Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C38H52N6O2.CH4O3S |
| Molecular Weight | 720.964 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.[H][C@@]12C[C@@H](C)[C@H](C(=O)CN3CCN(CC3)C4=CC(=NC(=N4)N5CCCC5)N6CCCC6)[C@@]1(C)CC=C7[C@@]2([H])CCC8=CC(=O)C=C[C@]78C
InChI
InChIKey=HPZOOQSXPMEJBV-ODCFVKFUSA-N
InChI=1S/C38H52N6O2.CH4O3S/c1-26-22-31-29-9-8-27-23-28(45)10-12-37(27,2)30(29)11-13-38(31,3)35(26)32(46)25-41-18-20-43(21-19-41)34-24-33(42-14-4-5-15-42)39-36(40-34)44-16-6-7-17-44;1-5(2,3)4/h10-12,23-24,26,29,31,35H,4-9,13-22,25H2,1-3H3;1H3,(H,2,3,4)/t26-,29-,31+,35-,37+,38+;/m1./s1
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C38H52N6O2 |
| Molecular Weight | 624.8585 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including:
http://www.ncbi.nlm.nih.gov/pubmed/10978061
http://www.ukmi.nhs.uk/applications/ndo/record_view_open.asp?newDrugID=2805
Curator's Comment: description was created based on several sources, including:
http://www.ncbi.nlm.nih.gov/pubmed/10978061
http://www.ukmi.nhs.uk/applications/ndo/record_view_open.asp?newDrugID=2805
Subarachnoid haemorrhage (SAH) following cerebral aneurysm rupture or trauma can result in the induction of secondary ischaemic brain damage via a decrease in microvascular perfusion, a disruption of the blood-brain barrier and consequent vasogenic oedema, and the delayed spasm of the major cerebral arteries (i.e. vasospasm). It is increasingly apparent that oxygen radical-induced, iron-catalyzed lipid peroxidation (LP) within the subarachnoid blood and vascular wall plays a key role in the occurrence of these secondary events. Tirilazad mesylate, is a nonglucocorticoid, 21-aminosteroid, is a potent cytoprotective inhibitor of LP that works by a combination of radical scavenging and membrane stabilizing properties. It has been demonstrated to attenuate the acute and delayed vascular consequences of SAH and to protect the brain against ischaemic insults. Tirilazad mesylate has been proposed to treat acute ischaemic stroke. When tested on animal models, tirilazad protects brain tissue, and reduces brain damage. However, the drug fails to treat, and even worsens a stroke when studied on a human being.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Tirilazad for acute ischaemic stroke. | 2001 |
|
| Role of free radicals in the neurodegenerative diseases: therapeutic implications for antioxidant treatment. | 2001 |
|
| Metaanalysis of trials of tirilazad mesylate in aneurysmal SAH. | 2001 |
|
| Correlation of aphasia and/or neglect with cortical infarction in a subpopulation of RANTTAS. | 2001 |
|
| A role for free radicals and nitric oxide in delayed recovery in aged rats with chronic constriction nerve injury. | 2001 Aug 15 |
|
| Pharmacological treatment of acute spinal cord injury: how do we build on past success? | 2001 Fall |
|
| Lazaroids: efficacy and mechanism of action of the 21-aminosteroids in neuroprotection. | 2001 Jan |
|
| Modulation of inflammation by reactive oxygen species: implications for aging and tissue repair. | 2001 Jan 1 |
|
| Tirilazad mesylate improve water immersion stress induced decrease in erythrocyte deformability in the rats. | 2001 Jan-Feb |
|
| Effects of immunosuppressive treatment on host responses against intracerebral porcine neural tissue xenografts in rats. | 2001 Jun 27 |
|
| Decreased red blood cells deformability in acute pancreatitis in the rat. Effect of tirilazad mesylate. | 2003 |
|
| Ultrastructural characterization of dissociated embryonic ventral mesencephalic tissue treated with neuroprotectants. | 2003 |
|
| The lazaroid tirilazad is a new inhibitor of direct and indirect UVA-induced lipid peroxidation in human dermal fibroblasts. | 2003 Dec |
|
| Effects of different steroid treatment on reperfusion-associated production of reactive oxygen species and arrhythmias during coronary surgery. | 2003 Jul |
|
| Drug development in spinal cord injury: what is the FDA looking for? | 2003 Jul-Aug |
|
| Brain trauma. | 2003 Jun |
|
| Neuroprotection in transient focal cerebral ischemia by combination drug therapy and mild hypothermia: comparison with customary therapeutic regimen. | 2003 Jun |
|
| Combination drug therapy and mild hypothermia after transient focal cerebral ischemia in rats. | 2003 Sep |
|
| Neuroprotection and acute spinal cord injury: a reappraisal. | 2004 Jan |
|
| Grading of subarachnoid hemorrhage: modification of the world World Federation of Neurosurgical Societies scale on the basis of data for a large series of patients. | 2004 Mar |
|
| Early vasospasm on admission angiography in patients with aneurysmal subarachnoid hemorrhage is a predictor for in-hospital complications and poor outcome. | 2004 Nov |
|
| Neuroprotection in ischemic stroke--combination drug therapy and mild hypothermia in a rat model of permanent focal cerebral ischemia. | 2004 Oct 15 |
|
| Re: Grading of subarachnoid hemorrhage: modification of the World Federation of Neurosurgical Societies scale on the basis of data for a large series of patients. | 2005 Mar |
|
| Relationship between 3-month National Institutes of Health Stroke Scale score and dependence in ischemic stroke patients. | 2006 |
|
| Some prognostic models for traumatic brain injury were not valid. | 2006 Feb |
|
| Evidence-based cerebral vasospasm management. | 2006 Sep 15 |
|
| Tirilazad amelioriates extracellular effects of photooxidative stress by sealing the membrane of UVA irradiated human dermal fibroblasts. | 2006 Sep-Oct |
|
| Clinical review: Prevention and therapy of vasospasm in subarachnoid hemorrhage. | 2007 |
|
| [Effect of combination therapy with hypothermia, magnesium and tirilazad in an experimental model of diffuse cerebral ischemia]. | 2007 Apr |
|
| Predictors of cerebral infarction in patients with aneurysmal subarachnoid hemorrhage. | 2007 Apr |
|
| Intraventricular hemorrhage from ruptured aneurysm: clinical characteristics, complications, and outcomes in a large, prospective, multicenter study population. | 2007 Aug |
|
| Outcome in patients with subarachnoid hemorrhage treated with antiepileptic drugs. | 2007 Aug |
|
| Traumatic brain injury: simple data collection will improve the outcome. | 2007 Feb |
|
| Subarachnoid clot volume correlates with age, neurological grade, and blood pressure. | 2007 Feb |
|
| Systematic review and meta-analysis of the efficacy of tirilazad in experimental stroke. | 2007 Feb |
|
| Comparison of treatment effects between animal experiments and clinical trials: systematic review. | 2007 Jan 27 |
|
| The combinations C1 esterase inhibitor with coagulation factor XIII and N-acetylcysteine with tirilazad mesylate reduce the leukocyte adherence in an experimental endotoxemia in rats. | 2008 |
|
| Mapping similarities in mTOR pathway perturbations in mouse lupus nephritis models and human lupus nephritis. | 2008 |
|
| Effects of N-acetylcysteine and tirilazad mesylate on intestinal functional capillary density, leukocyte adherence, mesenteric plasma extravasation and cytokine levels in experimental endotoxemia in rats. | 2008 |
|
| Predicting outcome after traumatic brain injury: development and international validation of prognostic scores based on admission characteristics. | 2008 Aug 5 |
|
| Impact of combined C1 esterase inhibitor/coagulation factor XIII or N-acetylcysteine/tirilazad mesylate administration on leucocyte adherence and cytokine release in experimental endotoxaemia. | 2008 Jul-Aug |
|
| Role of cytochrome P450 in drug interactions. | 2008 Oct 18 |
|
| Metaanalysis of tirilazad mesylate in patients with aneurysmal subarachnoid hemorrhage. | 2009 |
|
| Molecular mechanisms of traumatic brain injury: the missing link in management. | 2009 Feb 2 |
|
| Granulocyte-colony stimulating factor for stroke treatment: mechanisms of action and efficacy in preclinical studies. | 2009 Oct 21 |
|
| Anticonvulsant drug therapy after aneurysmal subarachnoid hemorrhage: a critically appraised topic. | 2010 Nov |
|
| External validity of risk models: Use of benchmark values to disentangle a case-mix effect from incorrect coefficients. | 2010 Oct 15 |
Patents
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:40:01 GMT 2023
by
admin
on
Fri Dec 15 16:40:01 GMT 2023
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| Record UNII |
19B418DV39
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| Record Status |
Validated (UNII)
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| Record Version |
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110101-67-2
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DTXSID40149144
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104902
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PARENT -> SALT/SOLVATE |
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SOLVATE->ANHYDROUS |
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ACTIVE MOIETY |
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