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Minoxidil sulfate

Clinical data
Other names	Minoxidil sulphate; Minoxidil sulfate ester; Minoxidil sulphate ester; Minoxidil N-O-sulfate; Minoxidil N-O-sulphate; U-58838
Identifiers
IUPAC name (2,6-diamino-4-piperidin-1-ylpyrimidin-1-ium-1-yl) sulfate
CAS Number	83701-22-8
PubChem CID	4202
ChemSpider	4057
UNII	2H6K6Y231J
ChEBI	CHEBI:143426
ChEMBL	ChEMBL906
ECHA InfoCard	100.163.834
Chemical and physical data
Formula	C9H15N5O4S
Molar mass	289.31 g·mol
3D model (JSmol)	Interactive image
SMILES C1CCN(CC1)C2=NC(=(C(=C2)N)OS(=O)(=O))N
InChI 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. Minoxidil acts as a prodrug of minoxidil sulfate. Minoxidil sulfate is formed from minoxidil via sulfotransferase enzymes, with the predominant enzyme responsible, at least in hair follicles, being SULT1A1. Minoxidil sulfate acts as a potassium channel opener, among other actions, and has vasodilating, hypotensive, and trichogenic or hypertrichotic (hair growth-promoting) effects. Its mechanism of action in terms of hair growth is still unknown, although multiple potential mechanisms have been implicated.

Minoxidil sulfate is a sulfate ester of minoxidil, not a sulfate salt of the compound. However, minoxidil sulfate forms an inner salt, which makes it more hydrophobic than minoxidil. This is in contrast to most sulfate esters, which are usually more hydrophilic than their non-ester forms. 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. Normally, sulfation tends to inactivate drugs by reducing their biological activity and increasing their excretion.

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. This has served as a limiting factor in its potential pharmaceutical use and therapeutic effectiveness. Moreover, minoxidil sulfate has a 40% higher molecular weight than minoxidil, and this may reduce its absorption into the scalp. In any case, a minoxidil sulfate-based topical formulation has been investigated for the treatment of scalp hair loss. Additionally, minoxidil-sulfate-based topical formulations appear to be available for medical use in some parts of the world, for instance in Brazil.

References

1. ^ Gupta AK, Talukder M, Venkataraman M, Bamimore MA (June 2022). "Minoxidil: a comprehensive review". The Journal of Dermatological Treatment. 33 (4): 1896–1906. doi:10.1080/09546634.2021.1945527. PMID 34159872. S2CID 235609487.
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". Journal of the European Academy of Dermatology and Venereology. 35 (7): 1485–1492. doi:10.1111/jdv.17216. PMID 33660357. S2CID 232115094.
3. ^ Meisheri KD, Johnson GA, Puddington L (January 1993). "Enzymatic and non-enzymatic sulfation mechanisms in the biological actions of minoxidil". Biochemical Pharmacology. 45 (2): 271–279. doi:10.1016/0006-2952(93)90061-z. PMID 8435087.
4. ^ 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. ^ 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 Disorders. 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 Design, Development and Therapy. 13: 2777–2786. doi:10.2147/DDDT.S214907. PMC 6691938. PMID 31496654.
7. Kelly Y, Tosti A (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. ISBN 978-3-030-21554-5. S2CID 203340151.

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