, O304 activated AMPK in the heart, increased cardiac glucose uptake, reduced cardiac glycogen levels, and improved left ventricular stroke volume in mice, but it did not increase heart weight in mice or rats. Thus, O304 exhibits a great potential as a novel drug to treat T2D and associated cardiovascular complications. Reference: JCI Insight. 2018 Jun 21;3(12):e99114. https://pubmed.ncbi.nlm.nih.gov/29925691/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	10.0	26.30
	DMSO	20.0	52.60
	DMSO:PBS (pH 7.2) (1:30)	0.0	0.08

Preparing Stock Solutions

The following data is based on the product molecular weight 380.243000000000000000000000000000 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. Zhu M, Shen W, Li J, Jia N, Xiong Y, Miao J, Xie C, Chen Q, Shen K, Meng P, Li X, Wu Q, Zhou S, Wang M, Kong Y, Zhou L. AMPK Activator O304 Protects Against Kidney Aging Through Promoting Energy Metabolism and Autophagy. Front Pharmacol. 2022 Mar 2;13:836496. doi: 10.3389/fphar.2022.836496. PMID: 35308246; PMCID: PMC8924548. 2. López-Pérez A, Norlin S, Steneberg P, Remeseiro S, Edlund H, Hörnblad A. Pan-AMPK activator O304 prevents gene expression changes and remobilisation of histone marks in islets of diet-induced obese mice. Sci Rep. 2021 Dec 23;11(1):24410. doi: 10.1038/s41598-021-03567-3. PMID: 34949756; PMCID: PMC8702551. 3. Das V, Basovich MB, Kroin JS, Buvanendran A, McCarthy RJ. Analgesic Effectiveness and Dorsal Root Ganglia Protein Modulation of a Peripheral Adenosine Monophosphate Kinase Alpha Activator (O304) Following Lumbar Disk Puncture in the Mouse. Anesth Analg. 2022 Dec 1;135(6):1293-1303. doi: 10.1213/ANE.0000000000006228. Epub 2022 Oct 6. PMID: 36201356. 4. Steneberg P, Lindahl E, Dahl U, Lidh E, Straseviciene J, Backlund F, Kjellkvist E, Berggren E, Lundberg I, Bergqvist I, Ericsson M, Eriksson B, Linde K, Westman J, Edlund T, Edlund H. PAN-AMPK activator O304 improves glucose homeostasis and microvascular perfusion in mice and type 2 diabetes patients. JCI Insight. 2018 Jun 21;3(12):e99114. doi: 10.1172/jci.insight.99114. PMID: 29925691; PMCID: PMC6124394.
In vitro protocol:	1. Zhu M, Shen W, Li J, Jia N, Xiong Y, Miao J, Xie C, Chen Q, Shen K, Meng P, Li X, Wu Q, Zhou S, Wang M, Kong Y, Zhou L. AMPK Activator O304 Protects Against Kidney Aging Through Promoting Energy Metabolism and Autophagy. Front Pharmacol. 2022 Mar 2;13:836496. doi: 10.3389/fphar.2022.836496. PMID: 35308246; PMCID: PMC8924548. 2. López-Pérez A, Norlin S, Steneberg P, Remeseiro S, Edlund H, Hörnblad A. Pan-AMPK activator O304 prevents gene expression changes and remobilisation of histone marks in islets of diet-induced obese mice. Sci Rep. 2021 Dec 23;11(1):24410. doi: 10.1038/s41598-021-03567-3. PMID: 34949756; PMCID: PMC8702551.
In vivo protocol:	1. Das V, Basovich MB, Kroin JS, Buvanendran A, McCarthy RJ. Analgesic Effectiveness and Dorsal Root Ganglia Protein Modulation of a Peripheral Adenosine Monophosphate Kinase Alpha Activator (O304) Following Lumbar Disk Puncture in the Mouse. Anesth Analg. 2022 Dec 1;135(6):1293-1303. doi: 10.1213/ANE.0000000000006228. Epub 2022 Oct 6. PMID: 36201356. 2. Steneberg P, Lindahl E, Dahl U, Lidh E, Straseviciene J, Backlund F, Kjellkvist E, Berggren E, Lundberg I, Bergqvist I, Ericsson M, Eriksson B, Linde K, Westman J, Edlund T, Edlund H. PAN-AMPK activator O304 improves glucose homeostasis and microvascular perfusion in mice and type 2 diabetes patients. JCI Insight. 2018 Jun 21;3(12):e99114. doi: 10.1172/jci.insight.99114. PMID: 29925691; PMCID: PMC6124394.

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1: Das V, Kroin JS, Moric M, McCarthy RJ, Buvanendran A. AMP-activated protein kinase (AMPK) activator drugs reduce mechanical allodynia in a mouse model of low back pain. Reg Anesth Pain Med. 2019 Sep 20. pii: rapm-2019-100839. doi: 10.1136/rapm-2019-100839. [Epub ahead of print] PubMed PMID: 31541009. 2: Das V, Kroin JS, Moric M, McCarthy RJ, Buvanendran A. Antihyperalgesia effect of AMP-activated protein kinase (AMPK) activators in a mouse model of postoperative pain. Reg Anesth Pain Med. 2019 Jun 21. pii: rapm-2019-100651. doi: 10.1136/rapm-2019-100651. [Epub ahead of print] PubMed PMID: 31229963. 3: D'Souza N, Balyasnikova S, Tudyka V, Lord A, Shaw A, Abulafi M, Tekkis P, Brown G. Variation in landmarks for the rectum: an MRI study. Colorectal Dis. 2018 Oct;20(10):O304-O309. doi: 10.1111/codi.14398. Epub 2018 Sep 26. PubMed PMID: 30176118. 4: Steneberg P, Lindahl E, Dahl U, Lidh E, Straseviciene J, Backlund F, Kjellkvist E, Berggren E, Lundberg I, Bergqvist I, Ericsson M, Eriksson B, Linde K, Westman J, Edlund T, Edlund H. PAN-AMPK activator O304 improves glucose homeostasis and microvascular perfusion in mice and type 2 diabetes patients. JCI Insight. 2018 Jun 21;3(12). pii: 99114. doi: 10.1172/jci.insight.99114. eCollection 2018 Jun 21. PubMed PMID: 29925691; PubMed Central PMCID: PMC6124394. 5: Riad NM, Zlotos DP, Holzgrabe U. Crystal structure of 5,11-di-hydro-pyrido[2,3-b][1,4]benzodiazepin-6-one. Acta Crystallogr E Crystallogr Commun. 2015 Apr 11;71(Pt 5):o304-5. doi: 10.1107/S2056989015006817. eCollection 2015 May 1. PubMed PMID: 25995917; PubMed Central PMCID: PMC4420050. 6: Ohno K, Fujihara T, Nagasawa A. An ortho-rhom-bic polymorph of N (1),N (4)-diphenyl-3,6-bis-(phenyl-imino)-cyclo-hexa-1,4-diene-1,4-di-amine. Acta Crystallogr Sect E Struct Rep Online. 2014 Mar 29;70(Pt 4):o495-6. doi: 10.1107/S1600536814006254. eCollection 2014 Apr 1. PubMed PMID: 24826185; PubMed Central PMCID: PMC3998558. 7: Yoon YK, Ali MA, Tan SC, Rosli MM, Razak IA. 3-{5-Eth-oxy-carbonyl-1-[3-(2-oxopyrrol-idin-1-yl)prop-yl]-1H-benzimidazol-2-yl}b enzoic acid. Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 1;69(Pt 2):o304. doi: 10.1107/S1600536813001116. Epub 2013 Jan 31. PubMed PMID: 23424569; PubMed Central PMCID: PMC3569823. 8: Yu Y. 7-Chloro-6,8-dinitro-quinazolin-4(3H)-one acetic acid monosolvate. Acta Crystallogr Sect E Struct Rep Online. 2012 Feb 1;68(Pt 2):o304. doi: 10.1107/S1600536811055735. Epub 2012 Jan 7. PubMed PMID: 22346942; PubMed Central PMCID: PMC3274997. 9: Loh WS, Fun HK, Sarveswari S, Vijayakumar V, Reddy BP. 6-Chloro-3-[5-(4-fluoro-phen-yl)-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl]-2-methyl-4 -phenyl-quinoline. Acta Crystallogr Sect E Struct Rep Online. 2010 Jan 9;66(Pt 2):o304. doi: 10.1107/S1600536810000218. PubMed PMID: 21579737; PubMed Central PMCID: PMC2979872. 10: Zhang M, Yuan XY, Liu XM. 2,2-Dimethyl-5-triphenyl-methyl-1,3-dioxane. Acta Crystallogr Sect E Struct Rep Online. 2009 Jan 14;65(Pt 2):o304. doi: 10.1107/S1600536809000294. PubMed PMID: 21581913; PubMed Central PMCID: PMC2968387. 11: Portalone G, Colapietro M. Nicotinohydrazide. Acta Crystallogr Sect E Struct Rep Online. 2007 Dec 18;64(Pt 1):o304. doi: 10.1107/S1600536807066561. PubMed PMID: 21200868; PubMed Central PMCID: PMC2915352. 12: Batsanov AS, Goeta AE, Howard JA, Soto B, Au-Alvarez O. 2-(4-Chloroanilino)- and 2-(4-methoxyanilino)-1,2-diphenylethanone. Acta Crystallogr C. 2006 May;62(Pt 5):o304-6. Epub 2006 Apr 29. PubMed PMID: 16679611.

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