Tirilazad Mesylate
Basic information
- CAS
110101-67-2- Standard SMILES
CS(=O)(=O)O.C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]2(C)[C@H]1C(=O)CN1CCN(c2cc(N3CCCC3)nc(N3CCCC3)n2)CC1- InChIKey
HPZOOQSXPMEJBV-ODCFVKFUSA-N- Molecular formula
- C39H56N6O5S
- Average molar mass
- 721 g/mol
- Monoisotopic mass
- 720.40329008
Overview
Tirilazad mesylate is a corticosteroid hormone.
Names & identifiers
- Preferred name
- Tirilazad Mesylate
- IUPAC
- (8S,10S,13S,14S,16R,17S)-17-[2-[4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)piperazin-1-yl]acetyl]-10,13,16-trimethyl-6,7,8,12,14,15,16,17-octahydrocyclopenta[a]phenanthren-3-one;methanesulfonic acid
- English name
- tirilazad
- Molecular formula
- C39H56N6O5S
- Molecular weight
- 720.97
Names & synonyms
Tirilazad mesylate110101-67-2FreedoxU-74006FTirilazad mesilateTIRILAZAD MESILATE ANHYDROUSTIRILAZAD MESYLATE ANHYDROUSTiralazad mesilate hydrateTiralazad mesylate hydrate19B418DV39DTXSID40149144PNU 74006F
Show more names
21-(4-(2,6-di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl)-16-methylpregna-1,4,9(11)-triene-3,20-dione monomethane sulfonateRefChem:190128DTXCID4071635PREGNA-1,4,9(11)-TRIENE-3,20-DIONE, 21-(4-(2,6-DI-1-PYRROLIDINYL-4-PYRIMIDINYL)-1-PIPERAZINYL)-16-METHYL-, (16ALPHA)-, MONOMETHANESULFONATE, MONOHYDRATE149042-61-5HXS259UWKWTirilazad mesylate hydrateTirilazad (mesylate)
Database identifiers
- CAS
110101-67-2- PubChem CID
- 104902
- DTXSID
DTXSID40149144- ChEMBL
CHEMBL3989513- ChEBI
CHEBI:32233- UNII
- 19B418DV39
Properties
Computed structural properties
- Topological polar surface area
- 136 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 6
- Heavy atoms
- 51
- Formal charge
- 0
- Complexity
- 1,380
Physicochemical properties
- FDA UNII
- 19 B418DV39 · 19B418DV39
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 280 · P280-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P280-P305+P351+P338
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues.
Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids.
Applications
DescriptionTirilazad mesylate, a novel 21 -aminosteroid derivative, has been marketed in Austria for the intravenous treatment of subarachnoid hemorrhage (SAH) in male patients. Studies have indicated involvement of lipid peroxidation and/or lipid hydrolysis in the genesis of SAH-initiated microvascular damage and prolonged vasospasm of the large cerebral vessels. Tirilazad mesylate is a highly lipophilic compound that localizes to the cell membrane. It is a potent inhibitor of lipid peroxidation induced by oxygen free radicals, purely through a mechanism similar to vitamin E by scavenging lipid peroxyl radicals, and is a stabilizer of biological membranes. Tirilazad mesylate has been demonstrated to have a positive effect in reducing symptomatic vasospasm, cerebral infarction, and neurological dysfunction. Clinically, it is reportedly effective in reducing mortality in male SAH patients relative to the control group. The title compound is also reportedly in clinical trials for ischemic stroke, spinal cord injury, and for non-systemic ocular applications. Little or no behavioral and physiological side effects have been reported.
Additional notes
DefinitionChEBI: Tirilazad mesylate is a corticosteroid hormone.
Related reactions
6 records
Compound notes
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