U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of MINOXIDIL TARTRATE

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

HIDE SMILES / InChI

Description
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.

Originator

Curator's Comment: Developed by then Upjohn Co. of Kalamazoo, Michigan, Minoxidil first came on the scene in 1960s

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.62 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Minoxidil

Approved Use

Because 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 Date

1987
Primary
ROGAINE

Approved Use

Women’s ROGAINE® is for general thinning of hair on the top of the scalp

Launch Date

1988
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
1.27 h
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

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
MINOXIDIL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
PubMed

PubMed

TitleDatePubMed
Clinical and haemodynamic effects of minoxidil in refractory hypertension.
1976
[Minoxidil in the treatment of malignant hypertension (author's transl)].
1977 Dec 2
The outpatient treatment of refractory hypertension with minoxidil.
1977 Jul
Cardiac hypertrophy and antihypertensive therapy.
1977 Sep
Minoxidil and cardiac enlargement.
1978 Oct 13
Experiences with the antihypertensive drug minoxidil.
1980
Long-term effects of minoxidil therapy on renal function of patients with refractory hypertension: the significance of albuminuria.
1980
Rebound hypertension following minoxidil withdrawal.
1980 Apr
Minoxidil.
1981 Jan
Minoxidil and pericardial effusion: an idiosyncratic reaction.
1981 Jul
Clinical experience of long-term treatment with minoxidil in severe arterial hypertension.
1982
Pleuropericardial effusion associated with minoxidil administration.
1982 May
Minoxidil in severe and moderately severe hypertension, in association with methyldopa and chlortalidone.
1982 Nov
Effects of acute and chronic minoxidil administration on rest and exercise hemodynamics and clinical status in patients with severe, chronic heart failure.
1982 Nov
Pericarditis: a complication of minoxidil therapy.
1983 Jun
Bilateral optic neuritis following minoxidil administration.
1983 Mar
Mode of antihypertensive action of nitrendipine.
1984
Topical minoxidil for extended areate alopecia.
1985
Felodipine can replace minoxidil in the treatment of refractory hypertension.
1985 Dec
Minoxidil in a once-a-day step-3 antihypertensive program.
1985 Mar
Topical tretinoin for hair growth promotion.
1986 Oct
[Minoxidil-induced pericardial effusion].
1987
Severe hypertrichosis of the external ear canal during minoxidil therapy.
1988 Aug
Orthostatic hypotension occurring after discontinuation of long-term minoxidil therapy.
1988 Aug
Minoxidil induced pericardial effusion.
1988 May
Review of cardiovascular findings in humans treated with minoxidil.
1989
Pathogenesis of cardiovascular alterations in dogs treated with minoxidil.
1989
[Polymyalgia induced by topical minoxidil].
1990
Polymyalgia and minoxidil.
1990 Aug 1
Unexpected first dose hypotensive reaction to enalapril.
1990 Dec
Cardiotoxicity of hydralazine and minoxidil in the rat. Influence of age.
1991 Feb
Minoxidil versus nitroglycerin: a prospective double-blind controlled trial in transcutaneous erection facilitation for organic impotence.
1991 Jul
Pericardial effusion associated with minoxidil therapy: case reports.
1992 Jan-Mar
Hyperfiltration and conservation of renal function in hypertensive nephrosclerosis patients.
1993 Apr
Transcutaneous minoxidil in the treatment of erectile dysfunctions in spinal cord injured men.
1993 Jan-Feb
Renin-angiotensin system and minoxidil-induced cardiac hypertrophy in rats.
1993 Nov
Structural and functional consequences of minoxidil-induced cardiac hypertrophy.
1994 Apr
Minoxidil accelerates heart failure development in rats with ascending aortic constriction.
1998 Jun
Use of M-mode and Doppler echocardiography to investigate the cardiotoxicity of minoxidil in beagle dogs.
2004 Jan
Minoxidil attenuates ischemia-induced apoptosis in cultured neonatal rat cardiomyocytes.
2004 Jun
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
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
A method for the determination of minoxidil in hair-regrowth formulations by micellar electrokinetic capillary chromatography.
2005 Oct
Does the hyperfiltration of minoxidil result in increased proteinuria and loss of renoprotection conferred by angiotensin inhibition?
2006
K+ channel activation with minoxidil stimulates nasal-epithelial ion transport and blunts exaggerated hypoxic pulmonary hypertension.
2006 Spring
Topical use of minoxidil in children and systemic side effects.
2007
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
Cardiovascular toxicity of minoxidil in the marmoset.
2008 Aug 28
[Systemic effects of topical minoxidil 2% in children].
2008 Aug-Sep
CRF receptor antagonist astressin-B reverses and prevents alopecia in CRF over-expressing mice.
2011 Feb 16
Patents

Sample Use Guides

In Vivo Use Guide
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
Minoxidil (0.1-100 uM) increased deer hair follicle growth
Name Type Language
MINOXIDIL TARTRATE
Common Name English
2,4-PYRIMIDINEDIAMINE, 6-(1-PIPERIDINYL)-, 3-OXIDE, (2R,3R)-2,3-DIHYDROXYBUTANEDIOATE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
70J7ZH7ECA
Created by admin on Sat Dec 16 07:57:02 GMT 2023 , Edited by admin on Sat Dec 16 07:57:02 GMT 2023
PRIMARY
CAS
158473-55-3
Created by admin on Sat Dec 16 07:57:02 GMT 2023 , Edited by admin on Sat Dec 16 07:57:02 GMT 2023
PRIMARY
EPA CompTox
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
PRIMARY