Details
Stereochemistry | ACHIRAL |
Molecular Formula | C14H10N4O5 |
Molecular Weight | 314.253 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[O-][N+](=O)C1=CC=C(C=C1)C2=CC=C(O2)\C=N\N3CC(=O)NC3=O
InChI
InChIKey=OZOMQRBLCMDCEG-VIZOYTHASA-N
InChI=1S/C14H10N4O5/c19-13-8-17(14(20)16-13)15-7-11-5-6-12(23-11)9-1-3-10(4-2-9)18(21)22/h1-7H,8H2,(H,16,19,20)/b15-7+
Molecular Formula | C14H10N4O5 |
Molecular Weight | 314.253 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/15023108Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9341133, http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/017443s043s046s048s049lbl.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15023108
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/9341133, http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/017443s043s046s048s049lbl.pdf
Dantrolene is a drug which was approved by FDA for the treatment of chronic spasticity and malignant hyperthermia (a rare life-threatening clinical syndrome). Dantrolene effect was shown both in vivo and in vitro and proved to be mediated by interaction with Ryanodine receptor 1. The drug has a potential for hepatotoxicity and should be used as indicated in the label.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15105208
Curator's Comment: Dantrolene crosses the blood-brain barrier and produces mild sedation
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P21817 Gene ID: 6261.0 Gene Symbol: RYR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/15023108 |
130.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | DANTRIUM Approved UseIn Chronic Spasticity: Dantrium is indicated in controlling the manifestations of clinical spasticity resulting from upper motor neuron disorders (e.g., spinal cord injury, stroke, cerebral palsy, or multiple sclerosis). In Malignant Hyperthermia: Oral Dantrium is also indicated preoperatively to prevent or attenuate the development of signs of malignant hyperthermia in known, or strongly suspect, malignant hyperthermia susceptible patients who require anesthesia and/or surgery. Launch Date1.27440003E11 |
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Preventing | DANTRIUM Approved UseIn Chronic Spasticity: Dantrium is indicated in controlling the manifestations of clinical spasticity resulting from upper motor neuron disorders (e.g., spinal cord injury, stroke, cerebral palsy, or multiple sclerosis). In Malignant Hyperthermia: Oral Dantrium is also indicated preoperatively to prevent or attenuate the development of signs of malignant hyperthermia in known, or strongly suspect, malignant hyperthermia susceptible patients who require anesthesia and/or surgery. Launch Date1.27440003E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9 μg/mL |
2.5 mg/kg single, intravenous dose: 2.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DANTROLENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
77.7 μg × h/mL |
2.5 mg/kg single, intravenous dose: 2.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DANTROLENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.7 h |
100 mg 1 times / day multiple, oral dose: 100 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
DANTROLENE blood | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
10.8 h |
2.5 mg/kg single, intravenous dose: 2.5 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
DANTROLENE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
25 mg 1 times / day steady, oral (starting) Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Hepatitis, Diarrhea... AEs leading to discontinuation/dose reduction: Hepatitis Sources: Diarrhea |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | Disc. AE | 25 mg 1 times / day steady, oral (starting) Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hepatitis | Disc. AE | 25 mg 1 times / day steady, oral (starting) Dose: 25 mg, 1 times / day Route: oral Route: steady Dose: 25 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Treatment of spastic cerebral-palsied children with sodium dantrolene. | 1975 Dec |
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Letter: Hallucinations associated with dantrolene sodium therapy. | 1975 Jan 25 |
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Dantrolene hepatitis. | 1976 Apr 12 |
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Hepatitis from dantrolene sodium. | 1979 Jan |
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Dantrolene and lymphocytic lymphoma. | 1980 Apr |
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[Neuroleptic malignant syndrome. Beneficial effects of dantrolene on hyperthermia and hypertonia (author's transl)]. | 1982 Mar 27 |
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Neuroleptic malignant syndrome: response to dantrolene sodium. | 1983 Feb |
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Pneumonitis, pleural effusion and pericarditis following treatment with dantrolene. | 1984 May |
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[Cardiac failure caused by an overdose of dantrolene]. | 1986 |
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Neuroleptic malignant syndrome induced by domperidone. | 1992 Jun |
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Successful treatment of levodopa-induced neuroleptic malignant syndrome (NMS) and disseminated intravascular coagulation (DIC) in a patient with Parkinson's disease. | 1992 Nov |
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Successful treatment of an episode of malignant hyperthermia using a large dose of dantrolene. | 1993 Jan-Feb |
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[Freeman-Sheldon syndrome: generalized muscular rigidity after anesthetic induction]. | 1994 May-Jun |
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Dantrolene treatment of opioid-induced myoclonus. | 1995 Dec |
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[A case of malignant syndrome triggered by the use of haloperidol and chrorpromazine]. | 1997 Apr |
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Vesl/Homer proteins regulate ryanodine receptor type 2 function and intracellular calcium signaling. | 2003 Sep |
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Atypical neuroleptic malignant syndrome caused by clozapine and venlafaxine: early brief treatment with dantrolene. | 2004 Jul |
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Drug-induced liver injury. | 2004 Mar 1 |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Prevention of succinylcholine-induced fasciculation and myalgia: a meta-analysis of randomized trials. | 2005 Oct |
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Early bicarbonate loading and dantroline for ziprasidone/haloperidol-induced neuroleptic malignant syndrome. | 2006 Apr |
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Insulin-like growth factors (IGF) I and II utilize different calcium signaling pathways in a primary human parathyroid cell culture model. | 2006 Mar |
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KATP channel knockout worsens myocardial calcium stress load in vivo and impairs recovery in stunned heart. | 2007 Apr |
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Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
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Quantitative investigation of the role of breast cancer resistance protein (Bcrp/Abcg2) in limiting brain and testis penetration of xenobiotic compounds. | 2008 Jun |
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Cellular imaging predictions of clinical drug-induced liver injury. | 2008 Sep |
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Dantrolene, a therapeutic agent for malignant hyperthermia, inhibits catecholaminergic polymorphic ventricular tachycardia in a RyR2(R2474S/+) knock-in mouse model. | 2010 Nov |
|
Stimulation of cytosolic and mitochondrial calcium mobilization by indomethacin in Caco-2 cells: modulation by the polyphenols quercetin, resveratrol and rutin. | 2012 Dec |
Sample Use Guides
For Use in Chronic Spasticity: 25 mg once daily for seven days, then 25 mg t.i.d. for seven days, 50 mg t.i.d. for seven days, 100 mg t.i.d. (adults). For Malignant Hyperthermia: administer 4 to 8 mg/kg/day of oral drug in 3 or 4 divided doses for one or two days prior to surgery, with the last dose being given approximately 3 to 4 hours before scheduled surgery with a minimum of water.
Route of Administration:
Oral
Whole skeletal muscle fascicles were incubated with dantrolene at concentrations of 5, 15 and 25 uM. Dantrolene inhibited twitch tensions of skeletal muscle fascicles, probably by indirectly preventing the release of calcium from the SR.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 14:59:19 UTC 2023
by
admin
on
Fri Dec 15 14:59:19 UTC 2023
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Record UNII |
F64QU97QCR
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175735
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LIVERTOX |
NBK548144
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NDF-RT |
N0000008953
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WHO-ATC |
M03CA01
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FDA ORPHAN DRUG |
713319
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WHO-VATC |
QM03CA01
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NCI_THESAURUS |
C29696
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NDF-RT |
N0000175738
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Code System | Code | Type | Description | ||
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780
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PRIMARY | |||
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SUB06903MIG
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CHEMBL1201288
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F64QU97QCR
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PRIMARY | |||
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N0000008953
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PRIMARY | Decreased Striated Muscle Contraction [PE] | ||
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C61697
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6914273
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833480-90-3
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ALTERNATIVE | |||
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DTXSID7022881
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D003620
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1163140
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DANTROLENE
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DB01219
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7261-97-4
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Dantrolene
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m4085
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100000083439
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N0000175735
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PRIMARY | Decreased Striated Muscle Tone [PE] | ||
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230-684-8
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4317
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4172
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3050
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3105
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PRIMARY | RxNorm | ||
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2317
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F64QU97QCR
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