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MedKoo Cat#: 562730 | Name: Methiothepin Maleate
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Description:

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

Methiothepin Maleate is an inhibitor of HCV infection and cell-to-cell transmission that acts by targeting the HCV E2 glycoprotein.

Chemical Structure

Methiothepin Maleate
Methiothepin Maleate
CAS#19728-88-2

Theoretical Analysis

MedKoo Cat#: 562730

Name: Methiothepin Maleate

CAS#: 19728-88-2

Chemical Formula: C24H28N2O4S2

Exact Mass: 472.1490

Molecular Weight: 472.62

Elemental Analysis: C, 60.99; H, 5.97; N, 5.93; O, 13.54; S, 13.57

Price and Availability

Size Price Availability Quantity
25mg USD 285.00 2 weeks
50mg USD 500.00 2 weeks
100mg USD 850.00 2 weeks
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Related CAS #
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Synonym
Methiothepin Maleate; Methiothepin Maleate salt; Metitepine; HCV-IN-281816; HCV IN 281816; HCVIN281816;
IUPAC/Chemical Name
1-Methyl-4-(3-methylsulfanyl-5,6-dihydrobenzo[b][1]benzothiepin-5-yl)piperazine Maleate
InChi Key
GEZNFWLEZPDMLH-BTJKTKAUSA-N
InChi Code
InChI=1S/C20H24N2S2.C4H4O4/c1-21-11-13-22(14-12-21)24-19-6-4-3-5-16(19)7-8-17-9-10-18(23-2)15-20(17)24;5-3(6)1-2-4(7)8/h3-5,7-10,15H,6,11-14H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-
SMILES Code
CSC1=CC=C2C=CC3=CC=CCC3=S(N4CCN(C)CC4)C2=C1.O=C(O)/C=C\C(O)=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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methiothepin Maleate is an inhibitor of HCV infection.
In vitro activity:
This study verified apoptotic cell death in prostate cancer cell lines after treatment with methiothepin mesylate (MET), an antagonist for serotonin receptor 5-HT1. MET induced hydrogen peroxide (H2O2) production and mitochondrial Ca2+ overload. Moreover, MET induced changes in the expression of proteins associated with endoplasmic reticulum stress, autophagy, and mitochondrial membrane potential. Reference: Free Radic Biol Med. 2020 Apr;150:12-22. https://pubmed.ncbi.nlm.nih.gov/32035100/
In vivo activity:
Fluorescence microscopy revealed that methiothepin treatment for 48 h in zebrafish embryos inhibited fluorescence signals in the inner optic circle, dorsal longitudinal vein, yolk sac, and caudal vein, compared to those of the solvent-treated control (Figure 7). These results suggest that methiothepin may have anti-angiogenic effects in the tumor microenvironment and contribute anti-metastatic functions in ovarian cancer cells. Reference: Pharmaceutics. 2020 Jul 20;12(7):686. https://pubmed.ncbi.nlm.nih.gov/32698407/
Solvent mg/mL mM comments
Solubility
DMF 30.0 63.48
DMSO 30.0 63.48
DMSO:PBS (pH 7.2) (1:2) 0.3 0.70
Ethanol 0.5 1.06
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 472.62 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. Yang C, Song G, Lim W. Methiothepin mesylate causes apoptosis of human prostate cancer cells by mediating oxidative stress and mitochondrial dysfunction. Free Radic Biol Med. 2020 Apr;150:12-22. doi: 10.1016/j.freeradbiomed.2020.01.187. Epub 2020 Feb 5. PMID: 32035100. 2. Pauwels PJ, Palmier C. Inhibition by 5-HT of forskolin-induced cAMP formation in the renal opossum epithelial cell line OK: mediation by a 5-HT1B like receptor and antagonism by methiothepin. Neuropharmacology. 1994 Jan;33(1):67-75. doi: 10.1016/0028-3908(94)90098-1. PMID: 7910388. 3. Lee JY, Yang C, Lim W, Song G. Methiothepin Suppresses Human Ovarian Cancer Cell Growth by Repressing Mitochondrion-Mediated Metabolism and Inhibiting Angiogenesis In Vivo. Pharmaceutics. 2020 Jul 20;12(7):686. doi: 10.3390/pharmaceutics12070686. PMID: 32698407; PMCID: PMC7407284. 4. Varanasi S, Chi J, Stephens RL Jr. Methiothepin attenuates gastric secretion and motility effects of vagal stimulants at the dorsal vagal complex. Eur J Pharmacol. 2002 Feb 1;436(1-2):67-73. doi: 10.1016/s0014-2999(01)01579-5. PMID: 11834248.
In vitro protocol:
1. Yang C, Song G, Lim W. Methiothepin mesylate causes apoptosis of human prostate cancer cells by mediating oxidative stress and mitochondrial dysfunction. Free Radic Biol Med. 2020 Apr;150:12-22. doi: 10.1016/j.freeradbiomed.2020.01.187. Epub 2020 Feb 5. PMID: 32035100. 2. Pauwels PJ, Palmier C. Inhibition by 5-HT of forskolin-induced cAMP formation in the renal opossum epithelial cell line OK: mediation by a 5-HT1B like receptor and antagonism by methiothepin. Neuropharmacology. 1994 Jan;33(1):67-75. doi: 10.1016/0028-3908(94)90098-1. PMID: 7910388.
In vivo protocol:
1. Lee JY, Yang C, Lim W, Song G. Methiothepin Suppresses Human Ovarian Cancer Cell Growth by Repressing Mitochondrion-Mediated Metabolism and Inhibiting Angiogenesis In Vivo. Pharmaceutics. 2020 Jul 20;12(7):686. doi: 10.3390/pharmaceutics12070686. PMID: 32698407; PMCID: PMC7407284. 2. Varanasi S, Chi J, Stephens RL Jr. Methiothepin attenuates gastric secretion and motility effects of vagal stimulants at the dorsal vagal complex. Eur J Pharmacol. 2002 Feb 1;436(1-2):67-73. doi: 10.1016/s0014-2999(01)01579-5. PMID: 11834248.
1: Miyazato M, Kaiho Y, Kamo I, Chancellor MB, Sugaya K, de Groat WC, Yoshimura N. Effect of duloxetine, a norepinephrine and serotonin reuptake inhibitor, on sneeze-induced urethral continence reflex in rats. Am J Physiol Renal Physiol. 2008 Jul;295(1):F264-71. doi: 10.1152/ajprenal.90241.2008. Epub 2008 May 14. PubMed PMID: 18480175; PubMed Central PMCID: PMC2494509. 2: Hudecki MS, Pollina CM, Bhargava AK, Hudecki RS. Screening of antiserotoninergic drugs with the genetically dystrophic chicken. Arch Neurol. 1980 Sep;37(9):545-50. PubMed PMID: 6448038. 3: Masala A, Devilla L, Delitala G, Alagna S, Rovasio PP, Capitanio GL. Action of the serotoninergic and dopaminergic antagonist methiothepin maleate on serum prolactin and growth hormone levels in man. Panminerva Med. 1979 Apr-Jun;21(2):65-8. PubMed PMID: 554040.