Minoxidil

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Minoxidil is a medication used for the treatment of high blood pressure and pattern hair loss.<ref name="Loniten SmPC" /><ref name="Regaine for Men SmPC" /><ref name="Regaine for Women SmPC" /> It is an antihypertensive and a vasodilator.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is available as a generic medication by prescription in oral tablet form and over-the-counter as a topical liquid or foam.<ref name="Minoxidil tablet FDA label">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="Minoxidil aerosol FDA label">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Medical uses

Minoxidil, when used for hypertension, is generally reserved for use in severe hypertension patients who do not respond to at least two agents and a diuretic.<ref name="pmid15133413" /> Minoxidil is also generally administered with a loop diuretic to prevent sodium retention and potassium retention.<ref name="pmid15133413" /> It may also cause a reflex tachycardia and thus is prescribed with a beta blocker.<ref name="pmid15133413" />

Hair loss

Minoxidil, when applied topically, is used for the treatment of hair loss.<ref name="Var2014" /> It is effective in helping promote hair growth in people with androgenic alopecia regardless of sex.<ref name="Var2014">Template:Cite journal</ref> Minoxidil must be used indefinitely for continued support of existing hair follicles and the maintenance of any experienced hair regrowth.<ref name="Regaine for Men SmPC" /><ref name="Regaine for Women SmPC" />

Low-dose oral minoxidil (LDOM) is used off-label against hair loss and to promote hair regrowth.<ref name=":0">Template:Cite news</ref> Oral minoxidil is an effective and well-tolerated treatment alternative for patients having difficulty with topical formulations.<ref name=":1">Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>

Side effects

File:Minoxidil and Finasteride side effects.jpg

Top 10 most common side effects.<ref name=pmid27738338>Template:Cite journal</ref>

Topically applied minoxidil is generally well tolerated, but common side effects include itching of the eyes, general itching, irritation at the treated area, and unwanted hair growth elsewhere on the body.<ref name=effects>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Alcohol and propylene glycol present in some topical preparations may dry the scalp, resulting in dandruff and contact dermatitis.<ref>Template:Cite journal</ref>

Side effects of oral minoxidil may include swelling of the face and extremities, rapid heartbeat, or lightheadedness. Cardiac lesions, such as focal necrosis of the papillary muscle and subendocardial areas of the left ventricle, have been observed in laboratory animals treated with minoxidil.<ref name="Minoxidil tablet FDA label" /> Pseudoacromegaly is an extremely rare side effect reported with large doses of oral minoxidil.<ref>Template:Cite journal</ref>

In 2013 or 2014, a seven-year-old girl was admitted to a children's hospital in Toulouse in France after accidentally ingesting a teaspoon of Alopexy (a brand name for minoxidil in France). The child vomited constantly after ingestion and showed hypotension and tachycardia for 40 hours.<ref>Template:Cite journal</ref> The authors of the report on the incident stressed that the product should be kept out of reach of children, and urged manufacturers to consider more secure child-resistant packaging.<ref>Template:Cite news</ref>

Pharmacology

Mechanism of action

The mechanism by which minoxidil promotes hair growth is not fully understood. Minoxidil is an adenosine 5'-triphosphate-sensitive potassium channel opener,<ref>Template:Cite journal</ref> causing hyperpolarization of cell membranes. Theoretically, by widening blood vessels and opening potassium channels, it allows more oxygen, blood, and nutrients to the follicles. Moreover, minoxidil contains a nitric oxide moiety and may act as a nitric oxide agonist. This may cause follicles in the telogen phase to shed, which are then replaced by thicker hairs in a new anagen phase. Minoxidil is a prodrug that is converted by sulfation via the sulfotransferase enzyme SULT1A1 to its active form, minoxidil sulfate. The effect of minoxidil is mediated by adenosine, which triggers intracellular signal transduction via both adenosine A₁ receptors and two sub-types of adenosine A₂ receptors (A_2A and A_2B receptors).<ref name="maru 2001">Template:Cite journal</ref> Minoxidil acts as an activator of the Kir6/SUR2 channel upon selective binding to SUR2.<ref>Template:Cite journal</ref> The expression of SUR2B in dermal papilla cells might play a role in the production of adenosine.<ref name="maru 2001"/> Minoxidil induces cell growth factors such as VEGF, HGF, IGF-1 and potentiates HGF and IGF-1 actions by the activation of uncoupled sulfonylurea receptor on the plasma membrane of dermal papilla cells.<ref>Template:Cite journal</ref>

A number of in vitro effects of minoxidil have been described in monocultures of various skin and hair follicle cell types including stimulation of cell proliferation, inhibition of collagen synthesis, and stimulation of vascular endothelial growth factor, prostaglandin synthesis and leukotriene B4 expression.<ref>Template:Cite journal</ref>

Minoxidil causes a redistribution of cellular iron through its apparent capacity to bind this metal ion. By binding iron in a Fenton-reactive form, intracellular hydroxyl radical production would ensue, but hydroxyl would be immediately trapped and scavenged by the minoxidil to generate a nitroxyl radical. It is presumed that this nitroxyl radical will be capable of reduction by glutathione to reform minoxidil. Such a process would cycle until the minoxidil is otherwise metabolized and would result in rapid glutathione depletion with glutathione disulphide formation and therefore with concomitant consumption of NADPH/NADH and other reducing equivalents.<ref>Template:Cite book</ref> Minoxidil inhibited PHD by interfering with the normal function of ascorbate, a cofactor of the enzyme, leading to a stabilization of HIF-1α protein and a subsequent activation of HIF-1. In an in vivo angiogenesis assay, millimolar minoxidil increased blood vessel formation in a VEGF-dependent manner. Minoxidil inhibition of PHD occurs via interrupting ascorbate binding to iron.<ref>Template:Cite journal</ref> The structural feature of positioning amines adjacent to nitric oxide may confer the ability of millimolar minoxidil to chelate iron, thereby inhibiting PHD. Minoxidil is capable of tetrahydrobiopterin inhibition as a cofactor for nitric oxide synthase.<ref>Template:Cite patent</ref>

Minoxidil stimulates prostaglandin E₂ production by activating COX-1<ref>Template:Cite journal</ref> and prostaglandin endoperoxide synthase-1 but inhibits prostacyclin production. Additionally, expression of the prostaglandin E₂ receptor, the most upregulated target gene in the β-catenin pathway of DP cells, was enhanced by minoxidil, which may enable hair follicles to grow continuously and maintain the anagen phase.<ref name="pmid31496654">Template:Cite journal</ref>

Due to the anti-fibrotic activity of minoxidil inhibition of enzyme lysyl hydroxylase present in fibroblast may result in the synthesis of a hydroxylysine-deficient collagen. Minoxidil can also potentially stimulate elastogenesis in aortic smooth muscle cells, and in skin fibroblasts in a dose-dependent manner. In hypertensive rats, minoxidil increases elastin levels in the mesenteric, abdominal, and renal arteries by a decrease in elastase enzyme activity in these tissues. In rats, potassium channel openers decrease calcium influx which inhibits elastin gene transcription through extracellular signal-regulated kinase 1/2 (ERK 1/2)-activator protein 1 signaling pathway. ERK 1/2 increases, through elastin gene transcription, adequately cross-linked elastic fiber content synthesized by smooth muscle cells, and decreases the number of cells in the aorta.<ref>Template:Cite journal</ref>

Minoxidil possesses α₂-adrenergic receptor agonist activity,<ref>Template:Cite journal</ref> stimulates the peripheral sympathetic nervous system (SNS) by way of carotid and aortic baroreceptor reflexes. Minoxidil administration also brings an increase in plasma renin activity, largely due to the aforementioned activation of the SNS. This activation of the renin-angiotensin axis further prompts increased biosynthesis of aldosterone; whereas plasma and urinary aldosterone levels are increased early in the course of treatment with minoxidil, over time these values tend to normalize presumably because of accelerated metabolic clearance of aldosterone in association with hepatic vasodilation.<ref name="pmid15133413">Template:Cite journal</ref>

Minoxidil may be involved in the inhibition of serotonin 5-HT₂ receptors.<ref>Template:Cite journal</ref>

Minoxidil might increase blood-tumor barrier permeability in a time-dependent manner by down-regulating tight junction protein expression and this effect could be related to ROS/RhoA/PI3K/PKB signal pathway.<ref>Template:Cite journal</ref> Minoxidil significantly increases ROS concentration when compared to untreated cells.Template:Medcn

In vitro Minoxidil treatment resulted in a 0.22 fold change for 5α-R2 (p < 0.0001). This antiandrogenic effect of minoxidil, shown by significant downregulation of 5α-R2 gene expression in HaCaT cells, may be one of its mechanisms of action in alopecia.<ref>Template:Cite journal</ref>

Minoxidil is less effective when the area of hair loss is large. In addition, its effectiveness has largely been demonstrated in younger men who have experienced hair loss for less than 5 years. Minoxidil use is indicated for central (vertex) hair loss only.<ref>Template:Cite journal</ref> Two clinical studies are being conducted in the US for a medical device that may allow patients to determine if they are likely to benefit from minoxidil therapy.<ref>Template:ClinicalTrialsGov</ref>

Conditions such as Cantú syndrome have been shown to mimic the pharmacological properties of minoxidil.<ref>Template:Cite journal</ref>

Chemistry

Minoxidil is an odorless, white to off-white, crystalline powder (crystals from methanol-acetonitrile). When heated to decomposition it emits toxic fumes of nitrogen oxides. It decomposes at 259-261 °C.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Solubility (mg/ml): propylene glycol 75, methanol 44, ethanol 29, 2-propanol 6.7, dimethylsulfoxide 6.5, water 2.2, chloroform 0.5, acetone <0.5, ethyl acetate <0.5, diethyl ether <0.5, benzene <0.5, acetonitrile <0.5.

<math chem="">\mathrm{p}K_\ce{a} =</math> 4.61

Synthesis

File:Minoxidil synthesis 1.svg

Another synthesis approach of Minoxidil<ref>Template:Cite journal</ref>

Minoxidil, 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine, is synthesized from barbituric acid, the reaction of which with phosphorus oxychloride gives 2,4,6-trichloropyrimidine. Upon reaction with ammonium, this turns into 2,4-diamino-6-chloropyrimidine. Next, the resulting 2,4-diamino-6-chloropyrimidine undergoes a reaction with 2,4-dichlorophenol in the presence of potassium hydroxide, giving 2,4-diamino-6-(2,4-dichlorophenoxy)-pyrimidine. Oxidation of this product with 3-chloroperbenzoic acid gives 2,4-diamino-6-(2,4-dichlorophenoxy)pyrimidine-3-oxide, the 2,4-dichlorophenoxyl group of which is replaced with a piperidine group at high temperature, giving minoxidil.<ref>Template:Cite book</ref>

History

Initial application

Minoxidil was developed in the late 1950s by the Upjohn Company (later became part of Pfizer) to treat ulcers. In trials using dogs, the compound did not cure ulcers but proved to be a powerful vasodilator. Upjohn synthesized over 200 variations of the compound, including the one it developed in 1963 and named minoxidil.<ref name="kahn" /> These studies resulted in the U.S. Food and Drug Administration (FDA) approving minoxidil (with the brand name Loniten) in the form of oral tablets to treat high blood pressure in 1979.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name="medical">Template:Cite book</ref>

Hair growth

When Upjohn received permission from the U.S. Food and Drug Administration (FDA) to test the new drug as medicine for hypertension they approached Charles A. Chidsey, at the University of Colorado School of Medicine.<ref name="kahn">Template:Cite news</ref> He conducted two studies,<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref> the second study showing unexpected hair growth. Puzzled by this side-effect, Chidsey consulted Guinter Kahn (who while a dermatology resident at the University of Miami had been the first to observe and report hair development on patients using the minoxidil patch) and discussed the possibility of using minoxidil for treating hair loss.Template:Cn

Kahn, along with his colleague Paul J. Grant, had obtained a certain amount of minoxidil and conducted their own research, since they were first to make the side effect observation. Neither Upjohn or Chidsey at the time were aware of the side effect of hair growth.<ref name="firstcl">Template:Cite journal</ref> The two doctors had been experimenting with a 1% solution of minoxidil mixed with several alcohol-based liquids.<ref name="gazette">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Both parties filed patents to use minoxidil for hair loss prevention, which resulted in a decade-long trial between Kahn and Upjohn, which ended with Kahn's name included in a consolidated patent (U.S. #4,596,812 Charles A Chidsey, III and Guinter Kahn) in 1986 and royalties from the company to both Kahn and Grant.<ref name="firstcl" />

Meanwhile, the effect of minoxidil on hair loss prevention was so clear that in the 1980s physicians were prescribing Loniten off-label to their balding patients.<ref name="medical" />

In August 1988, the FDA approved minoxidil for treating baldness in men<ref name="medical" /><ref name="gazette" /> under the brand name "Rogaine" (FDA rejected Upjohn's first choice, Regain, as misleading<ref name="hair">Template:Cite book (Google Books)</ref>). The agency concluded that although "the product will not work for everyone", 39% of the men studied had "moderate to dense hair growth on the crown of the head".<ref name="hair" /> "Men's Rogaine", marketed by Johnson & Johnson went off-patent on January 20, 2006.<ref name=":6">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

In 1991, Upjohn made the product available for women.<ref name="gazette" /> "Women's Rogaine", marketed by Johnson & Johnson, went off-patent in February 2014.<ref name=":6" />

Pericardial effusion

Minoxidil has been implicated in causing pericardial effusions<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> including life-threatening cases of cardiac tamponade.<ref name = "Oye_2021">Template:Cite journal</ref> There have been case reports dating back to the 1980s describing this phenomenon, including topical<ref name = "Oye_2021" /> and oral formulations.<ref>Template:Cite journal</ref> The frequency of these occurrences has previously been reported at 3% but the true frequency is difficult to determine as a large proportion of patients in this cohort also had renal insufficiency and may have had an effusion preceding the use of minoxidil.<ref>Template:Cite journal</ref>

Society and culture

Economics

In February 1996, the FDA approved both the over-the-counter sale and the production of generic formulations of minoxidil.<ref name="medical" /> Upjohn replied to that by lowering prices to half the price of the prescription drug<ref name="gazette" /> and by releasing a prescription 5% formula of Rogaine in 1997.<ref name="medical" /><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> In 1998, a 5% formulation of minoxidil was approved for nonprescription sale by the FDA.<ref>Template:Cite book (Google Books)</ref> The 5% aerosol foam formula was approved for medical use in the US in 2006.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The generic versions of the 5% aerosol foam formula were approved in 2017.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

In 2017, a study of pharmacy prices in four states for 41 over-the-counter minoxidil products which were "gender-specified" found that the mean price for minoxidil solutions was the same for women and men even though the women's formulations were 2% and the men's were 5%, while the mean price for minoxidil foams, which were all 5%, was 40% higher for women. The authors noted this was the first time gender-based pricing had been shown for a medication.<ref>Template:Cite journal</ref>

Brand names

Template:As of, Minoxidil is sold under many brand names worldwide, including but not limited to: Alomax, Alopek, Alopexy, Alorexyl, Alostil, Aloxid, Aloxidil, Anagen, Apo-Gain, Axelan, Belohair, Boots Hair Loss Treatment, Botafex, Capillus, Carexidil, Coverit, Da Fei Xin, Dilaine, Dinaxcinco, Dinaxil, Ebersedin, Eminox, Folcare, Follixil, Guayaten, Hair Grow, Hair-Treat, Hairgain, Hairgaine, Hairgrow, Hairway, Headway, Inoxi, Ivix, Keranique, Lacovin, Locemix, Loniten, Lonnoten, Lonolox, Lonoten, Loxon, M E Medic, Maev-Medic, Mandi, Manoxidil, Mantai, Men's Rogaine, Minodil, Minodril, Minostyl, Minovital, Minox, Minoxi, Minoxidil, Minoxidilum, Minoximen, Minoxiten, Minscalp, Mintop, Modil, Morr, Moxidil, Neo-Pruristam, Neocapil, Neoxidil, Nherea, Nioxin, Noxidil, Oxofenil, Pilfud, Pilogro, Pilomin, Piloxidil, Re-Stim, Re-Stim+, Recrea, Regain, Regaine, Regaxidil, Regro, Regroe, Regrou, Regrowth, Relive, Renobell Locion, Reten, Rexidil, Rogaine, Rogan, Scalpmed, Si Bi Shen, Splendora, Superminox, Trefostil, Tricolocion, Tricoplus, Tricovivax, Tricoxane, Trugain, Tugain, Unipexil, Vaxdil, Vius, Women's Regaine, Xenogrow, Xtreme Boost, Xtreme Boost+, Xue Rui, Ylox, and Zeldilon.<ref name=generic>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is also sold as a combination medication with amifampridine under the brand names Gainehair and Hair 4 U; and as a combination with tretinoin and clobetasol under the brand name Sistema GB.<ref name=generic/>

Research

Minoxidil is being investigated as a potential treatment for ovarian cancer.<ref name=":2">Template:ClinicalTrialsGov</ref>

Toxicity to animals

Minoxidil is highly toxic to dogs and cats, even in doses as small as a drop or lick.<ref>Template:Cite journal</ref>Template:Unreliable source? There are reported cases of cats dying shortly after coming in contact with minimal amounts of the substance.<ref>Template:Cite journal</ref>

There is no specific antidote, but lipid rescue has been used successfully.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>

External links

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