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)
| Molecular Formula | C9H15N5O |
| Molecular Weight | 209.2483 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|||
| 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 |
|---|---|---|
| Minoxidil accelerates heart failure development in rats with ascending aortic constriction. | 1998-06 |
|
| Age dependence of the cardiac lesions induced by minoxidil in the rat. | 1996-06-17 |
|
| Structural and functional consequences of minoxidil-induced cardiac hypertrophy. | 1994-04 |
|
| Effects of the arterial vasodilator minoxidil on cardiovascular structure and sympathetic activity in spontaneously hypertensive rats. | 1993-12 |
|
| Renin-angiotensin system and minoxidil-induced cardiac hypertrophy in rats. | 1993-11 |
|
| Hyperfiltration and conservation of renal function in hypertensive nephrosclerosis patients. | 1993-04 |
|
| Transcutaneous minoxidil in the treatment of erectile dysfunctions in spinal cord injured men. | 1993-01-01 |
|
| Severe hypertrichosis of the external ear canal during minoxidil therapy. | 1988-08 |
|
| Orthostatic hypotension occurring after discontinuation of long-term minoxidil therapy. | 1988-08 |
|
| Minoxidil induced pericardial effusion. | 1988-05 |
|
| Examination of minoxidil-induced acute cardiotoxicity in miniature swine. | 1988-01 |
|
| Minoxidil-associated pericardial effusion. | 1987-09 |
|
| [Minoxidil-induced pericardial effusion]. | 1987 |
|
| Topical tretinoin for hair growth promotion. | 1986-10 |
|
| Prolonged hypotension after initial minoxidil dose. | 1986-10 |
|
| Minoxidil-associated pericarditis and fatal cardiac tamponade. | 1985-10 |
|
| Pericarditis after minoxidil reinstitution. | 1985-10 |
|
| Minoxidil in a once-a-day step-3 antihypertensive program. | 1985-03 |
|
| Cardiac morphologic alterations in acute minoxidil cardiotoxicity in miniature swine. | 1984-08 |
|
| Mode of antihypertensive action of nitrendipine. | 1984 |
|
| Pericarditis: a complication of minoxidil therapy. | 1983-06 |
|
| Bilateral optic neuritis following minoxidil administration. | 1983-03 |
|
| Minoxidil in severe and moderately severe hypertension, in association with methyldopa and chlortalidone. | 1982-11 |
|
| Effects of acute and chronic minoxidil administration on rest and exercise hemodynamics and clinical status in patients with severe, chronic heart failure. | 1982-11 |
|
| Vasodilators in the treatment of hypertension. | 1982-11 |
|
| [Pericardial effusion during long-term treatment with minoxidil]. | 1982-10 |
|
| [Fluid retention with pericardial effusion in minoxidil therapy (author's transl)]. | 1982-06-25 |
|
| Pleuropericardial effusion associated with minoxidil administration. | 1982-05 |
|
| Chest pain and abnormal electrocardiogram associated with minoxidil. | 1982-05 |
|
| Clinical experience of long-term treatment with minoxidil in severe arterial hypertension. | 1982 |
|
| Pericardial effusion associated with minoxidil therapy. | 1981-11 |
|
| Minoxidil and pericardial effusion: an idiosyncratic reaction. | 1981-07 |
|
| Minoxidil. | 1981-01 |
|
| Minoxidil in the management of intractable hypertension. | 1981 |
|
| Divergent effects of propranolol and furosemide pretreatment on acute cardiomyopathy induced by minoxidil in beagle dogs. | 1981 |
|
| Effect of minoxidil on sympathetic nervous activity in clonidine-treated hypertensive patients. | 1981 |
|
| Rebound hypertension following minoxidil withdrawal. | 1980-04 |
|
| Pericardial effusion associated with minoxidil therapy in dialyzed patients. | 1980-01 |
|
| Experiences with the antihypertensive drug minoxidil. | 1980 |
|
| Renal function in long-term minoxidil-treated patients. | 1980 |
|
| Long-term effects of minoxidil therapy on renal function of patients with refractory hypertension: the significance of albuminuria. | 1980 |
|
| Renal function and vascular resistance during long-term minoxidil treatment of severe hypertension. | 1980 |
|
| Hypertrichosis due to minoxidil. | 1979-11 |
|
| Reversible renal failure during treatment with captopril. | 1979-09-08 |
|
| Acute cardiomyopathy induced by the vasodilating antihypertensive agent minoxidil. | 1979-03-15 |
|
| Pericardial effusions associated with minoxidil. | 1977-12-24 |
|
| The outpatient treatment of refractory hypertension with minoxidil. | 1977-07 |
|
| Minoxidil in refractory hypertension: benefits, risks. | 1977 |
|
| The effect of minoxidil on blood pressure and plasma renin activity in patients with essential and renal hypertension. | 1976-08-01 |
|
| Clinical and haemodynamic effects of minoxidil in refractory hypertension. | 1976 |
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
| Substance Class |
Chemical
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5965120SH1
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Validated (UNII)
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NCI_THESAURUS |
C270
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N0000175379
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QC02DC01
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C02DC01
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D11AX01
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NBK548394
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QD11AX01
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N0000175564
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C29707
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4254
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16317-69-4
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DB00350
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CHEMBL802
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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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ACTIVE MOIETY |
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