CICLETANINE

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

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

Description

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

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567	Primary		Approved 8,429	TENSTATEN

C_max

Value	Dose	Analyte	Population
20 μg/mL	300 mg single, oral	CICLETANINE plasma	Homo sapiens
14 μg/mL	300 mg single, oral	CICLETANINE plasma	Homo sapiens
13 μg/mL	300 mg single, oral	CICLETANINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
115 μg × h/mL	300 mg single, oral	CICLETANINE plasma	Homo sapiens
81 μg × h/mL	300 mg single, oral	CICLETANINE plasma	Homo sapiens
109 μg × h/mL	300 mg single, oral	CICLETANINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
7.4 h	300 mg single, oral	CICLETANINE plasma	Homo sapiens
12.4 h	300 mg single, oral	CICLETANINE plasma	Homo sapiens
31 h	300 mg single, oral	CICLETANINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
7%			CICLETANINE plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
100 mg 1 times / day multiple, oral Studied dose	unhealthy, ADULT
150 mg single, oral Studied dose	healthy, ADULT

Showing 1 to 2 of 2 entries

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PubMed

Show entries

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
Nitric oxide, peroxynitrite and cGMP in atherosclerosis-induced hypertension in rabbits: beneficial effects of cicletanine.	2001 Jan-Feb	11173993
Updated meta-analytical approach to the efficacy of antihypertensive drugs in reducing blood pressure.	2007	17914893
Emerging therapies for the treatment of pulmonary hypertension.	2010 Mar	20216170

Showing 1 to 5 of 5 entries

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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.