Isosorbide 5-mononitrate

Iupac Name：[(3S,3aR,6R,6aS)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate

Molecular Weight：191.139

Modify Date.: 2022-11-01 04:58

Introduction: Isosorbide 5-mononitrate is a crystalline solid. Isosorbide 5-mononitrate is very flammable and may be toxic by ingestion. View more+

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1. Names and Identifiers

1.1 Name: Isosorbide 5-mononitrate
1.2 Synonyms: (3R,3aS,6S,6aR)-6-Hydroxyhexahydrofuro[3,2-b]fur-3-ylnitrat (3R,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl nitrate 1,4:3,6-Dianhydro-5-O-nitro-D-glucitol 1,4:3,6-Dianhydro-D-glucitol 5-nitrate 1,4:3,6-dianhydro-D-glucitol-5-nitrate 5-ismn ahr4698 CORANGIN Coronu D-Glucitol, 1,4:3,6-dianhydro-, 5-nitrate EINECS 240-197-2 ELAN ELANTAN IMDUR IS-5-MN ISMN Ismo ISOSORBIDE 5-NITRATE ISOSORBIDE MONONITRATE isosorbide nitrate isosorbide-5-mononitrate MFCD00143462 Momt Monicor Monit Monoclair MONOKET Mono-Mack Monosorb nitrate de (3R,3aS,6S,6aR)-6-hydroxyhexahydrofuro[3,2-b]fur-3-yle Olicard Pentacard

1.3 CAS No.: 16051-77-7

1.4 CID: 27661

1.5 EINECS(EC#): 240-197-2

1.6 Molecular Formula: C6H9NO6 (isomer)

1.7 Inchi: InChI=1S/C6H9NO6/c8-3-1-11-6-4(13-7(9)10)2-12-5(3)6/h3-6,8H,1-2H2/t3-,4+,5+,6+/m0/s1

1.8 InChkey: YWXYYJSYQOXTPL-SLPGGIOYSA-N

1.9 Canonical Smiles: C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O

1.10 Isomers Smiles: C1[C@@H]([C@@H]2[C@H](O1)[C@@H](CO2)O[N+](=O)[O-])O

2. Properties

2.1 Density: 1.56

2.1 Melting point: 88-93℃

2.1 Boiling point: 364.5°Cat760mmHg

2.1 Refractive index: 145 ° (C=5, H2O)

2.1 Flash Point: 174.2°C

2.1 Precise Quality: 191.04300

2.1 PSA: 93.74000

2.1 logP: -0.75500

2.1 Appearance: white crystalline powder

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: white to light yellow crystal powde

2.4 Physical: Isosorbide-5-mononitrate; is a crystalline solid. It is very flammable and may be toxic by ingestion.

2.5 pKa: 13.09±0.40(Predicted)

2.6 Water Solubility: soluble

2.7 Stability: Stable under normal temperatures and pressures.

2.8 StorageTemp: -20°C Freezer

3. Use and Manufacturing

3.1 General Description: Isosorbide 5-mononitrate is a crystalline solid. Isosorbide 5-mononitrate is very flammable and may be toxic by ingestion.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 24 companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H228 (87.5%): Flammable solid [Danger Flammable solids]
H242 (12.5%): Heating may cause a fire [Danger Self-reactive substances and mixtures; and Organic peroxides]
H302 (20.83%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (12.5%): Causes skin irritation [Warning Skin corrosion/irritation]
H361 (62.5%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P201, P202, P210, P220, P234, P240, P241, P264, P270, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P332+P313, P362, P370+P378, P403+P235, P405, P411, P420, and P501

3.3 Usage: antidepressant, 5HT reuptake inhibitor

4. Safety and Handling

4.1 Hazard Codes: F

4.1 Risk Statements: R11;R36/37/38

4.1 Safety Statements: S15;S16;S37/39

4.1 Packing Group: III

4.1 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. Isosorbide 5-mononitrate Preparation Products And Raw materials Raw materials

4.2 Hazard Class: 1.1A

4.2 RIDADR: UN 3251

4.2 RTECS: LZ4386500

4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LZ4386500

CAS REGISTRY NUMBER :: 16051-77-7

LAST UPDATED :: 199706

DATA ITEMS CITED :: 13

MOLECULAR FORMULA :: C6-H9-N-O6

MOLECULAR WEIGHT :: 191.16

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2010 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Kidney, Ureter, Bladder - urine volume increased Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 29,327,1985

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1760 mg/kg

TOXIC EFFECTS :: Sense Organs and Special Senses (Eye) - lacrimation Behavioral - altered sleep time (including change in righting reflex) Nutritional and Gross Metabolic - body temperature decrease

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 29,327,1985

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1750 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 29,327,1985

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

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1771 mg/kg

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

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 128,74,1989

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1810 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 29,327,1985

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

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1820 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 29,327,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 147 gm/kg/26W-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - other changes in urine composition Endocrine - changes in spleen weight Blood - other changes

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 33,171,1987

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 182 gm/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - other changes

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 30,1079,1985 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 91 gm/kg

SEX/DURATION :: male 91 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 30,1079,1985

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 27 gm/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Fertility - pre-implantation mortality (e.g. reduction in number of implants per female; total number of implants per corpora lutea) Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,6911,1986

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 27 gm/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - physical Reproductive - Effects on Newborn - delayed effects

REFERENCE :: KSRNAM Kiso to Rinsho. Clinical Report. (Yubunsha Co., Ltd., 1-5, Kanda Suda-Cho, Chiyoda-ku, KS Bldg., Tokyo 101, Japan) V.1- 1960- Volume(issue)/page/year: 20,6911,1986

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

DOSE :: 860 ug/m3

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - hepatobiliary system Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: TOVEFN Toksikologicheskii Vestnik. (18-20 Vadkovskii per. Moscow, 101479, Russia) History Unknown Volume(issue)/page/year: (5),28,1996

TYPE OF TEST :: TCLo - Lowest published toxic concentration

ROUTE OF EXPOSURE :: Inhalation

DOSE :: 100 ug/m3

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Newborn - delayed effects

REFERENCE :: TOVEFN Toksikologicheskii Vestnik. (18-20 Vadkovskii per. Moscow, 101479, Russia) History Unknown Volume(issue)/page/year: (5),28,1996

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable solids, Category 2

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H228 Flammable solid H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P280 Wear protective gloves/protective clothing/eye protection/face protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P370+P378 In case of fire: Use ... to extinguish. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

16051-77-7Total: 10 Synthesis Route

87-33-2 146 Suppliers

16051-77-7 181 Suppliers

Literatures:
Bhar, Debjani; Chandrasekaran, Srinivasan Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1997 , vol. 36, # 9 p. 793 - 795
Yield: ~69%

87-33-2 146 Suppliers

16051-77-7 181 Suppliers

Literatures:
Arzneimittel-Forschung/Drug Research, , vol. 34, # 12 p. 1779 - 1782
Yield: null

87-33-2 146 Suppliers

16051-77-7 181 Suppliers

652-67-5 164 Suppliers

Literatures:
Brown, Chris; Marston, Richard W.; Quigley, Paul F.; Roberts, Stanley M. Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 12 p. 1809 - 1810
Yield: ~52%

View all

8. Precursor and Product

precursor:

84207-83-0

79-31-2

87-33-2

13042-38-1

75648-24-7

652-67-5

13042-39-2

39813-48-4

9. Other Information

9.0 Uses: Isosorbide 5-Mononitrate is a metabolite of Isosorbide Dinitrate; used as an antianginal.

9.1 Usage: A coronary vasodilator that does not require hepatic biotransformation

9.2 Merck: 5225

9.3 Chemical Properties: white to light yellow crystal powde

9.4 Uses: antidepressant, 5HT reuptake inhibitor

9.5 Uses: A metabolite of Isosorbide Dinitrate. Used as an antianginal

9.6 Brand name: Imdur (Schering-Plough); Ismo (Dr. Reddy’s); Monoket (Schwarz Pharma) .

9.7 General Description: Isosorbide 5-mononitrate is a crystalline solid. Isosorbide 5-mononitrate is very flammable and may be toxic by ingestion.

9.8 Air & Water Reactions: Highly flammable.

9.9 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.

9.10 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.

9.11 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.

10. Computational chemical data

Molecular Weight: 191.139g/mol
Molecular Formula: C₆H₉NO₆
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 191.04298701
Monoisotopic Mass: 191.04298701
Complexity: 216
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 6
Topological Polar Surface Area: 93.7
Heavy Atom Count: 13
Defined Atom Stereocenter Count: 4
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBiOAAAAAAAAAAAAAAAAAAAASJAAAAAAAAAAAASAAAAAAAAGgAECAAACBSggAIAAAAARgABAAAAAQAAAAAAAAAAAAAAAAABEAIAAAACQAAFAAADAAHAYAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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