Selenium disulfide

Mixture of selenium sulfides

Pharmaceutical compound

Selenium disulfideClinical data

Trade names| Selseb, Selsun Blue, others
Other names| Selenium sulfide
AHFS/Drugs.com| Monograph
MedlinePlus| a682258
Routes of
administration| Topical
ATC code|

* D01AE13 (WHO)

Legal status
Legal status|

* AU: S5 (Caution)
* UK: P (Pharmacy medicines)
* US: OTC / Rx-only

Identifiers
CAS Number|

* 7488-56-4  Y

PubChem CID|

* 24087

DrugBank|

* DB00971

ChemSpider|

* 22519

UNII|

* Z69D9E381Q

KEGG|

* D05815

ChEBI|

* CHEBI:135934

ChEMBL|

* ChEMBL1200680

ECHA InfoCard| 100.028.458
Chemical and physical data
Formula| S2Se
Molar mass| 143.09 g·mol−1
3D model (JSmol)|

* Interactive image

Density| 3 g/cm3
Melting point| 111 °C (232 °F)
Boiling point| 118 to 119 °C (244 to 246 °F) (decomposes)
Solubility in water| negligible mg/mL (20 °C)

SMILES

* S=[Se]=S

InChI

* InChI=1S/S2Se/c1-3-2

* Key:JNMWHTHYDQTDQZ-UHFFFAOYSA-N

Selenium disulfide, also known as selenium sulfide, is a chemical compound and medication used to treat seborrheic dermatitis, dandruff, and pityriasis versicolor.[1][2] It is applied to the affected area as a lotion or shampoo.[3] Symptoms frequently return if treatment is stopped.[4]

Side effects may include hair discoloration, skin irritation, and risk of systemic absorption and toxicity, among others.[1] Use is not recommended in children less than 2–5 years old.[1][4] Use in pregnancy or breastfeeding has not been studied.[5] It consists of a mixture of inorganic covalent compounds having an approximate empirical formulas of SeS2.[6] Selenium disulfide acts as a keratolytic and antifungal agent.[7][8][9]

Selenium disulfide was approved for medical use in the United States at least as early as 1951.[4] It is on the World Health Organization's List of Essential Medicines.[10] Selenium disulfide is available as a generic medication and over the counter.[3]

## Medical uses

[edit]

Selenium disulfide is sold as an antifungal agent in shampoos (such as Selsun Blue) for the treatment of dandruff and seborrheic dermatitis associated in the scalp with fungi of genus Malassezia.[11][12][13] It is also used on the body to treat tinea versicolor (pityriasis versicolor), a type of fungal skin infection caused by a different species of Malassezia.[2][14]

A 2015 systematic review of topical treatments for seborrheic dermatitis of the scalp identified only a single randomized controlled trial evaluating selenium disulfide for the condition.[15] It was a three-arm trial of 246 people with moderate to severe dandruff and compared treatment with 2% ketoconazole shampoo (n=97), 2.5% selenium disulfide shampoo (n=100), and placebo (shampoo base with no antiseborrheic agent) (n=49) for 29 days.[15][16] The study found a 73% reduction in dandruff score with ketoconazole, a 67% reduction with selenium disulfide, and a 45% reduction with placebo.[15][16] Based on the study, the systematic review concluded that selenium disulfide may be effective in the treatment of dandruff but that the available evidence is limited and overall evidence quality is low.[15] It also found that while selenium disulfide has infrequent side effects, it seems to have more side effects than ketoconazole shampoo.[15] Consequently, the review concluded that selenium disulfide should not be considered as a first-line therapy but instead should be used as an alternative treatment after other therapies like ketoconazole shampoo have proven not effective.[15]

A 2015 review recommended topical antifungal agents, topical corticosteroids, and topical calcineurin inhibitors like tacrolimus as the main treatments for seborrheic dermatitis based on good-quality evidence, rather than selenium disulfide for which evidence is much more limited.[17] However, the review did suggest use of over-the-counter selenium disulfide shampoos as an inexpensive option for managing mild symptoms of seborrheic dermatitis.[17]

### Available forms

[edit]

Selenium disulfide is available in the form of a prescription drug as a 2.25% medical shampoo.[18][19] In the United States, a 1% strength is available over-the-counter, and a 2.5% strength is also available with a prescription.[19] In Canada, the 2.5% strength is available over-the-counter.[19] Selsun Blue is an over-the-counter shampoo for dandruff with 1% selenium disulfide as its active ingredient.[20][19]

## Side effects

[edit]

Side effects of selenium disulfide shampoo for dandruff appear to be infrequent.[15][16] A randomized controlled trial of 100 people who received selenium disulfide reported side effects of itching or burning sensation of the scalp (3 people), eruption near the hairline (1 person), psoriasis (1 person), lightening or bleaching of hair color (2 people), orange staining of the scalp (1 person), and a chemical taste while shampooing (1 person).[15][16]

Selenium disulfide can cause discoloration of nails and light hair[7] and can alter the color of hair dyes. Several scattered case reports of orange to red–brown scalp discoloration with selenium sulfide shampoo exist.[7][21] The discoloration resolved shortly following discontinuation of selenium disulfide shampoo and its removal could be facilitated by lightly swabbing with isopropyl alcohol.[21] Selenium disulfide may also discolor metallic jewellery. Case reports of temporary diffuse hair loss with selenium disulfide shampoo exist as well.[22][23] Excessive environmental or occupational exposure to selenium has also been associated with hair loss and other adverse effects.[22] However, hair loss has not been reported with topical selenium disulfide in several large studies.[21]

Selenium disulfide should not be applied to damaged skin as there is a risk of systemic absorption and associated toxicity.[1] Systemic symptoms may include tremors, weakness, lethargy, lower abdominal pain, and occasional vomiting.[1] These symptoms usually resolve within 10 days following exposure.[1]

## Pharmacology

[edit]

### Pharmacodynamics

[edit]

Selenium disulfide acts as an antifungal and keratolytic agent to treat seborrheic dermatitis and dandruff.[7][8][9]

### Pharmacokinetics

[edit]

The systemic absorption and toxicity of orally administered selenium sulfide has been studied in animals.[24][7] Topical use of selenium sulfide in the form of a shampoo or lotion in humans does not appear to normally increase circulating or urinary selenium levels.[25][26][27][28][29] However, application of selenium disulfide to damaged skin can result in systemic absorption and has been associated with cases of toxicity.[1] Selenium disulfide appears to be much less toxic than other selenium salts, which may be attributed to its low aqueous solubility and very poor systemic absorption.[7]

## Chemistry

[edit]

### Composition

[edit]

Structure of 1,2,3-Se3S5, illustrative of selenium sulfide

Selenium disulfide has a composition that approximates to SeS2 and is sometimes called selenium sulfide. However, as used in proprietary formulations, it is not a pure chemical compound but a mixture of eight-membered-ring compounds where the overall Se:S ratio is 1:2. The specific chemicals contain a variable number of S and Se atoms, SenS8−n.[30]

Many selenium sulfides are known, as indicated by 77Se-NMR spectroscopy.[31]

## History

[edit]

Selenium sulfide was introduced for medical use in the United States in 1951.[4][19]

Selenium monosulfide, along with elemental selenium and sulfur, has been used in medicinal preparations in the past,[32] causing confusion and contradiction[33] as to exactly what form selenium is in any given topical preparation.

## Society and culture

[edit]

### Popular culture

[edit]

In the film Evolution selenium was mentioned as an active ingredient of Head & Shoulders. A group of academics, therefore, tried to use this brand of shampoo to stop an alien invasion after discovering that the alien life form was sensitive to selenium.[34]

## Research

[edit]

Selenium disulfide has been suggested to be effective as a treatment for hyperkeratosis based on a small case series of three treated patients.[35] It has also been reported to be effective in the treatment of scalp psoriasis based on clinical observation of over 100 treated patients and two case reports of dramatic response.[36]

Selenium sulfide is under development for the treatment of meibomianitis (meibomian gland dysfunction) and dry eyes in topical and ophthalmic formulations.[37][38][19] As of March 2021, it is in phase 2/3 clinical trials for meibomianitis and phase 2 trials for dry eyes.[37] The developmental code name of selenium sulfide for these uses is AZR-MD-001 and it is being developed by Azura Ophthalmics.[37]

## References

[edit]

1. ^ a b c d e f g World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 297\. hdl:10665/44053. ISBN 9789241547659.
2. ^ a b Faergemann J (2000). "Management of seborrheic dermatitis and pityriasis versicolor". American Journal of Clinical Dermatology. 1 (2): 75–80\. doi:10.2165/00128071-200001020-00001. PMID 11702314. S2CID 43516330.
3. ^ a b Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 194\. ISBN 9781284057560.
4. ^ a b c d "Selenium Sulfide". The American Society of Health-System Pharmacists. Archived from the original on 18 January 2017. Retrieved 8 January 2017.
5. ^ "Selenium sulfide topical Use During Pregnancy". Drugs.com. Archived from the original on 16 January 2017. Retrieved 13 January 2017.
6. ^ Mitchell SC (2003). Biological Interactions Of Sulfur Compounds. CRC Press. p. 174\. ISBN 9780203362525. Archived from the original on 16 January 2017.
7. ^ a b c d e f Mitchell SC, Nickson RM, Waring RH (August 1993). "The Biological Activity of Selenium Sulfide". Sulfur Reports. 13 (2): 279–289\. doi:10.1080/01961779308048957. eISSN 1029-0508. ISSN 0196-1772.
8. ^ a b Borda LJ, Perper M, Keri JE (March 2019). "Treatment of seborrheic dermatitis: a comprehensive review". The Journal of Dermatological Treatment. 30 (2): 158–169\. doi:10.1080/09546634.2018.1473554. PMID 29737895. S2CID 13686180.
9. ^ a b Gupta AK, Madzia SE, Batra R (2004). "Etiology and management of Seborrheic dermatitis". Dermatology. 208 (2): 89–93\. doi:10.1159/000076478. PMID 15056994. S2CID 22432032.
10. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
11. ^ "Selenium(IV) sulfide". Pharmacy Codes. Archived from the original on 1 April 2008.
12. ^ "Chemicals of Selenium". selenium.se. Archived from the original on 3 April 2008.
13. ^ "Selenium sulfide". DermNet NZ. New Zealand Dermatological Society Incorporated. Archived from the original on 26 December 2008. Retrieved 24 December 2007.
14. ^ Savin R (August 1996). "Diagnosis and treatment of tinea versicolor". The Journal of Family Practice. 43 (2): 127–132\. PMID 8708621.
15. ^ a b c d e f g h Naldi L, Diphoorn J (May 2015). "Seborrhoeic dermatitis of the scalp". BMJ Clinical Evidence. 2015. PMC 4445675. PMID 26016669.
16. ^ a b c d Danby FW, Maddin WS, Margesson LJ, Rosenthal D (December 1993). "A randomized, double-blind, placebo-controlled trial of ketoconazole 2% shampoo versus selenium sulfide 2.5% shampoo in the treatment of moderate to severe dandruff". Journal of the American Academy of Dermatology. 29 (6): 1008–1012\. doi:10.1016/0190-9622(93)70282-x. PMID 8245236.
17. ^ a b Clark GW, Pope SM, Jaboori KA (February 2015). "Diagnosis and treatment of seborrheic dermatitis". American Family Physician. 91 (3): 185–190\. PMID 25822272.
18. ^ "Selenium sulfide shampoo". Bi-Coastal Pharma International LLC. January 2022. Archived from the original on 29 May 2023. Retrieved 29 May 2023 – via DailyMed.
19. ^ a b c d e f Gupta PK, Periman LM, Lain E, Donnenfeld E, Hovanesian J, Kim T, et al. (2021). "Meibomian Gland Dysfunction: A Dermatological Perspective on Pathogenesis and Treatment Outlook". Clinical Ophthalmology. 15: 4399–4404\. doi:10.2147/OPTH.S327407. PMC 8590836. PMID 34785886.
20. ^ Rapaport M (1981). "A randomized, controlled clinical trial of four anti-dandruff shampoos". The Journal of International Medical Research. 9 (2): 152–156\. doi:10.1177/030006058100900213. PMID 7014286. S2CID 41649828.
21. ^ a b c Gilbertson K, Jarrett R, Bayliss SJ, Berk DR (2012). "Scalp discoloration from selenium sulfide shampoo: a case series and review of the literature". Pediatric Dermatology. 29 (1): 84–88\. doi:10.1111/j.1525-1470.2011.01410.x. PMID 21453309. S2CID 42996869.
22. ^ a b Vinceti M, Wei ET, Malagoli C, Bergomi M, Vivoli G (2001). "Adverse health effects of selenium in humans". Reviews on Environmental Health. 16 (4): 233–251\. doi:10.1515/reveh.2001.16.4.233. hdl:11380/310575. PMID 12041880. S2CID 6596336.
23. ^ Grover RW (April 1956). "Diffuse hair loss associated with selenium (selsun) sulfide shampoo". Journal of the American Medical Association. 160 (16): 1397–1398\. doi:10.1001/jama.1956.02960510023006. PMID 13306564.
24. ^ Henschler D, Kirschner U (1969). "[On the absorption and toxicity of selenium sulfide]" [On the absorption and toxicity of selenium sulfide]. Archiv für Toxikologie (in German). 24 (4): 341–344\. doi:10.1007/BF00577584. PMID 5795758. S2CID 30908076.
25. ^ Noisel N, Bouchard M, Carrier G (May 2010). "Disposition kinetics of selenium in healthy volunteers following therapeutic shampoo treatment". Environmental Toxicology and Pharmacology. 29 (3): 252–259\. Bibcode:2010EnvTP..29..252N. doi:10.1016/j.etap.2010.02.001. PMID 21787610.
26. ^ Kalivas J (May 1993). "Lack of serum selenium rise after overnight application of selenium sulfide". Archives of Dermatology. 129 (5): 646–648\. doi:10.1001/archderm.1993.01680260118023. PMID 8481030.
27. ^ Sánchez JL, Torres VM (August 1984). "Selenium sulfide in tinea versicolor: blood and urine levels". Journal of the American Academy of Dermatology. 11 (2 Pt 1): 238–241\. doi:10.1016/s0190-9622(84)70156-3. PMID 6480923.
28. ^ Cummins LM, Kimura ET (September 1971). "Safety evaluation of selenium sulfide antidandruff shampoos". Toxicology and Applied Pharmacology. 20 (1): 89–96\. Bibcode:1971ToxAP..20...89C. doi:10.1016/0041-008x(71)90092-5. PMID 5110829.
29. ^ Slinger WN, Hubbard DM (July 1951). "Treatment of seborrheic dermatitis with a shampoo containing selenium disulfide". A.M.A. Archives of Dermatology and Syphilology. 64 (1): 41–48\. doi:10.1001/archderm.1951.01570070044007. PMID 14837491.
30. ^ Cyclic selenium sulfides R. Steudel, R. Laitinen, Topics in Current Chemistry, (1982), 102, 177-197
31. ^ Pekonen P, Hiltunen Y, Laitinen RS, Pakkanen TA (1991). "Chalcogen ring interconversion pathways. 77Se NMR spectroscopic study of the decomposition of 1,2,3,4,5-Se5S2 to 1,2,3,4,5,6-Se6S2 and 1,2,3,4-Se4S2". Inorganic Chemistry. 30 (19): 3679. doi:10.1021/ic00019a022.
32. ^ "Definition: selenium sulfide". Online Medical Dictionary.
33. ^ "Selenium Sulfide". DrugBank. DB00971. Archived from the original on 27 April 2007.
34. ^ "Evolution (2001)". IMDb. Archived from the original on 8 November 2020. Retrieved 19 May 2020.
35. ^ Cohen PR, Anderson CA (December 2018). "Topical Selenium Sulfide for the Treatment of Hyperkeratosis". Dermatology and Therapy. 8 (4): 639–646\. doi:10.1007/s13555-018-0259-9. PMC 6261123. PMID 30203232.
36. ^ Borglund E, Enhamre A (November 1987). "Treatment of psoriasis with topical selenium sulphide". The British Journal of Dermatology. 117 (5): 665–666\. doi:10.1111/j.1365-2133.1987.tb07503.x. PMID 3689688. S2CID 36783670.
37. ^ a b c "AZR MD 001". AdisInsight. Springer Nature Switzerland AG.
38. ^ "ARVO 2021: Investigational Agent Containing Selenium Sulfide Shows Promise for Meibomian Gland Dysfunction". PracticeUpdate. Archived from the original on 11 February 2022. Retrieved 11 February 2022.

## Further reading

[edit]

* Danby FW, Maddin WS, Margesson LJ, Rosenthal D (December 1993). "A randomized, double-blind, placebo-controlled trial of ketoconazole 2% shampoo versus selenium sulfide 2.5% shampoo in the treatment of moderate to severe dandruff". Journal of the American Academy of Dermatology. 29 (6): 1008–1012\. doi:10.1016/0190-9622(93)70282-x. PMID 8245236. Archived from the original on 14 April 2013.
* Grover RW (April 1956). "Diffuse hair loss associated with selenium (selsun) sulfide shampoo". Journal of the American Medical Association. 160 (16): 1397–1398\. doi:10.1001/jama.1956.02960510023006. PMID 13306564.
* Givens TG, Murray MM, Baker RC (July 1995). "Comparison of 1% and 2.5% selenium sulfide in the treatment of tinea capitis". Archives of Pediatrics & Adolescent Medicine. 149 (7): 808–811\. doi:10.1001/archpedi.1995.02170200098016. PMID 7795774.
* Ransone JW, Scott NM, Knoblock EC (February 1961). "Selenium sulfide intoxication". The New England Journal of Medicine. 264 (8): 384–385\. doi:10.1056/NEJM196102232640806. PMID 13739506.
* Laitinen RS, Pakkanen TA (1987). "77Se NMR spectroscopic characterization of selenium sulfide ring molecules SenS8−n". Inorganic Chemistry. 26 (16): 2598. doi:10.1021/ic00263a010.

* v
* t
* e

Selenium compounds

Se(−II)|

* Se2−
* H2Se
* Al2Se3
* Sb2Se3
* As2Se3
* Bi2Se3
* CdSe
* CaSe
* CSe2
* OCSe
* CrSe
* CoSe
* CuSe
* (CH3)2Se
* GaSe
* Ga2Se3
* GeSe
* In2Se3
* FeSe
* PbSe
* MgSe
* MnSe
* MnSe2
* HgSe
* MoSe2
* NiSe
* NbSe2
* NbSe3
* PxSey
* PuSe
* ReSe2
* Sm2Se3
* Ag2Se
* Na2Se
* SnSe
* TiSe2
* WSe2
* USe2
* ZnSe

Se(0,I)|

* Se3S5

Se(I)|

* Se2S6
* Se2Cl2
* C3H7NO2Se

Se(II)|

* SeBr2
* SeCl2
* SeS2

Se(IV)|

* SeO2−3
* SeBr4
* SeCl4
* SeF4
* SeO2
* SeS2
* SeOF2
* SeOCl2
* SeOBr2
* H2SeO3

Se(VI)|

* SeO2−4
* SeF6
* SeO3
* SeO2F2
* H2SeO4

Se(IV,VI)|

* SeO2−4 \+ SeO2−3

* v
* t
* e

Sulfides (S2−)

| H2S |  |  |  | He

|
|
|
|

Li2S | BeS | B2S3
+BO3 | CS2
COS | (NH4)SH | O  | F  | Ne
Na2S | MgS | Al2S3 | SiS
SiS2
-Si | PxSy
-P | -S2−
2 | Cl  | Ar
K2S | CaS |  | ScS
Sc2S3 | TiS
TiS2
Ti2S3 | VS
VS2
V2S3 | CrS
Cr2S3 | MnS
MnS2 | FeS
Fe3S4 | CoxSy | NixSy | Cu2S
CuS | ZnS | GaS
Ga2S3 | GeS
GeS2
-Ge | As2S3
As2S5
As4S3
-As | SeS2
+Se | Br  | Kr
Rb2S | SrS |  | Y2S3 | ZrS2 | NbS2 | MoS2
MoS3 | TcS2
Tc2S7 | Ru  | Rh2S3 | PdS | Ag2S | CdS | In2S3 | SnS
SnS2
-Sn | Sb2S3
Sb2S5
-Sb | TeS2 | I  | Xe
Cs2S | BaS | *  | LuS
Lu2S3 | HfS2 | TaS2 | WS2
WS3 | ReS2
Re2S7 | OsS
4 | Ir2S3
IrS2 | PtS
PtS2 | Au2S
Au2S3 | HgS | Tl2S | PbS
PbS2 | Bi2S3 | PoS | At  | Rn
Fr  | Ra  | **  | Lr  | Rf  | Db  | Sg  | Bh  | Hs  | Mt  | Ds  | Rg  | Cn  | Nh  | Fl  | Mc  | Lv  | Ts  | Og

*  | LaS
La2S3 | CeS
Ce2S3 | PrS
Pr2S3 | NdS
Nd2S3 | PmS
Pm2S3 | SmS
Sm2S3 | EuS
Eu2S3 | GdS
Gd2S3 | TbS
Tb2S3 | DyS
Dy2S3 | HoS
Ho2S3 | ErS
Er2S3 | TmS
Tm2S3 | YbS
Yb2S3
**  | Ac2S3 | ThS
Th2S3
Th7S12
ThS2 | Pa  | US
U2S3
U3S5
US2 | NpS
Np2S3
Np3S5
NpS2 | PuS
Pu2S3 | AmS
Am2S3 | CmS
Cm2S3 | Bk2S3 | Cf2S3 | Es  | Fm  | Md  | No

* 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

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

*[AU]: Australia
*[UK]: United Kingdom
*[US]: United States
*[CID]: Compound ID
*[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