HMN-176

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

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

10mg
Not available
100mg
Not available
1g
Ask price
Size
Price

25mg
Not available
200mg
Not available
2g
Ask price
Size
Price

50mg
Not available
500mg
Not available
5g
Ask price

HMN-176 is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

img

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).

Harmonized System Code:
293490


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.