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Details

Stereochemistry ACHIRAL
Molecular Formula C9H15N5O
Molecular Weight 209.2487
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MINOXIDIL

SMILES

C1CCN(CC1)c2cc(N)n(=O)c(=N)[nH]2

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)

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

5.41641605E11
Primary
ROGAINE

Approved Use

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

Launch Date

5.8769277E11
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 refractory hypertension: benefits, risks.
1977
The outpatient treatment of refractory hypertension with minoxidil.
1977 Jul
Need for beta-blockade in hypertension reduced with long-term minoxidil.
1978 Aug 5
Acute cardiomyopathy induced by the vasodilating antihypertensive agent minoxidil.
1979 Mar 15
Hypertrichosis due to minoxidil.
1979 Nov
Reversible renal failure during treatment with captopril.
1979 Sep 8
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
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
Effect of minoxidil on sympathetic nervous activity in clonidine-treated hypertensive patients.
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
Vasodilators in the treatment of hypertension.
1982 Nov
[Pericardial effusion during long-term treatment with minoxidil].
1982 Oct
Pericarditis: a complication of minoxidil therapy.
1983 Jun
Bilateral optic neuritis following minoxidil administration.
1983 Mar
Mode of antihypertensive action of nitrendipine.
1984
Cardiac morphologic alterations in acute minoxidil cardiotoxicity in miniature swine.
1984 Aug
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
Prolonged hypotension after initial minoxidil dose.
1986 Oct
[Minoxidil-induced pericardial effusion].
1987
Minoxidil-associated pericardial effusion.
1987 Sep
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
[Massive pericardial effusion following minoxidil].
1989 Jun 1
Hyperfiltration and conservation of renal function in hypertensive nephrosclerosis patients.
1993 Apr
Renin-angiotensin system and minoxidil-induced cardiac hypertrophy in rats.
1993 Nov
Structural and functional consequences of minoxidil-induced cardiac hypertrophy.
1994 Apr
Age dependence of the cardiac lesions induced by minoxidil in the rat.
1996 Jun 17
Minoxidil accelerates heart failure development in rats with ascending aortic constriction.
1998 Jun
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
EP   HSDB   INCI   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INCI   INN  
Official Name English
MINOXIDIL [USP MONOGRAPH]
Common Name English
MINOXIDIL [JAN]
Common Name English
TRICOXIDIL
Brand Name English
MINOXIDIL [USP-RS]
Common Name English
2,4-PYRIMIDINEDIAMINE, 6-(1-PIPERIDINYL)-, 3-OXIDE
Systematic Name English
MINOXIDIL [USAN]
Common Name English
MINOXIDIL [EP MONOGRAPH]
Common Name English
MINOXIDIL [WHO-DD]
Common Name English
2,4-DIAMINO-6-PIPERIDINOPYRIMIDINE 3-OXIDE.
Common Name English
ALOPEXIL
Brand Name English
NSC-757106
Code English
MINTOP
Brand Name English
MINOXIDIL [MART.]
Common Name English
LONITEN
Brand Name English
MINOXIMEN
Brand Name English
MINOXIDIL [VANDF]
Common Name English
ROGAINE
Brand Name English
U-10,858
Code English
PIERMINOX
Brand Name English
NORMOXIDIL
Brand Name English
MINOXIDIL [MI]
Common Name English
MINOXIDIL [INCI]
Common Name English
MINOXIDIL [HSDB]
Common Name English
THEROXIDIL
Brand Name English
MINOXIDIL [INN]
Common Name English
ALOSTIL
Brand Name English
LONOLOX
Brand Name English
MINOXIDIL [ORANGE BOOK]
Common Name English
MINODYL
Brand Name English
U-10858
Code English
RIUP
Brand Name English
PREXIDIL
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C270
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
NDF-RT N0000175379
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-VATC QC02DC01
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-ATC C02DC01
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-ATC D11AX01
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
LIVERTOX 641
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-VATC QD11AX01
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
NDF-RT N0000175564
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
NCI_THESAURUS C29707
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
Code System Code Type Description
RXCUI
6984
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY RxNorm
IUPHAR
4254
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
USP_CATALOG
1444208
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY USP-RS
CAS
16317-69-4
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
ALTERNATIVE
FDA UNII
5965120SH1
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
MESH
D008914
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
HSDB
6538
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
CAS
38304-91-5
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
EPA CompTox
38304-91-5
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
DRUG BANK
DB00350
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
INN
2987
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
DRUG CENTRAL
1814
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
ChEMBL
CHEMBL802
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
MERCK INDEX
M7555
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY Merck Index
LACTMED
Minoxidil
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
ECHA (EC/EINECS)
253-874-2
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
WIKIPEDIA
MINOXIDIL
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
NCI_THESAURUS
C47623
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
EVMPD
SUB08982MIG
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY