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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 of CICLETANINE

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

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

Ipsen
13
Curator's Comment: In october 2005 Ipsen and Recordati announced the signature of an agreement by which Ipsen grants to Recordati the exclusive marketing and selling rights in France of Tenstaten (cicletanine).

Approval Year

Unknown
139594
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
TENSTATEN

Approved Use

Hypertension.

Launch Date

5.22892804E11
PubMed

PubMed

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

Patents

CA2042421 C
2
US5026855 A
2

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 UTC 2023
Edited
by admin
on Fri Dec 15 16:12:19 UTC 2023
Record UNII
CHG7QC509W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CICLETANINE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
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
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
NCI_THESAURUS C448
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
WHO-ATC C03BX03
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C77557
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
SMS_ID
100000081885
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
DRUG CENTRAL
634
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
USAN
BB-93
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
RXCUI
21914
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY RxNorm
EVMPD
SUB06237MIG
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
FDA UNII
CHG7QC509W
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
EPA CompTox
DTXSID70868972
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
MESH
C038068
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
PUBCHEM
54910
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
CAS
89943-82-8
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
MERCK INDEX
m3537
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY Merck Index
INN
5596
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
WIKIPEDIA
CICLETANINE
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
DRUG BANK
DB12766
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
ChEMBL
CHEMBL191886
Created by admin on Fri Dec 15 16:12:19 UTC 2023 , Edited by admin on Fri Dec 15 16:12:19 UTC 2023
PRIMARY
Related Record Type Details
Structure of CICLETANINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of CICLETANINE, (R)-
ENANTIOMER -> RACEMATE
Structure of CICLETANINE, (S)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of CICLETANINE
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