WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H527070
CAS#: 2038-35-9
Description: Phenamil is an irreversible inhibitor of amiloride-sensitive Na channels; derivative of amiloride, synergizing bone formation with BMP2 and inhibits BMP2 induced cyst-like bone formation.
Hodoodo Cat#: H527070
Name: Phenamil
CAS#: 2038-35-9
Chemical Formula: C12H12ClN7O
Exact Mass: 305.08
Molecular Weight: 305.726
Elemental Analysis: C, 47.14; H, 3.96; Cl, 11.60; N, 32.07; O, 5.23
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Synonym: Phenamil
IUPAC/Chemical Name: 3,5-Diamino-6-chloro-N-[imino(phenylamino)methyl]pyrazinecarboxamide
InChi Key: NIOHELZQFBGCEO-UHFFFAOYSA-N
InChi Code: InChI=1S/C12H12ClN7O/c13-8-10(15)19-9(14)7(18-8)11(21)20-12(16)17-6-4-2-1-3-5-6/h1-5H,(H4,14,15,19)(H3,16,17,20,21)
SMILES Code: ClC1=C(N)N=C(N)C(C(NC(NC2=CC=CC=C2)=N)=O)=N1
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:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 305.73 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.
| 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 |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Fan J, Pi-Anfruns J, Guo M, Im DCS, Cui ZK, Kim S, Wu BM, Aghaloo TL, Lee M. Small molecule-mediated tribbles homolog 3 promotes bone formation induced by bone morphogenetic protein-2. Sci Rep. 2017 Aug 8;7(1):7518. doi: 10.1038/s41598-017-07932-z. PubMed PMID: 28790361; PubMed Central PMCID: PMC5548928.
2: Lee JH, Mandakhbayar N, El-Fiqi A, Kim HW. Intracellular co-delivery of Sr ion and phenamil drug through mesoporous bioglass nanocarriers synergizes BMP signaling and tissue mineralization. Acta Biomater. 2017 Sep 15;60:93-108. doi: 10.1016/j.actbio.2017.07.021. Epub 2017 Jul 14. PubMed PMID: 28713017.
3: Cui ZK, Sun JA, Baljon JJ, Fan J, Kim S, Wu BM, Aghaloo T, Lee M. Simultaneous delivery of hydrophobic small molecules and siRNA using Sterosomes to direct mesenchymal stem cell differentiation for bone repair. Acta Biomater. 2017 Aug;58:214-224. doi: 10.1016/j.actbio.2017.05.057. Epub 2017 May 31. PubMed PMID: 28578107; PubMed Central PMCID: PMC5537024.
4: Gonzalez RJ, Jones SL, Nguyen TV. Ionoregulatory Characteristics of Non-Rio Negro Characiforms and Cichlids. Physiol Biochem Zool. 2017 May/Jun;90(3):407-414. doi: 10.1086/690306. Epub 2017 Feb 8. PubMed PMID: 28384425.
5: Price TR, Moncada K, Leyva-Jimenez H, Park KW, Tontonoz P, Walzem RL. Phenamil, an amiloride derivative, restricts long bone growth and alters keeled-sternum bone architecture in growing chickens. Poult Sci. 2017 Jul 1;96(7):2471-2479. doi: 10.3382/ps/pex034. PubMed PMID: 28340021.
6: Phung S, Lee C, Hong C, Song M, Yi JK, Stevenson RG, Kang MK, Shin KH, Park NH, Kim RH. Effects of Bioactive Compounds on Odontogenic Differentiation and Mineralization. J Dent Res. 2017 Jan;96(1):107-115. doi: 10.1177/0022034516675152. Epub 2016 Oct 25. PubMed PMID: 28033065.
7: Fan J, Guo M, Im CS, Pi-Anfruns J, Cui ZK, Kim S, Wu BM, Aghaloo TL, Lee M. Enhanced Mandibular Bone Repair by Combined Treatment of Bone Morphogenetic Protein 2 and Small-Molecule Phenamil. Tissue Eng Part A. 2017 Mar;23(5-6):195-207. doi: 10.1089/ten.TEA.2016.0308. Epub 2016 Nov 28. PubMed PMID: 27771997; PubMed Central PMCID: PMC5346908.
8: Regassa A, Park KW, Kim WK. Phenamil enhances the adipogenic differentiation of hen preadipocytes. Cell Biol Int. 2016 Oct;40(10):1123-8. doi: 10.1002/cbin.10651. Epub 2016 Aug 9. PubMed PMID: 27460177.
9: Snell HD, Gonzales EB. 5-(N, N-Hexamethylene) amiloride is a GABA-A ρ1 receptor positive allosteric modulator. Channels (Austin). 2016 Nov;10(6):498-506. doi: 10.1080/19336950.2016.1207021. Epub 2016 Jul 1. PubMed PMID: 27367557; PubMed Central PMCID: PMC5034777.
10: Zadeh-Tahmasebi M, Bui P, Donini A. FLUID AND ION SECRETION BY MALPIGHIAN TUBULES OF LARVAL CHIRONOMIDS, Chironomus riparius: EFFECTS OF REARING SALINITY, TRANSPORT INHIBITORS, AND SEROTONIN. Arch Insect Biochem Physiol. 2016 Oct;93(2):67-85. doi: 10.1002/arch.21342. Epub 2016 Jun 30. PubMed PMID: 27357470.
11: Nguyen VT, Farman N, Maubec E, Nassar D, Desposito D, Waeckel L, Aractingi S, Jaisser F. Re-Epithelialization of Pathological Cutaneous Wounds Is Improved by Local Mineralocorticoid Receptor Antagonism. J Invest Dermatol. 2016 Oct;136(10):2080-2089. doi: 10.1016/j.jid.2016.05.101. Epub 2016 Jun 1. PubMed PMID: 27262545.
12: Fan J, Im CS, Guo M, Cui ZK, Fartash A, Kim S, Patel N, Bezouglaia O, Wu BM, Wang CY, Aghaloo TL, Lee M. Enhanced Osteogenesis of Adipose-Derived Stem Cells by Regulating Bone Morphogenetic Protein Signaling Antagonists and Agonists. Stem Cells Transl Med. 2016 Apr;5(4):539-51. doi: 10.5966/sctm.2015-0249. Epub 2016 Mar 8. PubMed PMID: 26956209; PubMed Central PMCID: PMC4798741.
13: Minamino T, Morimoto YV, Hara N, Aldridge PD, Namba K. The Bacterial Flagellar Type III Export Gate Complex Is a Dual Fuel Engine That Can Use Both H+ and Na+ for Flagellar Protein Export. PLoS Pathog. 2016 Mar 4;12(3):e1005495. doi: 10.1371/journal.ppat.1005495. eCollection 2016 Mar. PubMed PMID: 26943926; PubMed Central PMCID: PMC4778876.
14: Leng TD, Si HF, Li J, Yang T, Zhu M, Wang B, Simon RP, Xiong ZG. Amiloride Analogs as ASIC1a Inhibitors. CNS Neurosci Ther. 2016 Jun;22(6):468-76. doi: 10.1111/cns.12524. Epub 2016 Feb 18. PubMed PMID: 26890278; PubMed Central PMCID: PMC4996284.
15: Guffey SC, Fliegel L, Goss GG. Cloning and characterization of Na(+)/H(+) Exchanger isoforms NHE2 and NHE3 from the gill of Pacific dogfish Squalus suckleyi. Comp Biochem Physiol B Biochem Mol Biol. 2015 Oct;188:46-53. doi: 10.1016/j.cbpb.2015.06.003. Epub 2015 Jun 23. PubMed PMID: 26112825.
16: Fan J, Im CS, Cui ZK, Guo M, Bezouglaia O, Fartash A, Lee JY, Nguyen J, Wu BM, Aghaloo T, Lee M. Delivery of Phenamil Enhances BMP-2-Induced Osteogenic Differentiation of Adipose-Derived Stem Cells and Bone Formation in Calvarial Defects. Tissue Eng Part A. 2015 Jul;21(13-14):2053-65. doi: 10.1089/ten.TEA.2014.0489. Epub 2015 May 20. PubMed PMID: 25869476; PubMed Central PMCID: PMC4507130.
17: Maubec E, Laouénan C, Deschamps L, Nguyen VT, Scheer-Senyarich I, Wackenheim-Jacobs AC, Steff M, Duhamel S, Tubiana S, Brahimi N, Leclerc-Mercier S, Crickx B, Perret C, Aractingi S, Escoubet B, Duval X, Arnaud P, Jaisser F, Mentré F, Farman N. Topical Mineralocorticoid Receptor Blockade Limits Glucocorticoid-Induced Epidermal Atrophy in Human Skin. J Invest Dermatol. 2015 Jul;135(7):1781-1789. doi: 10.1038/jid.2015.44. Epub 2015 Feb 10. PubMed PMID: 25668238.
18: González Y, Camarena L, Dreyfus G. Induction of the lateral flagellar system of Vibrio shilonii is an early event after inhibition of the sodium ion flux in the polar flagellum. Can J Microbiol. 2015 Mar;61(3):183-91. doi: 10.1139/cjm-2014-0579. Epub 2014 Nov 27. PubMed PMID: 25639364.
19: Rubino JG, Zimmer AM, Wood CM. Intestinal ammonia transport in freshwater and seawater acclimated rainbow trout (Oncorhynchus mykiss): evidence for a Na+ coupled uptake mechanism. Comp Biochem Physiol A Mol Integr Physiol. 2015 May;183:45-56. doi: 10.1016/j.cbpa.2014.12.037. Epub 2014 Dec 27. PubMed PMID: 25545914.
20: Nadella SR, Patel D, Ng A, Wood CM. An in vitro investigation of gastrointestinal Na(+) uptake mechanisms in freshwater rainbow trout. J Comp Physiol B. 2014 Dec;184(8):1003-19. doi: 10.1007/s00360-014-0855-7. Epub 2014 Sep 3. PubMed PMID: 25183198.
