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

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
Structure of MINOXIDIL

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)

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 refractory hypertension: benefits, risks.
1977
[Minoxidil in the treatment of malignant hypertension (author's transl)].
1977 Dec 2
The outpatient treatment of refractory hypertension with minoxidil.
1977 Jul
Need for beta-blockade in hypertension reduced with long-term minoxidil.
1978 Aug 5
Reversible renal failure during treatment with captopril.
1979 Sep 8
Divergent effects of propranolol and furosemide pretreatment on acute cardiomyopathy induced by minoxidil in beagle dogs.
1981
Minoxidil.
1981 Jan
Pericardial effusion associated with minoxidil therapy.
1981 Nov
Minoxidil in the management of intractable hypertension.
1981 Spring
Pleuropericardial effusion associated with minoxidil administration.
1982 May
Vasodilators in the treatment of hypertension.
1982 Nov
Pericarditis: a complication of minoxidil therapy.
1983 Jun
Cardiac morphologic alterations in acute minoxidil cardiotoxicity in miniature swine.
1984 Aug
Renal and cardiovascular effects of acute and chronic administration of felodipine to SHR.
1985 Jul 11
Minoxidil-associated pericarditis and fatal cardiac tamponade.
1985 Oct
Pericarditis after minoxidil reinstitution.
1985 Oct
Severe hypertrichosis of the external ear canal during minoxidil therapy.
1988 Aug
[Massive pericardial effusion following minoxidil].
1989 Jun 1
Polymyalgia and minoxidil.
1990 Aug 1
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
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
Renin-angiotensin system and minoxidil-induced cardiac hypertrophy in rats.
1993 Nov
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
Induction of rat hepatic aryl sulfotransferase (SULT1A1) gene expression by triamcinolone acetonide: impact on minoxidil-mediated hypotension.
2000 May 1
Enzymatic characterization and interspecies difference of phenol sulfotransferases, ST1A forms.
2001 Mar
Use of M-mode and Doppler echocardiography to investigate the cardiotoxicity of minoxidil in beagle dogs.
2004 Jan
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
Cardiovascular toxicity of minoxidil in the marmoset.
2008 Aug 28
[Systemic effects of topical minoxidil 2% in children].
2008 Aug-Sep
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
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
Minoxidil [WHO-DD]
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 Dec 15 15:48:58 GMT 2023 , Edited by admin on Fri Dec 15 15:48:58 GMT 2023
NDF-RT N0000175379
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WHO-VATC QC02DC01
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WHO-ATC C02DC01
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WHO-ATC D11AX01
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LIVERTOX NBK548394
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WHO-VATC QD11AX01
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NDF-RT N0000175564
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NCI_THESAURUS C29707
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Code System Code Type Description
RXCUI
6984
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PRIMARY RxNorm
IUPHAR
4254
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PRIMARY
CAS
16317-69-4
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ALTERNATIVE
FDA UNII
5965120SH1
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PRIMARY
MESH
D008914
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PRIMARY
HSDB
6538
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PRIMARY
SMS_ID
100000090366
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PRIMARY
CAS
38304-91-5
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PRIMARY
EPA CompTox
DTXSID9040685
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PRIMARY
DRUG BANK
DB00350
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PRIMARY
RS_ITEM_NUM
1444208
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PRIMARY
INN
2987
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PRIMARY
CHEBI
6942
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PRIMARY
DRUG CENTRAL
1814
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PRIMARY
DAILYMED
5965120SH1
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PRIMARY
ChEMBL
CHEMBL802
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PRIMARY
MERCK INDEX
m7555
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PRIMARY Merck Index
LACTMED
Minoxidil
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PRIMARY
ECHA (EC/EINECS)
253-874-2
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PRIMARY
WIKIPEDIA
MINOXIDIL
Created by admin on Fri Dec 15 15:48:58 GMT 2023 , Edited by admin on Fri Dec 15 15:48:58 GMT 2023
PRIMARY
NCI_THESAURUS
C47623
Created by admin on Fri Dec 15 15:48:58 GMT 2023 , Edited by admin on Fri Dec 15 15:48:58 GMT 2023
PRIMARY
NSC
757106
Created by admin on Fri Dec 15 15:48:58 GMT 2023 , Edited by admin on Fri Dec 15 15:48:58 GMT 2023
PRIMARY
EVMPD
SUB08982MIG
Created by admin on Fri Dec 15 15:48:58 GMT 2023 , Edited by admin on Fri Dec 15 15:48:58 GMT 2023
PRIMARY