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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
Synonyms
SynonymLanguageCode
[Fe(CN)5(NO)](2-)Not AvailableNot Available
NitroferricyanideNot AvailableNot 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 KeyASPOIVQEUUCDQT-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
Not Available
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

Targets

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

Enzymes

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

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