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A7410

Sigma-Aldrich

Amiloride hydrochloride hydrate

≥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)
MDL number:
MFCD03703482
UNSPSC Code:
12352200
PubChem Substance ID:
24277817
NACRES:
NA.77

product name

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

Quality Level

200

Assay

≥98% (HPLC)

form

powder

color

yellow

mp

285-288 °C (dec.)

solubility

H2O: 50 mg/mL, clear, yellow-green

originator

Perrigo

storage temp.

room temp

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

Gene Information

human ... ABP1(26) , ACCN1(40) , ACCN2(41) , PLAU(5328) , SCNN1A(6337) , SCNN1B(6338) , SCNN1D(6339) , SCNN1G(6340) , SLC9A1(6548) , TNF(7124)
mouse ... Abp1(76507) , Accn1(11418) , Accn2(11419) , Plau(18792) , Scnn1a(20276) , Scnn1b(20277) , Scnn1d(140501) , Scnn1g(20278) , Slc9a1(20544)
rat ... Abp1(65029) , Accn1(25364) , Accn2(79123) , Plau(25619) , Scnn1a(25122) , Scnn1b(24767) , Scnn1g(24768) , Slc9a1(24782)

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

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.

Caution

Protect from light.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
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
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
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
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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