Minoxidil

Base Information

• Chemical Name: Minoxidil
• CAS No.: 38304-91-5
• Molecular Formula: C9H15N5O
• Molecular Weight: 209.251
• Hs Code.: 29335990
• European Community (EC) Number: 253-874-2
• NSC Number: 757106
• UNII: 5965120SH1
• DSSTox Substance ID: DTXSID9040685
• Wikipedia: Minoxidil
• Wikidata: Q424165
• NCI Thesaurus Code: C47623
• RXCUI: 6984
• Pharos Ligand ID: AFG3C2FGTMXZ
• Metabolomics Workbench ID: 53298
• ChEMBL ID: CHEMBL802,CHEMBL609587,CHEMBL1372483
• Mol file: 38304-91-5.mol

Synonyms:Loniten;Minoxidil;Regaine;Rogaine;U 10858

Chemical Property of Minoxidil

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 272-274 °C (dec.)(lit.)
• Refractive Index: 1.724
• Boiling Point: 351.7 °C at 760 mmHg
• PKA: 4.61(at 25℃)
• Flash Point: 166.5 °C
• PSA: 91.16000
• Density: 1.52 g/cm³
• LogP: 0.91830
• Storage Temp.: Store at RT
• Solubility.: Slightly soluble in water, soluble in methanol and in propylene glycol.
• Water Solubility.: Soluble in water (2.2 mg/ml), 100% ethanol (29 mg/ml), propylene glycol, acetone, DMSO (6.5 mg/ml), and methanol.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 209.12766012
• Heavy Atom Count: 15
• Complexity: 329

Purity/Quality:

99% ^*data from raw suppliers

PDP ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, T+
• Hazard Codes: Xn,T+
• Statements: 22-36/37/38-26/27/28
• Safety Statements: 26-36-45-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antihypertensive Agents
• Canonical SMILES: C1CCN(CC1)C2=NC(=N)N(C(=C2)N)O
• Recent ClinicalTrials: Bioavailability Clinical Trial of Oral Minoxidil 1 mg
• Recent EU Clinical Trials: A Phase 2, multicenter, prospective, randomized, double-blind, Minoxidil and vehicle controlled, dose-ranging study to evaluate the efficacy and safety of CB-03-01 (Cortexolone 17α-propionate) solution for the treatment of androgenetic alopecia in females
• Recent NIPH Clinical Trials: Investigation of therapy for congenital hypotrichosis and woolly hair
• Chemical Structure and Formulation: Minoxidil is a piperidino-pyrimidine derivative with the chemical structure: 2,6-diamino-4-piperidinopyrimidine-1-oxide. It is formulated as a solution containing inactive ingredients such as water, ethanol, and propylene glycol to enhance solubility.
• Mechanism of Action: Acts as a potent arteriolar vasodilator by opening potassium channels on smooth muscles of peripheral arteries, leading to hyperpolarization of the cell membrane.; Widens blood vessels and opens potassium channels, allowing more oxygen, blood, and nutrients to reach the hair follicles.
• History and Development: Developed by the Upjohn Company in the late 1950s initially for treating ulcers but later found to be a powerful vasodilator. FDA approved minoxidil in 1979 to treat high blood pressure in oral tablet form under the brand name "Loniten". In 1988, FDA approved 2% topical minoxidil (known as Rogaine) for male pattern baldness (androgenetic alopecia) treatment, and in 1992, its use was approved for female pattern hair loss.; Minoxidil is the only topical drug approved for both male and female pattern hair loss treatment in the US. Approved over-the-counter (OTC) at a maximum concentration of 5%.
• Clinical Use: Acts through multiple pathways including vasodilation, anti-inflammatory effects, induction of Wnt/β-catenin signaling pathway, and antiandrogenic activity. Approximately 1.4% of topical minoxidil is absorbed through the skin, and it is metabolized to minoxidil sulfate, the active form.; Needs to be applied regularly once or twice daily for hair regrowth maintenance. Can cause increased hair loss initially due to synchronization of the hair cycle induced by treatment.

Technology Process of Minoxidil

There total 4 articles about Minoxidil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

2,6-diamino-4-chloro-pyrimidine N-oxide (35139-67-4) → 2,4-diamino-6-piperidinopyrimidine 3-oxide (38304-91-5)

Guidance literature:

at 106 ℃; for 2h;

DOI:10.3906/kim-1903-46

Reference yield:

ketoconazole (65277-42-1) → 2,4-diamino-6-piperidinopyrimidine 3-oxide (38304-91-5)

Guidance literature:

Reference yield:

piperidine (110-89-4) + 2,6-diamino-4-chloro-pyrimidine N-oxide (35139-67-4) → 2,4-diamino-6-piperidinopyrimidine 3-oxide (38304-91-5)

Guidance literature:

In dimethyl sulfoxide; at 80 ℃; Rate constant; Thermodynamic data; various temp.; ΔH*, ΔS*;

DOI:10.1021/jo00113a025

upstream raw materials:

piperidine

2,6-diamino-4-chloro-pyrimidine N-oxide

ketoconazole

Refernces

• 1、 -. "METHOD OF ENHANCING HAIR GROWTH". . . Retrieved 2012/12/13.
• 2、 -. "3-deoxyglucosone and skin". . . Retrieved 2008/06/13.