関: ethacrynate、ethacrynic acid

WordNet

street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/10/03 21:58:20」(JST)

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Etacrynic acid (INN) or ethacrynic acid (USAN), trade name Edecrin, is a loop diuretic used to treat high blood pressure and the swelling caused by diseases like congestive heart failure, liver failure, and kidney failure.

Unlike the other loop diuretics, etacrynic acid is not a sulfonamide^[1] and thus, its use is not contraindicated in those with sulfa allergies.

Ethacrynic acid is a phenoxyacetic acid derivative containing a ketone group and a methylene group. A cysteine adduct is formed with the methylene group and this is the active form.

Medical use

Ethacrynic acid is a diuretic that is used to treat edema when a stronger agent is required. It is available as a pill or injected form. The pill is used to treat edema associated with congestive heart failure, cirrhosis and renal disease, accumulation of liquid in the belly associated with cancer or edema, and management of hospitalized children with congenital heart disease or nephrotic syndrome. The injected form is used to rapidly remove water from the body when needed - for example in acute pulmonary edema - or when a person cannot take the medicine in pill form.^[2]

Adverse effects

As a diuretic, ethacrynic acid can cause frequent urination, but this usually resolves after taking the drug for a few weeks.

Ethacrynic acid can also cause low potassium levels, which may manifest as muscle cramps or weakness. It has also been known to cause reversible or permanent hearing loss (ototoxicity)^[3] and liver damage^[4] when administered in extremely high dosages. On oral administration, it produces diarrhea; intestinal bleeding may occur at higher doses.

Mechanism of action

Ethacrynic acid acts by inhibiting NKCC2 in the thick ascending loop of Henle and the Macula Densa. Loss of potassium ions is less marked but chances of hypochloremic alkalosis are greater. The dose response curve of ethacrynic acid is steeper than that of furosemide and, in general, it is less manageable; dose range is 50-150mg.

Ethacrynic acid and its glutathione-adduct are potent inhibitors of glutathione S-transferase family members, which are enzymes involved in xenobiotic metabolism. This family of enzymes has recently been shown to have a high rate of genetic variability.

References

^ Somberg JC, Molnar J; Molnar (January 2009). "The Pleiotropic Effects of Ethacrynic Acid". Am J Ther. 16 (1): 102–4. doi:10.1097/MJT.0b013e3181961264. PMID 19142157.
^ Merck and FDA Etacrynic acid Label. Last updated February 2005 per FDA site for NDA 016093 injected form and FDA site for NDA 016092 oral form per index here, each accessed January 16, 2016
^ Bosher SK (1980). "The nature of the ototoxic actions of ethacrynic acid upon the mammalian endolymph system. I. Functional aspects". Acta Otolaryngol. 89 (5–6): 407–18. doi:10.3109/00016488009127156. PMID 7446061.
^ Datey, KK; Deshmukh, SN; Dalvi, CP; Purandare, NM (1967). "Hepatocellular damage with ethacrynic acid". Br. Med. J. 3 (5558): 152–153. doi:10.1136/bmj.3.5558.152. PMC 1842848. PMID 6028103.

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1. ループ利尿剤：最大有効量および主な副作用 loop diuretics maximum effective dose and major side effects
2. 利尿剤の作用機序 mechanism of action of diuretics
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4. 成人における難治性浮腫の治療 treatment of refractory edema in adults
5. 成人における浮腫に対する治療の一般原則 general principles of the treatment of edema in adults

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Mechanism of Reductive Metabolism and Chiral Inversion of Proton Pump Inhibitors.

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Drug metabolism and disposition: the biological fate of chemicals. 2019 Jun;47(6)657-664.
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リンク元	「ethacrynate」

「ethacrynate」

Etacrynic acid
Systematic (IUPAC) name
	[2,3-dichloro-4-(2-methylenebutanoyl)phenoxy]acetic acid
Clinical data
Trade names	Edecrin
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682857
Routes of; administration	Oral, IV
Legal status
Legal status	℞ (Prescription only);
Pharmacokinetic data
Protein binding	> 98%
Identifiers
CAS Number	58-54-8
ATC code	C03CC01 (WHO)
PubChem	CID 3278
IUPHAR/BPS	7179
DrugBank	DB00903
ChemSpider	3163
UNII	M5DP350VZV
KEGG	D00313
ChEBI	CHEBI:4876
ChEMBL	CHEMBL456
Chemical data
Formula	C13H12Cl2O4
Molar mass	303.138 g/mol
	SMILES Clc1c(C(=O)\C(=C)CC)ccc(OCC(=O)O)c1Cl ;
	InChI InChI=1S/C13H12Cl2O4/c1-3-7(2)13(18)8-4-5-9(12(15)11(8)14)19-6-10(16)17/h4-5H,2-3,6H2,1H3,(H,16,17) ; Key:AVOLMBLBETYQHX-UHFFFAOYSA-N ;
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関: etacrynic acid、ethacrynic acid

ethacrynic acid

[pmid19142157-1] Somberg JC, Molnar J; Molnar (January 2009). "The Pleiotropic Effects of Ethacrynic Acid". Am J Ther. 16 (1): 102–4. doi:10.1097/MJT.0b013e3181961264. PMID 19142157.

[Label-2] Merck and FDA Etacrynic acid Label. Last updated February 2005 per FDA site for NDA 016093 injected form and FDA site for NDA 016092 oral form per index here, each accessed January 16, 2016

[pmid7446061-3] Bosher SK (1980). "The nature of the ototoxic actions of ethacrynic acid upon the mammalian endolymph system. I. Functional aspects". Acta Otolaryngol. 89 (5–6): 407–18. doi:10.3109/00016488009127156. PMID 7446061.

[pmid6028103-4] Datey, KK; Deshmukh, SN; Dalvi, CP; Purandare, NM (1967). "Hepatocellular damage with ethacrynic acid". Br. Med. J. 3 (5558): 152–153. doi:10.1136/bmj.3.5558.152. PMC 1842848. PMID 6028103.

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etacrynic acid