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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
[Fe(CN)5(NO)](2-)
Nitroferricyanide
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nipridesolution25 mgintravenousHospira Healthcare Corporation2011-05-17Not applicableCanada
Nipridepowder for solution50 mgintravenousHospira Healthcare Corporation1975-12-312011-08-05Canada
Sodium Nitroprusside for Injectionsolution25 mgintravenousSterimax IncNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nitropressinjection, solution, concentrate50 mg/2mLintravenousValeant Pharmaceuticals North America LLC2013-12-01Not applicableUs
Nitropressinjection, solution, concentrate50 mg/2mLintravenousMarathon Pharmaceuticals, LLC2013-12-01Not applicableUs
Nitropressinjection, solution, concentrate50 mg/2mLintravenousHospira, Inc.1988-08-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Sodium nitroprusside
ThumbNot applicableDBSALT000839
Categories
UNII169D1260KM
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
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.
Related Articles
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 inhibitorNon-inhibitor0.8599
CYP450 2D6 inhibitorNon-inhibitor0.9186
CYP450 2C19 inhibitorNon-inhibitor0.8218
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 solutionintravenous50 mg
Solutionintravenous25 mg
Injection, solution, concentrateintravenous50 mg/2mL
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 ReferencesNot Available
External Links
ATC CodesC02DD01
AHFS Codes
  • 24:08.20
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (79 KB)
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Nitroprusside.
AlfuzosinAlfuzosin may increase the hypotensive activities of Nitroprusside.
AmifostineNitroprusside may increase the hypotensive activities of Amifostine.
AmlodipineAmlodipine may increase the hypotensive activities of Nitroprusside.
AmrinoneAmrinone may increase the hypotensive activities of Nitroprusside.
BepridilBepridil may increase the hypotensive activities of Nitroprusside.
BrimonidineBrimonidine may increase the antihypertensive activities of Nitroprusside.
ButabarbitalButabarbital may increase the hypotensive activities of Nitroprusside.
ButethalButethal may increase the hypotensive activities of Nitroprusside.
ClevidipineClevidipine may increase the hypotensive activities of Nitroprusside.
DapsoneThe risk or severity of adverse effects can be increased when Dapsone is combined with Nitroprusside.
DiazoxideDiazoxide may increase the hypotensive activities of Nitroprusside.
DiltiazemDiltiazem may increase the hypotensive activities of Nitroprusside.
DuloxetineNitroprusside may increase the orthostatic hypotensive activities of Duloxetine.
FelodipineFelodipine may increase the hypotensive activities of Nitroprusside.
FlunarizineFlunarizine may increase the hypotensive activities of Nitroprusside.
GabapentinGabapentin may increase the hypotensive activities of Nitroprusside.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Nitroprusside.
HexobarbitalHexobarbital may increase the hypotensive activities of Nitroprusside.
IsradipineIsradipine may increase the hypotensive activities of Nitroprusside.
LamotrigineLamotrigine may increase the hypotensive activities of Nitroprusside.
LercanidipineLercanidipine may increase the hypotensive activities of Nitroprusside.
LevodopaNitroprusside may increase the orthostatic hypotensive activities of Levodopa.
Magnesium SulfateMagnesium Sulfate may increase the hypotensive activities of Nitroprusside.
MethohexitalMethohexital may increase the hypotensive activities of Nitroprusside.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Nitroprusside.
MolsidomineMolsidomine may increase the hypotensive activities of Nitroprusside.
MoxonidineMoxonidine may increase the hypotensive activities of Nitroprusside.
NicardipineNicardipine may increase the hypotensive activities of Nitroprusside.
NicorandilNicorandil may increase the hypotensive activities of Nitroprusside.
NifedipineNifedipine may increase the hypotensive activities of Nitroprusside.
NimodipineNimodipine may increase the hypotensive activities of Nitroprusside.
NisoldipineNisoldipine may increase the hypotensive activities of Nitroprusside.
NitrendipineNitrendipine may increase the hypotensive activities of Nitroprusside.
Nitric OxideThe risk or severity of adverse effects can be increased when Nitric Oxide is combined with Nitroprusside.
ObinutuzumabNitroprusside may increase the hypotensive activities of Obinutuzumab.
PentobarbitalPentobarbital may increase the hypotensive activities of Nitroprusside.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Nitroprusside.
PerhexilinePerhexiline may increase the hypotensive activities of Nitroprusside.
PhenelzinePhenelzine may increase the hypotensive activities of Nitroprusside.
PrenylaminePrenylamine may increase the hypotensive activities of Nitroprusside.
PrilocaineThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Prilocaine.
PrimidonePrimidone may increase the hypotensive activities of Nitroprusside.
QuinineQuinine may increase the hypotensive activities of Nitroprusside.
RisedronateRisedronate may increase the hypotensive activities of Nitroprusside.
RisperidoneNitroprusside may increase the hypotensive activities of Risperidone.
RituximabNitroprusside may increase the hypotensive activities of Rituximab.
SecobarbitalSecobarbital may increase the hypotensive activities of Nitroprusside.
Sodium NitriteThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Sodium Nitrite.
TadalafilTadalafil may increase the antihypertensive activities of Nitroprusside.
TranylcypromineTranylcypromine may increase the hypotensive activities of Nitroprusside.
TreprostinilTreprostinil may increase the hypotensive activities of Nitroprusside.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Nitroprusside.
VardenafilVardenafil may increase the antihypertensive activities of Nitroprusside.
VerapamilVerapamil may increase the hypotensive activities of Nitroprusside.
YohimbineYohimbine may decrease the antihypertensive activities of Nitroprusside.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Protein kinase activity
Specific Function:
Receptor for the atrial natriuretic peptide NPPA/ANP and the brain natriuretic peptide NPPB/BNP which are potent vasoactive hormones playing a key role in cardiovascular homeostasis. Has guanylate cyclase activity upon binding of the ligand.
Gene Name:
NPR1
Uniprot ID:
P16066
Molecular Weight:
118918.11 Da
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:16902599 ]
  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:17016498 ]
  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:15093694 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Vitamin d 24-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics.
Gene Name:
CYP1A1
Uniprot ID:
P04798
Molecular Weight:
58164.815 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N...
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular Weight:
58293.76 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:09