U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C25H23N9O6S
Molecular Weight 577.572
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLAZOSENTAN

SMILES

COC1=CC=CC=C1OC2=C(OCCO)N=C(N=C2NS(=O)(=O)C3=NC=C(C)C=C3)C4=CC=NC(=C4)C5=NN=NN5

InChI

InChIKey=LFWCJABOXHSRGC-UHFFFAOYSA-N
InChI=1S/C25H23N9O6S/c1-15-7-8-20(27-14-15)41(36,37)32-24-21(40-19-6-4-3-5-18(19)38-2)25(39-12-11-35)29-22(28-24)16-9-10-26-17(13-16)23-30-33-34-31-23/h3-10,13-14,35H,11-12H2,1-2H3,(H,28,29,32)(H,30,31,33,34)

HIDE SMILES / InChI

Molecular Formula C25H23N9O6S
Molecular Weight 577.572
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Clazosentan is an endothelin receptor antagonist, developed by the Swiss pharmaceutical company Actelion, and licensed to its spin-off, Idorsia. The drug was designed to inhibit endothelin-mediated cerebral vasospasm and associated delayed ischaemic neurological deficit. The drug has been investigated in a phase III clinical trials in patients with aneurysmal subarachnoid hemorrhage. Clazosentan at 5 mg/h had no significant effect on mortality and vasospasm-related morbidity or functional outcome. Clinical investigation of a higher dose of the drug is underway.

Approval Year

PubMed

PubMed

TitleDatePubMed
Profile of past and current clinical trials involving endothelin receptor antagonists: the novel "-sentan" class of drug.
2006 Jun
Clazosentan (Actelion).
2006 Mar
Effect of gender on the tolerability, safety and pharmacokinetics of clazosentan following long-term infusion.
2007
Clinical review: Prevention and therapy of vasospasm in subarachnoid hemorrhage.
2007
Effects of the selective endothelin A (ET(A)) receptor antagonist Clazosentan on cerebral perfusion and cerebral oxygenation following severe subarachnoid hemorrhage - preliminary results from a randomized clinical series.
2007
Tolerability, pharmacokinetics, and pharmacodynamics of clazosentan, a parenteral endothelin receptor antagonist.
2007 Feb
Effect of delayed cerebral vasospasm on cerebrovascular endothelin A receptor expression and function.
2007 Jul
Cerebral vasospasm: looking beyond vasoconstriction.
2007 Jun
Cerebral vasospasm after subarachnoid hemorrhage: the emerging revolution.
2007 May
[Systemic treatments of the vasospasm].
2007 Nov
Influence of ethnic origin and sex on the pharmacokinetics of clazosentan.
2007 Nov
Vasospasm after aneurysmal subarachnoid hemorrhage: need for further study.
2008
Clazosentan, an endothelin receptor antagonist, prevents early hypoperfusion during the acute phase of massive experimental subarachnoid hemorrhage: a laser Doppler flowmetry study in rats.
2008 Dec
IL-33 mediates antigen-induced cutaneous and articular hypernociception in mice.
2008 Feb 19
Clazosentan: an endothelin receptor antagonist for treatment of vasospasm after subarachnoid hemorrhage.
2008 Nov
Clazosentan to overcome neurological ischemia and infarction occurring after subarachnoid hemorrhage (CONSCIOUS-1): randomized, double-blind, placebo-controlled phase 2 dose-finding trial.
2008 Nov
Diagnosis and management of vasospasm.
2009 Apr 29
Effect of endothelin-receptor antagonists on delayed cerebral ischemia after aneurysmal subarachnoid hemorrhage remains unclear.
2009 Dec
Delayed cerebral ischemia after aneurysmal subarachnoid hemorrhage: is angiographic vasospasm an epiphenomenon?
2009 Feb
Cortical spreading ischaemia is a novel process involved in ischaemic damage in patients with aneurysmal subarachnoid haemorrhage.
2009 Jul
In vitro and in vivo pharmacokinetic characteristics of clazosentan, an intravenous endothelin receptor antagonist, in humans.
2009 Mar
Therapeutic approaches to cerebral vasospasm complicating ruptured aneurysm.
2009 Nov 16
Preventing vasospasm improves outcome after aneurysmal subarachnoid hemorrhage: rationale and design of CONSCIOUS-2 and CONSCIOUS-3 trials.
2010 Dec
Patient age and vasospasm after subarachnoid hemorrhage.
2010 Oct
Impact of systemic inflammatory response syndrome on vasospasm, cerebral infarction, and outcome after subarachnoid hemorrhage: exploratory analysis of CONSCIOUS-1 database.
2010 Oct
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 17:48:25 GMT 2023
Edited
by admin
on Sat Dec 16 17:48:25 GMT 2023
Record UNII
3DRR0X4728
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLAZOSENTAN
INN   MI   WHO-DD  
USAN   INN  
Official Name English
RO-61-1790
Code English
AXV-343434
Code English
2-PYRIDINESULFONAMIDE, N-(6-(2-HYDROXYETHOXY)-5-(2-METHOXYPHENOXY)-2-(2-(1H-TETRAZOL-5-YL)-4-PYRIDINYL)-4-PYRIMIDINYL)-5-METHYL-
Systematic Name English
Clazosentan [WHO-DD]
Common Name English
RO 61-1790
Code English
AXV-034343
Code English
CLAZOSENTAN [USAN]
Common Name English
clazosentan [INN]
Common Name English
CLAZOSENTAN [MI]
Common Name English
N-(6-(2-HYDROXYETHOXY)-5-(2-METHOXYPHENOXY)-2-(2-(1H-TETRAZOL-5-YL)PYRIDIN-4-YL)PYRIMIDIN-4-YL)-5-METHYLPYRIDINE-2-SULFONAMIDE
Systematic Name English
VML-588
Code English
ACT-108475
Code English
Classification Tree Code System Code
FDA ORPHAN DRUG 217105
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
Code System Code Type Description
FDA UNII
3DRR0X4728
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
INN
8397
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
CAS
180384-56-9
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
ChEMBL
CHEMBL109648
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
DRUG BANK
DB06677
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
EVMPD
SUB25412
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
USAN
GH-137
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
EPA CompTox
DTXSID60170955
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
WIKIPEDIA
Clazosentan
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
MERCK INDEX
m3610
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY Merck Index
SMS_ID
100000089436
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
PUBCHEM
6433095
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
MESH
C109641
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
NCI_THESAURUS
C79486
Created by admin on Sat Dec 16 17:48:25 GMT 2023 , Edited by admin on Sat Dec 16 17:48:25 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY