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16051-77-7

16051-77-7 Structure

16051-77-7 Structure
IdentificationMore
[Name]

Isosorbide 5-mononitrate
[CAS]

16051-77-7
[Synonyms]

1,4:3,6-DIANHYDRO-D-GLUCITOL 5-MONONITRATE
5-ISOSORBIDE MONONITRATE
CORANGIN
ELAN
ELANTAN
IMDUR
IS-5-MN
ISOSORBIDE 5-MONONITRATE
ISOSORBIDE 5-NITRATE
ISOSORBIDE MONONITRATE
MONOCEDOCARD
MONOCLAIR
MONOSORB
1,4:3,6-dianhydro-,5-nitrate,d-glucito
1,4:3,6-dianhydro-d-glucito5-nitrate
1,4:3,6-dianhydro-d-glucitol5-nitrate
5-ismn
ahr4698
bm22-145
Ososoribide-5-mononitrate
[EINECS(EC#)]

240-197-2
[Molecular Formula]

C6H9NO6
[MDL Number]

MFCD00143462
[Molecular Weight]

191.14
[MOL File]

16051-77-7.mol
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystal powde
[Melting point ]

88-93 °C
[alpha ]

170 º (c=1, EtOH)
[Boiling point ]

326.86°C (rough estimate)
[density ]

1.5784 (rough estimate)
[refractive index ]

145 ° (C=5, H2O)
[storage temp. ]

-20°C Freezer
[solubility ]

Undiluted isosorbide mononitrate is freely soluble in water, in acetone, in ethanol (96 per cent) and in methylene chloride. The solubility of the diluted product depends on the diluent and its concentration.
[form ]

Solid
[pka]

13.09±0.40(Predicted)
[color ]

White to Off-White
[Water Solubility ]

soluble
[Usage]

A metabolite of Isosorbide Dinitrate. Used as an antianginal
[Merck ]

5225
[InChIKey]

YWXYYJSYQOXTPL-SLPGGIOYSA-N
[CAS DataBase Reference]

16051-77-7(CAS DataBase Reference)
[EPA Substance Registry System]

16051-77-7(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Flame (GHS02)
GHS02
[Signal word ]

Danger
[Hazard statements ]

H228
[Precautionary statements ]

P210-P240-P241-P280-P370+P378
[Hazard Codes ]

Xi-F,Xi,F
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
R11:Highly Flammable.
[Safety Statements ]

S37/39:Wear suitable gloves and eye/face protection .
S16:Keep away from sources of ignition-No smoking .
S15:Keep away from heat .
[RIDADR ]

3251
[RTECS ]

LZ4386500
[HazardClass ]

4.1
[PackingGroup ]

III (ISOSORBIDE-5-MONONITRATE)
[HS Code ]

2932999000
[Toxicity]

LD50 oral in rat: 2010mg/kg
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Sorbitol-->D-Sorbitol-->Isosorbide dinitrate-->Isosorbide-->(3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl acetate-->Silver nitrate-->Ethyl acetate-->Thionyl chloride
Hazard InformationBack Directory
[General Description]

ISOSORBIDE-5-MONONITRATE(16051-77-7) is a crystalline solid. ISOSORBIDE-5-MONONITRATE(16051-77-7) is very flammable and may be toxic by ingestion.
[Reactivity Profile]

The dinitrate, a heart drug, can detonate when dry, but is non explosive with 30% of water [J. Haz.. Mater., 1992, 32(1), 87]. The mononitrate would be expected to be less reactive.
[Air & Water Reactions]

Highly flammable.
[Health Hazard]

Fire may produce irritating and/or toxic gases. Contact may cause burns to skin and eyes. Contact with molten substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.
[Fire Hazard]

Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.
[Chemical Properties]

white to light yellow crystal powde
[Uses]

A metabolite of Isosorbide Dinitrate. Used as an antianginal
[Uses]

antidepressant, 5HT reuptake inhibitor
[Definition]

ChEBI: Isosorbide mononitrate is a nitrate ester and a glucitol derivative. It has a role as a nitric oxide donor and a vasodilator agent.
[Brand name]

Imdur (Schering-Plough); Ismo (Dr. Reddy’s); Monoket (Schwarz Pharma) .
[Clinical Use]

Vasodilator:
Treatment and prophylaxis of angina
Adjunct in congestive heart failure
[Synthesis]

Isosorbide

652-67-5

ISOSORBIDE 2-MONONITRATE

16106-20-0

The general procedure for the synthesis of isosorbide 2-nitrate from isosorbide (stored below +4°C) is as follows: 146 g of dehydrated sorbitol was dissolved in 880 mL of anhydrous ethyl acetate, stirred well, and then cooled to -5 to 0°C. Subsequently, 170 g of silver nitrate solids were added, stirring was continued, and 120 g of thionyl chloride was added dropwise at a slow rate. After the dropwise addition was completed, the reaction mixture was stirred at the same temperature for 10 hours. Upon completion of the reaction, the reaction process was monitored by high performance liquid chromatography (HPLC). The reaction solution was filtered by suction filtration. The filtrate was washed to neutrality with 500 mL of water to purify the product. The organic phase was dried with 20 g of anhydrous magnesium sulfate for 4 hours. After drying, the magnesium sulfate was removed by filtration and the filtrate was decolorized by adding 17.6 g of activated carbon and heated to reflux for 30 minutes. After the decolorization was completed, the activated carbon was removed by filtration and the filtrate was concentrated to dryness by decompression to give 170 g of isosorbide 2-nitrate solid. The purity of the product was 99.85% and the yield was 89.0% by HPLC analysis.

[Drug interactions]

Potentially hazardous interactions with other drugs Avanafil: hypotensive effect significantly enhanced - avoid. Levosimendan: possible severe hypotension. Riociguat: avoid concomitant use due to risk of hypotension. Sildenafil: hypotensive effect significantly enhanced - avoid. Tadalafil: hypotensive effect significantly enhanced - avoid. Vardenafil: hypotensive effect significantly enhanced - avoid.
[Metabolism]

Unlike isosorbide dinitrate, isosorbide mononitrate does not undergo first-pass hepatic metabolism. Isosorbide mononitrate is taken up by smooth muscle cells of blood vessels and the nitrate group is cleaved to inorganic nitrite and then to nitric oxide. Isosorbide mononitrate is metabolised to inactive metabolites, including isosorbide and isosorbide glucuronide
[storage]

Store at -20°C
[References]

[1] Patent: CN107011354, 2017, A. Location in patent: Paragraph 0042-0057
[2] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 12, p. 1809 - 1810
[3] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997, vol. 36, # 9, p. 793 - 795
[4] ChemMedChem, 2015, vol. 10, # 10, p. 1724 - 1732
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

Isosorbide 5-mononitrate(16051-77-7).msds
Spectrum DetailBack Directory
[Spectrum Detail]

Isosorbide 5-mononitrate(16051-77-7)1HNMR
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