A7410

Amiloride hydrochloride hydrate

Name: Amiloride hydrochloride hydrate
Brand: SIGMA

≥98% (HPLC), powder, T-type calcium channel blocker

Synonym(s):

N-Amidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):

C₆H₈ClN₇O · HCl · xH₂O

CAS Number:

2016-88-8

Molecular Weight:

266.09 (anhydrous basis)

UNSPSC Code:

12352200

PubChem Substance ID:

24277817

NACRES:

NA.77

MDL number:

MFCD03703482

Key Documents

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Product Name

Amiloride hydrochloride hydrate, ≥98% (HPLC), powder

SMILES string

O.Cl.NC(=N)NC(=O)c1nc(Cl)c(N)nc1N

InChI

1S/C6H8ClN7O.ClH.H2O/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11;;/h(H4,8,9,13)(H4,10,11,14,15);1H;1H2

InChI key

WDZJJRLYFQNCQL-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

, White to Yellow and Faint Green to Green and Yellow-Green

mp

285-288 °C (dec.)

solubility

H₂O: 50 mg/mL, hazy (Very Faint Yellow to Dark Yellow and Very Faint Green-Yellow to Dark Green-Yellow and Very Faint Brown-Yellow to Dark Brown-Yellow)

originator

Perrigo

storage temp.

room temp

Quality Level

200

Gene Information

Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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Show Differences

1 of 4

This Item	A4562	B2417	SML0460
Sigma-Aldrich A7410 Amiloride hydrochloride hydrate	Sigma-Aldrich A4562 5-(N,N-Dimethyl)amiloride hydrochloride	Sigma-Aldrich B2417 Benzamil hydrochloride hydrate	Sigma-Aldrich SML0460 Methylhexanamine hydrochloride
form powder	form powder	form solid	form powder
assay ≥98% (HPLC)	assay -	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 200	Quality Level 200	Quality Level 100	Quality Level 100
storage temp. room temp	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. room temp
solubility H₂O: 50 mg/mL, clear, yellow-green	solubility -	solubility methanol: 10 mg/mL, DMSO: >20 mg/mL	solubility H₂O: 5 mg/mL (clear solution)
color yellow	color -	color yellow	color white to beige

Application

Amiloride is a selective T-type calcium channel blocker, an epithelial sodium channel blocker and a selective inhibitor of urokinase plasminogen activator (uPA). Amiloride has been used in a study to develop an alternative treatment for constipation.

Biochem/physiol Actions

Selective T-type Ca²⁺ and epithelial sodium channel blocker

Selective T-type calcium channel blocker and blocker of epithelial sodium channel. Selective inhibitor of urokinase plasminogen activator (uPA).

Disclaimer

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Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the Acid-Sensing (Proton-gated) Ion Channels (ASICs) and Imidazoline Binding Sites pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Perrigo. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Deficiency of renal cortical EGF increases ENaC activity and contributes to salt-sensitive hypertension.

Tengis S Pavlov et al.

Journal of the American Society of Nephrology : JASN, 24(7), 1053-1062 (2013-04-20)

Various stimuli, including hormones and growth factors, modulate epithelial sodium channels (ENaCs), which fine-tune Na(+) absorption in the kidney. Members of the EGF family are important for maintaining transepithelial Na(+) transport, but whether EGF influences ENaC, perhaps mediating salt-sensitive hypertension

Fibrinolytic cross-talk: a new mechanism for plasmin formation.

Tiphaine Dejouvencel et al.

Blood, 115(10), 2048-2056 (2009-12-10)

Fibrinolysis and pericellular proteolysis depend on molecular coassembly of plasminogen and its activator on cell, fibrin, or matrix surfaces. We report here the existence of a fibrinolytic cross-talk mechanism bypassing the requirement for their molecular coassembly on the same surface.

Involvement of the epithelial sodium channel in initiation of mechanically evoked swallows in anaesthetized rats.

Takanori Tsujimura et al.

The Journal of physiology, 597(11), 2949-2963 (2019-04-30)

Afferents carried by the superior laryngeal nerve play a primary role in the initiation of laryngeal mechanically evoked swallows in anaesthetized rats. Amiloride and its analogues inhibit swallowing evoked by mechanical stimulation, but not swallowing evoked by chemical and electrical

TAZ expression as a prognostic indicator in colorectal cancer.

Hiu-Fung Yuen et al.

PloS one, 8(1), e54211-e54211 (2013-02-02)

The Hippo pathway restricts the activity of transcriptional coactivators TAZ (WWTR1) and YAP. TAZ and YAP are reported to be overexpressed in various cancers, however, their prognostic significance in colorectal cancers remains unstudied. The expression levels of TAZ and YAP

Ca2+ permeability and Na+ conductance in cellular toxicity caused by hyperactive DEG/ENaC channels.

Cristina Matthewman et al.

American journal of physiology. Cell physiology, 311(6), C920-C930 (2016-10-21)

Hyperactivated DEG/ENaC channels cause neuronal death mediated by intracellular Ca2+ overload. Mammalian ASIC1a channels and MEC-4(d) neurotoxic channels in Caenorhabditis elegans both conduct Na+ and Ca2+, raising the possibility that direct Ca2+ influx through these channels contributes to intracellular Ca2+

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