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Nitropress
Also known as: 15078-28-1, Pentacyanidonitrosylferrate(2-), Iron(4+);nitroxyl anion;pentacyanide, Pentacyano(nitroso)iron(2-), Chebi:7596, Pentacyanidonitrosylferrate(iii)
Molecular Formula
C5FeN6O-2
Molecular Weight
215.94  g/mol
InChI Key
PAORBFBZBNPTCL-UHFFFAOYSA-N

A powerful vasodilator used in emergencies to lower blood pressure or to improve cardiac function. It is also an indicator for free sulfhydryl groups in proteins.
1 2D Structure

Nitropress

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
iron(4+);nitroxyl anion;pentacyanide
2.1.2 InChI
InChI=1S/5CN.Fe.NO/c5*1-2;;1-2/q5*-1;+4;-1
2.1.3 InChI Key
PAORBFBZBNPTCL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[N-]=O.[Fe+4]
2.2 Synonyms
2.2.1 MeSH Synonyms

1. Cyanonitrosylferrate

2. Disodium Salt Nitroprusside

3. Ketostix

4. Naniprus

5. Nipride

6. Nipruton

7. Nitriate

8. Nitropress

9. Nitroprussiat Fides

10. Nitroprusside

11. Nitroprusside, Disodium Salt

12. Nitroprusside, Disodium Salt, Dihydrate

13. Nitroprusside, Sodium

14. Sodium Nitroprusside

2.2.2 Depositor-Supplied Synonyms

1. 15078-28-1

2. Pentacyanidonitrosylferrate(2-)

3. Iron(4+);nitroxyl Anion;pentacyanide

4. Pentacyano(nitroso)iron(2-)

5. Chebi:7596

6. Pentacyanidonitrosylferrate(iii)

7. [fe(cn)5(no)](2-)

8. Bdbm50377921

9. Db00325

10. Ncgc00166055-01

11. Ncgc00166055-04

12. Sbi-0206675.p002

13. C07269

14. Ab00920709_03

15. Ferrate(2-), Pentakis(cyano-.kappa.c)-nitrosyl

2.2.3 Other Synonyms

1. Nitroprusside Sodium

2. Nitroprusside Sodium Dihydrate

2.3 Create Date
2006-12-13
3 Chemical and Physical Properties
Molecular Weight 215.94 g/mol
Molecular Formula C5FeN6O-2
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count12
Rotatable Bond Count0
Exact Mass215.948294 g/mol
Monoisotopic Mass215.948294 g/mol
Topological Polar Surface Area137 Ų
Heavy Atom Count13
Formal Charge-2
Complexity119
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count7
4 Drug and Medication Information
4.1 Drug Indication

For immediate reduction of blood pressure of patients in hypertensive crises, reduce bleeding during surgery, and for the treatment of acute congestive heart failure


5 Pharmacology and Biochemistry
5.1 Pharmacology

Nitroprusside a powerful vasodilator relaxes the vascular smooth muscle and produce consequent dilatation of peripheral arteries and veins. Other smooth muscle (e.g., uterus, duodenum) is not affected. Sodium nitroprusside is more active on veins than on arteries.


5.2 MeSH Pharmacological Classification

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)


Indicators and Reagents

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)


Nitric Oxide Donors

A diverse group of agents, with unique chemical structures and biochemical requirements, which generate NITRIC OXIDE. These compounds have been used in the treatment of cardiovascular diseases and the management of acute myocardial infarction, acute and chronic congestive heart failure, and surgical control of blood pressure. (Adv Pharmacol 1995;34:361-81) (See all compounds classified as Nitric Oxide Donors.)


Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)


5.3 Absorption, Distribution and Excretion

Route of Elimination

One molecule of sodium nitroprusside is metabolized by combination with hemoglobin to produce one molecule of cyanmethemoglobin and four CN ions, thiosulfate reacts with cyanide to produce thiocyanate, thiocyanate is eliminated in the urine.


5.4 Metabolism/Metabolites

Metabolized by reaction with hemoglobin to produce cyanmethemoglobin and cynide ions


5.5 Biological Half-Life

Approximately 2 minutes


5.6 Mechanism of Action

One molecule of sodium nitroprusside is metabolized by combination with hemoglobin to produce one molecule of cyanmethemoglobin and four CN- ions; methemoglobin, obtained from hemoglobin, can sequester cyanide as cyanmethemoglobin; thiosulfate reacts with cyanide to produce thiocyanate; thiocyanate is eliminated in the urine; cyanide not otherwise removed binds to cytochromes. Cyanide ion is normally found in serum; it is derived from dietary substrates and from tobacco smoke. Cyanide binds avidly (but reversibly) to ferric ion (Fe+++), most body stores of which are found in erythrocyte methemoglobin (metHgb) and in mitochondrial cytochromes. When CN is infused or generated within the bloodstream, essentially all of it is bound to methemoglobin until intraerythrocytic methemoglobin has been saturated. Sodium nitroprusside is further broken down in the circulation to release nitric oxide (NO), which activates guanylate cyclase in the vascular smooth muscle. This leads to increased production of intracellular cGMP, which stimulates calcium ion movement from the cytoplasm to the endoplasmic reticulum, reducing the level of available calcium ions that can bind to calmodulin. This ultimately results in vascular smooth muscle relaxation and vessel dilation.


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