Agomelatine | Valdoxan | Thymanax | Melitor | AGO-178 | S-20098 | CAS#138112-76-2

MedKoo Cat#: 315211 | Name: Agomelatine

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Description:

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

Agomelatine (BAN, rINN; trade names Valdoxan, Melitor, Thymanax) is a melatonergic antidepressant developed by the pharmaceutical company Servier. It is marketed for the treatment of major depressive disorder and has been reported to not produce discontinuation syndrome and have no sexual side effects compared to SSRIs, SNRIs and the older tricyclic antidepressants. Agomelatine may also have positive effects on sleep. Agomelatine is a melatonergic agonist (MT1 and MT2 receptors) and 5-HT2C antagonist. Binding studies indicate that it has no effect on monoamine uptake and no affinity for α, β adrenergic, histaminergic, cholinergic, dopaminergic and benzodiazepine receptors.

Chemical Structure

Agomelatine

CAS#138112-76-2 (free base)

Theoretical Analysis

MedKoo Cat#: 315211

Name: Agomelatine

CAS#: 138112-76-2 (free base)

Chemical Formula: C15H17NO2

Exact Mass: 243.1259

Molecular Weight: 243.31

Elemental Analysis: C, 74.05; H, 7.04; N, 5.76; O, 13.15

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 350.00	2 Weeks
5g	USD 650.00	2 Weeks
10g	USD 950.00	2 Weeks

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Related CAS #

138112-76-2 (free base) 1176316-99-6 (HCl)

Synonym

Valdoxan; Thymanax; Melitor; AGO 178; AGO-178; AGO178; N-(2-(7-methoxy-1-naphthyl)ethyl)acetamide; S 20098; S-20098; S20098.

IUPAC/Chemical Name

N-[2-(7-methoxynaphthalen-1-yl)ethyl]acetamide

InChi Key

YJYPHIXNFHFHND-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H17NO2/c1-11(17)16-9-8-13-5-3-4-12-6-7-14(18-2)10-15(12)13/h3-7,10H,8-9H2,1-2H3,(H,16,17)

SMILES Code

CC(=O)NCCC1=CC=CC2=C1C=C(C=C2)OC

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Agomelatine (S-20098) is a specific agonist of MT1 and MT2 receptors with Kis of 0.1, 0.06, 0.12, and 0.27 nM for CHO-hMT1, HEK-hMT1, CHO-hMT2, and HEK-hMT2, respectively. It is a selective 5-HT2C receptor antagonist with pKis of 6.4 and 6.2 at native (porcine) and cloned, human 5-HT2C receptors, respectively.

In vitro activity:

The half maximal inhibitory concentration (IC50) value of cisplatin was calculated with free Quest Graph™ IC50 Calculator (AAT Bioquest, Inc., California, USA). After determination of IC50 value of cisplatin as 5.5 µM, cells were co-treated with cisplatin (5.5 µM) and agomelatine in different concentrations (1 µM, 2 µM, 4 µM, 8 µM and 16 µM) (Fig. 1) (Supp material 1. Fig. S1). Although agomelatine 1 µM, 2 µM, 4 µM did not affect cisplatin-induced cellular death, 8 µM and 16 µM concentrations of agomelatine significantly rescued cellular loss against cisplatin toxicity (Supp material 3.1, p < 0.001) (Fig. 1). Reference: Metab Brain Dis. 2021 Feb;36(2):339-349. https://pubmed.ncbi.nlm.nih.gov/33165734/

In vivo activity:

In the present study, the effects of Ago (Agomelatine) treatment during the early stage of AD progression on anxiety, depressive-like behavior, spatial memory as well as Aβ-induced cellular loss in crucial brain structures in an icvAβ1–42 rat model was studied. The results showed that Ago exerted beneficial effects on concomitant behavioral impairments and caused area-specific neuroprotection. Both treatments approaches applied (Ago being administered during the early or the late stage of AD) successfully attenuated icvAβ1–42-induced accumulation of this toxic peptide in the FC and the hippocampus mainly through decreasing the concentration of the γ-secretase in the hippocampus. Reference: Physiol Behav. 2021 Jul 6:113525. https://pubmed.ncbi.nlm.nih.gov/34242671/

	Solvent	mg/mL	mM
Solubility
	DMSO	59.3	243.85
	DMF	30.0	123.30
	Ethanol	39.0	160.29
	Ethanol:PBS (pH 7.2) (1:1)	0.5	2.05

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 243.31 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. Cankara FN, Günaydın C, Çelik ZB, Şahin Y, Pekgöz Ş, Erzurumlu Y, Gülle K. Agomelatine confers neuroprotection against cisplatin-induced hippocampal neurotoxicity. Metab Brain Dis. 2021 Feb;36(2):339-349. doi: 10.1007/s11011-020-00634-y. Epub 2020 Nov 9. PMID: 33165734. 2. Yao K, Zhao YF, Zu HB. Melatonin receptor stimulation by agomelatine prevents Aβ-induced tau phosphorylation and oxidative damage in PC12 cells. Drug Des Devel Ther. 2019 Jan 21;13:387-396. doi: 10.2147/DDDT.S182684. PMID: 30718944; PMCID: PMC6345325. 3. Ilieva K, Atanasova M, Atanasova D, Kortenska L, Tchekalarova J. Chronic agomelatine treatment alleviates icvAβ-induced anxiety and depressive-like behavior through affecting Aβ metabolism in the hippocampus in a rat model of Alzheimer's disease. Physiol Behav. 2021 Jul 6:113525. doi: 10.1016/j.physbeh.2021.113525. Epub ahead of print. PMID: 34242671. 4. Köse D, Yüksel TN, Halıcı Z, Çadırcı E, Gürbüz MA. The Effects of Agomelatine Treatment on Lipopolysaccharide-Induced Septic Lung Injuries in Rats. Eurasian J Med. 2021 Jun;53(2):127-131. doi: 10.5152/eurasianjmed.2021.20342. PMID: 34177296; PMCID: PMC8184031.

In vitro protocol:

In vivo protocol:

1. Ilieva K, Atanasova M, Atanasova D, Kortenska L, Tchekalarova J. Chronic agomelatine treatment alleviates icvAβ-induced anxiety and depressive-like behavior through affecting Aβ metabolism in the hippocampus in a rat model of Alzheimer's disease. Physiol Behav. 2021 Jul 6:113525. doi: 10.1016/j.physbeh.2021.113525. Epub ahead of print. PMID: 34242671. 2. Köse D, Yüksel TN, Halıcı Z, Çadırcı E, Gürbüz MA. The Effects of Agomelatine Treatment on Lipopolysaccharide-Induced Septic Lung Injuries in Rats. Eurasian J Med. 2021 Jun;53(2):127-131. doi: 10.5152/eurasianjmed.2021.20342. PMID: 34177296; PMCID: PMC8184031.

1: Kumar H, Sharma BM, Sharma B. Benefits of agomelatine in behavioral, neurochemical and blood brain barrier alterations in prenatal valproic acid induced autism spectrum disorder. Neurochem Int. 2015 Oct 20. pii: S0197-0186(15)30057-7. doi: 10.1016/j.neuint.2015.10.007. [Epub ahead of print] PubMed PMID: 26498253. 2: Avila A, Cardona X, Martin-Baranera M, Leon L, Caballol N, Millet P, Bello J. Agomelatine for Depression in Parkinson Disease: Additional Effect on Sleep and Motor Dysfunction. J Clin Psychopharmacol. 2015 Oct 5. [Epub ahead of print] PubMed PMID: 26444951. 3: Li M, Tang F, Xie F, Lv Y, Yu P, Liu Z, Cheng Z. Development and validation a LC-MS/MS method for the simultaneous determination of agomelatine and its metabolites, 7-desmethyl-agomelatine and 3-hydroxy-agomelatine in human plasma: Application to a bioequivalence study. J Chromatogr B Analyt Technol Biomed Life Sci. 2015 Oct 15;1003:60-6. doi: 10.1016/j.jchromb.2015.09.018. Epub 2015 Sep 18. PubMed PMID: 26409931. 4: Stuhec M, Oravecz R. Moclobemide as add-on therapy to agomelatine in a patient with treatment-resistant major depressive disorder: a psychopharmacological case. Wien Klin Wochenschr. 2015 Sep 24. [Epub ahead of print] PubMed PMID: 26404738. 5: Plasencia-García BO, Romero-Guillena SL, Quirós-López A, Ruiz-Doblado S. Agomelatine and migraine management: a successfully treated case series. Ther Adv Psychopharmacol. 2015 Aug;5(4):243-5. doi: 10.1177/2045125315584869. PubMed PMID: 26301081; PubMed Central PMCID: PMC4535043. 6: Montejo AL, Deakin J, Gaillard R, Harmer C, Meyniel F, Jabourian A, Gabriel C, Gruget C, Klinge C, MacFayden C, Milligan H, Mullings E, Goodwin G. Better sexual acceptability of agomelatine (25 and 50 mg) compared to escitalopram (20 mg) in healthy volunteers. A 9-week, placebo-controlled study using the PRSexDQ scale. J Psychopharmacol. 2015 Oct;29(10):1119-28. doi: 10.1177/0269881115599385. Epub 2015 Aug 12. PubMed PMID: 26268533. 7: Komaram RB, Nukala S, Palla J, Nambaru LR, Kasturi SM. A Comparative Study of Efficacy and Safety of Agomelatine and Escitalopram in Major Depressive Disorder. J Clin Diagn Res. 2015 Jun;9(6):VC05-VC08. doi: 10.7860/JCDR/2015/12371.6092. Epub 2015 Jun 1. PubMed PMID: 26266196; PubMed Central PMCID: PMC4525586. 8: Yeh TC, Kao LC, Tzeng NS, Kuo TB, Huang SY, Chang CC, Chang HA. Heart rate variability in major depressive disorder and after antidepressant treatment with agomelatine and paroxetine: Findings from the Taiwan Study of Depression and Anxiety (TAISDA). Prog Neuropsychopharmacol Biol Psychiatry. 2016 Jan 4;64:60-7. doi: 10.1016/j.pnpbp.2015.07.007. Epub 2015 Jul 26. PubMed PMID: 26216863. 9: Domotor E, Hermanne EF. [The temporal accuracy of agomelatine administration and comparison of antidepressant effect of agomelatine and escitalopram in major depression, a retrospective investigation at a psychiatric outpatient clinic]. Neuropsychopharmacol Hung. 2015 Jun;17(2):59-67. Hungarian. PubMed PMID: 26192899. 10: Pringle A, Bogdanovskaya M, Waskett P, Zacharia S, Cowen PJ, Harmer CJ. Does melatonin treatment change emotional processing? Implications for understanding the antidepressant mechanism of agomelatine. J Psychopharmacol. 2015 Oct;29(10):1129-32. doi: 10.1177/0269881115592341. Epub 2015 Jul 14. PubMed PMID: 26174133.