Sodium salicylate: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
⚫	\| verifiedrevid = ~~401613201~~
			\| Watchedfields = changed
	\| ImageFile = SodiumSalicylate.png
		⚫	\| verifiedrevid = 476997079
⚫	\| ImageSize =
	\| ~~IUPACName~~ = Sodium ~~salicylate~~		\| ImageFile = Sodium salicylate2DCSD.svg
		⚫	\| ImageSize = 100px
⚫	\| OtherNames = Salsonin, Monosodium salicylate, Sodium o~~-hydroxybenzoate, Sodium 2~~-hydroxybenzoate, Salicylic acid sodium salt, Monosodium 2-hydroxybenzoate, Diuratin,
			\| PIN = Sodium 2-hydroxybenzoate
⚫	\| Section1 = {{Chembox Identifiers
		⚫	\| OtherNames = Salsonin, Monosodium salicylate, Sodium ''o''-hydroxybenzoate, Salicylic acid sodium salt, Monosodium 2-hydroxybenzoate, Diuratin
⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
		⚫	\|Section1={{Chembox Identifiers
		⚫	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 5689		\| ChemSpiderID = 5689
	\| UNII_Ref = {{fdacite\|correct\|FDA}}		\| UNII_Ref = {{fdacite\|correct\|FDA}}
Line 18:		Line 20:
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\| CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 54-21-7		\| CASNo = 54-21-7
	\| EINECS = 200-198-0		\| EINECS = 200-198-0
			\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}
⚫	\| PubChem = ~~5900~~
	\| ~~DrugBank~~ = ~~DB01398~~		\| ChEMBL = 447868
		⚫	\| PubChem = 16760658
			\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
			\| DrugBank = DB01398
	\| SMILES = .O=C()c1ccccc1O		\| SMILES = .O=C()c1ccccc1O
	\| InChI = 1/C7H6O3.Na/c8-6-4-2-1- 3-5(6)7(9)10;/h1-4,8H,(H,9,10); /q;+1/p-1/fC7H5O3.Na/q-1;m		\| InChI = 1/C7H6O3.Na/c8-6-4-2-1- 3-5(6)7(9)10;/h1-4,8H,(H,9,10); /q;+1/p-1/fC7H5O3.Na/q-1;m
			\| KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D00566
	\| RTECS = VO5075000		\| KEGG = D00566
			\| RTECS = VO5075000
	}}		}}
	\| Section2 = {{Chembox Properties		\|Section2={{Chembox Properties
			\| C=7 \| H=5 \| Na=1 \| O=3
	\| Formula = C<sub>7</sub>H<sub>5</sub>NaO<sub>3</sub>
	\| ~~MolarMass~~ = ~~160.11~~ g/mol		\| MolarMassUnit = g/mol
	\| Appearance = White crystals		\| Appearance = White crystals
	\| Density =		\| Density =
	\| ~~MeltingPt~~ = 200 °C		\| MeltingPtC = 200
	\| BoilingPt =		\| BoilingPt =
			\| Solubility = 25.08{{nbsp}}g/100{{nnbsp}}g (-1.5{{nbsp}}°C)<br> 107.9{{nbsp}}g/100{{nnbsp}}g (15{{nbsp}}°C)<br> 124.6{{nbsp}}g/100{{nnbsp}}g (25{{nbsp}}°C)<br> 141.8{{nbsp}}g/100{{nnbsp}}g (78.5{{nbsp}}°C)<br> 179{{nbsp}}g/100{{nnbsp}}g (114{{nbsp}}°C)<ref name=chemister>{{cite web\|url=http://chemister.ru/Database/properties-en.php?dbid=1&id=2993\|title=sodium salicylate\|website=chemister.ru\|access-date=8 April 2018\|archive-date=24 May 2014\|archive-url=https://web.archive.org/web/20140524024107/http://chemister.ru/Database/properties-en.php?dbid=1&id=2993\|url-status=live}}</ref>
	\| Solubility = ~ 660 g/l at 20 °C
			\| SolubleOther = Soluble in ], ], ]<ref name=chemister />
			\| Solubility1 = 26.28{{nbsp}}g/100{{nnbsp}}g (15{{nbsp}}°C)<br> 34.73{{nbsp}}g/100{{nnbsp}}g (67.2{{nbsp}}°C)<ref name=chemister />
			\| Solvent1 = methanol
	}}		}}
	\| ~~Section3~~ = {{Chembox ~~Hazards~~		\|Section6={{Chembox Pharmacology
			\| ATCCode_prefix = N02
⚫	\| MainHazards = Harmful
	\| ~~FlashPt~~ =		\| ATCCode_suffix = BA04
			}}
	\| Autoignition = > 250 °C
			\|Section7={{Chembox Hazards
⚫	\| NFPA-H = 1
			\| GHSPictograms = {{GHS07}}
⚫	\| NFPA-F = 1
			\| GHS_ref = <ref name="sigma">], . Retrieved on 2014-05-26.</ref>
⚫	\| NFPA-R = 0
			\| GHSSignalWord = Warning
⚫	\| NFPA-O =
	\| ~~RPhrases~~ = {{~~R22}}, {{R36/37/38~~}}		\| HPhrases = {{H-phrases\|314\|331\|400}}
			\| PPhrases = {{P-phrases\|210\|261\|273\|280\|305+351+338\|310}}
	\| SPhrases = {{S24/25}}, {{S26}}, {{S36/37/39}}
		⚫	\| MainHazards = Harmful
			\| EyeHazard = Irritant
			\| FlashPt =
			\| AutoignitionPtC = 250
		⚫	\| NFPA-H = 1
		⚫	\| NFPA-F = 1
		⚫	\| NFPA-R = 0
		⚫	\| NFPA-S =
			\| LD50 = 930 mg/kg (rats, oral)<ref>{{cite web\|url=https://chem.nlm.nih.gov/chemidplus/rn/54-21-7\|title=ChemIDplus - 54-21-7 - ABBQHOQBGMUPJH-UHFFFAOYSA-M - Sodium salicylate - Similar structures search, synonyms, formulas, resource links, and other chemical information.\|first=Michael\|last=Chambers\|website=chem.sis.nlm.nih.gov\|access-date=8 April 2018\|archive-date=9 April 2018\|archive-url=https://web.archive.org/web/20180409171616/https://chem.nlm.nih.gov/chemidplus/rn/54-21-7\|url-status=live}}</ref>
	}}		}}
	}}		}}

	'''Sodium salicylate''' is a ] salt of ]. It can be prepared from ] and ] under higher temperature and pressure. Historically, it has been synthesized ~~from~~ ] (~~found in~~ ] ~~plants or the bark of ] tree~~) ~~by reacting it~~ with an excess of ] ~~and heating it under reflux~~.<ref>Lehman, J.W., Operational Organich Chemistry, 4th ed., New Jersey, Prentice Hall, 2009</ref>		'''Sodium salicylate''' is a ] salt of ]. It can be prepared from ] and ] under higher temperature and pressure. Historically, it has been synthesized by refluxing ] (] oil) with an excess of ].<ref>Lehman, J.W., Operational Organich Chemistry, 4th ed., New Jersey, Prentice Hall, 2009</ref>

	==Properties==		==Properties==
			{{Expand section\|date=July 2024}}
	Sodium salicylate is of the ] family and thiscompound is known to trigger ] in children and adults, usually following a viral infection such as influenza or chicken pox. Productscontaining such salicylates should not be given to children under the age of 19.{{Citation needed\|date=February 2011}}
			Sodium salicylate is of the ] family. It is a shiny white powder with an aromatic taste.<ref>{{Cite web \|title=Sodium salicylate {{!}} 54-21-7 \|url=https://m.chemicalbook.com/ChemicalProductProperty_EN_CB1255762.htm \|access-date=2024-09-02 \|website=ChemicalBook \|language=en \|archive-date=2024-09-02 \|archive-url=https://web.archive.org/web/20240902235509/https://m.chemicalbook.com/ChemicalProductProperty_EN_CB1255762.htm \|url-status=live }}</ref>

	==Uses==		==Uses==
	It is used in medicine as an ] and ]. Sodium salicylate also acts as ] (NSAID), and induces ] in cancer cells <ref>{{cite journal \| title = Sodium Salicylate Activates Caspases and Induces Apoptosis of Myeloid Leukemia Cell Lines \| journal = Blood \| date = 1999-04-01 \| first = Lidija \| last = Klampfer \| ~~coauthors~~ = Jörg Cammenga, Hans-Georg Wisniewski, Stephen D. Nimer \| volume = 93 \| issue = 7 \| pages = 2386–94\| id = ~~\| url = http:~~/~~/bloodjournal~~.~~hematologylibrary~~.~~org/cgi/content/full/93/~~7/2386 ~~\| accessdate = 2011-02-21~~ \| pmid=10090950}}</ref><ref>{{cite journal \| title = Elevated NF-κB responses and FLIP levels in leukemic but not normal lymphocytes: reduction by salicylate allows TNF-induced apoptosis \| journal = Proceedings of the National Academy of Sciences of the USA \| date = 2007-07-31 \| first = Colin \| last = Rae \| ~~coauthors~~ = Susana Langa, Steven J. Tucker, David J. MacEwan \| volume = 104 \| issue = 31 \| pages = 12790–5~~\| id = \| url = http://www.pnas.org/content/104/31/12790 \| accessdate = 2011-02-21~~ \| pmid=17646662 \| pmc = 1937545 \| doi=10.1073/pnas.0701437104}}</ref><ref>{{cite journal \| title = Aspirin activates the NF-κB signalling pathway and induces apoptosis in intestinal neoplasia in two in vivo models of human colorectal cancer \| journal = Carcinogenesis \| date = 2007~~-05~~ \| first = Lesley A. \| last = Stark ~~\| coauthors = et al~~ \| volume = 28 \| issue = 5 \| pages = 968–76\| id = \| ~~url~~ = ~~http:/~~/carcin~~.oxfordjournals.org~~/~~content/28/5/968~~ \| ~~accessdate~~ = ~~2011~~-~~02-21~~ ~~\| pmid~~=~~17132819~~ \| ~~doi=10.1093/carcin/bgl220~~}}</ref> and also ].<ref>{{cite journal \| title = Inhibition of Tumor Necrosis Factor-induced p42/p44 Mitogen-Activated Protein Kinase Activation by Sodium Salicylate \| journal = The Journal of Biological Chemistry \| date = 1996-04-05 \| first = Paul \| last = Schwenger \| ~~coauthors~~ = Edward Y. Skolnik, Jan Vilcek \| volume = 271 \| issue = 14 \| pages = 8089–94~~\| id = \| url = http://www.jbc.org/content/271/14/8089 \| accessdate = 2011-02-21~~ \| pmid=8626494 \| doi=10.1074/jbc.271.14.8089}}</ref> It is also a potential replacement for aspirin for people sensitive to it.		It is used in medicine as an ] and ].<ref>{{Cite web \|title=Sodium salicylate {{!}} 54-21-7 \|url=https://m.chemicalbook.com/ChemicalProductProperty_EN_CB1255762.htm \|access-date=2024-09-02 \|website=ChemicalBook \|language=en \|archive-date=2024-09-02 \|archive-url=https://web.archive.org/web/20240902235509/https://m.chemicalbook.com/ChemicalProductProperty_EN_CB1255762.htm \|url-status=live }}</ref> Sodium salicylate also acts as ] (NSAID), and induces ] in cancer cells <ref>{{cite journal \| title = Sodium Salicylate Activates Caspases and Induces Apoptosis of Myeloid Leukemia Cell Lines \| journal = Blood \| date = 1999-04-01 \| first = Lidija \| last = Klampfer \|author2=Jörg Cammenga \|author3=Hans-Georg Wisniewski \|author4=Stephen D. Nimer \| volume = 93 \| issue = 7 \| pages = 2386–94\| doi = 10.1182/blood.V93.7.2386 \| pmid=10090950}}</ref><ref>{{cite journal \| title = Elevated NF-κB responses and FLIP levels in leukemic but not normal lymphocytes: reduction by salicylate allows TNF-induced apoptosis \| journal = Proceedings of the National Academy of Sciences of the USA \| date = 2007-07-31 \| first = Colin \| last = Rae \|author2=Susana Langa \|author3=Steven J. Tucker \|author4=David J. MacEwan \| volume = 104 \| issue = 31 \| pages = 12790–5\| pmid=17646662 \| pmc = 1937545 \| doi=10.1073/pnas.0701437104\| bibcode = 2007PNAS..10412790R \| doi-access = free }}</ref><ref>{{cite journal \| title = Aspirin activates the NF-κB signalling pathway and induces apoptosis in intestinal neoplasia in two in vivo models of human colorectal cancer \| journal = Carcinogenesis \| date = May 2007 \| first = Lesley A. \| last = Stark \| volume = 28 \| issue = 5 \| pages = 968–76\| pmid=17132819 \| doi=10.1093/carcin/bgl220\|display-authors=etal\| doi-access = free }}</ref> and also ].<ref>{{cite journal \| title = Inhibition of Tumor Necrosis Factor-induced p42/p44 Mitogen-Activated Protein Kinase Activation by Sodium Salicylate \| journal = The Journal of Biological Chemistry \| date = 1996-04-05 \| first = Paul \| last = Schwenger \|author2=Edward Y. Skolnik \|author3=Jan Vilcek \| volume = 271 \| issue = 14 \| pages = 8089–94\| pmid=8626494 \| doi=10.1074/jbc.271.14.8089\| doi-access = free }}</ref> It is also a potential replacement for ] for people sensitive to it. It may also be used as a phosphor for the detection of ] radiation and ].<ref>{{cite web\|last=Samson\|first=James\|title=Vacuum Ultraviolet Spectroscopy\|url=http://www.mcphersoninc.com/detectors/Sodium%20Salicylate.pdf\|publisher=Pied Publications\|access-date=July 26, 2012\|url-status=dead\|archive-url=https://web.archive.org/web/20061016104429/http://www.mcphersoninc.com/detectors/Sodium%20Salicylate.pdf\|archive-date=October 16, 2006}}</ref>

	==References==		==References==
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	== External links ==		== External links ==
			{{Commons category}}
	*		*
	*		*
			*
	*		* {{Webarchive\|url=https://web.archive.org/web/20060523222443/http://physchem.ox.ac.uk/MSDS/SO/sodium_salicylate.html \|date=2006-05-23 }}
	*		*

	{{Anti-inflammatory and antirheumatic products}}		{{Anti-inflammatory and antirheumatic products}}
	{{NSAIDs}}
	{{Analgesics}}		{{Analgesics}}
	{{Sodium compounds}}		{{Sodium compounds}}
	{{Salicylates}}		{{Salicylates}}
			{{Prostanoidergics}}

	{{DEFAULTSORT:Sodium Salicylate}}		{{DEFAULTSORT:Sodium Salicylate}}
	]		]
	]		]
			]

	]
	]
	]
	]
	]
	]
	]
	]
	]
	]

Latest revision as of 05:42, 23 November 2024

Sodium salicylate
Names

Preferred IUPAC name Sodium 2-hydroxybenzoate
Other names Salsonin, Monosodium salicylate, Sodium o-hydroxybenzoate, Salicylic acid sodium salt, Monosodium 2-hydroxybenzoate, Diuratin
Identifiers
CAS Number	54-21-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL447868
ChemSpider	5689
DrugBank	DB01398
ECHA InfoCard	100.000.181
EC Number	200-198-0
KEGG	D00566
PubChem CID	16760658
RTECS number	VO5075000
UNII	WIQ1H85SYP
CompTox Dashboard (EPA)	DTXSID5021708
InChI InChI=1S/C7H6O3.Na/c8-6-4-2-1-3-5(6)7(9)10;/h1-4,8H,(H,9,10);/q;+1/p-1Key: ABBQHOQBGMUPJH-UHFFFAOYSA-M InChI=1/C7H6O3.Na/c8-6-4-2-1- 3-5(6)7(9)10;/h1-4,8H,(H,9,10); /q;+1/p-1/fC7H5O3.Na/q-1;m InChI=1/C7H6O3.Na/c8-6-4-2-1-3-5(6)7(9)10;/h1-4,8H,(H,9,10);/q;+1/p-1Key: ABBQHOQBGMUPJH-REWHXWOFAO
SMILES .O=C()c1ccccc1O
Properties
Chemical formula	C₇H₅NaO₃
Molar mass	160.104 g/mol
Appearance	White crystals
Melting point	200 °C (392 °F; 473 K)
Solubility in water	25.08 g/100 g (-1.5 °C) 107.9 g/100 g (15 °C) 124.6 g/100 g (25 °C) 141.8 g/100 g (78.5 °C) 179 g/100 g (114 °C)
Solubility	Soluble in glycerol, 1,4-Dioxane, alcohol
Solubility in methanol	26.28 g/100 g (15 °C) 34.73 g/100 g (67.2 °C)
Pharmacology
ATC code	N02BA04 (WHO)
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful
Eye hazards	Irritant
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H314, H331, H400
Precautionary statements	P210, P261, P273, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	1 1 0
Autoignition temperature	250 °C (482 °F; 523 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	930 mg/kg (rats, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Sodium salicylate is a sodium salt of salicylic acid. It can be prepared from sodium phenolate and carbon dioxide under higher temperature and pressure. Historically, it has been synthesized by refluxing methyl salicylate (wintergreen oil) with an excess of sodium hydroxide.

Properties

This section needs expansion. You can help by adding to it. (July 2024)

Sodium salicylate is of the salicylate family. It is a shiny white powder with an aromatic taste.

Uses

It is used in medicine as an analgesic and antipyretic. Sodium salicylate also acts as non-steroidal anti-inflammatory drug (NSAID), and induces apoptosis in cancer cells and also necrosis. It is also a potential replacement for aspirin for people sensitive to it. It may also be used as a phosphor for the detection of vacuum ultraviolet radiation and beta radiation.

References

^ "sodium salicylate". chemister.ru. Archived from the original on 24 May 2014. Retrieved 8 April 2018.
Chambers, Michael. "ChemIDplus - 54-21-7 - ABBQHOQBGMUPJH-UHFFFAOYSA-M - Sodium salicylate [USP:JAN] - Similar structures search, synonyms, formulas, resource links, and other chemical information". chem.sis.nlm.nih.gov. Archived from the original on 9 April 2018. Retrieved 8 April 2018.
Sigma-Aldrich Co., Sodium salicylate. Retrieved on 2014-05-26.
Lehman, J.W., Operational Organich Chemistry, 4th ed., New Jersey, Prentice Hall, 2009
"Sodium salicylate | 54-21-7". ChemicalBook. Archived from the original on 2024-09-02. Retrieved 2024-09-02.
"Sodium salicylate | 54-21-7". ChemicalBook. Archived from the original on 2024-09-02. Retrieved 2024-09-02.
Klampfer, Lidija; Jörg Cammenga; Hans-Georg Wisniewski; Stephen D. Nimer (1999-04-01). "Sodium Salicylate Activates Caspases and Induces Apoptosis of Myeloid Leukemia Cell Lines". Blood. 93 (7): 2386–94. doi:10.1182/blood.V93.7.2386. PMID 10090950.
Rae, Colin; Susana Langa; Steven J. Tucker; David J. MacEwan (2007-07-31). "Elevated NF-κB responses and FLIP levels in leukemic but not normal lymphocytes: reduction by salicylate allows TNF-induced apoptosis". Proceedings of the National Academy of Sciences of the USA. 104 (31): 12790–5. Bibcode:2007PNAS..10412790R. doi:10.1073/pnas.0701437104. PMC 1937545. PMID 17646662.
Stark, Lesley A.; et al. (May 2007). "Aspirin activates the NF-κB signalling pathway and induces apoptosis in intestinal neoplasia in two in vivo models of human colorectal cancer". Carcinogenesis. 28 (5): 968–76. doi:10.1093/carcin/bgl220. PMID 17132819.
Schwenger, Paul; Edward Y. Skolnik; Jan Vilcek (1996-04-05). "Inhibition of Tumor Necrosis Factor-induced p42/p44 Mitogen-Activated Protein Kinase Activation by Sodium Salicylate". The Journal of Biological Chemistry. 271 (14): 8089–94. doi:10.1074/jbc.271.14.8089. PMID 8626494.
Samson, James. "Vacuum Ultraviolet Spectroscopy" (PDF). Pied Publications. Archived from the original (PDF) on October 16, 2006. Retrieved July 26, 2012.

External links

v t e Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A, also N02BA)
pyrazolones / pyrazolidines	Aminophenazone Ampyrone Azapropazone Clofezone Difenamizole Famprofazone Feprazone Kebuzone Metamizole Mofebutazone Morazone Nifenazone Oxyphenbutazone Phenazone Phenylbutazone Propyphenazone Sulfinpyrazone Suxibuzone
salicylates	Aspirin (acetylsalicylic acid) Aloxiprin Benorylate Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Methyl salicylate Salsalate Salicin Salicylamide Salicylic acid (salicylate) Sodium salicylate
acetic acid derivatives and related substances	Aceclofenac Acemetacin Alclofenac Amfenac Bendazac Bromfenac Bufexamac Bumadizone Diclofenac Difenpiramide Etodolac Felbinac Fenclozic acid Fentiazac Indometacin Indometacin farnesil Isoxepac Ketorolac Lonazolac Mofezolac Oxametacin Prodolic acid Proglumetacin Sulindac Tiopinac Tolmetin Zomepirac
oxicams	Ampiroxicam Droxicam Isoxicam Lornoxicam Meloxicam Piroxicam Pivoxicam Tenoxicam
propionic acid derivatives (profens)	Alminoprofen Benoxaprofen Carprofen Dexibuprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Oxaprozin Pelubiprofen Piketoprofen Pirprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid Vedaprofen Zaltoprofen COX-inhibiting nitric oxide donator: Naproxcinod
n-arylanthranilic acids (fenamates)	Azapropazone Clonixin Etofenamate Floctafenine Flufenamic acid Flunixin Flutiazin Glafenine Meclofenamic acid Mefenamic acid Morniflumate Niflumic acid Tolfenamic acid
COX-2 inhibitors (coxibs)	Apricoxib Celecoxib (+tramadol) Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Robenacoxib Rofecoxib Valdecoxib
other	Aminopropionitrile Benzydamine Chondroitin sulfate Diacerein Fluproquazone Glucosamine Glycosaminoglycan Hyperforin Nabumetone Nimesulide Oxaceprol Proquazone Superoxide dismutase / orgotein Tenidap
NSAID combinations	Ibuprofen/famotidine Ibuprofen/hydrocodone Ibuprofen/oxycodone Ibuprofen/paracetamol Meloxicam/bupivacaine Naproxen/diphenhydramine Naproxen/esomeprazole
Key: underline indicates initially developed first-in-class compound of specific group; WHO-Essential Medicines; withdrawn drugs; veterinary use.
category commons portal

Analgesics (N02A, N02B)

Opioids

Opiates/opium	Codeine +aspirin +paracetamol Morphine (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Diamorphine (heroin) Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol, +ibuprofen, +aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tilidine Tramadol (+celecoxib, +paracetamol) Viminol

Paracetamol-type

NSAIDs

Propionates	Benoxaprofen Fenoprofen Flurbiprofen Ibuprofen (Dexibuprofen) (+paracetamol) Ketoprofen (Dexketoprofen) Loxoprofen Naproxen Oxaprozin Suprofen Tiaprofenic acid Zaltoprofen
Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib Parecoxib Rofecoxib Valdecoxib
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid) (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Cannabinoids

Ion channel
modulators

Calcium blockers

Sodium blockers

Carbamazepine
Lacosamide
Local anesthetics (e.g., cocaine, lidocaine)
Mexiletine
Nefopam
Tricyclic antidepressants (e.g., amitriptyline)

Na_v1.7/1.8-selective: DSP-2230
Funapide
PF-05089771

Potassium openers

Flupirtine

Myorelaxants

Others

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

Sodium compounds

Inorganic

Halides	NaF NaHF₂ NaCl NaBr NaI NaAt
Chalcogenides	NaO₃ NaO₂ Na₂O Na₂O₂ NaOH NaOD Na₂S NaSH Na₂Se NaSeH Na₂Te NaHTe Na₂Po
Pnictogenides	Na₃N NaN₃ NaNH₂ Na₃P Na₃As
Oxyhalides	NaClO NaClO₂ NaClO₃ NaClO₄ NaBrO NaBrO₂ NaBrO₃ NaBrO₄ NaIO NaIO₃ NaIO₄
Oxychalcogenides	Na₂SO₃ Na₂SO₄ NaHSO₃ NaHSO₄ Na₂S₂O₃ Na₂S₂O₄ Na₂S₂O₅ Na₂S₂O₆ Na₂S₂O₇ Na₂S₂O₈ Na₂SeO₃ Na₂SeO₄ NaHSeO₃ Na₂TeO₃
Oxypnictogenides	NaNO₂ NaNO₃ Na₂N₂O₂ NaH₂PO₄ NaPO₂H₂ Na₂HPO₃ Na₂PO₃F Na₃PS₂O₂ Na₃PO₄ Na₅P₃O₁₀ Na₄P₂O₇ Na₂H₂P₂O₇ Na₃AsO₃ Na₃AsO₄ Na₂HAsO₄ NaH₂AsO₄ NaSbO₃
Others	NaAlH₄ NaAlO₂ Na₃AlF₆ NaAl(SO₄)₂ NaAuCl₄ NaSbF₆ NaAsF₆ Na₂TiF₆ NaBH₄ NaBH₃(CN) NaBO₂ Na₂B₄O₇ Na₂B₂O₉ Na₂B₈O₁₃ NaBiO₃ NaCN NaCNO NaCoO₂ NaH NaHCO₃ Na₄XeO₆ NaHXeO₄ NaMnO₄ NaOCN NaReO₄ NaSCN NaTcO₃ NaTcO₄ NaVO₃ Na₂CO₃ Na₂C₂O₄ Na₂C₃S₅ Na₂CrO₄ Na₂Cr₂O₇ Na₂Cr₃O₁₀ Na₂GeO₃ Na₂He Na₂ Na₂MnO₄ Na₂MoO₄ Na₃IrCl₆ Na₂PtCl₆ Na₂O(UO₃)₂ Na₂S₄O₆ Na₂SiO₃ Na₂TiO₃ Na₂U₂O₇ Na₂WO₄ Na₂Zn(OH)₄ Na₃VO₄ Na₆V₁₀O₂₈ Na₄Fe(CN)₆ Na₃Fe(CN)₆ Na₃Fe(C₂O₄)₃ Na₄SiO₄ Na₂SiF₆ Na₃[Co(NO₂)₆] NaNSi₂(CH₃)₆ Na₂PdCl₄

Organic

v t e Salicylates
Salicylic acid Aspirin Aloxiprin Methyl salicylate Magnesium salicylate Ethyl salicylate Isopropyl salicylate Bismuth subsalicylate Sodium salicylate Salicylamide Salicin Benorilate Salsalate Ethenzamide Diflunisal Trolamine salicylate Homosalate Salicylmethylecgonine 2-Ethylhexyl salicylate Aluminon Benzyl salicylate Copper aspirinate Potassium salicylate

Prostanoid signaling modulators

Receptor
(ligands)

DP (D₂)Tooltip Prostaglandin D2 receptor

DP₁Tooltip Prostaglandin D2 receptor 1

Agonists: Prostaglandin D₂
Treprostinil

DP₂Tooltip Prostaglandin D2 receptor 2

Agonists: Indometacin
Prostaglandin D₂

EP (E₂)Tooltip Prostaglandin E2 receptor

EP₁Tooltip Prostaglandin EP1 receptor	Agonists: Beraprost Enprostil Iloprost (ciloprost) Latanoprost Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Sulprostone Antagonists: AH-6809 ONO-8130 SC-19220 SC-51089 SC-51322
EP₂Tooltip Prostaglandin EP2 receptor	Agonists: Butaprost Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Treprostinil Antagonists: AH-6809 PF-04418948 TG 4-155
EP₃Tooltip Prostaglandin EP3 receptor	Agonists: Beraprost Carbacyclin Cicaprost Enprostil Iloprost (ciloprost) Isocarbacyclin Latanoprost Misoprostol Prostaglandin D₂ Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) Remiprostol Ricinoleic acid Sulprostone Antagonists: L-798106
EP₄Tooltip Prostaglandin EP4 receptor	Agonists: Lubiprostone Misoprostol Prostaglandin E₁ (alprostadil) Prostaglandin E₂ (dinoprostone) TCS-2510 Antagonists: Grapiprant GW-627368 L-161982 ONO-AE3-208
Unsorted	Agonists: 16,16-Dimethyl Prostaglandin E₂ Aganepag Carboprost Evatanepag Gemeprost Nocloprost Omidenepag Prostaglandin F_2α (dinoprost) Simenepag Taprenepag

FP (F_2α)Tooltip Prostaglandin F receptor

IP (I₂)Tooltip Prostacyclin receptor

Agonists: ACT-333679
AFP-07
Beraprost
BMY-45778
Carbacyclin
Cicaprost
Iloprost (ciloprost)
Isocarbacyclin
MRE-269
NS-304
Prostacyclin (prostaglandin I₂, epoprostenol)
Prostaglandin E₁ (alprostadil)
Ralinepag
Selexipag
Taprostene
TRA-418
Treprostinil

Antagonists: RO1138452

TP (TX_A2)Tooltip Thromboxane receptor

Agonists: Carbocyclic thromboxane A₂
I-BOP
Thromboxane A₂
U-46619
Vapiprost

Unsorted

Enzyme
(inhibitors)

COX (PTGS)	Salicylic acids: Aloxiprin Aspirin (acetylsalicylic acid) Benorilate (benorylate) Carbasalate calcium Diflunisal Dipyrocetyl Ethenzamide Guacetisal Magnesium salicylate Mesalazine (5-aminosalicylic acid) Methyl salicylate Salacetamide Salicin Salicylamide Salicylate (salicylic acid) Salsalate Sodium salicylate Triflusal; Acetic acids: Aceclofenac Acemetacin Aclofenac Amfenac Alclofenac Bendazac Bromfenac Bufexamac Bumadizone Cinmetacin Clometacin Diclofenac Difenpiramide Etodolac Felbinac Fenclofenac Fentiazac Glucametacin Indometacin (indomethacin) Indometacin farnesil Ketorolac Lonazolac Mofezolac Nabumetone Oxametacin Oxindanac Proglumetacin Sulindac Sulindac sulfide Tolmetin Zidometacin Zomepirac; Propionic acids: Alminoprofen Benoxaprofen Bucloxic acid (blucloxate) Butibufen Carprofen Dexibuprofen Dexindoprofen Dexketoprofen Fenbufen Fenoprofen Flunoxaprofen Flurbiprofen Ibuprofen Ibuproxam Indoprofen Ketoprofen Loxoprofen Miroprofen Naproxen Naproxcinod Oxaprozin Pirprofen Pranoprofen Suprofen Tarenflurbil Tepoxalin Tiaprofenic acid (tiaprofenate) Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate) Floctafenic acid (floctafenate) Flufenamic acid (flufenamate) Meclofenamic acid (meclofenamate) Mefenamic acid (mefenamate) Morniflumic acid (morniflumate) Niflumic acid (niflumate) Talinflumic acid (talinflumate) Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone Dipyrone Isopyrin Oxyphenbutazone Phenylbutazone; Enolic acids (oxicams): Ampiroxicam Droxicam Enolicam Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam; 4-Aminoquinolines: Antrafenine Floctafenine Glafenine; Quinazolines: Fluproquazone Proquazone; Aminonicotinic acids: Clonixeril Clonixin Flunixin; Sulfonanilides: Flosulide Nimesulide; Aminophenols (anilines): Acetanilide AM-404 (N-arachidonoylaminophenol) Bucetin Paracetamol (acetaminophen) Parapropamol Phenacetin Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib Celecoxib Cimicoxib Deracoxib Etoricoxib Firocoxib Lumiracoxib Mavacoxib Parecoxib Polmacoxib Robenacoxib Rofecoxib Tilmacoxib Valdecoxib; Others/unsorted: Anitrazafen Clobuzarit Curcumin DuP-697 FK-3311 Flumizole FR-122047 Glimepiride Hyperforin Itazigrel L-655240 L-670596 Licofelone Menatetrenone (vitamin K₂) NCX-466 NCX-4040 NS-398 Pamicogrel Resveratrol Romazarit Rosmarinic acid Rutecarpine Satigrel SC-236 SC-560 SC-58125 Tenidap Tiflamizole Timegadine Trifenagrel Tropesin
PGD₂STooltip Prostaglandin D synthase	Retinoids Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
PGESTooltip Prostaglandin E synthase	HQL-79
PGFSTooltip Prostaglandin F synthase	Bimatoprost
PGI₂STooltip Prostacyclin synthase	Tranylcypromine
TXASTooltip Thromboxane A synthase	Camonagrel Dazmegrel Dazoxiben Furegrelate Isbogrel Midazogrel Nafagrel Nicogrelate Ozagrel Picotamide Pirmagrel Ridogrel Rolafagrel Samixogrel Terbogrel U63557A

Others

See also: Receptor/signaling modulators; Leukotriene signaling modulators

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