Clazosentan

Clazosentan (INN, brand name Pivlaz^[1]) is a drug belonging to the class of endothelin receptor antagonists.

Clazosentan

Clinical data
Trade names	Pivlaz
ATC code	C04AX33 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name 5-methyl-pyridin-2-sulfonic acid{6-(2-hydroxy-ethoxy)-5-(2-methoxy-phenoxy)-2-[2-(1H-tetrazol-5-yl)-pyridin-4-yl]-pyrimidin-4-yl}amide
CAS Number	180384-56-9
PubChem CID	6433095
DrugBank	DB06677
ChemSpider	4938283
UNII	3DRR0X4728
KEGG	D11664
ChEMBL	ChEMBL109648
CompTox Dashboard (EPA)	DTXSID60170955
Chemical and physical data
Formula	C25H23N9O6S
Molar mass	577.58 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CN=C(C=C1)S(=O)(=O)NC2=C(C(=NC(=N2)C3=CC(=NC=C3)C4=NNN=N4)OCCO)OC5=CC=CC=C5OC
InChI 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) Key:LFWCJABOXHSRGC-UHFFFAOYSA-N

Mechanism

The endothelin 1 receptor is one of the strongest known vasoconstrictors. After subarachnoidal bleedings, irritation of the blood vessels can lead to a vasospasm and thus to an ischaemia, an insufficient blood supply to brain tissue. One possible effect of this is, in turn, an ischaemic stroke.

Trials

In a randomized trial with patients who had aneurysmal subarachnoid bleeding and were being treated with endovascular coiling, 15 mg/h clazosentan significantly reduced vasospasm-related morbidity and all-cause mortality. Clazosentan, however, did not improve the neurological outcome as measured by the extended Glascow Outcome Scale.^[2]