Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H15N5O |
Molecular Weight | 209.2483 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=CC(N)=[N+]1[O-])N2CCCCC2
InChI
InChIKey=ZFMITUMMTDLWHR-UHFFFAOYSA-N
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)
DescriptionSources: http://www.drugbank.ca/drugs/DB00350Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/minoxidil.html
Sources: http://www.drugbank.ca/drugs/DB00350
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/minoxidil.html
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. 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. Minoxidil is used 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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2095198 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11886528 |
0.62 µM [IC50] | ||
Target ID: CHEMBL1293292 Sources: http://www.drugbank.ca/drugs/DB00350 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Minoxidil Approved UseBecause of the potential for serious adverse effects, Minoxidil tablets are indicated only in the treatment of hypertension that is symptomatic or associated with target organ damage and is not manageable with maximum therapeutic doses of a diuretic plus two other antihypertensive drugs. At the present time use in milder degrees of hypertension is not recommended because the benefit-risk relationship in such patients has not been defined. Launch Date1987 |
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Primary | ROGAINE Approved UseWomen’s ROGAINE® is for general thinning of hair on the top of the scalp Launch Date1988 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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2.13 ng/mL |
50 mg 2 times / day multiple, topical dose: 50 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
MINOXIDIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
37.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2715373 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
MINOXIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.71 ng × h/mL |
50 mg 2 times / day multiple, topical dose: 50 mg route of administration: Topical experiment type: MULTIPLE co-administered: |
MINOXIDIL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
55.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2715373 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
MINOXIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.27 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2715373 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
MINOXIDIL plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
100% |
MINOXIDIL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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Minoxidil in refractory hypertension: benefits, risks. | 1977 |
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[Minoxidil in the treatment of malignant hypertension (author's transl)]. | 1977 Dec 2 |
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The outpatient treatment of refractory hypertension with minoxidil. | 1977 Jul |
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Need for beta-blockade in hypertension reduced with long-term minoxidil. | 1978 Aug 5 |
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Reversible renal failure during treatment with captopril. | 1979 Sep 8 |
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Divergent effects of propranolol and furosemide pretreatment on acute cardiomyopathy induced by minoxidil in beagle dogs. | 1981 |
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Minoxidil. | 1981 Jan |
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Pericardial effusion associated with minoxidil therapy. | 1981 Nov |
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Minoxidil in the management of intractable hypertension. | 1981 Spring |
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Pleuropericardial effusion associated with minoxidil administration. | 1982 May |
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Vasodilators in the treatment of hypertension. | 1982 Nov |
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Pericarditis: a complication of minoxidil therapy. | 1983 Jun |
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Cardiac morphologic alterations in acute minoxidil cardiotoxicity in miniature swine. | 1984 Aug |
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Renal and cardiovascular effects of acute and chronic administration of felodipine to SHR. | 1985 Jul 11 |
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Minoxidil-associated pericarditis and fatal cardiac tamponade. | 1985 Oct |
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Pericarditis after minoxidil reinstitution. | 1985 Oct |
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Severe hypertrichosis of the external ear canal during minoxidil therapy. | 1988 Aug |
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[Massive pericardial effusion following minoxidil]. | 1989 Jun 1 |
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Polymyalgia and minoxidil. | 1990 Aug 1 |
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Minoxidil versus nitroglycerin: a prospective double-blind controlled trial in transcutaneous erection facilitation for organic impotence. | 1991 Jul |
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Pericardial effusion associated with minoxidil therapy: case reports. | 1992 Jan-Mar |
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Effects of the arterial vasodilator minoxidil on cardiovascular structure and sympathetic activity in spontaneously hypertensive rats. | 1993 Dec |
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Transcutaneous minoxidil in the treatment of erectile dysfunctions in spinal cord injured men. | 1993 Jan-Feb |
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Renin-angiotensin system and minoxidil-induced cardiac hypertrophy in rats. | 1993 Nov |
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Age dependence of the cardiac lesions induced by minoxidil in the rat. | 1996 Jun 17 |
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Minoxidil accelerates heart failure development in rats with ascending aortic constriction. | 1998 Jun |
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Induction of rat hepatic aryl sulfotransferase (SULT1A1) gene expression by triamcinolone acetonide: impact on minoxidil-mediated hypotension. | 2000 May 1 |
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Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms. | 2001 Mar |
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Use of M-mode and Doppler echocardiography to investigate the cardiotoxicity of minoxidil in beagle dogs. | 2004 Jan |
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A method for the determination of minoxidil in hair-regrowth formulations by micellar electrokinetic capillary chromatography. | 2005 Oct |
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Does the hyperfiltration of minoxidil result in increased proteinuria and loss of renoprotection conferred by angiotensin inhibition? | 2006 |
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Cardiovascular toxicity of minoxidil in the marmoset. | 2008 Aug 28 |
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[Systemic effects of topical minoxidil 2% in children]. | 2008 Aug-Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/minoxidil.html
Curator's Comment: can also be used topically for hair loss treatment http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/019501Orig1s029lbl.pdf
Usual Adult Dose for Hypertension
Initial dose: 5 mg orally once a day.
Maintenance dose: 10-40 mg in 1-2 divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15816824
Minoxidil (0.1-100 uM) increased deer hair follicle growth
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NCI_THESAURUS |
C270
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NDF-RT |
N0000175379
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QC02DC01
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C02DC01
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D11AX01
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LIVERTOX |
NBK548394
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QD11AX01
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N0000175564
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NCI_THESAURUS |
C29707
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6984
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4254
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16317-69-4
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5965120SH1
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D008914
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38304-91-5
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DTXSID9040685
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DB00350
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1444208
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m7555
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Minoxidil
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253-874-2
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MINOXIDIL
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C47623
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757106
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SUB08982MIG
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ACTIVE MOIETY
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)