ニトロプルシド。ニトロプルシドナトリウム, sodium nitroprusside SNP

WordNet

a silvery soft waxy metallic element of the alkali metal group; occurs abundantly in natural compounds (especially in salt water); burns with a yellow flame and reacts violently in water; occurs in sea water and in the mineral halite (rock salt) (同)Na, atomic number 11

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ソジウム,ナトリウム(金属元素;化学記号はNa)

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/10/29 23:56:44」(JST)

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Sodium nitroprusside is the inorganic compound with the formula Na₂[Fe(CN)₅NO]·2H₂O.^[1] This red-coloured salt, which is often abbreviated SNP, is a potent vasodilator. The sodium salt dissolves in water and to a lesser extent in ethanol to give solutions containing the dianion [Fe(CN)₅NO]²⁻.

Preparation[edit]

Sodium nitroprusside can be synthesized by boiling potassium ferrocyanide in concentrated nitric acid:^[2]

K₄[Fe(CN)₆] + 6 HNO₃ → H₂[Fe(CN)₅(NO)] + CO₂ + NH₄NO₃ + 4 NaNO₃

H₂[Fe(CN)₅NO] + Na₂CO₃ → Na₂[Fe(CN)₅(SO)] + NO₂ + H₂O

Or with nitrites:^[3]

[Fe(CN)₆]^4- + H₂O + NO₂^- → [Fe(CN)₅(NO)]^2- + CN^- + 2 OH^-

Structure and properties[edit]

Nitroprusside is a complex anion that features an octahedral ferrous centre surrounded by five tightly bound cyanide ligands and one linear nitric oxide ligand. The molecular symmetry is C_4v. Linear nitrosyl ligands are assigned a single positive charge, thus the iron is assigned an oxidation state of 2+. As such it has a low-spin d⁶ electron configuration and is diamagnetic; together with the relatively short N-O distance of 113pm and the relatively high stretching wavenumber of 1947 cm⁻¹, the complex is formulated as containing an [NO]⁺ ligand.^[3]

The chemical reactions of sodium nitroprusside are mainly associated with the NO ligand.^[4] For example, addition of S^2- ion to [Fe(CN)₅(NO)]^2- produces the red [Fe(CN)₅(NOS)]^4- ion, which is the basis for a sensitive test for S^2- ions. An analogous reaction also exists with OH^- ions, giving [Fe(CN)₅(NO₂)]^4-.^[3]

Ball-and-stick model of part of the crystal structure of sodium nitroprusside dihydrate^[5]

Medical pharmacology[edit]

Sodium nitroprusside (Abbreviated SNP, brand name: Nitropress) has potent vasodilating effects in arterioles and venules (venules more than arterioles, but this selectivity is much less marked than that of nitroglycerin).^[6] It is administered intravenously in cases of acute hypertensive emergency. SNP breaks down in circulation to release nitric oxide (NO). NO activates guanylate cyclase in vascular smooth muscle and increases intracellular production of cGMP. cGMP activates Protein Kinase G which activates phosphatases which inactivate Myosin light chains. Myosin light chains are involved in muscle contraction. The end result is vascular smooth muscle relaxation, which allow vessels to dilate.

In the human heart, nitric oxide reduces both total peripheral resistance as well as venous return, thus decreasing both preload and afterload. For this reason, it can be used in severe cardiogenic heart failure where this combination of effects can act to increase cardiac output. In situations where cardiac output is normal, the effect is to reduce blood pressure.

Metabolism and toxicity[edit]

Sodium nitroprusside slowly breaks down to release 5 cyanide ions, especially upon exposure to UV light. Despite the toxic potential of cyanide, nitroprusside remains an effective drug in certain clinical circumstances such as malignant hypertension or for rapid control of blood pressure during vascular surgery and neurosurgery. The cyanide can be detoxified by reaction with a sulfur-donor such as thiosulfate, catalysed by the enzyme rhodanese. In the absence of sufficient thiosulfate, cyanide ions can quickly reach toxic levels.^[7] The half-life of nitroprusside is 1–2 minutes, but the metabolite thiocyanate has an excretion half-life of several days.

Use in research[edit]

In physiology research, sodium nitroprusside is frequently used to test endothelium-independent vasodilation. Iontophoresis, for example, allows local administration of the drug, preventing the systemic effects listed above but still inducing local microvascular vasodilation.

Sodium nitroprusside is also used in the presence of buffers as a reagent for ketone strips, which test the ketone levels in the urine of a diabetic. Colour change on the strip indicates the relative concentration of ketones.

Sodium nitroprusside spectrum is used to calibrate Mössbauer spectrometers

Sodium nitroprusside is often used as a reference compound for the calibration of Mössbauer spectrometer. It is also used as an analytical reagent in qualitative organic analysis.

In combination with acetaldehyde it is also used as a colour reagent in the development of thin layer chromatography plates, particularly for N-heterocyclic compounds.

Sodium nitroprusside is also used in a urinalysis test, called the cyanide nitroprusside test, also known as Brand's test. In this test sodium cyanide is added first to urine and let stand for approximately 10 minutes. In this time disulfide bonds will be broken by the released cyanide. The destruction of disulfide bonds liberates cysteine from cystine and homocysteine from homocystine. Next sodium nitroprusside is added to the solution and it reacts with the newly freed sulfhydryl groups. The test will turn a red/purple colour if the test is positive indicating that there was significant amounts of amino acid in the urine (aminoaciduria). Cysteine, cystine, homocysteine and homocystine all react when present in the urine when this test is performed. This test can indicate inborn errors of amino acid transporters such as cystinuria, which results from pathology in the transport of dibasic amino acids.

SNP is also used in microbiology, where it has been linked with the dispersal of Pseudomonas aeruginosa biofilms by acting as a nitric oxide donor.^[8]

Use in forensic science[edit]

Sodium nitroprusside is used by forensic chemists in a preliminary test in the identification of illicit substances.^[9] The test, called Simon's test, is performed by adding 1 volume of a solution of SNP and acetaldehyde in deionized water to a suspected drug, followed by the addition of 2 volumes of an aqueous sodium carbonate solution. The test turns blue for some secondary amines. The most common secondary amines encountered in forensic chemistry include 3,4-methylenedioxymethamphetamine (MDMA, the main component in Ecstasy) and phenethylamines such as methamphetamine.

References[edit]

^ A. R. Butler, I. L. Megson (2002). "Non-Heme Iron Nitrosyls in Biology". Chemical Reviews 102 (4): 1155–1165. doi:10.1021/cr000076d.
^ "Sodium Nitrosyl Cyanoferrate" in Handbook of Preparative Inorganic Chemistry, 2nd Ed. Edited by G. Brauer, Academic Press, 1963, NY. Vol. 1. p. 1768.
^ ^a ^b ^c Catherine E. Housecroft; Alan G. Sharpe (2008). "Chapter 22: d-Block metal chemistry: the first row metals". Inorganic Chemistry, 3rd Edition. Pearson. p. 721. ISBN 978-0-13-175553-6.
^ Coppens, P.; Novozhilova, I.; Kovalevsky, A. (2002). "Photoinduced Linkage Isomers of Transition-Metal Nitrosyl Compounds and Related Complexes". Chem. Rev. 102 (4): 861–883. doi:10.1021/cr000031c.
^ A. Navaza, G. Chevrier, P. M. Alzari, P. J. Aymonino (1989). "Single-crystal neutron diffraction structure of sodium pentacyanonitrosylferrate(2−) (sodium nitroprusside) dihydrate". Acta Cryst. 45 (6): 839–841. doi:10.1107/S0108270188013691.
^ http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=2402
^ Nitropress (Nitroprusside Sodium) Drug Information: User Reviews, Side Effects, Drug Interactions and Dosage at RxList. Rxlist.com. Retrieved on 2010-12-11.
^ Barraud, N; Hassett, DJ; Hwang, SH; Rice, SA; Kjelleberg, S; Webb, JS (2006). "Involvement of nitric oxide in biofilm dispersal of Pseudomonas aeruginosa". Journal of bacteriology 188 (21): 7344–53. doi:10.1128/JB.00779-06. PMC 1636254. PMID 17050922.
^ Carol L. O’Neala, Dennis J. Croucha, Alim A. Fatahb (2000). "Validation of twelve chemical spot tests for the detection of drugs of abuse". Forensic Science International 109: 189–201. doi:10.1016/S0379-0738(99)00235-2. PMID 10725655.

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English Journal

The mediation of platelet quiescence by NO-releasing polymers via cGMP-induced serine 239 phosphorylation of vasodilator-stimulated phosphoprotein.

Major TC, Handa H, Brisbois EJ, Reynolds MM, Annich GM, Meyerhoff ME, Bartlett RH.SourceDepartment of Surgery, University of Michigan Medical Center, Ann Arbor, MI, USA. Electronic address: tcmajor@umich.edu.
Biomaterials.Biomaterials.2013 Nov;34(33):8086-96. doi: 10.1016/j.biomaterials.2013.07.041. Epub 2013 Jul 29.
Nitric oxide (NO) releasing (NORel) materials have been shown to create localized increases in NO concentration by the release of NO from a diazeniumdiolate-containing or S-nitrosothiol-containing polymer coating and the improvement of extracorporeal circulation (ECC) hemocompatibility. However, the
PMID 23906514

Complement activation is critical for placental ischemia-induced hypertension in the rat.

Lillegard KE, Johnson AC, Lojovich SJ, Bauer AJ, Marsh HC, Gilbert JS, Regal JF.SourceDepartment of Biomedical Sciences, University of Minnesota Medical School Duluth, Duluth, MN 55812, USA. lille067@umn.edu
Molecular immunology.Mol Immunol.2013 Nov;56(1-2):91-7. doi: 10.1016/j.molimm.2013.04.009. Epub 2013 May 15.
Preeclampsia is a major obstetric problem defined by new-onset hypertension and proteinuria associated with compromised placental perfusion. Although activation of the complement system is increased in preeclampsia compared to normal pregnancy, it remains unclear whether excess complement activation
PMID 23685261

Do iodinated nano-emulsions designed for preclinical vascular imaging alter the vascular reactivity in rat aorta?

Anton N, Atzenhoffer M, Daubeuf F, Li X, Schini-Kerth VB, Delmotte B, Vandamme TF, Chataigneau T.SourceUMR 7199 CNRS, Laboratoire de Conception et Application de Molécules Bioactives, équipe de Pharmacie Biogalénique, Université de Strasbourg, Faculté de Pharmacie, 74 route du Rhin, BP 60024, 67401 Illkirch Cedex, France.
International journal of pharmaceutics.Int J Pharm.2013 Sep 15;454(1):143-8. doi: 10.1016/j.ijpharm.2013.07.007. Epub 2013 Jul 10.
This study proposes a new methodology to evaluate the putative consequences of the long-lasting circulation in the blood pool of nanoparticulate systems widely used in nanomedicine, Indeed, the blood pool contrast agent for micro-computed tomography, i.e. iodinated nano-emulsions, have recently been
PMID 23850235

Japanese Journal

Autologous Bone-Marrow Mesenchymal Stem Cell Implantation and Endothelial Function in a Rabbit Ischemic Limb Model

Mikami Shinsuke,Nakashima Ayumu,Nakagawa Keigo,Maruhashi Tatsuya,Iwamoto Yumiko,Kajikawa Masato,Matsumoto Takeshi,Kihara Yasuki,Chayama Kazuaki,Noma Kensuke,Ochi Mitsuo,Nishimura Masahiro,Tsuji Koichiro,Kato Yukio,Goto Chikara,Higashi Yukihito
PLoS ONE 8(7), e67739, 2013-07-04
… Background:The purpose of this study was to determine whether autologous mesenchymal stem cells (MSCs) implantation improves endothelial dysfunction in a rabbit ischemic limb model.Methods:We evaluated the effect of MSC implantation on limb blood flow (LBF) responses to acetylcholine (ACh), an endothelium-dependent vasodilator, and sodium nitroprusside (SNP), an endothelium-independent vasodilator, in rabbits with limb ischemia in which cultured MSCs were implanted (n = 20) or saline was injected as a control group (n = 20). …
NAID 120005311939

Effect of Overexpression of the Brain-Specific Na+/Ca2+ Exchanger Splice Variant NCX1.5 on NO Cytotoxicity in HEK293 Cells

Ota Yuki,Kawanai Takuya,Watanabe Ryo,Nishimura Akira,Ago Yukio,Takuma Kazuhiro,Matsuda Toshio
Journal of Pharmacological Sciences 121(4), 351-354, 2013
… There was no difference in the cytotoxic effects of the NO donors sodium nitroprusside and S-nitroso-N-acetylpenicillamine between control and transfected cells. …
NAID 130003382585

Protective Effect of Luteolin on an Oxidative-Stress Model Induced by Microinjection of Sodium Nitroprusside in Mice

Nazari Qand Agha,Kume Toshiaki,Takada-Takatori Yuki [他],Izumi Yasuhiko,Akaike Akinori
Journal of Pharmacological Sciences 122(2), 109-117, 2013
… The purpose of this study was to examine whether luteolin can protect against sodium nitroprusside (SNP)-induced oxidative damage in mouse brain. …
NAID 130003362709

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リンク元	「ニトロプルシド」「SNP」

「ニトロプルシド」

Sodium nitroprusside
	IUPAC name Sodium pentacyanonitrosylferrate(II)
	Other names Sodium nitroprusside; Sodium nitroferricyanide; Sodium pentacyanonitrosylferrate; SNP
Identifiers
CAS number	14402-89-2 , (anhydrous); 13755-38-9 (dihydrate)
PubChem	26256
EC number	238-373-9
DrugBank	DB00325
ChEMBL	CHEMBL136478 , CHEMBL74115
RTECS number	LJ8750000
ATC code	C02DD01
Properties
Molecular formula	Na2[Fe(CN)5NO]
Molar mass	261.92 g/mol (anhydrous); 297.95 g/mol (dihydrate)
Appearance	red powder
Density	1.72
Solubility in water	good
Solubility in ethanol	soluble
Structure
Coordination; geometry	octahedral at Fe
Pharmacology
Routes of; administration	Intravenous
Metabolism	Circulatory
Elimination; half-life	2 minutes (metabolites: several days)
Excretion	Renal
Legal status	; ℞ Prescription only
Pregnancy; category	C
Hazards
EU Index	Not listed
NFPA 704	0 1 0
Flash point	Non-flammable
	(verify) (what is: /?); Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
	Infobox references

　　[★]

英: nitroprusside
化: ニトロプルシドナトリウム, sodium nitroprusside SNP
商: ニトプロ、Nipride

血管拡張薬・緊急降圧薬、グアニル酸シクラーゼ活性化

「SNP」

　　[★]

[1] A. R. Butler, I. L. Megson (2002). "Non-Heme Iron Nitrosyls in Biology". Chemical Reviews 102 (4): 1155–1165. doi:10.1021/cr000076d.

[2] "Sodium Nitrosyl Cyanoferrate" in Handbook of Preparative Inorganic Chemistry, 2nd Ed. Edited by G. Brauer, Academic Press, 1963, NY. Vol. 1. p. 1768.

[InorgChem-3] Catherine E. Housecroft; Alan G. Sharpe (2008). "Chapter 22: d-Block metal chemistry: the first row metals". Inorganic Chemistry, 3rd Edition. Pearson. p. 721. ISBN 978-0-13-175553-6.

[4] Coppens, P.; Novozhilova, I.; Kovalevsky, A. (2002). "Photoinduced Linkage Isomers of Transition-Metal Nitrosyl Compounds and Related Complexes". Chem. Rev. 102 (4): 861–883. doi:10.1021/cr000031c.

[5] A. Navaza, G. Chevrier, P. M. Alzari, P. J. Aymonino (1989). "Single-crystal neutron diffraction structure of sodium pentacyanonitrosylferrate(2−) (sodium nitroprusside) dihydrate". Acta Cryst. 45 (6): 839–841. doi:10.1107/S0108270188013691.

[6] ttp://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=2402

[7] Nitropress (Nitroprusside Sodium) Drug Information: User Reviews, Side Effects, Drug Interactions and Dosage at RxList. Rxlist.com. Retrieved on 2010-12-11.

[8] Barraud, N; Hassett, DJ; Hwang, SH; Rice, SA; Kjelleberg, S; Webb, JS (2006). "Involvement of nitric oxide in biofilm dispersal of Pseudomonas aeruginosa". Journal of bacteriology 188 (21): 7344–53. doi:10.1128/JB.00779-06. PMC 1636254. PMID 17050922.

[9] Carol L. O’Neala, Dennis J. Croucha, Alim A. Fatahb (2000). "Validation of twelve chemical spot tests for the detection of drugs of abuse". Forensic Science International 109: 189–201. doi:10.1016/S0379-0738(99)00235-2. PMID 10725655.

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sodium nitroprusside