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MedKoo Cat#: 597303 | Name: Spicamycin

Description:

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

Spicamycin is a potent inducer of differentiation of human myeloid leukemia cells (HL-60) and murine myeloid leukemia cells (M1).

Chemical Structure

Spicamycin
Spicamycin
CAS#87099-85-2

Theoretical Analysis

MedKoo Cat#: 597303

Name: Spicamycin

CAS#: 87099-85-2

Chemical Formula: C30H51N7O7

Exact Mass: 621.3850

Molecular Weight: 621.78

Elemental Analysis: C, 57.95; H, 8.27; N, 15.77; O, 18.01

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
Spicamycin;
IUPAC/Chemical Name
N-(2-((6-((7H-purin-6-yl)amino)-2-(1,2-dihydroxyethyl)-4,5-dihydroxytetrahydro-2H-pyran-3-yl)amino)-2-oxoethyl)-14-methylpentadecanamide
InChi Key
YBZRLMLGUBIIDN-UHFFFAOYSA-N
InChi Code
1S/C30H51N7O7/c1-19(2)13-11-9-7-5-3-4-6-8-10-12-14-21(40)31-15-22(41)36-23-25(42)26(43)30(44-27(23)20(39)16-38)37-29-24-28(33-17-32-24)34-18-35-29/h17-20,23,25-27,30,38-39,42-43H,3-16H2,1-2H3,(H,31,40)(H,36,41)(H2,32,33,34,35,37)
SMILES Code
CC(CCCCCCCCCCCCC(NCC(NC1C(O)C(O)C(Nc2ncnc3nc[nH]c23)OC1C(O)CO)=O)=O)C
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 621.78 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
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PubMed PMID: 24643053. 4: 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. Epub 2011 Oct 7. PubMed PMID: 21983265. 5: 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. Epub 2011 Sep 9. PubMed PMID: 21902681. 6: Mizumura Y. [Spicamycin derivative]. Nihon Rinsho. 2006 Feb;64(2):322-8. Review. Japanese. PubMed PMID: 16454188. 7: Igarashi Y, Ootsu K, Onaka H, Fujita T, Uehara Y, Furumai T. Anicemycin, a new inhibitor of anchorage-independent growth of tumor cells from Streptomyces sp. TP-A0648. J Antibiot (Tokyo). 2005 May;58(5):322-6. PubMed PMID: 16060384. 8: Borsook D, Edwards AD. Antineuropathic effects of the antibiotic derivative spicamycin KRN5500. Pain Med. 2004 Mar;5(1):104-8. PubMed PMID: 14996243. 9: Mons S, Fleet GW. An approach to the generation of simple analogues of the antitumour agent spicamycin. Org Biomol Chem. 2003 Nov 7;1(21):3685-91. PubMed PMID: 14649899. 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: 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. 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: 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. 14: DiLorenzo L, Kobierski L, Moore KA, Borsook D. A water-soluble synthetic spicamycin derivative (San-Gly) decreases mechanical allodynia in a rodent model of neuropathic pain. Neurosci Lett. 2002 Sep 13;330(1):37-40. PubMed PMID: 12213629. 15: Suzuki T, Suzuki ST, Yamada I, Koashi Y, Yamada K, Chida N. Total synthesis of spicamycin. J Org Chem. 2002 May 3;67(9):2874-80. PubMed PMID: 11975540. 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: 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. 18: 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. 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; PubMed Central PMCID: PMC5926402. 20: Suzuki T, Tanaka S, Yamada I, Koashi Y, Yamada K, Chida N. Total synthesis of spicamycin amino nucleoside. Org Lett. 2000 Apr 20;2(8):1137-40. PubMed PMID: 10804573.