Identification

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Name
Nitroprusside
Accession Number
DB00325  (APRD01143)
Type
Small Molecule
Groups
Approved, Investigational
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.

Structure
Thumb
Synonyms
  • Nitroferricyanide
Product Ingredients
IngredientUNIICASInChI Key
Sodium nitroprussideEAO03PE1TC13755-38-9OIRZWVYIQXBRFC-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NipridePowder, for solutionIntravenousHospira Healthcare Ulc1975-12-312011-08-05Canada
NiprideSolutionIntravenousPfizer Canada Ulc2011-05-17Not applicableCanada
Nipride RtuInjection, solution0.2 mg/1mLIntravenousExela Pharma Sciences, LLC2018-07-20Not applicableUs
Nipride RtuInjection, solution0.2 mg/1mLIntravenousExela Pharma Sciences, LLC2018-02-092019-08-30Us
Nipride RtuInjection, solution0.5 mg/1mLIntravenousExela Pharma Sciences, LLC2017-03-20Not applicableUs
Sodium Nitroprusside for InjectionSolutionIntravenousMarcan Pharmaceuticals Inc2019-04-15Not applicableCanada
Sodium Nitroprusside for InjectionSolutionIntravenousSterimax IncNot applicableNot applicableCanada
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NitropressInjection, solution, concentrate50 mg/2mLIntravenousHospira, Inc.2005-06-072015-07-01Us
NitropressInjection, solution, concentrate50 mg/2mLIntravenousMarathon Pharmaceuticals2013-12-012016-05-31Us
NitropressInjection, solution, concentrate50 mg/2mLIntravenousBausch Health Americas, Inc.2013-12-01Not applicableUs
Sodium NitroprussideInjection, solution, concentrate25 mg/1mLIntravenousMedicure International Inc.2018-08-10Not applicableUs
Sodium NitroprussideInjection50 mg/2mLIntravenousAmphastar Pharmaceuticals, Inc.2017-12-18Not applicableUs
Sodium NitroprussideInjection, solution, concentrate25 mg/1mLIntravenousSagent Pharmaceuticals2017-12-012020-09-30Us
Sodium NitroprussideInjection, solution, concentrate25 mg/1mLIntravenousSomerset Therapeutics, Llc2018-08-17Not applicableUs
Sodium nitroprussideInjection25 mg/1mLIntravenousAmneal Pharmaceuticals LLC2017-11-07Not applicableUs
Sodium nitroprussideInjection, solution, concentrate25 mg/1mLIntravenousMylan Institutional2018-08-10Not applicableUs
Sodium NitroprussideInjection25 mg/1mLIntravenousNexus Pharmaceuticals Inc2017-05-29Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
UNII
169D1260KM
CAS number
15078-28-1
Weight
Average: 215.938
Monoisotopic: 215.948300785
Chemical Formula
C5FeN6O
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

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

Associated Conditions
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
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Metabolized by reaction with hemoglobin to produce cyanmethemoglobin and cynide ions

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
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.

Affected organisms
  • Humans and other mammals
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
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid may decrease the antihypertensive activities of Nitroprusside.
1-benzylimidazole1-benzylimidazole may decrease the antihypertensive activities of Nitroprusside.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the antihypertensive activities of Nitroprusside.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the antihypertensive activities of Nitroprusside.
3-Aza-2,3-Dihydrogeranyl DiphosphateNitroprusside can cause a decrease in the absorption of 3-Aza-2,3-Dihydrogeranyl Diphosphate resulting in a reduced serum concentration and potentially a decrease in efficacy.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the antihypertensive activities of Nitroprusside.
4-Methoxyamphetamine4-Methoxyamphetamine may decrease the antihypertensive activities of Nitroprusside.
5-methoxy-N,N-dimethyltryptamine5-methoxy-N,N-dimethyltryptamine may decrease the antihypertensive activities of Nitroprusside.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the hypotensive activities of Nitroprusside.
AbacavirNitroprusside may decrease the excretion rate of Abacavir which could result in a higher serum level.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
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Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014470
KEGG Compound
C07269
PubChem Compound
11963622
PubChem Substance
46508965
ChemSpider
21607452
BindingDB
50377921
ChEBI
7596
ChEMBL
CHEMBL2097081
Therapeutic Targets Database
DNC001351
PharmGKB
PA451406
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Nitroprusside
ATC Codes
C02DD01 — Nitroprusside
AHFS Codes
  • 24:08.20 — Direct Vasodilators
MSDS
Download (79 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingBasic ScienceReceptor Blockade1
0RecruitingBasic ScienceArterial Stiffness / Vasodilation1
0RecruitingBasic ScienceVasoconstriction / Vasodilation1
1Active Not RecruitingScreeningAutonomic Nervous System Diseases / Dopamine Beta-Hydroxylase Deficiency / Orthostatic Hypotension / Orthostatic Intolerance1
1CompletedNot AvailableAging1
1CompletedBasic ScienceCardiovascular Disease (CVD) / Cardiovascular Risk Factors / Vasoconstriction1
1CompletedBasic ScienceSarcopenia2
1CompletedBasic ScienceSchizophrenic Disorders1
1RecruitingBasic ScienceCardiovascular Disease (CVD) / Cardiovascular Risk Factors / Vasoconstriction1
1RecruitingBasic ScienceChronic Obstructive Pulmonary Disease (COPD) / Heart Failure / High Blood Pressure (Hypertension) / Pulmonary Arterial Hypertension (PAH)1
1TerminatedOtherInflammatory Reaction1
1Unknown StatusEducational/Counseling/TrainingHealthy Volunteers1
1Unknown StatusTreatmentAcute Lung Injury (ALI) / Acute Respiratory Distress Syndrome (ARDS) / Arterial hypoxia / Respiratory Failure / Sodium Nitroprusside1
1, 2RecruitingPreventionBreast Cancer / Leukemias / Malignant Lymphomas1
2CompletedPreventionST Elevation Myocardial Infarction (STEMI)1
2CompletedTreatmentCerebral Oxygenation1
2CompletedTreatmentHigh Blood Pressure (Hypertension)1
2CompletedTreatmentHypotension1
2CompletedTreatmentSchizophrenic Disorders2
2RecruitingPreventionPost Traumatic Stress Disorder (PTSD)1
2RecruitingTreatmentAnemias1
2RecruitingTreatmentDepression1
2TerminatedDiagnosticHyperlipidemias1
2, 3CompletedTreatmentMyocardial Infarction1
3CompletedTreatmentHeart Failure / High Blood Pressure (Hypertension)1
3CompletedTreatmentHigh Blood Pressure (Hypertension)1
4RecruitingTreatmentHemorrhagic Strokes1
4TerminatedPreventionMyocardial Infarction1
4Unknown StatusScreeningNitroprusside / Thyroid Hormones1
4WithdrawnTreatmentAcute Heart Failure (AHF)1
Not AvailableCompletedNot AvailableEndothelial Dysfunction / High Blood Pressure (Hypertension) / Malignancies1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableHypotension, Controlled1
Not AvailableCompletedNot AvailableIntracerebral Hemorrhage / Subarachnoid Hemorrhage1
Not AvailableCompletedNot AvailableLeiomyomas1
Not AvailableCompletedBasic ScienceGlaucoma1
Not AvailableCompletedBasic ScienceHealthy Male Subjects1
Not AvailableCompletedBasic ScienceHeart Diseases / Heart Failure / Vasodilation1
Not AvailableCompletedBasic ScienceHeart Diseases / Vasodilation1
Not AvailableCompletedBasic ScienceLeprosy, Lepromatous1
Not AvailableCompletedDiagnosticBlood Flow in Healthy Volunteers1
Not AvailableCompletedTreatmentCerebrovascular Accident / Intracerebral Hemorrhage / Intracranial Hemorrhages1
Not AvailableCompletedTreatmentType 2 Diabetes Mellitus1
Not AvailableRecruitingPreventionElective Percutaneous Coronary Intervention / ST Segment Elevation Myocardial Infarction (STEMI)1
Not AvailableRecruitingPreventionPrimary Percutaneous Coronary Intervention / ST Segment Elevation Myocardial Infarction (STEMI)1
Not AvailableTerminatedBasic ScienceHealthy Volunteers1
Not AvailableTerminatedBasic ScienceProphylaxis of cardiomyopathy / Stress-induced (Takotsubo) Cardiomyopathy1
Not AvailableUnknown StatusNot AvailableDiabetes Mellitus (DM)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
Powder, for solutionIntravenous
Injection, solutionIntravenous0.2 mg/1mL
Injection, solutionIntravenous0.5 mg/1mL
Injection, solution, concentrateIntravenous50 mg/2mL
InjectionIntravenous25 mg/1mL
InjectionIntravenous50 mg/2mL
Injection, solution, concentrateIntravenous25 mg/1mL
SolutionIntravenous
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

Taxonomy

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
Organic transition metal salt / Organic nitrogen compound / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organonitrogen compound / Organometallic compound / Organic transition metal moeity / Organic anion
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
iron coordination entity (CHEBI:7596)

Targets

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. [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
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. [PubMed:8170947]

Drug created on June 13, 2005 07:24 / Updated on November 15, 2019 02:02