Salicylic acid

Chemical compound used in medicines and industry

Salicylic acid  | Skeletal formula of salicylic acid | Ball-and-stick model of salicylic acid

|

Salicylic acid
Names
Preferred IUPAC name

2-Hydroxybenzoic acid[1]

Identifiers

CAS Number

* 69-72-7 Y

3D model (JSmol)

* Interactive image

ChEBI |

* CHEBI:16914 Y

ChEMBL |

* ChEMBL424 Y

ChemSpider |

* 331 Y

DrugBank |

* DB00936

ECHA InfoCard | 100.000.648
EC Number |

* 200-712-3

IUPHAR/BPS

* 4306

KEGG |

* D00097 Y

PubChem CID

* 338

RTECS number |

* VO0525000

UNII |

* O414PZ4LPZ Y

CompTox Dashboard (EPA)

* DTXSID7026368

InChI

* InChI=1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10) Y

Key: YGSDEFSMJLZEOE-UHFFFAOYSA-N Y

* InChI=1/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)

Key: YGSDEFSMJLZEOE-UHFFFAOYAQ

SMILES

* O=C(O)c1ccccc1O

Properties

Chemical formula

| C7H6O3
Molar mass | 138.122 g/mol
Appearance  | Colorless to white crystalline powder
Odor | Odorless
Density | 1.443 g/cm3 (20 °C)[2]
Melting point | 158.6 °C (317.5 °F; 431.8 K)
Boiling point | 211 °C (412 °F; 484 K)
at 20 mmHg[2][3]

Sublimation
conditions

| Sublimes at 76 °C[3]

Solubility in water

* 1.24 g/L (0 °C)
* 2.48 g/L (25 °C)
* 4.14 g/L (40 °C)
* 17.41 g/L (75 °C)[3]
* 77.79 g/L (100 °C)[4]

Solubility | Soluble in ether, CCl4, benzene, propanol, acetone, ethanol, oil of turpentine, toluene
Solubility in benzene |

* 0.46 g/100 g (11.7 °C)
* 0.775 g/100 g (25 °C)
* 0.991 g/100 g (30.5 °C)
* 2.38 g/100 g (49.4 °C)
* 4.4 g/100 g (64.2 °C)[3][4]

Solubility in chloroform |

* 2.22 g/100 mL (25 °C)[4]
* 2.31 g/100 mL (30.5 °C)[3]

Solubility in methanol |

* 40.67 g/100 g (−3 °C)
* 62.48 g/100 g (21 °C)[3]

Solubility in olive oil | 2.43 g/100 g (23 °C)[3]
Solubility in acetone | 39.6 g/100 g (23 °C)[3]
log P | 2.26
Vapor pressure | 10.93 mPa[3]
Acidity (pKa)  |

1. 2.97 (25 °C)[5]
2. 13.82 (20 °C)[3]

UV-vis (λmax)  | 210 nm, 234 nm, 303 nm (4 mg/dL in ethanol)[3]

Magnetic susceptibility (χ)

| −72.23·10−6 cm3/mol

Refractive index (nD)

| 1.565 (20 °C)[2]

Dipole moment

| 2.65 D
Thermochemistry

Std enthalpy of
formation (ΔfH⦵298)

| −589.9 kJ/mol

Std enthalpy of
combustion (ΔcH⦵298)

| −3.025 MJ/mol[6]
Pharmacology

ATC code

| A01AD05 (WHO) B01AC06 (WHO) D01AE12 (WHO) N02BA01 (WHO) S01BC08 (WHO)
Hazards
Occupational safety and health (OHS/OSH):

Eye hazards

| Severe irritation

Skin hazards

| Mild irritation
GHS labelling:[7]

Pictograms

Signal word

| Danger

Hazard statements

| H302, H318

Precautionary statements

| P280, P305+P351+P338
NFPA 704 (fire diamond)  |

Flash point | 157 °C (315 °F; 430 K)
closed cup[3]

Autoignition
temperature

| 540 °C (1,004 °F; 813 K)[3]
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 480 mg/kg (mice, oral)
Safety data sheet (SDS)  | MSDS
Related compounds

Related compounds

| Methyl salicylate,
Benzoic acid,
Phenol, Aspirin,
4-Hydroxybenzoic acid,
Magnesium salicylate,
Choline salicylate,
Bismuth subsalicylate,
Sulfosalicylic acid

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)

Infobox references

Chemical compound

Salicylic acid is an organic compound with the formula HOC6H4COOH.[3] A colorless (or white), bitter-tasting solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin).[3] It is a plant hormone,[8] and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen.[9] The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.[3]

## Uses

[edit]

### Medicine

[edit]

Main article: Medical uses of salicylic acid

Cotton pads soaked in salicylic acid can be used to chemically exfoliate skin.

Salicylic acid as a medication is commonly used to remove the outermost layer of the skin. As such, it is used to treat warts, psoriasis, acne vulgaris, ringworm, dandruff, and ichthyosis.[3][10][11]

Similar to other hydroxy acids, salicylic acid is an ingredient in many skincare products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis, and warts.[12]

### Uses in manufacturing

[edit]

Salicylic acid is used as a food preservative, a bactericide, and an antiseptic.[13][14]

Salicylic acid is used in the production of other pharmaceuticals, including 4-aminosalicylic acid, sandulpiride, and landetimide (via salethamide).[15] It is also used in picric acid production.[16]

Salicylic acid has long been a key starting material for making acetylsalicylic acid (ASA or aspirin).[8] ASA is prepared by the acetylation of salicylic acid with the acetyl group from acetic anhydride or acetyl chloride.[17] ASA is the standard to which all the other non-steroidal anti-inflammatory drugs (NSAIDs) are compared. In veterinary medicine, this group of drugs is mainly used for treatment of inflammatory musculoskeletal disorders.[18]

Bismuth subsalicylate, a salt of bismuth and salicylic acid, "displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic".[3] It is an active ingredient in stomach-relief aids such as Pepto-Bismol and some formulations of Kaopectate.

Other derivatives include methyl salicylate, used as a liniment to soothe joint and muscle pain, and choline salicylate, which is used topically to relieve the pain of mouth ulcers.[3][19][20] Aminosalicylic acid is used to induce remission in ulcerative colitis, and has been used as an antitubercular agent often administered in association with isoniazid.[21]

Sodium salicylate is a useful phosphor in the vacuum ultraviolet spectral range, with nearly flat quantum efficiency for wavelengths between 10 and 100 nm.[22] It fluoresces in the blue at 420 nm. It is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.[citation needed]

## Mechanism of action

[edit]

Salicylic acid modulates COX-1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins. Salicylate may competitively inhibit prostaglandin formation.

Salicylic acid, when applied to the skin surface, works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with NADH and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid to the phenolic acceptor.[23]

The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis.[5]

## Safety

[edit]

Main article: Salicylate poisoning

If high concentrations of salicylic ointment are used topically, high levels of salicylic acid can enter the blood. In such cases , hemodialysis would be required to avoid further complications.[24]

Cosmetic applications of the drug pose no significant risk.[25] Even in a worst-case use scenario in which one was using multiple salicylic acid-containing topical products, the aggregate plasma concentration of salicylic acid was well below what was permissible for acetylsalicylic acid (aspirin).[25] Since oral aspirin (which produces much higher salicylic acid plasma concentrations than dermal salicylic acid applications) poses no significant adverse pregnancy outcomes in terms of frequency of stillbirth, birth defects or developmental delay, use of salicylic acid containing cosmetics is safe for pregnant women.[25] Salicylic acid is present in most fruits and vegetables as for example in greatest quantities in berries and in beverages like tea.

## Production and chemical reactions

[edit]

### Biosynthesis

[edit]

Salicylic acid is biosynthesized from the amino acid phenylalanine. In Arabidopsis thaliana, it can be synthesized via a phenylalanine-independent pathway.

### Chemical synthesis

[edit]

Commercial vendors prepare sodium salicylate by treating sodium phenolate (the sodium salt of phenol) with carbon dioxide at high pressure (100 atm) and high temperature (115 °C) – a method known as the Kolbe-Schmitt reaction. Acidifying the product with sulfuric acid gives salicylic acid:

At the laboratory scale, it can also be prepared by the hydrolysis of aspirin (acetylsalicylic acid)[26] or methyl salicylate (oil of wintergreen) with a strong acid or base; these reactions reverse those chemicals' commercial syntheses.

### Reactions

[edit]

Upon heating, salicylic acid converts to phenyl salicylate:[27][8]

2 HOC6H4CO2H → C6H5O2C6H4OH + CO2 \+ H2O

Further heating gives xanthone.[8]

Salicylic acid as its conjugate base is a chelating agent, with an affinity for iron(III).[28]

Salicylic acid slowly degrades to phenol and carbon dioxide at 200–230 °C:[29]

C6H4OH(CO2H) → C6H5OH + CO2

All isomers of chlorosalicylic acid and of dichlorosalicylic acid are known. 5-Chlorosalicylic acid is produced by direct chlorination of salicylic acid.[8]

## History

[edit]

Main article: History of aspirin

White willow (Salix alba) is a natural source of salicylic acid.

Willow has long been used for medicinal purposes. Dioscorides, whose writings were highly influential for more than 1,500 years,[30] used "Itea" (which was possibly a species of willow) as a treatment for "painful intestinal obstructions", birth control, for "those who spit blood", to remove calluses and corns and, externally, as a "warm pack for gout". William Turner, in 1597, repeated this, saying that willow bark, "being burnt to ashes, and steeped in vinegar, takes away corns and other like risings in the feet and toes".[31] Some of these cures may describe the action of salicylic acid, which can be derived from the salicin present in willow. It is, however, a modern myth that Hippocrates used willow as a painkiller.[32]

Hippocrates, Galen, Pliny the Elder, and others knew that decoctions containing salicylate could ease pain and reduce fevers.[33][34]

It was used in Europe and China to treat these conditions.[35] This remedy is mentioned in texts from Ancient Egypt, Sumer, and Assyria.[36]

The Cherokee and other Native Americans use an infusion of the bark for fever and other medicinal purposes.[37] In 2014, archaeologists identified traces of salicylic acid on seventh-century pottery fragments found in east-central Colorado.[38]

Edward Stone, a vicar from Chipping Norton, Oxfordshire, England, reported in 1763 that the bark of the willow was effective in reducing a fever.[39]

Letter from Florence Nightingale on "salicylic silk" as a dressing for cancer patients[40]

An extract of willow bark, called salicin, after the Latin name for the white willow (Salix alba), was isolated and named by German chemist Johann Andreas Buchner in 1828.[41] A larger amount of the substance was isolated in 1829 by Henri Leroux, a French pharmacist.[42] Raffaele Piria, an Italian chemist, was able to convert the substance into a sugar and a second component, which on oxidation becomes salicylic acid.[43][44] Salicylic acid was also isolated from the herb meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839.[45] Their extract caused digestive problems such as gastric irritation, bleeding, diarrhea, and even death when consumed in high doses.

In 1874 the Scottish physician Thomas MacLagan experimented with salicin as a treatment for acute rheumatism, with considerable success, as he reported in The Lancet in 1876.[46] Meanwhile, German scientists tried sodium salicylate with less success and more severe side effects.[47][48]

In 1979, salicylates were found to be involved in induced defenses of tobacco against tobacco mosaic virus.[49] In 1987, salicylic acid was identified as the long-sought signal that causes thermogenic plants, such as the voodoo lily, Sauromatum guttatum, to produce heat.[50]

## Dietary sources

[edit]

Salicylic acid occurs in plants as free salicylic acid and its carboxylated esters and phenolic glycosides. Several studies suggest that humans metabolize salicylic acid in measurable quantities from these plants.[51] High-salicylate beverages and foods include beer, coffee, tea, numerous fruits and vegetables, sweet potato, nuts, and olive oil.[19] Meat, poultry, fish, eggs, dairy products, sugar, breads and cereals have low salicylate content.[19][52]

Some people with sensitivity to dietary salicylates may have symptoms of allergic reaction, such as bronchial asthma, rhinitis, gastrointestinal disorders, or diarrhea, so may need to adopt a low-salicylate diet.[19]

## Plant hormone

[edit]

Salicylic acid is a phenolic phytohormone, and is found in plants with roles in plant growth and development, photosynthesis, transpiration, and ion uptake and transport.[53] Salicylic acid is involved in endogenous signaling, mediating plant defense against pathogens.[54] It plays a role in the resistance to pathogens (i.e. systemic acquired resistance) by inducing the production of pathogenesis-related proteins and other defensive metabolites.[55] SA's defense signaling role is most clearly demonstrated by experiments which do away with it: Delaney et al. 1994, Gaffney et al. 1993, Lawton et al. 1995, and Vernooij et al. 1994 each use Nicotiana tabacum or Arabidopsis expressing nahG, for salicylate hydroxylase. Pathogen inoculation did not produce the customarily high SA levels, SAR was not produced, and no pathogenesis-related (PR) genes were expressed in systemic leaves. Indeed, the subjects were more susceptible to virulent – and even normally avirulent – pathogens.[53]

Exogenously, salicylic acid can aid plant development via enhanced seed germination, bud flowering, and fruit ripening, though too high of a concentration of salicylic acid can negatively regulate these developmental processes.[56]

The volatile methyl ester of salicylic acid, methyl salicylate, can also diffuse through the air, facilitating plant-plant communication.[57] Methyl salicylate is taken up by the stomata of the nearby plant, where it can induce an immune response after being converted back to salicylic acid.[58]

### Signal transduction

[edit]

A number of proteins have been identified that interact with SA in plants, especially salicylic acid binding proteins (SABPs) and the NPR genes (nonexpressor of pathogenesis-related genes), which are putative receptors.[59]

## References

[edit]

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* Leroux H (1830). "Mémoire relatif à l'analyse de l'écorce de saule et à la découverte d'un principe immédiat propre à remplacer le sulfate de quinine" [Memoir concerning the analysis of willow bark and the discovery of a substance immediately likely to replace quinine sulfate]. Journal de Chimie Médicale, de Pharmacie et de Toxicologie. 6: 340–342.
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56. ^ Koo YM, Heo AY, Choi HW (February 2020). "Salicylic Acid as a Safe Plant Protector and Growth Regulator". The Plant Pathology Journal. 36 (1): 1–10\. doi:10.5423/PPJ.RW.12.2019.0295. PMC 7012573. PMID 32089657.
57. ^ Taiz L, Zeiger E (2002). Plant physiology. Sunderland, Mass: Sinauer Associates. p. 306\. ISBN 0-87893-823-0. OCLC 50002466. Archived from the original on 5 March 2014.
58. ^ Chamovitz D (2012). What A Plant Knows - A Field Guide to the Senses of your Garden - and Beyond. Oxford, England: Oneworld. ISBN 978-1-85168-910-1. OCLC 775030365.
59. ^ Kumar, D. 2014. Salicylic acid signaling in disease resistance. Plant Science 228:127–134.

## Further reading

[edit]

* Schrör K (2016). Acetylsalicylic Acid (2 ed.). John Wiley & Sons. pp. 9–10\. ISBN 978-3-527-68502-8.

## External links

[edit]

Wikimedia Commons has media related to Salicylic acid.

* "On the syntheses of salicylic acid" Archived 2020-08-06 at the Wayback Machine: English Translation of Hermann Kolbe's seminal 1860 German article "Ueber Synthese der Salicylsäure" in Annalen der Chemie und Pharmacie at MJLPHD Archived 2020-10-18 at the Wayback Machine

* v
* t
* e

Acne-treating agents (D10)

Antibacterial|

* Azelaic acid
* Benzoyl peroxide#
* 8-Hydroxyquinoline
* Blue light therapy
* Tea tree oil

Keratolytic|

* Glycolic acid
* Salicylic acid#
* Sulfur
* Benzoyl peroxide#

Anti-inflammatory|

* Niacinamide
* Ibuprofen#
* Aspirin#
* Red light therapy

Antibiotics|

* Clindamycin
* Dapsone
* Erythromycin
* Sulfacetamide
* Tetracyclines (Lymecycline
* Minocycline
* Doxycycline)

Hormonal|

* Antiandrogens
* Bicalutamide
* Cyproterone acetate
* Drospirenone
* Flutamide
* Spironolactone)
* Estrogens
* Estradiol
* Ethinylestradiol

Retinoids|

* Adapalene
* Isotretinoin
* Motretinide
* Tazarotene
* Tretinoin
* Trifarotene

Other|

* Epristeride
* Mesulfen
* Pelretin
* Stridex
* Tioxolone

Combinations|

* Adapalene/benzoyl peroxide
* Clindamycin/adapalene/benzoyl peroxide
* Clindamycin/benzoyl peroxide
* Clindamycin/tretinoin
* Erythromycin/benzoyl peroxide
* Erythromycin/isotretinoin
* Sulfacetamide/sulfur
* Tretinoin/benzoyl peroxide

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* v
* t
* e

Ancient anaesthesia

Plants / animals|

* Aconitum (aconite)
* Atropa belladonna (belladonna)
* Cannabis
* medical use
* Castoreum
* Coca
* Conium (hemlock)
* Datura innoxia (thorn-apple)
* Datura metel (devil's trumpet)
* Hyoscyamus niger (henbane)
* Lactucarium
* Mandragora officinarum (mandrake)
* Opium
* Saussurea (saw-wort)
* Willow

Preparations|

* Beer
* Wine

Compounds|

* Ethanol (medical use)
* Aconitine
* Atropine
* Cocaine
* Coniine
* Hyoscine
* Δ9-THC
* Hyoscyamine
* Morphine
* Salicylate

People|

* Abulcasis
* Avenzoar
* Avicenna
* Celsus
* Dioscorides
* Galen
* Hippocrates
* Rhazes
* Sabuncuoğlu
* Sushrutha
* Theophrastus
* Zhang

* v
* t
* e

Antifungals (D01 and J02)

Wall/
membrane|

| Ergosterol
inhibitors|

| Azoles (lanosterol 14α-
demethylase inhibitors)|

| Imidazoles|

* Topical: bifonazole‡
* butoconazole
* chlormidazole‡
* climbazole
* clotrimazole#
* croconazole‡
* eberconazole
* econazole
* fenticonazole‡
* flutrimazole
* isoconazole
* ketoconazole
* luliconazole
* miconazole#
* neticonazole‡
* omoconazole‡
* oxiconazole
* sertaconazole
* sulconazole
* tioconazole

* Systemic: ketoconazole

|

Triazoles|

* Topical: efinaconazole
* fluconazole#
* terconazole

* Systemic: fluconazole#
* fosfluconazole
* fosravuconazole
* hexaconazole‡
* isavuconazole
* itraconazole#
* oteseconazole
* posaconazole
* voriconazole#

* Unknown: albaconazole‡
* ravuconazole†

Thiazoles|

* Topical: abafungin‡

Polyene antimycotics
(ergosterol binding)|

* Topical: hamycin‡
* natamycin
* nystatin#
Systemic: amphotericin B#, hamycin‡

Squalene monooxygenase
inhibitors|

| Allylamines|

* Topical: naftifine
* terbinafine
Systemic: terbinafine

|

Benzylamines|

* Topical: butenafine

Others|

* Topical: amorolfine

β-glucan synthase
inhibitors|

* Systemic: echinocandins (anidulafungin
* caspofungin
* cilofungin
* micafungin
* rezafungin)
* ibrexafungerp

Intracellular|

| Pyrimidine analogues/
thymidylate synthase inhibitors|

* Systemic: flucytosine#

|

Mitotic inhibitors|

* Systemic: griseofulvin#

Aminoacyl tRNA synthetase inhibitors|

* Topical: tavaborole

Others|

* bromochlorosalicylanilide
* chlorophetanol
* chlorphenesin
* ciclopirox
* crystal violet
* dimazole
* ethylparaben
* haloprogin‡
* polynoxylin
* potassium iodide#
* salicylic acid
* selenium disulfide#
* sodium thiosulfate#
* sulbentine
* taurolidine
* ticlatone
* tolciclate
* tolnaftate
* tribromometacresol
* undecylenic acid
* Whitfield's ointment#

* citronella oil
* lemon grass
* lemon myrtle
* orange oil
* patchouli
* tea tree oil
* PCP: atovaquone
* dapsone
* pentamidine

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* 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
* Meloxicam/rizatriptan
* 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

* v
* t
* e

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|

* Acetanilide‡
* Bucetin‡
* Butacetin‡
* Paracetamol (acetaminophen)#
* +aspirin/caffeine
* +codeine
* +hydrocodone
* +ibuprofen
* +metoclopramide
* +oxycodone
* +propyphenazone/caffeine
* +tramadol
* Parapropamol‡
* Phenacetin‡
* Propacetamol‡

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|

* Cannabidiol
* Cannabis
* Nabilone
* Nabiximols
* Tetrahydrocannabinol (dronabinol)

Ion channel
modulators|

| Calcium blockers|

* Alcohol (ethanol)
* Gabapentin
* Gabapentin enacarbil
* Leconotide
* Mirogabalin
* Pregabalin
* Ziconotide

|

Sodium blockers|

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

* Nav1.7/1.8-selective: DSP-2230§
* Funapide§
* PF-05089771§
* Suzetrigine

Potassium openers|

* Flupirtine‡

Myorelaxants|

* Carisoprodol
* Chlorzoxazone
* Cyclobenzaprine
* Mephenoxalone
* Methocarbamol
* Orphenadrine

Others|

* Analgecine
* Analgesic adjuvant
* Bedinvetmab
* Camphor
* Capsaicin
* Clonidine
* Frunevetmab
* Ketamine
* Menthol
* Methoxyflurane
* Phenazopyridine
* Proglumide
* Rimazolium
* Tanezumab

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* v
* t
* e

Plant hormones

* Abscisic acid
* Auxins
* Brassinosteroids
* Cytokinins
* Ethylene
* Gibberellins

* 24-Epibrassinolide
* Florigen
* Jasmonates
* Karrikins
* Plant peptide hormones
* Polyamine
* Salicylic acid
* Strigolactones

* 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

* v
* t
* e

Phenolic acids (C6-C1) and their glycosides

Monohydroxybenzoic acids|

* 3-Hydroxybenzoic acid
* 4-Hydroxybenzoic acid
* Salicylic acid (2-Hydroxybenzoic acid)

| Glycosides|

* p-Hydroxybenzoic acid glucoside

|

Alkylated|

* Methylparaben (Methyl-p-hydroxybenzoic acid)

Dihydroxybenzoic acids|

* 2,3-Dihydroxybenzoic acid (Hypogallic acid)
* 2,4-Dihydroxybenzoic acid
* 2,5-Dihydroxybenzoic acid (Gentisic acid)
* 2,6-Dihydroxybenzoic acid
* 3,4-Dihydroxybenzoic acid (Protocatechuic acid)
* 3,5-Dihydroxybenzoic acid

| Alkylated|

* Ethyl protocatechuate
* Orsellinic acid

|

Trihydroxybenzoic acids|

* Gallic acid
* Phloroglucinol carboxylic acid

| Glycosides|

* Bergenin
* Norbergenin
* Theogallin
* Chebulic acid

|

Alkylated|

* Ethyl gallate
* Eudesmic acid
* Methyl gallate
* Syringic acid

* v
* t
* e

Prostanoid signaling modulators

Receptor
(ligands)|

| DP (D2)Tooltip Prostaglandin D2 receptor|

| DP1Tooltip Prostaglandin D2 receptor 1|

* Agonists: Prostaglandin D2
* Treprostinil

* Antagonists: Asapiprant
* Laropiprant
* Vidupiprant

|

DP2Tooltip Prostaglandin D2 receptor 2|

* Agonists: Indometacin
* Prostaglandin D2

* Antagonists: ADC-3680
* AZD-1981
* Bay U3405
* Fevipiprant
* MK-1029
* MK-7246
* QAV-680
* Ramatroban
* Setipiprant
* Timapiprant
* TM30089
* Vidupiprant

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 F2α (dinoprost)
* Simenepag
* Taprenepag

FP (F2α)Tooltip Prostaglandin F receptor|

* Agonists: Alfaprostol
* Bimatoprost
* Carboprost
* Cloprostenol
* Enprostil
* Fluprostenol
* Latanoprost
* Prostaglandin D2
* Prostaglandin F2α (dinoprost)
* Sulotroban
* Tafluprost
* Travoprost
* Unoprostone

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 (TXA2)Tooltip Thromboxane receptor|

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

* Antagonists: 12-HETE
* 13-APA
* AA-2414
* Argatroban
* Bay U3405
* BMS-180,291
* Daltroban
* Domitroban
* EP-045
* GR-32191
* ICI-185282
* ICI-192605
* Ifetroban
* Imitrodast
* L-655240
* L-670596
* Linotroban
* Mipitroban
* ONO-3708
* ONO-11120
* Picotamide
* Pinane thromboxane A2
* Ramatroban
* Ridogrel
* S-145
* Samixogrel
* Seratrodast
* SQ-28,668
* SQ-29,548
* Sulotroban
* Terbogrel
* Terutroban
* TRA-418

Unsorted|

* Arbaprostil
* Ataprost
* Ciprostene
* Clinprost
* Cobiprostone
* Delprostenate
* Deprostil
* Dimoxaprost
* Doxaprost
* Ecraprost
* Eganoprost
* Enisoprost
* Eptaloprost
* Esuberaprost
* Etiproston
* Fenprostalene
* Flunoprost
* Froxiprost
* Lanproston
* Limaprost
* Luprostiol
* Meteneprost
* Mexiprostil
* Naxaprostene
* Nileprost
* Nocloprost
* Ornoprostil
* Oxoprostol
* Penprostene
* Pimilprost
* Piriprost
* Posaraprost
* Prostalene
* Rioprostil
* Rivenprost
* Rosaprostol
* Spiriprostil
* Tiaprost
* Tilsuprost
* Tiprostanide
* Trimoprostil
* Viprostol

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|

* Precursors: Linoleic acid
* γ-Linolenic acid (gamolenic acid)
* Dihomo-γ-linolenic acid
* Diacylglycerol
* Arachidonic acid
* Prostaglandin G2
* Prostaglandin H2

See also
Receptor/signaling modulators
Leukotriene signaling modulators

Portal:

* Medicine

Authority control databases: National |

* Germany
* United States
* France
* BnF data
* Japan
* Israel

|

*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[H302]: H302: Harmful if swallowed
*[H318]: H318: Causes serious eye damage
*[P280]: P280: Wear protective gloves/protective clothing/eye protection/face protection.
*[P305+P351+P338]: P305+P351+P338: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do. Continue rinsing.
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[DP (D2)]: Prostaglandin D2 receptor
*[DP1]: Prostaglandin D2 receptor 1
*[DP2]: Prostaglandin D2 receptor 2
*[EP (E2)]: Prostaglandin E2 receptor
*[EP1]: Prostaglandin EP1 receptor
*[EP2]: Prostaglandin EP2 receptor
*[EP3]: Prostaglandin EP3 receptor
*[EP4]: Prostaglandin EP4 receptor
*[FP (F2α)]: Prostaglandin F receptor
*[IP (I2)]: Prostacyclin receptor
*[TP (TXA2)]: Thromboxane receptor
*[COX]: Cyclooxygenase
*[PTGS]: prostaglandin G/H synthase
*[PGD2S]: Prostaglandin D synthase
*[PGES]: Prostaglandin E synthase
*[PGFS]: Prostaglandin F synthase
*[PGI2S]: Prostacyclin synthase
*[TXAS]: Thromboxane A synthase