Synonym
NSC-60339; NSC 60339; NSC60339; Phthalanilide; Wander;
IUPAC/Chemical Name
2-Chloro-4',4''-di-2-imidazolin-2-yl-terephthalanilide
InChi Key
UJQGBYRKCZQJJS-UHFFFAOYSA-N
InChi Code
InChI=1S/C26H23ClN6O2/c27-22-15-18(25(34)32-19-6-1-16(2-7-19)23-28-11-12-29-23)5-10-21(22)26(35)33-20-8-3-17(4-9-20)24-30-13-14-31-24/h1-10,15H,11-14H2,(H,28,29)(H,30,31)(H,32,34)(H,33,35)
SMILES Code
O=C(NC1=CC=C(C2=NCCN2)C=C1)C3=CC=C(C(NC4=CC=C(C5=NCCN5)C=C4)=O)C=C3Cl
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
>2 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
More Info
In Gram-negative bacteria, efflux pumps are able to prevent effective cellular concentrations from being achieved for a number of antibiotics. Small molecule adjuvants that act as efflux pump inhibitors (EPIs) have the potential to reinvigorate existing antibiotics that are currently ineffective due to efflux mechanisms.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
486.96
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: Haynes KM, Abdali N, Jhawar V, Zgurskaya HI, Parks JM, Green AT, Baudry J, Rybenkov VV, Smith JC, Walker JK. Identification and Structure-Activity Relationships of Novel Compounds that Potentiate the Activities of Antibiotics in Escherichia coli. J Med Chem. 2017 Jul 27;60(14):6205-6219. doi: 10.1021/acs.jmedchem.7b00453. Epub 2017 Jul 11. PubMed PMID: 28650638; PubMed Central PMCID: PMC5783635.
2: Yesair DW, HOFook C. The retention or efflux of phthalanilide (NSC 60339)-lipid complexes by sensitive or resistant murine tumor cells and Escherichia coli B. Cancer Res. 1968 Feb;28(2):314-9. PubMed PMID: 4868016.
3: Yesair DW, Kohner FA, Rogers WI, Baronowsky PE, Kensler CJ. Relationship of phthalanilide-lipid complexes to uptake and retention of 2-chloro-4',4"-di(2-imidazolin-2-yl)terephthalanilide (NSC 60339) by sensitive and resistant P388 leukemia cells. Cancer Res. 1966 Feb;26(2):202-7. PubMed PMID: 5903172.
4: BOOTH J, BOYLAND E, GELLHORN A. SEARCH FOR METABOLITES OF ANTILEUKEMIC PHTHALANILIDES, 2-CHLORO-4',4"-DI-2-IMIDAZOLIN-2-YLTEREPHTHALANILIDE (NSC-60339) AND 2-AMINO-4',-4"-DI-2-IMIDAZOLIN-2-YLTEREPHTHALANILIDE DIHYDROCHLORIDE (NSC-50469). Cancer Chemother Rep. 1964 Dec;43:11-8. PubMed PMID: 14250645.
