IUPAC/Chemical Name
Bis(3-nitrophenyl) disulphide
InChi Key
ODOFDWDUSSFUMN-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H8N2O4S2/c15-13(16)9-3-1-5-11(7-9)19-20-12-6-2-4-10(8-12)14(17)18/h1-8H
SMILES Code
O=[N+](C1=CC(SSC2=CC=CC([N+]([O-])=O)=C2)=CC=C1)[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:
Nitrophenide is a bioactive chemical.
In vitro activity:
Treatment of E. tenella-infected chickens with nitrophenide resulted in a 90% reduction in oocyst shedding. The remaining oocysts displayed significant morphological abnormalities and were largely incapable of further development. Isolated oocysts from chickens treated with nitrophenide exhibited a dose-dependent reduction in mannitol, suggesting in vivo inhibition of parasite mannitol biosynthesis.
Reference: J Parasitol. 2001 Dec;87(6):1441-8. https://pubmed.ncbi.nlm.nih.gov/11780835/
In vivo activity:
Nitrophenide-mediated inhibition of MIPDH was observed in vitro using purified native enzyme. These data suggest that nitrophenide blocks parasite development at the sexual stages by targeting M1PDH.
Reference: J Parasitol. 2001 Dec;87(6):1441-8. https://pubmed.ncbi.nlm.nih.gov/11780835/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
308.33
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:
Allocco JJ, Nare B, Myers RW, Feiglin M, Schmatz DM, Profous-Juchelka H. Nitrophenide (Megasul) blocks Eimeria tenella development by inhibiting the mannitol cycle enzyme mannitol-1-phosphate dehydrogenase. J Parasitol. 2001 Dec;87(6):1441-8. doi: 10.1645/0022-3395(2001)087[1441:NMBETD]2.0.CO;2. PMID: 11780835.
In vitro protocol:
Allocco JJ, Nare B, Myers RW, Feiglin M, Schmatz DM, Profous-Juchelka H. Nitrophenide (Megasul) blocks Eimeria tenella development by inhibiting the mannitol cycle enzyme mannitol-1-phosphate dehydrogenase. J Parasitol. 2001 Dec;87(6):1441-8. doi: 10.1645/0022-3395(2001)087[1441:NMBETD]2.0.CO;2. PMID: 11780835.
In vivo protocol:
Allocco JJ, Nare B, Myers RW, Feiglin M, Schmatz DM, Profous-Juchelka H. Nitrophenide (Megasul) blocks Eimeria tenella development by inhibiting the mannitol cycle enzyme mannitol-1-phosphate dehydrogenase. J Parasitol. 2001 Dec;87(6):1441-8. doi: 10.1645/0022-3395(2001)087[1441:NMBETD]2.0.CO;2. PMID: 11780835.
1: Wyatt TT, van Leeuwen MR, Wösten HA, Dijksterhuis J. Mannitol is essential for the development of stress-resistant ascospores in Neosartorya fischeri (Aspergillus fischeri). Fungal Genet Biol. 2014 Mar;64:11-24. doi: 10.1016/j.fgb.2013.12.010. Epub 2014 Jan 9. PubMed PMID: 24412483.
2: Zimnicka M, Wileńska B, Sekiguchi O, Uggerud E, Danikiewicz W. Reactions of nitrophenide and halonitrophenide ions with acrylonitrile and alkyl acrylates in the gas phase: addition to the carbonyl group versus Michael addition. J Mass Spectrom. 2012 Apr;47(4):425-38. doi: 10.1002/jms.2042. PubMed PMID: 22689618.
3: Danikiewicz W, Bieńkowski T, Kozłowska D, Zimnicka M. Aromatic nucleophilic substitution (SNAr) reactions of 1,2- and 1,4-halonitrobenzenes and 1,4-dinitrobenzene with carbanions in the gas phase. J Am Soc Mass Spectrom. 2007 Aug;18(8):1351-63. Epub 2007 Apr 25. PubMed PMID: 17555982.
4: Danikiewicz W, Bieńkowski T, Poddebniak D. Generation and reactions of anionic sigma-adducts of 1,3-dinitrobenzene and 1,3,5-trinitrobenzene with carbanions in a gas phase, using an electrospray ion source as the chemical reactor. J Am Soc Mass Spectrom. 2004 Jun;15(6):927-33. PubMed PMID: 15144984.
5: Allocco JJ, Nare B, Myers RW, Feiglin M, Schmatz DM, Profous-Juchelka H. Nitrophenide (Megasul) blocks Eimeria tenella development by inhibiting the mannitol cycle enzyme mannitol-1-phosphate dehydrogenase. J Parasitol. 2001 Dec;87(6):1441-8. PubMed PMID: 11780835.
6: Schmatz DM. The mannitol cycle in Eimeria. Parasitology. 1997;114 Suppl:S81-9. Review. PubMed PMID: 9309770.
7: HUANG TC, MARSHAK RR, McCAY CM. Nitrophenide and other anticoccidial studies with dogs. J Am Vet Med Assoc. 1954 Mar;124(924):212-4. PubMed PMID: 13142958.
8: GARDINER JL, FARR MM, WEHR EE. The coccidiostatic action of nitrophenide on Eimeria tenella. J Parasitol. 1952 Dec;38(6):517-24. PubMed PMID: 13023502.
9: PETERSON EH, HYMAS TA. Sulfaquinoxaline, nitrofurazone and nitrophenide in the prophylaxis of experimental Eimeria necatrix infection. Am J Vet Res. 1950 Jul;11(40):278-83. PubMed PMID: 15425753.
