Synonym
Arsthinenol; Arsthinol; Balarsen; Mercaptoarsenol;
IUPAC/Chemical Name
N-(2-hydroxy-5-(4-(hydroxymethyl)-1,3,2-dithiarsolan-2-yl)phenyl)acetamide
InChi Key
MRUDSZSRLQAPOG-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
OC1=CC=C([As](S2)SCC2CO)C=C1NC(C)=O
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
Biological target:
Arsthinol is an antiprotozoal agent which may have anti-cancer activity.
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/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
0.0 |
0.00 |
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
347.28
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. Ajana I, Astier A, Gibaud S. Arsthinol nanosuspensions: pharmacokinetics and anti-leukaemic activity on NB4 promyelocytic leukaemia cells. J Pharm Pharmacol. 2009 Oct;61(10):1295-301. doi: 10.1211/jpp/61.10.0004. PMID: 19814860.
2. . Becherirat S, Lanhers MC, Socha M, Yemloul M, Astier A, Loboda C, Aniceto N, Gibaud S. The antitumor effects of an arsthinol-cyclodextrin complex in a heterotopic mouse model of glioma. Eur J Pharm Biopharm. 2013 Nov;85(3 Pt A):560-8. doi: 10.1016/j.ejpb.2013.06.021. Epub 2013 Jul 4. PMID: 23831266.
In vitro protocol:
1. Ajana I, Astier A, Gibaud S. Arsthinol nanosuspensions: pharmacokinetics and anti-leukaemic activity on NB4 promyelocytic leukaemia cells. J Pharm Pharmacol. 2009 Oct;61(10):1295-301. doi: 10.1211/jpp/61.10.0004. PMID: 19814860.
In vivo protocol:
1. . Becherirat S, Lanhers MC, Socha M, Yemloul M, Astier A, Loboda C, Aniceto N, Gibaud S. The antitumor effects of an arsthinol-cyclodextrin complex in a heterotopic mouse model of glioma. Eur J Pharm Biopharm. 2013 Nov;85(3 Pt A):560-8. doi: 10.1016/j.ejpb.2013.06.021. Epub 2013 Jul 4. PMID: 23831266.
1: Becherirat S, Lanhers MC, Socha M, Yemloul M, Astier A, Loboda C, Aniceto N, Gibaud S. The antitumor effects of an arsthinol-cyclodextrin complex in a heterotopic mouse model of glioma. Eur J Pharm Biopharm. 2013 Nov;85(3 Pt A):560-8. doi: 10.1016/j.ejpb.2013.06.021. Epub 2013 Jul 4. PMID: 23831266.
2: Ajana I, Astier A, Gibaud S. Speciation of arsenic in urine following intravenous administration of arsthinol in mice. Eur J Drug Metab Pharmacokinet. 2010 Sep;35(1-2):59-65. doi: 10.1007/s13318-010-0009-6. PMID: 21495268.
3: Ajana I, Astier A, Gibaud S. Arsthinol nanosuspensions: pharmacokinetics and anti-leukaemic activity on NB4 promyelocytic leukaemia cells. J Pharm Pharmacol. 2009 Oct;61(10):1295-301. doi: 10.1211/jpp/61.10.0004. PMID: 19814860.
4: Gibaud S, Astier A. Organoarséniés dérivés du 2-phényl- [1,3,2]dithiarsolane-4-yl)-méthanol (AsIII) à propriétés antileucémiques: des trypanosomicides aux anticancéreux [Organoarsenicals derived from 2-phenyl-[1,3,2]dithiarsolan-4-yl)-methanol (AsIII) with antileukaemic properties: from trypanosomicides to anticancer drugs]. Ann Pharm Fr. 2007 May;65(3):162-8. French. doi: 10.1016/s0003-4509(07)90031-0. PMID: 17489071.
5: Hiskey CF, Cantwell FF. Ultraviolet spectrum correlations with the conjugate acid-base species of acetarsone and arsthinol. J Pharm Sci. 1968 Dec;57(12):2105-11. doi: 10.1002/jps.2600571217. PMID: 5708352.
6: GOLDMAN L, PRESTON RH, MEISTER M. Arsthinol (Balarsen) in dermatology. Dermatologica. 1956 Dec;113(6):369-74. doi: 10.1159/000256212. PMID: 13414432.
7: BROWN CH, GEBHART WF, REICH A. Intestinal amebiasis; incidence, symptoms, and treatment with arsthinol (balarsen). J Am Med Assoc. 1956 Feb 4;160(5):360-3. doi: 10.1001/jama.1956.02960400018005. PMID: 13278204.
8: KUHN BH. Balarsen: a new oral arsenical in the treatment of pustular bacterid; case report. W V Med J. 1956 Feb;52(2):48-9. PMID: 13291781.
9: RAVINA A. Une nouvelle médication de l'amibiase, le mercaptoarsenical [A new amebiasis medication, the mercapto-arsenical]. Presse Med. 1956 Jan 7;64(2):29-30. French. PMID: 13289703.
10: LOUGHLIN EH, JOSEPH AA, MULLIN WG. The treatment of amebiasis with arsthinol (N.N.R) (balarsen). Antibiot Chemother (Northfield). 1954 Jun;4(6):647-8. PMID: 24543096.
11: MOST H, VAN ASSENDELFT F, MILLER J, MILBERG MB, ROSSMAN EB. Arsthinol (balarsen), a new trivalent arsenical for the treatment of intestinal amebiasis and other intestinal protozoa. Am J Trop Med Hyg. 1954 Mar;3(2):262-5. PMID: 13138828.
12: NEW and nonofficial remedies; arsthinol. J Am Med Assoc. 1953 Jun 6;152(6):531. PMID: 13044569.
13: LINDNER E. Obrat na hlavi6cku p6ri poloze podélné koncem pánevnäm [Rotation of the head in pelvic presentation]. Cesk Gynekol. 1953 Jun;18(3):222-31. Undetermined Language. PMID: 13082581.
