Nitroprusside

Identification

Summary

Nitroprusside is a direct acting vasodilator used to treat hypertension, to induce controlled hypotension to reduce postoperative bleeding, and to manage acute heart failure.

Brand Names
Nipride, Nipride RTU, Nitropress
Generic Name
Nitroprusside
DrugBank Accession Number
DB00325
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 215.938
Monoisotopic: 215.948300785
Chemical Formula
C5FeN6O
Synonyms
  • Nitroferricyanide

Pharmacology

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

Pharmacology
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Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

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.

TargetActionsOrganism
AAtrial natriuretic peptide receptor 1
agonist
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Metabolized by reaction with hemoglobin to produce cyanmethemoglobin and cynide ions

Hover over products below to view reaction partners

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.

Half-life

Approximately 2 minutes

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Overdosage 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.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirNitroprusside may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcebutololNitroprusside may increase the hypotensive activities of Acebutolol.
AceclofenacThe therapeutic efficacy of Nitroprusside can be decreased when used in combination with Aceclofenac.
AcemetacinThe therapeutic efficacy of Nitroprusside can be decreased when used in combination with Acemetacin.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Nitroprusside.
AcetazolamideAcetazolamide may increase the excretion rate of Nitroprusside which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Nitroprusside.
AclidiniumNitroprusside may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineNitroprusside may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirAcyclovir may decrease the excretion rate of Nitroprusside which could result in a higher serum level.
Interactions
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Food Interactions
No interactions found.

Products

Products2
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Product Ingredients
IngredientUNIICASInChI Key
Sodium nitroprussideEAO03PE1TC13755-38-9SPBWMYPZWNFWES-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NipridePowder, for solution50 mg / vialIntravenousHospira Healthcare Ulc1975-12-312011-08-05Canada flag
NiprideSolution25 mg / mLIntravenousPfizer Canada Ulc2011-05-17Not applicableCanada flag
Nipride RtuInjection, solution0.2 mg/1mLIntravenousExela Pharma Sciences, LLC2018-02-092019-08-30US flag
Nipride RtuInjection, solution0.5 mg/1mLIntravenousExela Pharma Sciences, LLC2017-03-20Not applicableUS flag
Nipride RtuInjection, solution0.2 mg/1mLIntravenousExela Pharma Sciences, LLC2018-07-20Not applicableUS flag
Sodium Nitroprusside for InjectionSolution25 mg / mLIntravenousSterimax Inc2021-04-26Not applicableCanada flag
Sodium Nitroprusside for InjectionSolution25 mg / mLIntravenousMarcan Pharmaceuticals Inc2019-04-15Not applicableCanada flag
Sodium Nitroprusside for InjectionSolution25 mg / mLIntravenousDr Reddy's Laboratories Ltd2021-05-26Not applicableCanada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NitropressInjection, solution, concentrate50 mg/2mLIntravenousHospira, Inc.2005-06-072015-07-01US flag
NitropressInjection, solution, concentrate50 mg/2mLIntravenousMarathon Pharmaceuticals2013-12-012016-05-31US flag
NitropressInjection, solution, concentrate50 mg/2mLIntravenousBausch Health US, LLC2013-12-01Not applicableUS flag
Sodium NitroprussideInjection25 mg/1mLIntravenousRenaissance Ssa, Llc2019-12-28Not applicableUS flag
Sodium NitroprussideInjection, solution, concentrate25 mg/1mLIntravenousSomerset Therapeutics, Llc2018-08-17Not applicableUS flag
Sodium NitroprussideInjection50 mg/2mLIntravenousBE Pharmaceuticals Inc.2021-07-12Not applicableUS flag
Sodium NitroprussideInjection, solution, concentrate50 mg/2mLIntravenousCipla USA Inc.2018-07-16Not applicableUS flag
Sodium NitroprussideInjection50 mg/2mLIntravenousCaplin Steriles Limited2019-12-05Not applicableUS flag
Sodium NitroprussideInjection50 mg/2mLIntravenousMicro Labs Limited2017-12-30Not applicableUS flag
Sodium NitroprussideInjection, solution, concentrate50 mg/2mLIntravenousSlate Run Pharmaceuticals, Llc2020-10-15Not applicableUS flag

Categories

ATC Codes
C02DD01 — Nitroprusside
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as organic transition metal salts. These are organic salt compounds containing a transition metal atom in its ionic form.
Kingdom
Organic compounds
Super Class
Organic salts
Class
Organic metal salts
Sub Class
Organic transition metal salts
Direct Parent
Organic transition metal salts
Alternative Parents
Organotransition metal compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Organic anions
Substituents
Aliphatic acyclic compound / Hydrocarbon derivative / Organic anion / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organic transition metal moeity / Organic transition metal salt / Organometallic compound / Organonitrogen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
iron coordination entity (CHEBI:7596)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
169D1260KM
CAS number
15078-28-1
InChI Key
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

References

General References
Not Available
Human Metabolome Database
HMDB0014470
KEGG Compound
C07269
PubChem Compound
11963622
PubChem Substance
46508965
ChemSpider
21607452
BindingDB
50377921
RxNav
7476
ChEBI
7596
ChEMBL
CHEMBL2097081
Therapeutic Targets Database
DNC001351
PharmGKB
PA451406
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Sodium_nitroprusside
MSDS
Download (79 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4RecruitingTreatmentHemorrhagic Stroke1
4TerminatedPreventionMyocardial Infarction1
4Unknown StatusScreeningNitroprusside / Thyroid Hormones1
4WithdrawnTreatmentAcute Heart Failure (AHF)1
3CompletedTreatmentHeart Failure / High Blood Pressure (Hypertension)1
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
2CompletedPreventionST Segment Elevation Myocardial Infarction (STEMI)1
2CompletedTreatmentCerebral Oxygenation1
2CompletedTreatmentDepression1
2CompletedTreatmentHigh Blood Pressure (Hypertension)1

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
  • Baxter International Inc.
  • Hospira Inc.
  • Physicians Total Care Inc.
  • Teva Pharmaceutical Industries Ltd.
Dosage Forms
FormRouteStrength
InjectionIntravenous25 mg/ml
Powder, for solutionIntravenous50 mg / vial
Injection, solutionIntravenous0.2 mg/1mL
Injection, solutionIntravenous0.5 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous50 mg
Injection, powder, for solutionParenteral
Injection, solutionIntravenous
Injection, solution, concentrateIntravenous50 mg/2mL
Injection, powder, for solutionIntravenous50 mg
InjectionParenteral25 mg
SolutionIntravenous50 mg
Powder50 mg/1vial
Powder, for solutionIntravenous
InjectionIntravenous25 mg/1mL
InjectionIntravenous50 mg/2mL
Injection, solutionIntravenous50 mg/2mL
Injection, solution, concentrateIntravenous25 mg/1mL
SolutionIntravenous25 mg / mL
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
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 ...
Gene Name
NPR1
Uniprot ID
P16066
Uniprot Name
Atrial natriuretic peptide receptor 1
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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Kind
Protein
Organism
Humans
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 un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Stadler J, Trockfeld J, Schmalix WA, Brill T, Siewert JR, Greim H, Doehmer J: Inhibition of cytochromes P4501A by nitric oxide. Proc Natl Acad Sci U S A. 1994 Apr 26;91(9):3559-63. doi: 10.1073/pnas.91.9.3559. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 19, 2021 07:39