Synonym
Diperodon HCl; Diperodon hydrochloride; NSC76069; NSC-76069; NSC 76069
IUPAC/Chemical Name
1,2-Propanediol, 3-(1-piperidinyl)-, bis(phenylcarbamate) (ester), monohydrochloride (9CI)
InChi Key
OWULVAZDMWJBLB-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H27N3O4.ClH/c26-21(23-18-10-4-1-5-11-18)28-17-20(16-25-14-8-3-9-15-25)29-22(27)24-19-12-6-2-7-13-19;/h1-2,4-7,10-13,20H,3,8-9,14-17H2,(H,23,26)(H,24,27);1H
SMILES Code
O=C(OC(CN1CCCCC1)COC(NC2=CC=CC=C2)=O)NC3=CC=CC=C3.[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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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:
Diperodon is a local anaesthetics, by the action of hydrolazes in blood serum is decomposed.
In vitro activity:
After preliminary experiments, this study selected 40μM as the optimal diperodon concentration for treatment of HL60 cells. Therefore, proliferation and differentiation of HL60 cells was assessed after treatment with ATRA alone (10nM), diperodon alone (40μM) or the ATRA-diperodon combination (10nM and 40μM, respectively). Treatment with ATRA alone slightly reduced proliferation of HL60 cells, whereas treatment with diperodon alone or with the ATRA-diperodon combination was much more effective; in particular, co-treated cells exhibited a 60% decrease of proliferation at day 6 (Fig. 1A).
Reference: Cell Cycle. 2015;14(16):2578-89. https://pubmed.ncbi.nlm.nih.gov/26102293/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
86.0 |
198.19 |
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
433.93
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. Manzotti G, Parenti S, Ferrari-Amorotti G, Soliera AR, Cattelani S, Montanari M, Cavalli D, Ertel A, Grande A, Calabretta B. Monocyte-macrophage differentiation of acute myeloid leukemia cell lines by small molecules identified through interrogation of the Connectivity Map database. Cell Cycle. 2015;14(16):2578-89. doi: 10.1080/15384101.2015.1033591. Epub 2015 Jun 23. PMID: 26102293; PMCID: PMC4614550.
2. Hrobonová K, Lehotay J, Cizmárik J, Armstrong DW. In vitro study of enzymatic hydrolysis of diperodon enantiomers in blood serum by two-dimensional LC. J Pharm Biomed Anal. 2002 Oct 15;30(3):875-80. doi: 10.1016/s0731-7085(02)00347-3. PMID: 12367714.
In vitro protocol:
1. Manzotti G, Parenti S, Ferrari-Amorotti G, Soliera AR, Cattelani S, Montanari M, Cavalli D, Ertel A, Grande A, Calabretta B. Monocyte-macrophage differentiation of acute myeloid leukemia cell lines by small molecules identified through interrogation of the Connectivity Map database. Cell Cycle. 2015;14(16):2578-89. doi: 10.1080/15384101.2015.1033591. Epub 2015 Jun 23. PMID: 26102293; PMCID: PMC4614550.
2. Hrobonová K, Lehotay J, Cizmárik J, Armstrong DW. In vitro study of enzymatic hydrolysis of diperodon enantiomers in blood serum by two-dimensional LC. J Pharm Biomed Anal. 2002 Oct 15;30(3):875-80. doi: 10.1016/s0731-7085(02)00347-3. PMID: 12367714.
1: Hrobonová K, Lehotay J, Cizmárik J, Armstrong DW. In vitro study of enzymatic hydrolysis of diperodon enantiomers in blood serum by two-dimensional LC. J Pharm Biomed Anal. 2002 Oct 15;30(3):875-80. doi: 10.1016/s0731-7085(02)00347-3. PMID: 12367714.
2: Dofek R, Vrba C, Kopácová L. Neue lokalanästhetisch wirksame Analoga des Diperodons [New local anesthetic-acting analogues of Diperodon]. Experientia. 1964 Oct 15;20(10):582-3. German. doi: 10.1007/BF02150310. PMID: 5861111.
3: Calnan CD. Allergy to the local anaesthetic diperodon. Contact Dermatitis. 1980 Aug;6(5):367. doi: 10.1111/j.1600-0536.1980.tb04981.x. PMID: 7418402.
4: Talibov VO, Fabini E, FitzGerald EA, Tedesco D, Cederfeldt D, Talu MJ, Rachman MM, Mihalic F, Manoni E, Naldi M, Sanese P, Forte G, Lepore Signorile M, Barril X, Simone C, Bartolini M, Dobritzsch D, Del Rio A, Danielson UH. Discovery of an Allosteric Ligand Binding Site in SMYD3 Lysine Methyltransferase. Chembiochem. 2021 Jan 5. doi: 10.1002/cbic.202000736. Epub ahead of print. PMID: 33400854.
5: Denderz N, Lehotay J. Application of the van't Hoff dependences in the characterization of molecularly imprinted polymers for some phenolic acids. J Chromatogr A. 2012 Dec 14;1268:44-52. doi: 10.1016/j.chroma.2012.10.025. Epub 2012 Oct 16. PMID: 23116796.
6: Cai SS, Hanold KA, Syage JA. Comparison of atmospheric pressure photoionization and atmospheric pressure chemical ionization for normal-phase LC/MS chiral analysis of pharmaceuticals. Anal Chem. 2007 Mar 15;79(6):2491-8. doi: 10.1021/ac0620009. Epub 2007 Feb 9. PMID: 17288463.
7: Hrobonová K, Lehotay J, Cizmárik J. HPLC stanovenie enantiomérov diperodonu v krvnom sére s pouzitím teikoplaninovej chiralnej stacionárnej fázy [HPLC determination of diperodon enantiomers in blood serum by using teicoplanin chiral stationary phase]. Ceska Slov Farm. 2004 Sep;53(5):225-7. Slovak. PMID: 15506704.
8: Denderz N, Lehotay J, Cižmárik J, Cibulková Z, Simon P. Thermodynamic study of molecularly imprinted polymer used as the stationary phase in high performance liquid chromatography. J Chromatogr A. 2012 Apr 27;1235:77-83. doi: 10.1016/j.chroma.2012.02.051. Epub 2012 Feb 28. PMID: 22429549.
9: Cizmárik J, Lehotay J, Hromuláková K. Study of local anaesthetics. Part 133. Determination of diperodon in blood serum in vitro by the HPLC method. Acta Pol Pharm. 1996 May-Jun;53(3):167-9. PMID: 8960289.
10: Zhao J, Lu X, Wang Y, Lv J. 'Click' preparation of a novel 'native- phenylcarbamoylated' bilayer cyclodextrin stationary phase for enhanced chiral differentiation. J Chromatogr A. 2015 Feb 13;1381:253-9. doi: 10.1016/j.chroma.2015.01.008. Epub 2015 Jan 14. PMID: 25614192.
