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MedKoo Cat#: 528806 | Name: KRN 5500

Description:

WARNING: This product is for research use only, not for human or veterinary use.

KRN 5500 is a derivative of the nucleoside antibiotic spicamycin with a wide range of antitumor activity against human cancer cell lines.

Chemical Structure

KRN 5500
KRN 5500
CAS#151276-95-8

Theoretical Analysis

MedKoo Cat#: 528806

Name: KRN 5500

CAS#: 151276-95-8

Chemical Formula: C28H43N7O7

Exact Mass: 589.3224

Molecular Weight: 589.69

Elemental Analysis: C, 57.03; H, 7.35; N, 16.63; O, 18.99

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
SPK-241; KRN-5500; NSC-650426; SPK241; KRN5500; NSC650426; SPK 241; KRN 5500; NSC 650426
IUPAC/Chemical Name
(2E,4E)-N-(2-(((2R,3R,4R,5R,6S)-6-((7H-purin-6-yl)amino)-2-((S)-1,2-dihydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)amino)-2-oxoethyl)tetradeca-2,4-dienamide
InChi Key
LQIPDFIUPOYMPR-BKYURJJWSA-N
InChi Code
InChI=1S/C28H43N7O7/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(38)29-14-20(39)34-21-23(40)24(41)28(42-25(21)18(37)15-36)35-27-22-26(31-16-30-22)32-17-33-27/h10-13,16-18,21,23-25,28,36-37,40-41H,2-9,14-15H2,1H3,(H,29,38)(H,34,39)(H2,30,31,32,33,35)/b11-10+,13-12+/t18-,21+,23+,24+,25-,28-/m0/s1
SMILES Code
CCCCCCCCC/C=C/C=C/C(NCC(N[C@H]1[C@H]([C@@H](O)CO)O[C@H](NC2=C3NC=NC3=NC=N2)[C@H](O)[C@@H]1O)=O)=O
Appearance
Solid powder
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

Preparing Stock Solutions

The following data is based on the product molecular weight 589.69 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.

Recalculate based on batch purity %
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: Kawai H. [Protein synthesis inhibitor--antitumor activity and mode of action of KRN 5500]. Gan To Kagaku Ryoho. 1997 Sep;24(11):1571-7. Review. Japanese. PubMed PMID: 9309156. 2: Weinstein SM, Abernethy AP, Spruill SE, Pike IM, True Kelly A, Jett LG. A spicamycin derivative (KRN5500) provides neuropathic pain relief in patients with advanced cancer: a placebo-controlled, proof-of-concept trial. J Pain Symptom Manage. 2012 Apr;43(4):679-93. doi: 10.1016/j.jpainsymman.2011.05.003. PubMed PMID: 21983265. 3: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2004 Apr;26(3):211-44. PubMed PMID: 15148527. 4: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Dec;25(10):831-55. PubMed PMID: 14735233. 5: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2003 Nov;25(9):747-71. PubMed PMID: 14685303. 6: Miki H, Ozaki S, Nakamura S, Oda A, Amou H, Ikegame A, Watanabe K, Hiasa M, Cui Q, Harada T, Fujii S, Nakano A, Kagawa K, Takeuchi K, Yata K, Sakai A, Abe M, Matsumoto T. KRN5500, a spicamycin derivative, exerts anti-myeloma effects through impairing both myeloma cells and osteoclasts. Br J Haematol. 2011 Nov;155(3):328-39. doi: 10.1111/j.1365-2141.2011.08844.x. PubMed PMID: 21902681. 7: Mizumura Y. [Spicamycin derivative]. Nihon Rinsho. 2006 Feb;64(2):322-8. Review. Japanese. PubMed PMID: 16454188. 8: Yokoyama M, Satoh A, Sakurai Y, Okano T, Matsumura Y, Kakizoe T, Kataoka K. Incorporation of water-insoluble anticancer drug into polymeric micelles and control of their particle size. J Control Release. 1998 Nov 13;55(2-3):219-29. PubMed PMID: 9795065. 9: Byrd JC, Lucas DM, Mone AP, Kitner JB, Drabick JJ, Grever MR. KRN5500: a novel therapeutic agent with in vitro activity against human B-cell chronic lymphocytic leukemia cells mediates cytotoxicity via the intrinsic pathway of apoptosis. Blood. 2003 Jun 1;101(11):4547-50. PubMed PMID: 12595316. 10: Supko JG, Eder JP Jr, Ryan DP, Seiden MV, Lynch TJ, Amrein PC, Kufe DW, Clark JW. Phase I clinical trial and pharmacokinetic study of the spicamycin analog KRN5500 administered as a 1-hour intravenous infusion for five consecutive days to patients with refractory solid tumors. Clin Cancer Res. 2003 Nov 1;9(14):5178-86. PubMed PMID: 14613997. 11: Mizumura Y, Matsumura Y, Yokoyama M, Okano T, Kawaguchi T, Moriyasu F, Kakizoe T. Incorporation of the anticancer agent KRN5500 into polymeric micelles diminishes the pulmonary toxicity. Jpn J Cancer Res. 2002 Nov;93(11):1237-43. PubMed PMID: 12460465. 12: Kobierski LA, Abdi S, DiLorenzo L, Feroz N, Borsook D. A single intravenous injection of KRN5500 (antibiotic spicamycin) produces long-term decreases in multiple sensory hypersensitivities in neuropathic pain. Anesth Analg. 2003 Jul;97(1):174-82, table of contents. PubMed PMID: 12818962. 13: Yamamoto N, Tamura T, Kamiya Y, Ono H, Kondoh H, Shirao K, Matsumura Y, Tanigawara Y, Shimada Y. Phase I and pharmacokinetic study of KRN5500, a spicamycin derivative, for patients with advanced solid tumors. Jpn J Clin Oncol. 2003 Jun;33(6):302-8. PubMed PMID: 12913085. 14: Gadgeel SM, Boinpally RR, Heilbrun LK, Wozniak A, Jain V, Redman B, Zalupski M, Wiegand R, Parchment R, LoRusso PM. A phase I clinical trial of spicamycin derivative KRN5500 (NSC 650426) using a phase I accelerated titration "2B" design. Invest New Drugs. 2003 Feb;21(1):63-74. PubMed PMID: 12795531. 15: Stine KC, Warren BA, Saylors RL, Becton DL. KRN5500 induces apoptosis (PCD) of myeloid leukemia cell lines and patient blasts. Leuk Res. 2000 Sep;24(9):741-9. Erratum in: Leuk Res 2000 Dec;24(12):1063. PubMed PMID: 10978778. 16: Takama H, Tanaka H, Sudo T, Tamura T, Tanigawara Y. Population pharmacokinetic modeling and model validation of a spicamycin derivative, KRN5500, in phase 1 study. Cancer Chemother Pharmacol. 2001 May;47(5):404-10. PubMed PMID: 11391855. 17: Kawasaki K, Murakami T, Ita M, Sasaki K, Furukawa S. KRN5500, a novel antitumor agent, induces apoptosis or cell differentiation in HL-60 cells. Cytometry. 2000 Mar 1;39(3):211-6. PubMed PMID: 10685078. 18: Abdi S, Vilassova N, Decosterd I, Feroz N, Borsook D. The effects of KRN5500, a spicamycin derivative, on neuropathic and nociceptive pain models in rats. Anesth Analg. 2000 Oct;91(4):955-9. PubMed PMID: 11004056. 19: Zhang WJ, Ohnishi K, Yoshida H, Pan L, Maksumova L, Muratkhodjaev F, Luo JM, Shigeno K, Fujisawa S, Naito K, Nakamura S, Shinjo K, Takeshita A, Ohno R. Spicamycin and KRN5500 induce apoptosis in myeloid and lymphoid cell lines with down-regulation of bcl-2 expression and modulation of promyelocytic leukemia protein. Jpn J Cancer Res. 2000 Jun;91(6):604-11. PubMed PMID: 10874212. 20: Kamishohara M, Kenney S, Domergue R, Vistica DT, Sausville EA. Selective accumulation of the endoplasmic reticulum-Golgi intermediate compartment induced by the antitumor drug KRN5500. Exp Cell Res. 2000 May 1;256(2):468-79. PubMed PMID: 10772819.