HMN-176
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MedKoo CAT#: 201480

CAS#: 173529-10-7

Description: HMN-176 is an active metabolite of the synthetic antitumor compound HMN-214. HMN-176 shows potent cytotoxicity toward various human tumor cell lines, and in mitotic cells, it causes cell cycle arrest at M phase through the destruction of spindle polar bodies, followed by the induction of DNA fragmentation. However, no direct interactions of HMN-176 with tubulin are observed. Moreover, in animal models, it was observed that oral administration of the prodrug HMN-214 caused no significant nerve toxicity, a severe side effect often associated with microtubule binding agents such as Taxol and VCR.3 In Phase I clinical trials, HMN-214 has caused sensory neuropathy and ileus in some patients. However, the grade and frequency of these adverse effects were much lower than those of typical microtubule binding agents. As expected from the mechanism of action of HMN-214 (induction of G2-M arrest in dividing cells), the main adverse effect was neutropenia. (Source: CANCER RESEARCH 63, 6942–6947).


Price and Availability

Size Price Shipping out time Quantity
10mg USD 150 2 Weeks
25mg USD 250 2 Weeks
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
200mg USD 1250 2 Weeks
500mg USD 1950 2 Weeks
1g USD 2950 2 Weeks
2g USD 4950 2 Weeks
5g USD 6950 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-26. Prices are subject to change without notice.

HMN-176, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 201480
Name: HMN-176
CAS#: 173529-10-7
Chemical Formula: C20H18N2O4S
Exact Mass: 382.09873
Molecular Weight: 382.43
Elemental Analysis: C, 62.81; H, 4.74; N, 7.33; O, 16.73; S, 8.38


Synonym: HMN176; HMN 176; HMN-176.

IUPAC/Chemical Name: (E)-4-(2-(4-methoxyphenylsulfonamido)styryl)pyridine 1-oxide

InChi Key: LBPNULPSVCDYRF-VOTSOKGWSA-N

InChi Code: InChI=1S/C20H18N2O4S/c1-26-18-8-10-19(11-9-18)27(24,25)21-20-5-3-2-4-17(20)7-6-16-12-14-22(23)15-13-16/h2-15,21H,1H3/b7-6+

SMILES Code: O=S(NC1=CC=CC=C1/C=C/C2=CC=[N+]([O-])C=C2)(C3=CC=C(OC)C=C3)=O


Technical Data

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, not in water

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


Additional Information

HMN-176 is a potential new cancer therapeutic known to retard the proliferation of tumor cell lines. This compound inhibits meiotic spindle assembly in surf clam oocytes and delays satisfaction of the spindle assembly checkpoint in human somatic cells by inducing the formation of short and/or multipolar spindles. HMN-176 does not affect centrosome assembly, nuclear envelope breakdown, or other aspects of meiotic or mitotic progression, nor does it affect the kinetics of Spisula or mammalian microtubule (MT) assembly in vitro. Notably, HMN-176 inhibits the formation of centrosome-nucleated MTs (i.e., asters) in Spisula oocytes and oocyte extracts, as well as from isolated Spisula or mammalian centrosomes in vitro. Together, these results reveal that HMN-176 is a first-in-class anticentrosome drug that inhibits proliferation, at least in part, by disrupting centrosome-mediated MT assembly during mitosis.  (source: Mol Cancer Ther. 2009 Mar;8(3):592-601. ).
 
 


References

1: DiMaio MA, Mikhailov A, Rieder CL, Von Hoff DD, Palazzo RE. The small organic compound HMN-176 delays satisfaction of the spindle assembly checkpoint by inhibiting centrosome-dependent microtubule nucleation. Mol Cancer Ther. 2009 Mar;8(3):592-601. doi: 10.1158/1535-7163.MCT-08-0876. Epub 2009 Mar 3. PubMed PMID: 19258425; PubMed Central PMCID: PMC2717217.

2: Garland LL, Taylor C, Pilkington DL, Cohen JL, Von Hoff DD. A phase I pharmacokinetic study of HMN-214, a novel oral stilbene derivative with polo-like kinase-1-interacting properties, in patients with advanced solid tumors. Clin Cancer Res. 2006 Sep 1;12(17):5182-9. PubMed PMID: 16951237.

3: Medina-Gundrum L, Cerna C, Gomez L, Izbicka E. Investigation of HMN-176 anticancer activity in human tumor specimens in vitro and the effects of HMN-176 on differential gene expression. Invest New Drugs. 2005 Jan;23(1):3-9. PubMed PMID: 15528975.

4: Takagi M, Honmura T, Watanabe S, Yamaguchi R, Nogawa M, Nishimura I, Katoh F, Matsuda M, Hidaka H. In vivo antitumor activity of a novel sulfonamide, HMN-214, against human tumor xenografts in mice and the spectrum of cytotoxicity of its active metabolite, HMN-176. Invest New Drugs. 2003 Nov;21(4):387-99. PubMed PMID: 14586206.

5: Tanaka H, Ohshima N, Ikenoya M, Komori K, Katoh F, Hidaka H. HMN-176, an active metabolite of the synthetic antitumor agent HMN-214, restores chemosensitivity to multidrug-resistant cells by targeting the transcription factor NF-Y. Cancer Res. 2003 Oct 15;63(20):6942-7. PubMed PMID: 14583495.