Minoxidil

Iupac Name：3-hydroxy-2-imino-6-piperidin-1-ylpyrimidin-4-amine

Molecular Weight：209.2483

Modify Date.: 2022-11-07 20:17

Introduction: Minoxidil is a peripheral vasodilator that directly relaxes vascular smooth musculature,thus, lowering systolic and diastolic pressure. Its action is linked to the activation of calciumchannels. Open calcium channels cause hyperpolarization of smooth muscle cells,which in turn, reduces the flow of calcium ions into the cell, which is necessary for supportingvascular tonicity. However, when taking minoxidil, tachycardia, elevated reninsecretion, and water and sodium ion retention all appear simultaneously with hypotension. View more+

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1. Names and Identifiers

1.1 Name: Minoxidil
1.2 Synonyms: (2E)-6-Amino-2-imino-4-(1-piperidinyl)-1(2H)-pyrimidinol 2,4-diamino-6-piperidinopyrimidine3-n-oxide 2,4-diamino-6-piperidino-pyrimidine-3-oxide 2,6-diamino-4-(piperidin-1-yl)pyrimidin-1-ium-1-olate 2,6-Diamino-4-(piperidin-1-yl)pyrimidine 1-oxide 2,6-Diamino-4-piperidinopyrimidine 1-Oxide 3-hydroxy-2-imino-6-piperidin-1-ylpyrimidin-4-amine 4-Pyrimidinamine, 2,3-dihydro-3-hydroxy-2-imino-6-(1-piperidinyl)-, (2E)- 4-pyrimidinediamine,6-(1-piperidinyl)-3-oxide 6-(1-Piperidinyl)-2,4-pyrimidinediamine 3-oxide (6-(1-Piperidinyl)pyrimidine-2,4-diamine 3-oxide 6-(1-Piperidinyl)-2,4-pyrimidinediamine 3-oxide 6-(1-Piperidinyl)pyrimidine-2,4-diamine 3-oxide 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine 6-piperidino-2,4-diaminopyrimidine3-oxide alopexil alostil EINECS 253-874-2 Loniten lonolox MFCD00063409 Minoximen Regaine Rogaine Theroxidil Tricoxidil

1.3 CAS No.: 38304-91-5

1.4 CID: 4201

1.5 EINECS(EC#): 253-874-2

1.6 Molecular Formula: C9H15N5O (isomer)

1.7 Inchi: InChI=1S/C9H15N5O/c10-7-6-8(12-9(11)14(7)15)13-4-2-1-3-5-13/h6,11,15H,1-5,10H2

1.8 InChkey: ZIMGGGWCDYVHOY-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CCN(CC1)C2=NC(=N)N(C(=C2)N)O

1.10 Isomers Smiles: C1CCN(CC1)C2=NC(=N)N(C(=C2)N)O

2. Properties

2.1 Density: 1.52

2.1 Melting point: 272-274 °C (dec.)(lit.)

2.1 Boiling point: 351.7 °C at 760 mmHg

2.1 Refractive index: 1.724

2.1 Flash Point: 166.5 °C

2.1 Precise Quality: 209.12800

2.1 PSA: 91.16000

2.1 logP: 0.91830

2.1 Appearance: White crystalline powder

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: White Crystalline Solid

2.4 Color/Form: Crystals from methanol-acetonitrile
White to off-white, crystalline powder

2.5 Decomposition: When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

2.6 Odor: Odorless

2.7 pKa: 4.61(at 25℃)

2.8 Water Solubility: Soluble in ethanol (29mg/ml), DMSO (6.5mg/ml), and water (2.2mg/ml)

2.9 Spectral Properties: Maximum absorption (ethanol): 230, 261, 285 nm (E= 35210, 11210, 11790); (0.01 N sulfuric acid: 232, 280 nm (E= 26350, 23850); (0.01 N potassium hydroxide): 231, 261.5, 285 nm (E= 36100, 11400, 12040).

2.10 Stability: Stable at normal temperatures and pressures.

2.11 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.

3.2 General Description: Minoxidil, 2,4-diamino-6-piperidinopyrimidine-3-oxide . It is converted to minoxidil sulfate in the liver bya sulfotransferase enzyme.The antihypertensive properties of minoxidil are similarto those of hydralazine hydrochloride, in that minoxidil candecrease arteriolar vascular resistance. Minoxidil exerts itsvasodilatory action by a direct effect on arteriolar smoothmuscle and appears to have no effect on the CNS or on theadrenergic nervous system in animals. The serum half-lifeis 4.5 hours, and the antihypertensive effect may last up to24 hours.

3.3 Usage: Used as an antihypertensive and antialopecia agent. Minoxidil activates ATP-activated K+ channels

4. Safety and Handling

4.1 Symbol: GHS07

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R36/37/38

4.1 Safety Statements: S26;S36;S45;S36/37/39;S22

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl minoxidil, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

4.2 Octanol/Water Partition Coefficient: log Kow = 1.24

4.3 Hazard Declaration: H302-H315-H319-H335

4.3 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.4 RIDADR: NONH for all modes of transport

4.4 Caution Statement: P261-P305 + P351 + P338

4.4 Formulations/Preparations: Tablets, 2.5 and 10 mg (Loniten). Topical soluton, 2% (Rogaine)
Oral tablets: 2.5 and 10 mg (scored)-Loniten (also Australia, United Kingdom).
Topical Solution, 2% Hair Regrowth /SRP: retail pharmaceutical distributor/; Rogaine Hair Regrowth Treatment for Men (with alcohol 60% and propylene glycol), Pharmacia; Rogaine Hair Regrowth Treatment for Women (with alcohol 60% and propylene glycol), Pharmacia. 5% Rogaine Extra Strength for Men (with alcohol 30% and propylene glycol), Pharmacia.
Oral Tablets, 2.5 mg, Loniten (scored), Pharmacia; 10 mg, Loniten (scored), Pharmacia.

4.5 WGK Germany: 3

4.5 RTECS: UV8200000

4.5 Safety: Hazard Codes:?Xn,T+
Risk Statements: 22-36/37/38-26/27/28?
R22:Harmful if swallowed.?
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-45-36/37/39-22?
S22:Do not breathe dust.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

4.6 Specification: ?Minoxidil?, its cas register number is 38304-91-5. It also can be called 6-(1-Piperidinyl)-2,4-pyrimidinediamine-3-oxide ; Loniten ; Regain ; Rogaine ; and 2,4-Diamino-6-piperidino-pyrimidine-3-oxide .?In 2007 a new foam-based formulation of 5% minoxidil was shown to be as effective as the liquid-based treatment for male pattern baldness.

4.7 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	LDLo	oral	69mg/kg/34W-I (69mg/kg)	CARDIAC: PERICARDITIS CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)	Western Journal of Medicine. Vol. 143, Pg. 527, 1985.
man	TDLo	oral	107ug/kg/3D-I (0.107mg/kg)	BLOOD: THROMBOCYTOPENIA	Annals of Internal Medicine. Vol. 92, Pg. 874, 1980.
mouse	LD50	intraperitoneal	560mg/kg (560mg/kg)	?	Bollettino Chimico Farmaceutico. Vol. 121, Pg. 16, 1982.
mouse	LD50	intravenous	51mg/kg (51mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 39, Pg. 1, 1977.
mouse	LD50	oral	> 1gm/kg (1000mg/kg)	?	Bollettino Chimico Farmaceutico. Vol. 121, Pg. 16, 1982.
rat	LD50	intraperitoneal	759mg/kg (759mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 39, Pg. 1, 1977.
rat	LD50	intravenous	49mg/kg (49mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 39, Pg. 1, 1977.
rat	LD50	oral	1321mg/kg (1321mg/kg)	?	Toxicology and Applied Pharmacology. Vol. 39, Pg. 1, 1977.
women	TDLo	oral	200ug/kg (0.2mg/kg)	VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION GASTROINTESTINAL: NAUSEA OR VOMITING	Archives of Internal Medicine. Vol. 146, Pg. 2075, 1986. ?

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

38304-91-5Total: 2 Synthesis Route

65277-42-1 545 Suppliers

38304-91-5 471 Suppliers

Literatures:
Bionanoplus, S.L. Patent: EP2510930 A1, 2012 ;
Yield: null

110-89-4

35139-67-4 27 Suppliers

38304-91-5 471 Suppliers

Literatures:
Maltese, M. Journal of Organic Chemistry, 1995 , vol. 60, # 8 p. 2436 - 2442
Yield: null

8. Precursor and Product

precursor:

65277-42-1

35139-67-4

9. Other Information

9.0 Merck: 14,6203

9.1 an antihypertensive vasodilator medication: Minoxidil is an antihypertensive vasodilator medication also claiming to slow or stop hair loss and promote hair regrowth. It is available over the counter for treatment of androgenic alopecia, among other baldness treatments, but measurable changes, if experienced, disappear within months after discontinuation of treatment.
Minoxidil was first sold as a drug for high blood pressure and was noted to have the interesting side-effect of increased body hair-growth, or in some cases, significant hair loss. Treatments for baldness and hair loss usually include a 5% concentration solution that is designed for men, whereas the 2% concentration solutions are designed for women.

9.2 Indications and Usage: Minoxidil is a type of oral drug that is clinically used to lower blood pressure, and it is also called Loniten and piperidine diamine. Minoxidil is an antihypertensive drug that is clinically used to treat intractable, primary or renal hypertension. It can also be used to treat severe hypertension that does not respond well to other antihypertensive drugs, but it needs to be used in combination with diuretic drugs to prevent water and sodium retention, and combined use with beta receptor blockers may increase its curative effects and reduce adverse effects. Minoxidil is also used to prevent grease-type alopecia and on livestock.

9.3 Mechanisms of Action: Minoxidil is a type of potassium channel opener and can directly relax smooth vascular muscles and has a strong small artery dilating effect. It can reduce peripheral resistance, dilate blood vessels, and lower blood pressure while having no effect on blood volume, thus promoting venous return. In addition, due to reflective regulation and positive frequency effects, it can increase cardiac output and heart rate, but will not cause orthostatic hypotension.

9.4 Adverse reactions: Long term use of Minoxidil may have the side effect of increased body hair, such as arm hair.
Adverse reactions to oral intake mainly include: weight gain and lower body swelling due to water and sodium retention, heart palpitations and arrhythmia due to reflexive sympathetic nervous excitement, and hirsuitism.
Adverse reactions to external use mainly include: skin irritation, red spots in applied areas, itching, and other skin inflammation reactions. Although only a small amount is absorbed, but there is also a slight possibility of causing a recurrence in patients with a history or heart disease. Use with caution if suffering from cerebrovascular disease, non-hypertensive heart failure, coronary heart disease, angina pectoris, myocardial infarction, pericardial effusion, renal dysfunction and other diseases.

9.5 Contradictions: Do not use if allergic to Minoxidil or suffering from pheochromocytoma.

9.6 Description: Minoxidil is a peripheral vasodilator that directly relaxes vascular smooth musculature, thus, lowering systolic and diastolic pressure. Its action is linked to the activation of calcium channels. Open calcium channels cause hyperpolarization of smooth muscle cells, which in turn, reduces the flow of calcium ions into the cell, which is necessary for supporting vascular tonicity. However, when taking minoxidil, tachycardia, elevated renin secretion, and water and sodium ion retention all appear simultaneously with hypotension.

9.7 Chemical Properties: White Crystalline Solid

9.8 Originator: Loniten ,Upjohn ,US ,1979

9.9 Uses: Used as an antihypertensive and antialopecia agent. Minoxidil activates ATP-activated K+ channels

9.10 Uses: A selective ATP dependent K+ (Kir6) channel activator

9.11 Definition: ChEBI: A pyrimidine N-oxide that is pyrimidine-2,4-diamine 3-oxide substituted by a piperidin-1-yl group at position 6.

9.12 Manufacturing Process: Barbituric acid is reacted with phosphorus oxychloride then with 2,4,6-trichloropyrimidine and that product with ammonia to give 4-chloro-2,6-diaminopyritnidine.
A 30 g (0.15 mol) quantity of 4-chloro-2,6-diaminopyrimidine is dissolved in600 ml of hot 3A alcohol, the solution cooled to 0°C to 10°C and 41.8 g (0.24mol) of m-chloroperbenzoic acid is added. The mixture is held at 0°C to 10°Cfor 4 hours and filtered. The solid is shaken for 2 hours in 0.24 mol of 10%sodium hydroxide and filtered. The solid is washed with water and dried toyield 193 g of crude product. This product is extracted for 1 hour with 900 mlof boiling acetonitrile to yield 14.8 g (44.7% yield) of 6-amino-4-chloro-1,2-dihydro-1-hydroxy-2-iminopyrimidine, melting point 193°C.
A mixture of 3.0 g (0.019 mol) of 6-amino-4-chloro-1,2-dihydro-1-hydroxy-2-iminopyrimidine and 35 ml of piperidine is refluxed for 1.5 hours, cooled andfiltered. The solid is shaken for 20 minutes in a solution of 0.8 g of sodiumhydroxide in 30 ml of water and filtered. The solid is washed with water andextracted with 800 ml of boiling acetonitrile and filtered to yield 3.5 g (89%)yield of 6-amino-4-chloro-1,2-dihydro-1-hydroxy-2-iminopyrimidine, meltingpoint 248°C, decomposition at 259°C to 261°C.

9.13 Brand name: Loniten (Pharmacia & Upjohn); Rogaine (Pharmacia & Upjohn); Minodyl (Quantum Pharmics).

9.14 Therapeutic Function: Antihypertensive

9.15 General Description: Minoxidil, 2,4-diamino-6-piperidinopyrimidine-3-oxide . It is converted to minoxidil sulfate in the liver bya sulfotransferase enzyme.
The antihypertensive properties of minoxidil are similarto those of hydralazine hydrochloride, in that minoxidil candecrease arteriolar vascular resistance. Minoxidil exerts itsvasodilatory action by a direct effect on arteriolar smoothmuscle and appears to have no effect on the CNS or on theadrenergic nervous system in animals. The serum half-lifeis 4.5 hours, and the antihypertensive effect may last up to24 hours.

9.16 Biological Activity: Antihypertensive. Antialopecia agent. K + channel (K ATP ) activator.

9.17 Biochem/physiol Actions: Activates ATP-activated K+ channels; vasodilator; slow or stop hair loss and promote hair regrowth.

9.18 Mechanism of action: Potassium channel openers are drugs that activate (i.e., open) ATP-sensitive K+ channels in the VSM. By opening these potassium channels, there is increased efflux of potassium ions from the cells, causing hyperpolarization of VSM, which closes the voltage-gated calcium channels and, thereby, decreases intracellular calcium. With less calcium available to combine with calmodulin, there is less activation of MLCK and phosphorylation of myosin light chains. This leads to relaxation and vasodilation. Because small arteries and arterioles normally have a high degree of smooth muscle tone, these drugs are particularly effective in dilating these resistance vessels, decreasing systemic vascular resistance, and lowering arterial pressure. The fall in arterial pressure leads to reflex cardiac stimulation (baroreceptor-mediated tachycardia).
Minoxidil, as its active metabolite minoxidil O-sulfate, prolongs the opening of the potassium channel, sustaining greater vasodilation on arterioles than on veins. The drug decreases blood pressure in both the supine and standing positions, and there is no orthostatic hypotension. Associated with the decrease in peripheral resistance and blood pressure is a reflex response that is accompanied by increased heart rate, cardiac output, and stroke volume, which can be attenuated by the coadministration of a β-blocker. Along with this decrease in peripheral resistance is increased plasma renin activity and sodium and water retention, which can result in expansion of fluid volume, edema, and congestive heart failure. The sodium- and water-retaining effects of minoxidil can be reversed by coadministration of a diuretic. When minoxidil is used in conjunction with a β-adrenergic blocker, pulmonary artery pressure remains essentially unchanged.

9.19 Pharmacokinetics: Minoxidil is absorbed from the GI tract and is metabolized to its active sulfate metabolite. Plasma concentrations for minoxidil sulfate peak within 1 hour and then decline rapidly. Following an oral dose of minoxidil, its hypotensive effect begins in 30 minutes, is maximal in 2 to 8 hours, and persists for approximately 2 to 5 days. The delayed onset of the hypotensive effect for minoxidil is attributed to its metabolism to its active metabolite. The drug is not bound to plasma proteins. The major metabolite for minoxidil is its N-O-glucuronide, which unlike the sulfate metabolite is inactive as a hypotensive agent. Approximately 10 to 20% of an oral dose of minoxidil is metabolized to its active metabolite, minoxidil O-sulfate, and approximately 20% of minoxidil is excreted unchanged.

9.20 Clinical Use: Minoxidil is used for severe hypertension that is difficultto control with other antihypertensive agents. The drug hassome of the characteristic side effects of direct vasodilatorydrugs. It causes sodium and water retention and may requirecoadministration of a diuretic. Minoxidil also causes reflextachycardia, which can be controlled by use of a -adrenergicblocking agent.
Minoxidil topical solution is used to treat alopecia androgenitica(male-pattern baldness). Although the mechanismis not clearly understood, topical minoxidil is believed to increasecutaneous blood flow, which may stimulate hairgrowth. The stimulation of hair growth is attributed to vasodilationin the vicinity of application of the drug, resultingin better nourishment of the local hair follicles.

9.21 Side effects: Adverse reactions include local irritation and contact dermatitis. If the treatment is discontinued, clinical regression occurs within 3 months to the state of hair thinning that would have occurred had the treatment not been started. Twice-daily treatment is more efficacious than once-daily application. Women who use the5%concentrationmay note the development of facial hair, which is reversible on discontinuation of the medication. The 5% concentration can be more irritating than the 2% solution.

9.22 Chemical Synthesis: Minoxidil, 6-amino-1,2-dihydro-1-hydroxy-2-imino-4-piperidinopyrimidine (22.8.5), is synthesized from barbituric acid, the reaction of which with phosphorous oxychloride gives 2,4,6-trichloropyrimidine (22.8.1). Upon reaction with ammonium, this turns into 2,4-diamino-6-chloropyrimidine (22.8.2). Next, the resulting 2,4-diamino-6- chloropyrimidine (22.8.2) undergoes reaction with 2,4-dichlorophenol in the presence of potassium hydroxide, giving 2,4-diamino-6-(2,4-dichlorophenoxy)-pyrimidine (22.8.3). Oxidation of this product with 3-chloroperbenzoic acid gives 2,4-diamino-6-(2,4- dichlorophenoxy)pyrimidine-3-oxide (22.8.4), the 2,4-dichlorophenoxyl group of which is replaced with a piperidine group at high temperature, giving minoxidil (22.8.5).

9.23 Drug interactions: When minoxidil is administered with diuretics or other hypotensive drugs, the hypotensive effect of minoxidil increases, and concurrent use may cause profound orthostatic hypotensive effects.

9.24 Usage: Minoxidil is used as antihypertensive, antialopecia agent. . It is administered orally for the treatment of severe hypertension and used topically to promote the regrowth of hair in male and female pattern baldness.

10. Computational chemical data

Molecular Weight: 209.2483g/mol
Molecular Formula: C₉H₁₅N₅O
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 209.12766012
Monoisotopic Mass: 209.12766012
Complexity: 329
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 88.9
Heavy Atom Count: 15
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBzoAAAAAAAAAAAAAAAAAAAAAAAAAAsQAAAAAAAAAAAAAAAHAAUCAAACADBAAQBAANQAACgACJiZACAAAGAAgABAAAYABCAAAIAiAAEAAAAAACAAAAQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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