7261-97-4

7261-97-4 structure

Name: Dantrolene
Chemical Name: dantrolene
CAS Number: 7261-97-4
Molecular Formula: C₁₄H₁₀N₄O₅
Molecular Weight: 314.25300
Catalog: Research Areas Inflammation/Immunology
Create Date: 2018-03-03 08:00:00
Modify Date: 2025-08-20 23:27:22
Dantrolene (F368), a muscle relaxant, non-competitively inhibits human erythrocyte glutathione reductase. Ki and IC50 values are 111.6 μM and 52.3 μM, respectively. Dantrolene is a ryanodine receptor antagonist and Ca2+ signaling stabilizer. Dantrolene can be used for the research of muscle spasticity, malignant hyperthermia, Huntington's disease and other neuroleptic malignant syndrome[1][2][3][4][5].

Name	dantrolene
Synonyms	Dantrium 1-[5-(4-nitro-phenyl)-furan-2-ylmethyleneamino]-imidazolidine-2,4-dione 1-[(E)-[5-(4-nitrophenyl)furan-2-yl]methylideneamino]imidazolidine-2,4-dione Dantroleno [INN-Spanish] Dantrolenum [INN-Latin] UNII-F64QU97QCR danthrolene Dantrium Intravenous Dantrolenum 1-[((5-(4-nitrophenyl)-2-furanyl)methylene)amino]-2,4-imidazolidinedione Dantroleno

Description	Dantrolene (F368), a muscle relaxant, non-competitively inhibits human erythrocyte glutathione reductase. Ki and IC50 values are 111.6 μM and 52.3 μM, respectively. Dantrolene is a ryanodine receptor antagonist and Ca2+ signaling stabilizer. Dantrolene can be used for the research of muscle spasticity, malignant hyperthermia, Huntington's disease and other neuroleptic malignant syndrome[1][2][3][4][5].
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Inflammation/Immunology Research Areas >> Neurological Disease
In Vitro	Dantrolene interferes with calcium release from the sarcoplasmic reticulum and thus to inhibit excitation--contraction coupling[1]. Dantrolene acts directly on the RYR1 to reduce the extent of channel activation by calmodulin (CaM) and thereby decreases the Ca2+ sensitivity of channel activation[2]. Dantrolene inhibits abnormal Ca2+ release from the sarcoplasmic reticulum[3]. Dantrolene depresses excitation-contraction coupling in muscle fibers by inhibiting calcium release from the sarcoplasmic reticulum[3]. Dantrolene also shows calcium channel blocker effect in the smooth muscle membrane as well as antioxidative and cytoprotective properties[3]. Dantrolene affects the membrane calcium channel of smooth muscle cells and inhibits calcium influx[3]. Dantrolene is a skeletal muscle-specific muscle relaxant that works on the cardiac muscle. Dantrolene (0.3 μM) binds to domain 601-620 of RyR2 and corrects defective inter-domain interaction within RyR2 in failing hearts. This in turn inhibits spontaneous Ca2++ leak/Ca2+ sparks, and improves cardiomyocyte function in failing hearts[4].
In Vivo	Dantrolene is neuroprotective in Huntington's disease transgenic mouse model[5]. Feeding dantrolene (5 mg/kg) twice a week to YAC128 mice between 2 months and 11.5 months of age resulted in significantly improved performance in the beam-walking and gait-walking assays[5]. Animal Model: YAC128 transgenic mice (FVBN/NJ background strain) and WT mice[5] Dosage: 5 mg/kg Administration: Fed orally twice per week from 2 to 11.5 months of age, followed by a washout period of 2 months (13.5 months of age) Result: Resulted in significantly improved performance in the beam-walking and gait-walking assays.
References	[1]. W J Meyler, et al. The effect of dantrolene sodium on rat skeletal muscle in relation to the plasma concentration. Eur J Pharmacol. 1979 Feb 1;53(4):335-42. [2]. F Zhao, et al. Dantrolene inhibition of ryanodine receptor Ca2+ release channels. Molecular mechanism and isoform selectivity. J Biol Chem. 2001 Apr 27;276(17):13810-6. [3]. Murat Sentürk, et al. Dantrolene inhibits human erythrocyte glutathione reductase. Biol Pharm Bull. 2008 Nov;31(11):2036-9. [4]. Shigeki Kobayashi, et al. Dantrolene, a therapeutic agent for malignant hyperthermia, markedly improves the function of failing cardiomyocytes by stabilizing interdomain interactions within the ryanodine receptor. J Am Coll Cardiol. 2009 May 26;53(21):1993-2005. [5]. Xi Chen, et al. Dantrolene is neuroprotective in Huntington's disease transgenic mouse model. Mol Neurodegener. 2011 Nov 25;6:81.

Density	1.57 g/cm3
Boiling Point	175-177ºC
Melting Point	279-280°C (lit.)
Molecular Formula	C₁₄H₁₀N₄O₅
Molecular Weight	314.25300
Exact Mass	314.06500
PSA	120.73000
LogP	2.53040
Index of Refraction	1.715

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MU3874000

CHEMICAL NAME :: Hydantoin, 1-((5-(p-nitrophenyl)furfurylidene)amino)-

CAS REGISTRY NUMBER :: 7261-97-4

BEILSTEIN REFERENCE NO. :: 0705189

LAST UPDATED :: 199612

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C14-H10-N4-O5

MOLECULAR WEIGHT :: 314.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >7 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 21,127,1978 ** TUMORIGENIC DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 9386 mg/kg/3Y-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Blood - lymphoma, including Hodgkin's disease

REFERENCE :: PGMJAO Postgraduate Medical Journal. (Blackwell Scientific Pub. Ltd., POB 88, Oxford, UK) V.1- 1925- Volume(issue)/page/year: 56,261,1980

Hazard Codes	Xi
RIDADR	NONH for all modes of transport

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