CICLETANINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C14H12ClNO2
Molecular Weight	261.704
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(O)C2=C(C=N1)C(OC2)C3=CC=C(Cl)C=C3

InChI

InChIKey=CVKNDPRBJVBDSS-UHFFFAOYSA-N

InChI=1S/C14H12ClNO2/c1-8-13(17)12-7-18-14(11(12)6-16-8)9-2-4-10(15)5-3-9/h2-6,14,17H,7H2,1H3

HIDE SMILES / InChI

Molecular Formula	C14H12ClNO2
Molecular Weight	261.704
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ipsen.com/websites/IPSENCOM-PROD/wp-content/uploads/2016/06/29140317/Ipsen_AR_2005_EN.pdf | https://www.ncbi.nlm.nih.gov/pubmed/10428010

Cicletanine is a diuretic, developed by Ipsen for the treatment of hypertension. The drug was marketed in France by Recordati under the name Tenstaten. The mechanism(s) by which cicletanine exerts its biological effects has not been definitely established. The salidiuretic activity appears to be the result of an action of the sulfoconjugated metabolite of cicletanine, which inhibits the apical Na+-dependent Cl-/HCO3- anion exchanger in the distal convoluted tubule. The mechanism of the vasodilating effect of cicletanine may include stimulation of vascular prostaglandin synthesis, inhibition of the low Km cyclic GMP phosphodiesterases, and blockade of Ca2+ channels either directly or indirectly. The drug has also been shown to interact with other proteins, including alpha-adrenergic, vascular histamine, and muscarinic receptors.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: https://www.has-sante.fr/portail/upload/docs/application/pdf/ct010354.pdf	Primary		Approved 8429	TENSTATEN Approved Use Hypertension. Launch Date 1986

PubMed

Title	Date	PubMed
[Comparison of the effects of cicletanine and captopril on kidney and heart lesions in spontaneously hypertensive rats (SHR-SP)].	1989 Nov	2514660
Renal-protective effect of nondepressor dose of cicletanine in diabetic rats with hypertension.	2000 Mar	10777035
Effect of cicletanine on the nitric oxide pathway in human umbilical vein endothelial cells.	2001 Aug	11483866
Nitric oxide, peroxynitrite and cGMP in atherosclerosis-induced hypertension in rabbits: beneficial effects of cicletanine.	2001 Jan-Feb	11173993
Cicletanine stimulates nitric oxide release and scavenges superoxide in endothelial cells.	2001 Jun	11392468
Diuretics in the therapy of hypertension.	2002 Mar	11986901
Myocardial PKC beta2 and the sensitivity of Na/K-ATPase to marinobufagenin are reduced by cicletanine in Dahl hypertension.	2003 Mar	12623951
Protective effect of cicletanine on renal function in diabetic spontaneously hypertensive rats.	2004 Nov	15672472
Insulin sensitization induced by oral cicletanine in conscious rabbits.	2006 Sep	16955283
Updated meta-analytical approach to the efficacy of antihypertensive drugs in reducing blood pressure.	2007	17914893
Cicletanine for the treatment of pulmonary arterial hypertension.	2008 Oct 27	18955648
Update on pulmonary hypertension complicating chronic obstructive pulmonary disease.	2009	19802350
Blood pressure lowering efficacy of loop diuretics for primary hypertension.	2009 Oct 7	19821314
Emerging therapies for the treatment of pulmonary hypertension.	2010 Mar	20216170

Patents

Sample Use Guides

In Vivo Use Guide

The treatment is initiated with 50 mg/day, but the effective dosage is usually 100 mg/day.

Route of Administration: Oral

In Vitro Use Guide

The effect of cicletanine on active tension was investigated in rat thoracic aortas. At concentrations from 3*10(-5) M to 3*10(-4) M the drug caused a concentration-related relaxation of noradrenaline, serotonin and prostaglandin F2alpha-induced contractions.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:12:19 GMT 2023` Edited by `admin` on `Fri Dec 15 16:12:19 GMT 2023`
Record UNII	CHG7QC509W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CICLETANINE

Official Name

English

(±)-BN-1270

Code

English

CICLETANINE [USAN]

Common Name

English

CICLETANINE [MI]

Common Name

English

cicletanine [INN]

Common Name

English

Cicletanine [WHO-DD]

Common Name

English

CICLETANINE [MART.]

Common Name

English

WIN 90,000

Code

English

BN-1270

Code

English

CYCLETANIDE

Common Name

English

WIN-90000

Code

English

Classification Tree Code System Code

WHO-VATC

QC03BX03