ALILUSEM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H15ClN2O5S
Molecular Weight	394.829
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(C=CC=C1)C(=O)N2CC\C(=N/OS(O)(=O)=O)C3=C2C=C(Cl)C=C3

InChI

InChIKey=QQCSUWGQBREWRO-XDJHFCHBSA-N

InChI=1S/C17H15ClN2O5S/c1-11-4-2-3-5-13(11)17(21)20-9-8-15(19-25-26(22,23)24)14-7-6-12(18)10-16(14)20/h2-7,10H,8-9H2,1H3,(H,22,23,24)/b19-15+

HIDE SMILES / InChI

Molecular Formula	C17H15ClN2O5S
Molecular Weight	394.829
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8283835
Curator's Comment: description was created based on several sources, including: http://www.ncbi.nlm.nih.gov/pubmed/8405100 https://www.ncbi.nlm.nih.gov/pubmed/15349965 http://www.ncbi.nlm.nih.gov/pubmed/12593763 https://www.ncbi.nlm.nih.gov/pubmed/17103337

Alilusem (M17055) is under development as a novel loop diuretic for oral administration. M17055 has a potent diuretic effect and can be categorized as a loop diuretic that inhibits both the cotransport of Na+, K+, and 2Cl- at the thick ascending Henle’s loop and the reabsorption of Na+ at the distal tubule cells in the kidney. Structure of M17055 is different from those of other loop diuretics; M17055, which has a sulfate group in its structure is soluble and well absorbed, and its bioavailability in humans is 42-60% (unpublished observation). Considering that the pKa of M17055 is 2.39, almost of M17055 would be in ionized form at physiological pH in the small intestine. In humans, the major elimination route of M17055 is renal excretion, 59-72% of the dose being recovered in unchanged form in urine; the remainder is thought to be metabolized by both CYP3A4 and CYP2C9.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
renal sodium ion transport 2 Target ID: GO:0003096 Sources: http://www.ncbi.nlm.nih.gov/pubmed/8405100	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8283835	Curative		Basic research	Unknown Approved Use Unknown
Left ventricular hypertrophy 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8283835	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Pharmacological properties of the novel highly potent diuretic 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone 4-oxime-O-sulfonic acid potassium salt.	1992 Dec	1337698
Loop and distal actions of a novel diuretic, M17055.	1993 Jul 20	8405100
Effect of a novel diuretic, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(IH)-quinolinone-4-oxime-o- sulfonic acid, potassium salt (M17055) on Na+ and K+ transport in the distal nephron segments.	1993 Sep	8396638
Effects of amiloride and a novel diuretic, 7-chloro-2,3-dihydro-1-(2-methylbenzoyl)-4(1H)-quinolinone-4-oxime-o-su lfonic acid, potassium salt (M17055), on calcium transport in the rabbit connecting tubule.	1993 Sep	8396639
Molecular effects of M17055, furosemide and thiazide on cardiac hypertrophy of spontaneously hypertensive rats.	1996 Nov	8930208
Studies on the metabolic fate of M17055, a novel diuretic (4): species difference in metabolic pathway and identification of human CYP isoform responsible for the metabolism of M17055.	2002	15618654
Studies on the metabolic fate of m17055, a novel diuretic (5): pharmacokinetics and pharmacodynamics of unchanged drug in rat and dog after intravenous administration of M17055.	2002	15618672
Studies on the metabolic fate of M17055, a novel diuretic (6). Assessment for drug-drug interactions of M17055 in metabolism, distribution and excretion.	2002 Dec	12593763
Characterization of renal excretion mechanism for a novel diuretic, M17055, in rats.	2004 Oct	15349965
Characterization of the uptake mechanism for a novel loop diuretic, M17055, in Caco-2 cells: involvement of organic anion transporting polypeptide (OATP)-B.	2007 Jan	17103337

Patents

Sample Use Guides

In Vivo Use Guide

dogs, 1 mg/kg per h

Route of Administration: Intravenous

In Vitro Use Guide

rabbit cortical thick, 1.0 - 10.0 uM

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:56:38 GMT 2023` Edited by `admin` on `Sat Dec 16 17:56:38 GMT 2023`
Record UNII	37376U135T
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ALILUSEM

Official Name

English

Alilusem [WHO-DD]

Common Name

English

alilusem [INN]

Common Name

English

7-CHLORO-1-(2-METHYLBENZOYL)-2,3-DIHYDROQUINOLIN-4(1H)-ONE (E)-O-SULFOOXIME

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C448