IUPAC/Chemical Name
3-Chloro-7-hydroxy-4-methylcoumarin bis(2-chloroethyl)phosphate
InChi Key
KULDXINYXFTXMO-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H14Cl3O6P/c1-9-11-3-2-10(8-12(11)22-14(18)13(9)17)23-24(19,20-6-4-15)21-7-5-16/h2-3,8H,4-7H2,1H3
SMILES Code
O=C1OC2=C(C=CC(OP(OCCCl)(OCCCl)=O)=C2)C(C)=C1Cl
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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
413.58
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 |
1: Sinko G, Bosak A, Kovarik Z, Simeon-Rudolf V. Structure-inhibition relationships in the interaction of butyrylcholinesterase with bambuterol, haloxon and their leaving groups. Chem Biol Interact. 2005 Dec 15;157-158:421-3. PubMed PMID: 16429568.
2: Radić Z, Taylor P. Peripheral site ligands accelerate inhibition of acetylcholinesterase by neutral organophosphates. J Appl Toxicol. 2001 Dec;21 Suppl 1:S13-4. PubMed PMID: 11920914.
3: Radić Z, Taylor P. The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases. Chem Biol Interact. 1999 May 14;119-120:111-7. PubMed PMID: 10421444.
4: Martin RJ. Modes of action of anthelmintic drugs. Vet J. 1997 Jul;154(1):11-34. Review. PubMed PMID: 9265850.
5: Schmuck G, Ahr HJ. Improved in vitro method for screening organophosphate-induced delayed polyneuropathy. Toxicol In Vitro. 1997 Jun;11(3):263-70. PubMed PMID: 20654312.
6: Nagayama M, Akahori F, Chiwata H, Shirai M, Motoya M, Masaoka T, Sakaguchi K. Effects of selected organophosphate insecticides on serum cholinesterase isoenzyme patterns in the rat. Vet Hum Toxicol. 1996 Jun;38(3):196-9. PubMed PMID: 8727219.
7: Bourke CA. The clinical differentiation of nervous and muscular locomotor disorders of sheep in Australia. Aust Vet J. 1995 Jun;72(6):228-34. Review. PubMed PMID: 8526819.
8: Bohuslavizki KH, Hänsel W, Kneip A, Koppenhöfer E, Niemöller E, Sanmann K. Mode of action of psoralens, benzofurans, acridinons, and coumarins on the ionic currents in intact myelinated nerve fibres and its significance in demyelinating diseases. Gen Physiol Biophys. 1994 Aug;13(4):309-28. PubMed PMID: 7890147.
9: Zahner H, Schares G. Experimental chemotherapy of filariasis: comparative evaluation of the efficacy of filaricidal compounds in Mastomys coucha infected with Litomosoides carinii, Acanthocheilonema viteae, Brugia malayi and B. pahangi. Acta Trop. 1993 Jan;52(4):221-66. Review. PubMed PMID: 8094587.
10: Radić Z, Reiner E, Taylor P. Role of the peripheral anionic site on acetylcholinesterase: inhibition by substrates and coumarin derivatives. Mol Pharmacol. 1991 Jan;39(1):98-104. PubMed PMID: 1987454.
11: Sharma RK, Singh K, Saxena KK. Effect of cambendazole and haloxon on the carbohydrate metabolism of Ascaridia galli and Heterakis gallinae (Nematoda). Angew Parasitol. 1990 May;31(2):101-5. PubMed PMID: 2389827.
12: Prichard RK. Anthelmintics and control. Vet Parasitol. 1988 Feb;27(1-2):97-109. Review. PubMed PMID: 3284172.
13: Sharma RK, Singh K, Saxena R, Saxena KK. Effect of some anthelmintics on malate dehydrogenase activity and mortality in two avian nematodes Ascaridia galli and Heterakis gallinae. Angew Parasitol. 1986 Aug;27(3):175-80. PubMed PMID: 3777528.
14: Prichard RK. Anthelmintics for cattle. Vet Clin North Am Food Anim Pract. 1986 Jul;2(2):489-501. PubMed PMID: 3488116.
15: Rew RS, Urban JF Jr, Douvres FW. Screen for anthelmintics, using larvae of Ascaris suum. Am J Vet Res. 1986 Apr;47(4):869-73. PubMed PMID: 3963590.
16: Radić Z, Reiner E, Simeon V. Binding sites on acetylcholinesterase for reversible ligands and phosphorylating agents. A theoretical model tested on haloxon and phosphostigmine. Biochem Pharmacol. 1984 Feb 15;33(4):671-7. PubMed PMID: 6704184.
17: Zahner H, Weidner E. Occurrence of microfilariae in various hollow organs and in the peritoneal cavity after treatment of Litomosoides carinii infected Mastomys natalensis with diethylcarbamazine and haloxon. Z Parasitenkd. 1983;69(3):387-92. PubMed PMID: 6880345.
18: Jortner BS, Pope AM, Heavner JE. Haloxon-induced delayed neurotoxicity: effect of plasma A (aryl) esterase activity on severity of lesions in sheep. Neurotoxicology. 1983 Summer;4(2):241-5. PubMed PMID: 6314214.
19: Hixson EJ. Consideration of dose levels for delayed neurotoxicity testing in hens: the relationship of neurotoxic dosages to acute LD50 values. Neurotoxicology. 1983 Spring;4(1):131-7. PubMed PMID: 6192368.
20: Wilson RD, Witzel DA, Verlander JM. Somatosensory-evoked response of ataxic Angora goats in suspected haloxon-delayed neurotoxicity. Am J Vet Res. 1982 Dec;43(12):2224-6. PubMed PMID: 7165170.