Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H15N5O.C4H6O6 |
Molecular Weight | 359.3351 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.NC1=NC(=CC(N)=[N+]1[O-])N2CCCCC2
InChI
InChIKey=SNCJAEVKCLODRY-LREBCSMRSA-N
InChI=1S/C9H15N5O.C4H6O6/c10-7-6-8(12-9(11)14(7)15)13-4-2-1-3-5-13;5-1(3(7)8)2(6)4(9)10/h6H,1-5,10H2,(H2,11,12);1-2,5-6H,(H,7,8)(H,9,10)/t;1-,2-/m.1/s1
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 |
---|---|---|---|
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 |
---|---|---|---|---|
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 |
---|---|---|---|---|
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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Clinical and haemodynamic effects of minoxidil in refractory hypertension. | 1976 |
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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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Cardiac hypertrophy and antihypertensive therapy. | 1977 Sep |
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Minoxidil and cardiac enlargement. | 1978 Oct 13 |
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Experiences with the antihypertensive drug minoxidil. | 1980 |
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Long-term effects of minoxidil therapy on renal function of patients with refractory hypertension: the significance of albuminuria. | 1980 |
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Rebound hypertension following minoxidil withdrawal. | 1980 Apr |
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Minoxidil. | 1981 Jan |
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Minoxidil and pericardial effusion: an idiosyncratic reaction. | 1981 Jul |
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Clinical experience of long-term treatment with minoxidil in severe arterial hypertension. | 1982 |
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Pleuropericardial effusion associated with minoxidil administration. | 1982 May |
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Minoxidil in severe and moderately severe hypertension, in association with methyldopa and chlortalidone. | 1982 Nov |
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Effects of acute and chronic minoxidil administration on rest and exercise hemodynamics and clinical status in patients with severe, chronic heart failure. | 1982 Nov |
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Pericarditis: a complication of minoxidil therapy. | 1983 Jun |
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Bilateral optic neuritis following minoxidil administration. | 1983 Mar |
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Mode of antihypertensive action of nitrendipine. | 1984 |
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Topical minoxidil for extended areate alopecia. | 1985 |
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Felodipine can replace minoxidil in the treatment of refractory hypertension. | 1985 Dec |
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Minoxidil in a once-a-day step-3 antihypertensive program. | 1985 Mar |
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Topical tretinoin for hair growth promotion. | 1986 Oct |
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[Minoxidil-induced pericardial effusion]. | 1987 |
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Severe hypertrichosis of the external ear canal during minoxidil therapy. | 1988 Aug |
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Orthostatic hypotension occurring after discontinuation of long-term minoxidil therapy. | 1988 Aug |
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Minoxidil induced pericardial effusion. | 1988 May |
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Review of cardiovascular findings in humans treated with minoxidil. | 1989 |
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Pathogenesis of cardiovascular alterations in dogs treated with minoxidil. | 1989 |
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[Polymyalgia induced by topical minoxidil]. | 1990 |
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Polymyalgia and minoxidil. | 1990 Aug 1 |
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Unexpected first dose hypotensive reaction to enalapril. | 1990 Dec |
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Cardiotoxicity of hydralazine and minoxidil in the rat. Influence of age. | 1991 Feb |
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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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Hyperfiltration and conservation of renal function in hypertensive nephrosclerosis patients. | 1993 Apr |
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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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Structural and functional consequences of minoxidil-induced cardiac hypertrophy. | 1994 Apr |
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Minoxidil accelerates heart failure development in rats with ascending aortic constriction. | 1998 Jun |
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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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Minoxidil attenuates ischemia-induced apoptosis in cultured neonatal rat cardiomyocytes. | 2004 Jun |
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Simultaneous effects of tocopheryl polyethylene glycol succinate (TPGS) on local hair growth promotion and systemic absorption of topically applied minoxidil in a mouse model. | 2005 Dec 8 |
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Development and validation of a procedure for the determination of minoxidil in hair-regrowth formulations using two variants of capillary zone electrophoresis. | 2005 Jun-Jul |
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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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K+ channel activation with minoxidil stimulates nasal-epithelial ion transport and blunts exaggerated hypoxic pulmonary hypertension. | 2006 Spring |
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Topical use of minoxidil in children and systemic side effects. | 2007 |
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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. | 2007 Nov |
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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 |
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CRF receptor antagonist astressin-B reverses and prevents alopecia in CRF over-expressing mice. | 2011 Feb 16 |
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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70J7ZH7ECA
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158473-55-3
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DTXSID60935925
Created by
admin on Sat Dec 16 07:57:02 GMT 2023 , Edited by admin on Sat Dec 16 07:57:02 GMT 2023
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ACTIVE MOIETY
SUBSTANCE RECORD