Synonym
KRH-3955; KRH 3955; KRH3955; KRH3955 Salt; KRH-3955 tartrate
IUPAC/Chemical Name
N1-(4-((((1H-imidazol-2-yl)methyl)((1-methyl-1H-imidazol-2-yl)methyl)amino)methyl)benzyl)-N1-methyl-N4,N4-dipropylbutane-1,4-diamine tris((2R,3R)-2,3-dihydroxysuccinate)
InChi Key
PVKNAUJEVORNRR-NOKJQLKVSA-N
InChi Code
InChI=1S/C28H45N7.3C4H6O6/c1-5-16-34(17-6-2)19-8-7-18-32(3)21-25-9-11-26(12-10-25)22-35(23-27-29-13-14-30-27)24-28-31-15-20-33(28)4;3*5-1(3(7)8)2(6)4(9)10/h9-15,20H,5-8,16-19,21-24H2,1-4H3,(H,29,30);3*1-2,5-6H,(H,7,8)(H,9,10)/t;3*1-,2-/m.111/s1
SMILES Code
CCCN(CCC)CCCCN(CC1=CC=C(CN(CC2=NC=CN2)CC3=NC=CN3C)C=C1)C.O=C(O)[C@H](O)[C@@H](O)C(O)=O.O=C(O)[C@H](O)[C@@H](O)C(O)=O.O=C(O)[C@H](O)[C@@H](O)C(O)=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
>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
KRH-3955 Salt (1097732-62-1) ; KRH-3955 free base (675135-77-0)
Preparing Stock Solutions
The following data is based on the
product
molecular weight
929.96
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: Hikichi Y, Yokoyama M, Takemura T, Fujino M, Kumakura S, Maeda Y, Yamamoto N, Sato H, Matano T, Murakami T. Increased HIV-1 sensitivity to neutralizing antibodies by mutations in the Env V3-coding region for resistance to CXCR4 antagonists. J Gen Virol. 2016 Jul 1. doi: 10.1099/jgv.0.000536. [Epub ahead of print] PubMed PMID: 27368421.
2: Iwanaga T, Iwasaki Y, Ohashi M, Ohinata R, Takahashi K, Yamaguchi T, Matsumoto H, Nakano D. [Inhibitory effect of CXCR4 blockers on a CXCR4-expressing gastric cancer cell line in nude mice]. Gan To Kagaku Ryoho. 2012 Nov;39(12):1788-90. Japanese. PubMed PMID: 23267887.
3: Nakasone T, Kumakura S, Yamamoto M, Murakami T, Yamamoto N. Single oral administration of the novel CXCR4 antagonist, KRH-3955, induces an efficient and long-lasting increase of white blood cell count in normal macaques, and prevents CD4 depletion in SHIV-infected macaques: a preliminary study. Med Microbiol Immunol. 2013 Apr;202(2):175-82. doi: 10.1007/s00430-012-0254-1. Epub 2012 Jul 8. PubMed PMID: 22772800.
4: De Clercq E. Recent advances on the use of the CXCR4 antagonist plerixafor (AMD3100, Mozobil™) and potential of other CXCR4 antagonists as stem cell mobilizers. Pharmacol Ther. 2010 Dec;128(3):509-18. doi: 10.1016/j.pharmthera.2010.08.009. Epub 2010 Sep 15. Review. PubMed PMID: 20826182.
5: Murakami T, Kumakura S, Yamazaki T, Tanaka R, Hamatake M, Okuma K, Huang W, Toma J, Komano J, Yanaka M, Tanaka Y, Yamamoto N. The novel CXCR4 antagonist KRH-3955 is an orally bioavailable and extremely potent inhibitor of human immunodeficiency virus type 1 infection: comparative studies with AMD3100. Antimicrob Agents Chemother. 2009 Jul;53(7):2940-8. doi: 10.1128/AAC.01727-08. Epub 2009 May 18. PubMed PMID: 19451305; PubMed Central PMCID: PMC2704660.
6: Iwasaki Y, Akari H, Murakami T, Kumakura S, Dewan MZ, Yanaka M, Yamamoto N. Efficient inhibition of SDF-1alpha-mediated chemotaxis and HIV-1 infection by novel CXCR4 antagonists. Cancer Sci. 2009 Apr;100(4):778-81. doi: 10.1111/j.1349-7006.2009.01104.x. Epub 2009 Feb 24. PubMed PMID: 19245436.
