Synonym
Stilbamidine dihydrochloride; NCI 174; NSC 35605;
IUPAC/Chemical Name
4-[(E)-2-(4-carbamimidoylphenyl)ethenyl]benzenecarboximidamide dihydrochloride
InChi Key
BJYYRSDXFXLJIV-SEPHDYHBSA-N
InChi Code
InChI=1S/C16H16N4.2ClH/c17-15(18)13-7-3-11(4-8-13)1-2-12-5-9-14(10-6-12)16(19)20;;/h1-10H,(H3,17,18)(H3,19,20);2*1H/b2-1+;;
SMILES Code
N=C(C1=CC=C(/C=C/C2=CC=C(C(N)=N)C=C2)C=C1)N.[H]Cl.[H]Cl
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
337.25
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: FULTON JD, MATHEW KK. Tracer studies of the distribution and trypanocidal action of stilbamidine in rats. Br J Pharmacol Chemother. 1959 Mar;14(1):137-41. PubMed PMID: 13651591; PubMed Central PMCID: PMC1481824.
2: Gresh N, Pullman B. A theoretical study of the nonintercalative binding of berenil and stilbamidine to double-stranded (dA-dT)n oligomers. Mol Pharmacol. 1984 May;25(3):452-8. PubMed PMID: 6727867.
3: SNAPPER I. Stilbamidine and pentamidine in multiple myeloma. J Am Med Assoc. 1947 Jan 18;133(3):157-61. PubMed PMID: 20278624.
4: FORGAN R. Stilbamidine in multiple myeloma. Lancet. 1947 Oct 18;2(6477):598. PubMed PMID: 20267355.
5: ALWALL N. Urethane and stilbamidine in multiple myeloma report on two cases. Lancet. 1947 Sep 13;2(6472):388. PubMed PMID: 20263550.
6: HAMPTON JW. The excretion of stilbamidine and some related compounds in experimental animals. Ann Trop Med Parasitol. 1947 Sep;41(2):226-33. PubMed PMID: 20267992.
7: SEAGER LD, CASTELNUOVO G. Toxicity of stilbamidine; a study of the effects of chronic intoxication. Arch Pathol (Chic). 1947 Sep;44(3):287-96. PubMed PMID: 20267695.
8: SCHOENBACH EB, MILLER JM, LONG PH. The treatment of systemic blastomycosis with stilbamidine. Ann Intern Med. 1952 Jul;37(1):31-47. PubMed PMID: 14933975.
9: NAPIER LE. Urethane and stilbamidine in multiple myeloma. Lancet. 1947 Sep 27;2(6474):489. PubMed PMID: 20344793.
10: GEPHARDT MC, HANLON TJ. Treatment of disseminated coccidiodomycosis with stilbamidine (case history). J Okla State Med Assoc. 1954 Mar;47(3):55-8. PubMed PMID: 13131168.
11: SNAPPER I, SCHNEID B. The development of basophilic inclusion bodies in myeloma cells after stilbamidine treatment. Ann Intern Med. 1947 Oct;27(4):541-7. PubMed PMID: 20268427.
12: MILLER JM, POGGE RC, SMITH GW. The toxicity of stilbamidine. J Med Assoc Ga. 1957 Feb;46(2):65. PubMed PMID: 13398750.
13: BERGMANN F, WILSON IB, NACHMANSOHN D. The inhibitory effect of stilbamidine, curare and related compounds and its relationship to the active groups of acetylcholine esterase; action of stilbamidine upon nerve impulse conduction. Biochim Biophys Acta. 1950 Sep;6(1):217-24. PubMed PMID: 14791412.
14: HARRELL ER, BOCOBO FC, CURTIS AC. A study of North American blastomycosis and its treatment with stilbamidine and 2-hydroxystilbamidine. Ann Intern Med. 1955 Nov;43(5):1076-91. PubMed PMID: 13268999.
15: MOHAMMED HAMAD SATI. Post-stilbamidine neuropathy, with reference to the retention of the drug in the body. Ann Trop Med Parasitol. 1949 Apr;43(1):4-12. PubMed PMID: 18121264.
16: FULTON JD, GRANT PT. Experiments on the mode of action of stilbamidine. Ann Trop Med Parasitol. 1956 Dec;50(4):381-4. PubMed PMID: 13395328.
17: HENRY AJ. The instability of stilbamidine. Br J Pharmacol Chemother. 1948 Jun;3(2):163-6. PubMed PMID: 18866997; PubMed Central PMCID: PMC1509815.
18: LIEBEN F. Effect of some reagents on the fluorescence of stilbamidine and 2 OH-hydroxystilbamidine in vitro. J Mt Sinai Hosp N Y. 1952 May-Jun;19(1):217-20. PubMed PMID: 14938991.
19: Mesa-Valle CM, Rodriguez-Cabezas MN, Moraleda-Lindez V, Craciunescu D, Sanchez-Moreno M, Osuna A. In vitro and in vivo activity of two Pt(IV) salts against leishmania donovani. Pharmacology. 1998 Sep;57(3):160-72. PubMed PMID: 9691236.
20: FINK JC, VANDERPLOEG DE, MOURSUND MP. Stilbamidine in the treatment of cutaneous blastomycosis. J Am Med Assoc. 1953 Apr 18;151(16):1395-7. PubMed PMID: 13034483.
