Cicletanine

Cicletanine
Clinical data
AHFS/Drugs.com	International Drug Names
Routes of; administration	Oral
ATC code	C03BX03 (WHO) ;
Pharmacokinetic data
Protein binding	99.6% for (-)cicletanine isomer; 87.5% for (+)cicletanine isomer
Elimination half-life	5.7 h. Also: Tmax = 0.750 hours. Plasma AUCinf = 29.0 μg·hr/mL. Cmax = 6.18 μg/mL. All figures are for a single oral dose of 150 mg.
Identifiers
	IUPAC name 3-(4-Chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol;
CAS Number	89943-82-8 ;
PubChem CID	54910;
ChemSpider	49583 ;
UNII	CHG7QC509W;
KEGG	D03487 ;
ChEMBL	ChEMBL191886 ;
CompTox Dashboard (EPA)	DTXSID70868972 ;
ECHA InfoCard	100.158.583
Chemical and physical data
Formula	C14H12ClNO2
Molar mass	261.71 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1)C3OCc2c3cnc(c2O)C;
	InChI 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 ; Key:CVKNDPRBJVBDSS-UHFFFAOYSA-N ;
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Cicletanine is a furopyridine compound approved in France for the treatment of hypertension.^[1] The drug is most commonly known as a diuretic drug, but has a broader range of cardiovascular and metabolic activity characterized extensively in the literature (see "Mechanism" below).

Cicletanine was originated and in 1986 launched in France by Paris-based Ipsen, who in 2005 licensed marketing rights in France to Milan-based Recordati for several years (at least until 2010). Ipsen and Recordati both marketed cicletanine under the trade name Tenstaten. The drug is no longer manufactured nor sold by IPSEN; it is currently marketed in France by three generics manufacturers: Viatris, Biogaran, and Teva Pharmaceuticals.

Cicletanine has been shown to be differentially effective in salt-sensitive hypertension.^[2]

^ Sassard J (1992). Genetic Hypertension. John Libbey Eurotext. ISBN 978-0-86196-313-3.
^ Bagrov AY, Dmitrieva RI, Dorofeeva NA, Fedorova OV, Lopatin DA, Lakatta EG, Droy-Lefaix MT (February 2000). "Cicletanine reverses vasoconstriction induced by the endogenous sodium pump ligand, marinobufagenin, via a protein kinase C dependent mechanism". Journal of Hypertension. 18 (2): 209–215. doi:10.1097/00004872-200018020-00012. PMID 10694190. S2CID 35374482.

[1] Sassard J (1992). Genetic Hypertension. John Libbey Eurotext. ISBN 978-0-86196-313-3.

[pmid10694190-2] Bagrov AY, Dmitrieva RI, Dorofeeva NA, Fedorova OV, Lopatin DA, Lakatta EG, Droy-Lefaix MT (February 2000). "Cicletanine reverses vasoconstriction induced by the endogenous sodium pump ligand, marinobufagenin, via a protein kinase C dependent mechanism". Journal of Hypertension. 18 (2): 209–215. doi:10.1097/00004872-200018020-00012. PMID 10694190. S2CID 35374482.

[1]

[2]

Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	C03BX03 (WHO)
Pharmacokinetic data
Protein binding	99.6% for (-)cicletanine isomer; 87.5% for (+)cicletanine isomer
Elimination half-life	5.7 h. Also: Tmax = 0.750 hours. Plasma AUCinf = 29.0 μg·hr/mL. Cmax = 6.18 μg/mL. All figures are for a single oral dose of 150 mg.
Identifiers
IUPAC name 3-(4-Chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol
CAS Number	89943-82-8^Y
PubChem CID	54910
ChemSpider	49583^Y
UNII	CHG7QC509W
KEGG	D03487^Y
ChEMBL	ChEMBL191886^Y
CompTox Dashboard (EPA)	DTXSID70868972
ECHA InfoCard	100.158.583
Chemical and physical data
Formula	C₁₄H₁₂ClNO₂
Molar mass	261.71 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Clc1ccc(cc1)C3OCc2c3cnc(c2O)C
InChI 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^Y Key:CVKNDPRBJVBDSS-UHFFFAOYSA-N^Y
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