5-(N,N-Hexamethylene)-amiloride
- CAS No.
- 1428-95-1
- Chemical Name:
- 5-(N,N-Hexamethylene)-amiloride
- Synonyms
- hma;Amilo;5-HMA;HMA-5;amipromizide;Hexamethyleneamiloride;5-(N,N-Hexamethylene)-amiloride;AMILORIDE,5-(N,N-HEXAMETHYLENE)-;HMA (5-(N,N-Hexamethylene)amiloride);5-(N,N-HEXAMETHYLENE)-AMILORIDE USP/EP/BP
- CBNumber:
- CB8418632
- Molecular Formula:
- C12H18ClN7O
- Molecular Weight:
- 311.77
- MDL Number:
- MFCD00069211
- MOL File:
- 1428-95-1.mol
- MSDS File:
- SDS
- TDS File:
- TDS
| Melting point | 224-225 °C |
|---|---|
| Density | 1.63±0.1 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| solubility | DMF: 3mg/mL; DMSO: 10mg/mL; DMSO:PBS (pH 7.2) (1:4): 0.2mg/mL |
| form | A crystalline solid |
| pka | 8.81±0.46(Predicted) |
| color | Light yellow to yellow |
| InChI | 1S/C12H18ClN7O/c13-8-10(20-5-3-1-2-4-6-20)18-9(14)7(17-8)11(21)19-12(15)16/h1-6H2,(H2,14,18)(H4,15,16,19,21) |
| InChIKey | RQQJJXVETXFINY-UHFFFAOYSA-N |
| SMILES | N\C(N)=N\C(=O)c1nc(Cl)c(nc1N)N2CCCCCC2 |
| UNSPSC Code | 12352200 |
| NACRES | NA.77 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H301+H311+H331 | |||||||||
| Precautionary statements | P261-P264-P280-P301+P310-P302+P352+P312-P304+P340+P311 | |||||||||
| PPE | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 23/24/25 | |||||||||
| Safety Statements | 22-36/37/39-45 | |||||||||
| RIDADR | 2811 | |||||||||
| WGK Germany | 3 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| Storage Class | 6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects |
|||||||||
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral |
|||||||||
| NFPA 704 |
|
5-(N,N-Hexamethylene)-amiloride price More Price(19)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | A9561 | 5-(N,N-Hexamethylene)amiloride | 1428-95-1 | 25mg | $124 | 2026-04-30 | Buy |
| Sigma-Aldrich | A9561 | 5-(N,N-Hexamethylene)amiloride | 1428-95-1 | 100mg | $417 | 2026-04-30 | Buy |
| Cayman Chemical | 29788 | 5-(N,N-hexamethylene)-Amiloride ≥98% | 1428-95-1 | 5mg | $44 | 2026-04-30 | Buy |
| Cayman Chemical | 29788 | 5-(N,N-hexamethylene)-Amiloride ≥98% | 1428-95-1 | 10mg | $80 | 2026-04-30 | Buy |
| Cayman Chemical | 29788 | 5-(N,N-hexamethylene)-Amiloride ≥98% | 1428-95-1 | 25mg | $120 | 2026-04-30 | Buy |
5-(N,N-Hexamethylene)-amiloride Chemical Properties, Uses, Production
Description
5-(N,N-hexamethylene)-Amiloride (HMA) is a derivative of amiloride with diverse biological activities. It is an allosteric antagonist of adenosine A2A receptors (Ki = 3.3 μM). HMA inhibits the cation-selective ion channel formed by the HIV-1 viral protein Vpu when used at a concentration of 50 μM, as well as budding of virus-like particles in HeLa cells expressing the HIV-1 proteins Gag and Vpu when used at a concentration of 10 μM. It also blocks the cation-selective ion channels formed by the hepatitis C virus (HCV) protein p7. HMA (40 μM) induces necrosis in and reduces the viability of MCF-7, MDA-MB-231, T47D, SK-BR-3, Met-1, and NDL breast cancer cells but not cardiomyocytes or uterine, pulmonary, and renal epithelial cells. HMA protects against post-ischemic contractile dysfunction and reduces coronary effluent creatine phosphokinase activity in a model of ischemia-reperfusion injury using isolated rat right ventricular free walls.
Uses
5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) derives from an amiloride and is a potent Na+/H+ exchanger inhibitor, which decreases the intracellular pH (pHi) and induces apoptosis in leukemic cells. 5-(N,N-Hexamethylene)-amiloride (Hexamethylene amiloride) is also an inhibitor of the HIV-1 Vpu virus ion channel and inhibits mouse hepatitis virus (MHV) replication and human coronavirus 229E (HCoV229E) replication in cultured L929 cells with EC50s of 3.91 μM and 1.34 μM, respectively[1][2].
Definition
ChEBI: A member of the class of pyrazines that is amiloride in which the two amino hydrogens at position N-5 are replaced by a hexamethylene moiety, resulting in the formation of an azepane ring.
Biochem/physiol Actions
Inhibitor of Na+/H+ antiport.
in vivo
5-(N,N-Hexamethylene)-amiloride (2.5 mg/kg; i.v.; single dose) shows short half-life and lowly oral bioavailability of 4.5%[3].
In vivo pharmacokinetics in mice or rat model[3]
Dosage: 2.5 mg/kg
Administration: Intravenous injection; single does; collected 10 min and 60 min after treatment.
| t1/2 (h) | Plasma CLint (mL/min/kg) | Plasma Vss (L/kg) | Plasma AUC0-inf (h·μM) | B/P ratio | Blood CL (mL/min/kg) | Blood Vss (L/kg) | |
| Female Balb/c mice | 0.62 | 86 | 2.0 | 1.5 | 1.5 | 59 | 1.4 |
| Sprague Dawley rats | 3.2 | 83.5 | 5.3 | 1.6 | 1.8 | 46.2 | 2.9 |
| % IV dose excreted in urine (0-24 h) | Renal Blood CL (mL/min/kg) | Non-Renal Blood CL (mL/min/kg) | |||||
| Sprague Dawley rats | 0.5 | 0.2 | 46.0 |
IC 50
HIV-1
References
[1] Rich IN, et al. Apoptosis of leukemic cells accompanies reduction in intracellular pH after targeted inhibition of the Na(+)/H(+) exchanger. Blood. 2000 Feb 15;95(4):1427-34. PMID:10666221
[2] Wilson L, et al. Hexamethylene amiloride blocks E protein ion channels and inhibits coronavirus replication. Virology. 2006 Sep 30;353(2):294-306. Epub 2006 Jul 3. DOI:10.1016/j.virol.2006.05.028
[3] Buckley BJ, et al. Systematic evaluation of structure-property relationships and pharmacokinetics in 6-(hetero)aryl-substituted matched pair analogs of amiloride and 5-(N,N-hexamethylene)amiloride. Bioorg Med Chem. 2021 May 1;37:116116. DOI:10.1016/j.bmc.2021.116116
5-(N,N-Hexamethylene)-amiloride Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| HangZhou YuHao Chemical Technology Co., Ltd. | 0571-82693216 | info@yuhaochemical.com | China | 1999 | 58 |
| Sigma-Aldrich | 021-61415566 800-8193336 | orderCN@merckgroup.com | China | 51389 | 80 |
| Beijing Solarbio Science & Tecnology Co., Ltd. | 17801761073 18101056239 | 3193328036@qq.com | China | 28150 | 68 |
| Shenzhen SUNGENING Bio-Medical Co., Ltd. | 0755-28967200 13631290199 | wxf@sungening.com | China | 9609 | 60 |
| Wuhan FengyaoTonghui Chemical Products Co., Ltd. | 027-87466105 15377573527 | 2678564200@qq.com | China | 17968 | 58 |
| Jinan Yaoyan Pharmaceutical Co., Ltd. | jnyaoyan@163.com | China | 3057 | 58 | |
| Shanghai Jizhi Biochemical Technology Co. Ltd. | 021-4009004166/18616739031 18616739031 | 3007523370@qq.com | China | 40000 | 58 |
| Fan De(Beijing) Biotechnology Co., Ltd. | 15911056312 | liming@bio-fount.com | China | 9718 | 58 |
| Lanzhou Kangyuxin Biotechnology Co., Ltd. | 0943-8293106 | sales@kyxpharma.com | China | 3552 | 58 |
| Nanjing Meihao Pharmaceutical Technology Co., Ltd. | meitaochem@126.com | meitaochem@126.com | China | 19087 | 58 |
View Latest Price from 5-(N,N-Hexamethylene)-amiloride manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2026-08-20 | 5-(N,N-HEXAMETHYLENE)-AMILORIDE USP/EP/BP
1428-95-1
|
$1.10 | 1g | 99.9% | 100 Tons Min | Dideu Industries Group Limited |
-
- 5-(N,N-HEXAMETHYLENE)-AMILORIDE USP/EP/BP
1428-95-1
- $1.10
- 99.9%
- Dideu Industries Group Limited
1428-95-1 (5-(N,N-Hexamethylene)-amiloride) Related Search:
1of3
