Description
Arsthinol is an antiprotozoal agent which may have anti-cancer activity. It was found that arsthinol, a trivalent organoarsenic compound (dithiarsolane), has been active in vitro on leukemia cell lines and offers a better therapeutic index than arsenic trioxide, as estimated by the ratio LD50/IC50. Arsthinol induced growth inhibition of NB4 cells at lower concentration (IC50 (concentration inhibiting growth by 50%) = 0.78 +/- 0.08 micromol/l after 24 h) than As(2)O(3) (IC50 = 1.60 +/- 0.23 micromol/l after 24 h) or melarsoprol (IC50 = 1.44 +/- 0.08 micromol/l after 24 h). Arsthinol-cyclodextrin complex demonstrated to have was more effective than arsenic trioxide (As2O3) and melarsoprol on the U87 MG cell line. Importantly, in the in vivo study, significant antitumor activity against heterotopic xenografts was observed after i.p. administration.
Synonyms
Arsthinenol; Arsthinol; Balarsen; Mercaptoarsenol
IUPAC Name
N-(2-hydroxy-5-(4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl)phenyl)acetamide
Molecular Formula
C11H14AsNO3S2
Canonical SMILES
OC1=CC=C([As](S2)SCC2CO)C=C1NC(C)=O
InChI
InChI=1S/C11H14AsNO3S2/c1-7(15)13-10-4-8(2-3-11(10)16)12-17-6-9(5-14)18-12/h2-4,9,14,16H,5-6H2,1H3,(H,13,15)
InChI Key
MRUDSZSRLQAPOG-UHFFFAOYSA-N
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Storage
Dry, dark and at 0-4 °C for short term (days to weeks) or -20 °C for long term (months to years).
Biological Target
Arsthinol is an antiprotozoal agent which may have anti-cancer activity.
Drug Formulation
This drug may be formulated in DMSO
Elemental Analysis
C, 38.04; H, 4.06; As, 21.57; N, 4.03; O, 13.82; S, 18.46
HS Tariff Code
2934.99.9001
In Vitro Activity
Arsthinol induced growth inhibition of NB4 cells at lower concentration (IC50 (concentration inhibiting growth by 50%) = 0.78 +/- 0.08 micromol/l after 24 h) than As(2)O(3) (IC50 = 1.60 +/- 0.23 micromol/l after 24 h) or melarsoprol (IC50 = 1.44 +/- 0.08 micromol/l after 24 h). When formulated as nanosuspension, arsthinol remained cytotoxic (IC50 = 1.33 +/- 0.30 micromol/l after 24 h). This formulation also reduced the drug's access to the brain (C(max) = 0.03 micromol/g) whereas bone marrow concentrations remained very high (C(max) = 2 micromol/g). In conclusion, nanosuspensions of arsthinol could be proposed for further studies in the treatment of acute promyelocytic leukaemia.
Reference: J Pharm Pharmacol. 2009 Oct;61(10):1295-301. https://pubmed.ncbi.nlm.nih.gov/19814860/
In Vivo Activity
During the treatment of the tumor-bearing mice, doses of 65% of the MTD for administration of i.p. STB*RAMEβCD (arsthinol-cyclodextrin complex), i.p. As2O3 and oral As2O3 were chosen for experiments. Compared with the control group, the average tumor volume increases more slowly after i.p. administration of As2O3 or STB*HPβCD. The differences between these two groups (i.e., As2O3 i.p. and STB*HPβCD i.p.) are significant (p = 0.049, log-rank [Mantel Cox] test). The median survival after As2O3 i.p. treatment was 15 days a very near that of the control group (14 days), whereas survival after STB*HPβCD i.p. treatment reached 21 days and was statistically different from that of the other groups (p < 0.05). The in vivo study did not show any signs of toxicity, and a significant antitumor activity after i.p. administration was observed.
Reference: Eur J Pharm Biopharm. 2013 Nov;85(3 Pt A):560-8. https://pubmed.ncbi.nlm.nih.gov/23831266/
Shipping
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.
Stock Solution Storage
0-4 °C for short term (days to weeks), or -20 °C for long term (months).
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