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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:44 UTC
HMDB IDHMDB14494
Secondary Accession NumbersNone
Metabolite Identification
Common NameMinoxidil
DescriptionMinoxidil is only found in individuals that have used or taken this drug. It is 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)Minoxidil is thought to promote the survival of human dermal papillary cells (DPCs) or hair cells by activating both extracellular signal-regulated kinase (ERK) and Akt and by preventing cell death by increasing the ratio of BCl-2/Bax. Minoxidil may stimulate the growth of human hairs by prolonging anagen through these proliferative and anti-apoptotic effects on DPCs. Minoxidil, when used as a vasodilator, acts by opening adenosine triphosphate-sensitive potassium channels in vascular smooth muscle cells. This vasodilation may also improve the viability of hair cells or hair follicles.
Structure
Thumb
Synonyms
ValueSource
AlostilChEBI
apo-GainChEBI
LonitenChEBI
LonoloxChEBI
MinoxidilumChEBI
MinoximenChEBI
NormoxidilChEBI
RegaineChEBI
RogaineChEBI
TricoxidilChEBI
Chemical FormulaC9H15N5O
Average Molecular Weight209.2483
Monoisotopic Molecular Weight209.127660127
IUPAC Name2,6-diamino-4-(piperidin-1-yl)pyrimidin-1-ium-1-olate
Traditional Namerogaine
CAS Registry Number38304-91-5
SMILES
NC1=CC(=NC(N)=[N+]1[O-])N1CCCCC1
InChI Identifier
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)
InChI KeyInChIKey=ZFMITUMMTDLWHR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassTertiary amines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Aminopyrimidine
  • Imidolactam
  • Pyrimidine
  • Primary aromatic amine
  • Piperidine
  • Heteroaromatic compound
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antihypertensive Agents
  • Vasodilator Agents
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point248 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.99e+01 g/LNot Available
LogP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility19.9 mg/mLALOGPS
logP1.24ALOGPS
logP1.3ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)4.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.63 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.74 m3·mol-1ChemAxon
Polarizability21.93 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00350
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00350
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00350
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10438564
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMinoxidil
NuGOwiki LinkHMDB14494
Metagene LinkHMDB14494
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDMXD
ChEBI ID6942
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. 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 Nov;57(5):767-74. Epub 2007 Aug 29. [17761356 ]

Enzymes

General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Kurbel S, Kurbel B, Zanic-Matanic D: Minoxidil and male-pattern alopecia: a potential role for a local regulator of sebum secretion with vasoconstrictive effects? Med Hypotheses. 1999 Nov;53(5):402-6. [10616041 ]
  2. Gaffar A, Scherl D, Afflitto J, Coleman EJ: The effect of triclosan on mediators of gingival inflammation. J Clin Periodontol. 1995 Jun;22(6):480-4. [7560228 ]
  3. Michelet JF, Commo S, Billoni N, Mahe YF, Bernard BA: Activation of cytoprotective prostaglandin synthase-1 by minoxidil as a possible explanation for its hair growth-stimulating effect. J Invest Dermatol. 1997 Feb;108(2):205-9. [9008235 ]
General function:
Involved in inward rectifier potassium channel activity
Specific function:
In the kidney, probably plays a major role in potassium homeostasis. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. This channel is activated by internal ATP and can be blocked by external barium
Gene Name:
KCNJ1
Uniprot ID:
P48048
Molecular weight:
44794.6
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Kirsten R, Nelson K, Kirsten D, Heintz B: Clinical pharmacokinetics of vasodilators. Part I. Clin Pharmacokinet. 1998 Jun;34(6):457-82. [9646008 ]
  4. Evans JM, Allan AK, Davies SA, Dow JA: Sulphonylurea sensitivity and enriched expression implicate inward rectifier K+ channels in Drosophila melanogaster renal function. J Exp Biol. 2005 Oct;208(Pt 19):3771-83. [16169954 ]
  5. Loffler-Walz C, Quast U: Binding of K(ATP) channel modulators in rat cardiac membranes. Br J Pharmacol. 1998 Apr;123(7):1395-402. [9579735 ]
  6. Bray KM, Quast U: A specific binding site for K+ channel openers in rat aorta. J Biol Chem. 1992 Jun 15;267(17):11689-92. [1601843 ]
  7. Black KL, Yin D, Konda BM, Wang X, Hu J, Ko MK, Bayan JA, Sacapano MR, Espinoza AJ, Ong JM, Irvin D, Shu Y: Different effects of KCa and KATP agonists on brain tumor permeability between syngeneic and allogeneic rat models. Brain Res. 2008 Aug 28;1227:198-206. Epub 2008 Jun 21. [18602898 ]