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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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nipridesolution25 mgintravenousHospira Healthcare CorporationNot AvailableNot AvailableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nitropressinjection, solution, concentrate50 mg/2mLintravenousHospira, Inc.1988-08-01Not AvailableUs
Nitropressinjection, solution, concentrate50 mg/2mLintravenousMarathon Pharmaceuticals, LLC2013-12-01Not AvailableUs
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixtures
Brand NameIngredients
Cora-Bosan B43Potassium Carbonate + Sodium Nitroprusside + Squill
Salts
Name/CASStructureProperties
Sodium nitroprusside
ThumbNot applicableDBSALT000839
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as organic metal salts. These are organic salt compounds containing a metal atom in its ionic form.
KingdomOrganic compounds
Super ClassOrganic salts
ClassOrganic metal salts
Sub ClassNot Available
Direct ParentOrganic metal salts
Alternative Parents
Substituents
  • Organic metal salt
  • Organic cyanide salt
  • Hydrocarbon derivative
  • Organic transition metal salt
  • Organonitrogen compound
  • Organometallic compound
  • Organic transition metal moeity
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption-0.8308
Blood Brain Barrier+0.9314
Caco-2 permeable-0.5269
P-glycoprotein substrateNon-substrate0.8966
P-glycoprotein inhibitor INon-inhibitor0.919
P-glycoprotein inhibitor IINon-inhibitor0.9767
Renal organic cation transporterNon-inhibitor0.9109
CYP450 2C9 substrateNon-substrate0.8573
CYP450 2D6 substrateNon-substrate0.8353
CYP450 3A4 substrateNon-substrate0.6675
CYP450 1A2 substrateNon-inhibitor0.6719
CYP450 2C9 substrateNon-inhibitor0.8599
CYP450 2D6 substrateNon-inhibitor0.9186
CYP450 2C19 substrateNon-inhibitor0.8218
CYP450 3A4 substrateNon-inhibitor0.9763
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9583
Ames testNon AMES toxic0.5204
CarcinogenicityCarcinogens 0.6595
BiodegradationNot ready biodegradable0.5759
Rat acute toxicity2.9543 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9345
hERG inhibition (predictor II)Non-inhibitor0.9596
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
Injection, solution, concentrateintravenous50 mg/2mL
Solutionintravenous25 mg
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 Area148.38 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.44 m3·mol-1ChemAxon
Polarizability16.52 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesC02DD01
AHFS Codes
  • 24:08.20
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (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