Minoxidil sulfate

Last updated
Minoxidil sulfate
Minoxidil sulfate.svg
Clinical data
Other namesMinoxidil sulphate; Minoxidil sulfate ester; Minoxidil sulphate ester; Minoxidil N-O-sulfate; Minoxidil N-O-sulphate; U-58838
Identifiers
  • (2,6-diamino-4-piperidin-1-ylpyrimidin-1-ium-1-yl) sulfate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
ECHA InfoCard 100.163.834 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C9H15N5O4S
Molar mass 289.31 g·mol−1
3D model (JSmol)
  • C1CCN(CC1)C2=NC(=[N+](C(=C2)N)OS(=O)(=O)[O-])N
  • InChI=1S/C9H15N5O4S/c10-7-6-8(13-4-2-1-3-5-13)12-9(11)14(7)18-19(15,16)17/h6H,1-5H2,(H4,10,11,12,15,16,17)
  • Key:OEOLOEUAGSPDLT-UHFFFAOYSA-N

Minoxidil sulfate, also known as minoxidil sulfate ester or minoxidil N-O-sulfate, is an active metabolite of minoxidil (Rogaine, Loniten, others) and is the active form of this agent. [1] [2] Minoxidil acts as a prodrug of minoxidil sulfate. [1] Minoxidil sulfate is formed from minoxidil via sulfotransferase enzymes, with the predominant enzyme responsible, at least in hair follicles, being SULT1A1. [1] [2] Minoxidil sulfate acts as a potassium channel opener, among other actions, and has vasodilating, hypotensive, and trichogenic or hypertrichotic (hair growth-promoting) effects. [1] [3] Its mechanism of action in terms of hair growth is still unknown, although multiple potential mechanisms have been implicated. [1]

Minoxidil sulfate is a sulfate ester of minoxidil, not a sulfate salt of the compound. [3] However, minoxidil sulfate forms an inner salt, which makes it more hydrophobic than minoxidil. [3] This is in contrast to most sulfate esters, which are usually more hydrophilic than their non-ester forms. [3] The bioactivation of minoxidil into minoxidil sulfate is very unusual and is among the only known instances of sulfation producing a more active drug form. [3] [4] Normally, sulfation tends to inactivate drugs by reducing their biological activity and increasing their excretion. [3] [4]

Minoxidil sulfate is highly unstable in aqueous solutions and alcohol-containing solvents, with a half-life of 6 hours in aqueous solutions and a further much lower half-life in alcohol-containing solvents. [3] This has served as a limiting factor in its potential pharmaceutical use and therapeutic effectiveness. [5] Moreover, minoxidil sulfate has a 40% higher molecular weight than minoxidil, and this may reduce its absorption into the scalp. [5] In any case, a minoxidil sulfate-based topical formulation has been investigated for the treatment of scalp hair loss. [6] [5] Additionally, minoxidil-sulfate-based topical formulations appear to be available for medical use in some parts of the world, for instance in Brazil. [5] [7]

Related Research Articles

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Alopecia areata, also known as spot baldness, is a condition in which hair is lost from some or all areas of the body. Often, it results in a few bald spots on the scalp, each about the size of a coin. Psychological stress and illness are possible factors in bringing on alopecia areata in individuals at risk, but in most cases there is no obvious trigger. People are generally otherwise healthy. In a few cases, all the hair on the scalp is lost, or all body hair is lost. Hair loss can be permanent, or temporary. It is distinct from pattern hair loss, which is common among males.

<span class="mw-page-title-main">Hair loss</span> Loss of hair from the head or body

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Telogen effluvium is a scalp disorder characterized by the thinning or shedding of hair resulting from the early entry of hair in the telogen phase. It is in this phase that telogen hairs begin to shed at an increased rate, where normally the approximate rate of hair loss is 125 hairs per day.

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<span class="mw-page-title-main">Azelaic acid</span> Chemical compound

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<span class="mw-page-title-main">Topilutamide</span> Chemical compound

Topilutamide, known more commonly as fluridil and sold under the brand name Eucapil, is an antiandrogen medication which is used in the treatment of pattern hair loss in men and women. It is used as a topical medication and is applied to the scalp. Topilutamide belongs to a class of molecules known as perfluoroacylamido-arylpropanamides.

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References

  1. 1 2 3 4 5 Gupta AK, Talukder M, Venkataraman M, Bamimore MA (June 2022). "Minoxidil: a comprehensive review". J Dermatolog Treat. 33 (4): 1896–1906. doi:10.1080/09546634.2021.1945527. PMID   34159872. S2CID   235609487.
  2. 1 2 Villani A, Fabbrocini G, Ocampo-Candiani J, Ruggiero A, Ocampo-Garza SS (July 2021). "Review of oral minoxidil as treatment of hair disorders: in search of the perfect dose". J Eur Acad Dermatol Venereol. 35 (7): 1485–1492. doi:10.1111/jdv.17216. PMID   33660357. S2CID   232115094.
  3. 1 2 3 4 5 6 7 Meisheri KD, Johnson GA, Puddington L (January 1993). "Enzymatic and non-enzymatic sulfation mechanisms in the biological actions of minoxidil". Biochem Pharmacol. 45 (2): 271–9. doi:10.1016/0006-2952(93)90061-z. PMID   8435087.
  4. 1 2 Richard B. Silverman (2 December 2012). The Organic Chemistry of Drug Design and Drug Action (2 ed.). Elsevier. pp. 543–. ISBN   978-0-08-051337-9. OCLC   1019583017.
  5. 1 2 3 4 Dias PC, Miot HA, Trüeb RM, Ramos PM (October 2018). "Use of Minoxidil Sulfate versus Minoxidil Base in Androgenetic Alopecia Treatment: Friend or Foe?". Skin Appendage Disord. 4 (4): 349–350. doi:10.1159/000488011. PMC   6219241 . PMID   30410915.
  6. ↑ Suchonwanit P, Thammarucha S, Leerunyakul K (2019). "Minoxidil and its use in hair disorders: a review". Drug Des Devel Ther. 13: 2777–2786. doi:10.2147/DDDT.S214907. PMC   6691938 . PMID   31496654.
  7. ↑ Kelly, Yanna; Tosti, Antonella (13 September 2019). "Androgenetic Alopecia: Clinical Treatment". Hair and Scalp Treatments. Springer International Publishing. pp. 91–108. doi:10.1007/978-3-030-21555-2_8.



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