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Identification
NameNitroprusside
Accession NumberDB00325  (APRD01143)
Typesmall molecule
Groupsapproved
Description

Nitroprusside serves as a source of nitric oxide, a potent peripheral vasodilator that affects both arterioles and venules (venules more than arterioles). Nitroprusside is often administered intravenously to patients who are experiencing a hypertensive emergency. [Wikipedia]

Structure
Thumb
SynonymsNot Available
Salts
Name/CAS Structure Properties
Sodium nitroprusside
Thumb Not applicable DBSALT000839
Brand names
NameCompany
NiprideNot Available
NitropressNot Available
Brand mixtures
Brand NameIngredients
Cora-Bosan B43Potassium Carbonate + Sodium Nitroprusside + Squill
CategoriesNot Available
CAS number15078-28-1
WeightAverage: 215.938
Monoisotopic: 215.948300785
Chemical FormulaC5FeN6O
InChI KeyInChIKey=ASPOIVQEUUCDQT-UHFFFAOYSA-N
InChI
InChI=1S/5CN.Fe.NO/c5*1-2;;1-2/q;;;;;2*-1
IUPAC Name
pentacyano(nitroso)irondiuide
SMILES
O=N[Fe--](C#N)(C#N)(C#N)(C#N)C#N
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganonitrogen Compounds
ClassAmines
SubclassPolyamines
Direct parentPolyamines
Alternative parentsNitriles; Organic Transition Metal Compounds
Substituentsorganometallic compound; organic transition metal moeity
Classification descriptionThis compound belongs to the polyamines. These are compounds containing more than one amine group.
Pharmacology
IndicationFor immediate reduction of blood pressure of patients in hypertensive crises, reduce bleeding during surgery, and for the treatment of acute congestive heart failure
PharmacodynamicsNitroprusside 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.
Mechanism of actionOne 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. Once activated to NO, it activates guanylate cyclase in vascular smooth muscle and increases intracellular production of cGMP. cGMP stimulates calcium movement from the cytoplasm to the endoplasmic reticulum and reduces calcium available to bind with calmodulin. This eventually leads to vascular smooth muscle relaxation and vessel dilatation.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolized by reaction with hemoglobin to produce cyanmethemoglobin and cynide ions

SubstrateEnzymesProduct
Nitroprusside
    cyanmethemoglobinDetails
    Route of eliminationOne 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.
    Half lifeApproximately 2 minutes
    ClearanceNot Available
    ToxicityOverdosage of nitroprusside can be manifested as excessive hypotension or cyanide toxicity or as thiocyanate toxicity. The acute intravenous mean lethal doses (LD50) of nitroprusside in rabbits, dogs, mice, and rats are 2.8, 5.0, 8.4, and 11.2 mg/kg, respectively.
    Affected organisms
    • Humans and other mammals
    PathwaysNot Available
    SNP Mediated EffectsNot Available
    SNP Mediated Adverse Drug ReactionsNot Available
    ADMET
    Predicted ADMET features
    Property Value Probability
    Human Intestinal Absorption - 0.8308
    Blood Brain Barrier + 0.9314
    Caco-2 permeable - 0.5269
    P-glycoprotein substrate Non-substrate 0.8966
    P-glycoprotein inhibitor I Non-inhibitor 0.919
    P-glycoprotein inhibitor II Non-inhibitor 0.9767
    Renal organic cation transporter Non-inhibitor 0.9109
    CYP450 2C9 substrate Non-substrate 0.8573
    CYP450 2D6 substrate Non-substrate 0.8353
    CYP450 3A4 substrate Non-substrate 0.6675
    CYP450 1A2 substrate Non-inhibitor 0.6719
    CYP450 2C9 substrate Non-inhibitor 0.8599
    CYP450 2D6 substrate Non-inhibitor 0.9186
    CYP450 2C19 substrate Non-inhibitor 0.8218
    CYP450 3A4 substrate Non-inhibitor 0.9763
    CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9583
    Ames test Non AMES toxic 0.5204
    Carcinogenicity Carcinogens 0.6595
    Biodegradation Not ready biodegradable 0.5759
    Rat acute toxicity 2.9543 LD50, mol/kg Not applicable
    hERG inhibition (predictor I) Weak inhibitor 0.9345
    hERG inhibition (predictor II) Non-inhibitor 0.9596
    Pharmacoeconomics
    Manufacturers
    • Hoffmann la roche inc
    • Abbott laboratories
    • Abbott laboratories pharmaceutical products div
    • Hospira inc
    • Abraxis pharmaceutical products
    • Baxter healthcare corp anesthesia and critical care
    • Teva parenteral medicines inc
    Packagers
    Dosage forms
    FormRouteStrength
    Powder, for solutionIntravenous
    PricesNot Available
    PatentsNot Available
    Properties
    Statesolid
    Experimental PropertiesNot Available
    Predicted Properties
    PropertyValueSource
    logP0.071ChemAxon
    pKa (strongest basic)-3.3ChemAxon
    physiological charge-2ChemAxon
    hydrogen acceptor count6ChemAxon
    hydrogen donor count0ChemAxon
    polar surface area148.38ChemAxon
    rotatable bond count1ChemAxon
    refractivity39.44ChemAxon
    polarizability16.52ChemAxon
    number of rings0ChemAxon
    bioavailability1ChemAxon
    rule of fiveYesChemAxon
    Ghose filterNoChemAxon
    Veber's ruleNoChemAxon
    MDDR-like ruleNoChemAxon
    Spectra
    SpectraNot Available
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    External Links
    ResourceLink
    KEGG CompoundC07269
    PubChem Compound11963622
    PubChem Substance46508965
    ChemSpider10137785
    ChEBI7596
    ChEMBLCHEMBL74115
    Therapeutic Targets DatabaseDNC001351
    PharmGKBPA451406
    Drug Product Database336459
    RxListhttp://www.rxlist.com/cgi/generic3/nitroprusside.htm
    Drugs.comhttp://www.drugs.com/mtm/nitroprusside.html
    WikipediaNitroprusside
    ATC CodesC02DD01
    AHFS Codes
    • 24:08.20
    PDB EntriesNot Available
    FDA labelNot Available
    MSDSshow(79 KB)
    Interactions
    Drug Interactions
    Drug
    TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
    Food InteractionsNot Available

    1. Atrial natriuretic peptide receptor 1

    Kind: protein

    Organism: Human

    Pharmacological action: yes

    Actions: agonist

    Components

    Name UniProt ID Details
    Atrial natriuretic peptide receptor 1 P16066 Details

    References:

    1. Fortin Y, De Lean A: Role of cyclic GMP and calcineurin in homologous and heterologous desensitization of natriuretic peptide receptor-A. Can J Physiol Pharmacol. 2006 May;84(5):539-46. Pubmed
    2. Madhani M, Okorie M, Hobbs AJ, MacAllister RJ: Reciprocal regulation of human soluble and particulate guanylate cyclases in vivo. Br J Pharmacol. 2006 Nov;149(6):797-801. Epub 2006 Oct 3. Pubmed
    3. Steinmetz M, Potthast R, Sabrane K, Kuhn M: Diverging vasorelaxing effects of C-type natriuretic peptide in renal resistance arteries and aortas of GC-A-deficient mice. Regul Pept. 2004 Jun 15;119(1-2):31-7. Pubmed

    1. Cytochrome P450 1A1

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 1A1 P04798 Details

    References:

    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    2. Cytochrome P450 1A2

    Kind: protein

    Organism: Human

    Pharmacological action: unknown

    Actions: inhibitor

    Components

    Name UniProt ID Details
    Cytochrome P450 1A2 P05177 Details

    References:

    1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

    Comments
    Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09