2,6-diamino-4-(piperidin-1-yl)pyrimidin-1-ium-1-olate

• ChemBase ID: 234
• Molecular Formular: C9H15N5O
• Molecular Mass: 209.2483
• Monoisotopic Mass: 209.12766013
• SMILES: c1(N2CCCCC2)cc([n+](c(n1)N)[O-])N
• Canonical SMILES: Nc1cc(nc([n+]1[O-])N)N1CCCCC1
• InChI: InChI=1S/C9H15N5O/c10-7-6-8(12-9(11)14(7)15)13-4-2-1-3-5-13/h6H,1-5,10H2,(H2,11,12)
• InChIKey: ZFMITUMMTDLWHR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,6-diamino-4-(piperidin-1-yl)pyrimidin-1-ium-1-olate
• IUPAC Traditional name: minoxidil; rogaine
• Brand Name: Alopexil; Alostil; Apo-Gain; Gen-Minoxidil; Loniten; Lonolox; Minodyl; Minoxigaine; Minoximen; Normoxidil; PDP; Pierminox; Prexidil; Regaine; Rogaine; Rogaine Extra Strength for Men; Rogaine for Men; Rogaine for Women; Theroxidil; Tricoxidil; Trocoxidil
• Synonyms: 2,6-diamino-4-(piperidin-1-yl)pyrimidin-1-ium-1-olate; Minoxidilum [INN-Latin]; Minossidile [Italian]; Minoxidil; 6-PIPERIDIN-1-YLPYRIMIDINE-2,4-DIAMINE 3-OXIDE; Regaine; Avacor and Mintop; 6-(1-Piperidinyl)-2,4-pyrimidinediamine 3-Oxide; 2,4-Diamino-6-piperidinopyrimidine 3-N-Oxide; Alopexil; Alostil; Loniten; Lonolox; Minoximen; Mintop; Rogaine; Tricoxidil; U 10858

Database IDs

• CAS Number: 38304-91-5
• MDL Number: MFCD00063409
• PubChem SID: 46508344; 160963697
• PubChem CID: 4201

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.219513
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.2723312
• LogD (pH = 7.4): 1.300422
• Log P: 1.3007929
• Molar Refractivity: 60.7351 cm^3
• Polarizability: 20.943834 Å^3
• Polar Surface Area: 93.63 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.24
• LOG S: -1.02
• Solubility (Water): 1.99e+01 g/l

PROPERTIES

Physical Property

• Solubility: 2200 mg/L; Sparingly soluble in DMSO and Methanol
• Apperance: White to Off-White Solid
• Melting Point: 254-259°C (dec.)
• Hydrophobicity(logP): 0.6; -1.614

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: lysyl hydroxylase

Product Information

• Purity: 95%; 95+%
• Salt Data: Free Base

DETAILS

DrugBank - DB08225

Drug information: experimental

DrugBank - DB00350

• Drug Groups: approved
• Description: A potent direct-acting peripheral vasodilator (vasodilator agents) that reduces peripheral resistance and produces a fall in blood pressure. (From Martindale, The Extra Pharmacopoeia, 30th ed, p371)
• Indication: For the treatment of severe hypertension and in the topical treatment (regrowth) of androgenic alopecia in males and females and stabilisation of hair loss in patients with androgenic alopecia.
• Pharmacology: Minoxidil is an orally effective direct acting peripheral vasodilator that reduces elevated systolic and diastolic blood pressure by decreasing peripheral vascular resistance. Minoxidil is also used topically to treat androgenetic alopecia. Microcirculatory blood flow in animals is enhanced or maintained in all systemic vascular beds. In man, forearm and renal vascular resistance decline; forearm blood flow increases while renal blood flow and glomerular filtration rate are preserved. The predominant site of minoxidil action is arterial. Venodilation does not occur with minoxidil; thus, postural hypotension is unusual with its administration. The antihypertensive activity of minoxidil is due to its sulphate metabolite, minoxidil sulfate.
• Toxicity: Oral LD₅₀ in rats has ranged from 1321-3492 mg/kg; in mice, 2456-2648 mg/kg. Side effects include cardiovascular effects associated with hypotension such as sudden weight gain, rapid heart beat, faintness or dizziness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Approximately 90% of the administered drug is metabolized, predominantly by conjugation with glucuronic acid at the N-oxide position in the pyrimidine ring, but also by conversion to more polar products. Known metabolites exert much less pharmacologic effect than minoxidil itself.
• Absorption: Minoxidil is at least 90% absorbed from the GI tract in experimental animals and man.
• Half Life: 4.2 hours
• Protein Binding: Minoxidil does not bind to plasma proteins.
• References: Olsen EA, Whiting D, Bergfeld W, Miller J, Hordinsky M, Wanser R, Zhang P, Kohut B: A multicenter, randomized, placebo-controlled, double-blind clinical trial of a novel formulation of 5% minoxidil topical foam versus placebo in the treatment of androgenetic alopecia in men. J Am Acad Dermatol. 2007 Aug 28;. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1383

Research Area: Endocrinology
Biological Activity:
Minoxidil is a vasodilator medication known for its ability 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 disappear within months after discontinuation of treatment. [1]

Toronto Research Chemicals - M345000

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

REFERENCES

• Olsen EA, Whiting D, Bergfeld W, Miller J, Hordinsky M, Wanser R, Zhang P, Kohut B: A multicenter, randomized, placebo-controlled, double-blind clinical trial of a novel formulation of 5% minoxidil topical foam versus placebo in the treatment of androgenetic alopecia in men. J Am Acad Dermatol. 2007 Aug 28;. Pubmed
• http://en.wikipedia.org/wiki/Minoxidil
• Franz, T.J., et al.: Arch. Dermatol., 121, 203 (1985)
• Gadwood, R.C., et al.: Annu. Rep. Med. Chem., 24, 187 (1985)
• Hautala, T., et al.: Biochem. J., 283, 51 (1985)