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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
[Minoxidil in the treatment of malignant hypertension (author's transl)].
1977 Dec 2
Pericardial effusions associated with minoxidil.
1977 Dec 24-31
The outpatient treatment of refractory hypertension with minoxidil.
1977 Jul
Need for beta-blockade in hypertension reduced with long-term minoxidil.
1978 Aug 5
Hypertrichosis due to minoxidil.
1979 Nov
Reversible renal failure during treatment with captopril.
1979 Sep 8
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
Renal function and vascular resistance during long-term minoxidil treatment of severe hypertension.
1980
Rebound hypertension following minoxidil withdrawal.
1980 Apr
Pericardial effusion associated with minoxidil therapy in dialyzed patients.
1980 Jan
Divergent effects of propranolol and furosemide pretreatment on acute cardiomyopathy induced by minoxidil in beagle dogs.
1981
Minoxidil.
1981 Jan
Minoxidil and pericardial effusion: an idiosyncratic reaction.
1981 Jul
Pericardial effusion associated with minoxidil therapy.
1981 Nov
Minoxidil in the management of intractable hypertension.
1981 Spring
Clinical experience of long-term treatment with minoxidil in severe arterial hypertension.
1982
[Fluid retention with pericardial effusion in minoxidil therapy (author's transl)].
1982 Jun 25
Pleuropericardial effusion associated with minoxidil administration.
1982 May
Chest pain and abnormal electrocardiogram associated with minoxidil.
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
[Pericardial effusion during long-term treatment with minoxidil].
1982 Oct
Topical minoxidil for extended areate alopecia.
1985
Felodipine can replace minoxidil in the treatment of refractory hypertension.
1985 Dec
Renal and cardiovascular effects of acute and chronic administration of felodipine to SHR.
1985 Jul 11
Minoxidil in a once-a-day step-3 antihypertensive program.
1985 Mar
The interaction of cimetidine with various antihypertensive agents in the spontaneously hypertensive rat.
1985 May
Minoxidil-associated pericarditis and fatal cardiac tamponade.
1985 Oct
Pericarditis after minoxidil reinstitution.
1985 Oct
Topical tretinoin for hair growth promotion.
1986 Oct
Severe hypertrichosis of the external ear canal during minoxidil therapy.
1988 Aug
Orthostatic hypotension occurring after discontinuation of long-term minoxidil therapy.
1988 Aug
Examination of minoxidil-induced acute cardiotoxicity in miniature swine.
1988 Jan
Minoxidil induced pericardial effusion.
1988 May
The safety of topical minoxidil solution in the treatment of pattern baldness: the results of a 27-center trial.
1988 Oct-Dec
A comparative study of minoxidil-induced myocardial lesions in beagle dogs and miniature swine.
1989
Review of cardiovascular findings in humans treated with minoxidil.
1989
[Massive pericardial effusion following minoxidil].
1989 Jun 1
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
Hyperfiltration and conservation of renal function in hypertensive nephrosclerosis patients.
1993 Apr
Effects of the arterial vasodilator minoxidil on cardiovascular structure and sympathetic activity in spontaneously hypertensive rats.
1993 Dec
Transcutaneous minoxidil in the treatment of erectile dysfunctions in spinal cord injured men.
1993 Jan-Feb
Structural and functional consequences of minoxidil-induced cardiac hypertrophy.
1994 Apr
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