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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

Molecular Formula C9H15N5O
Molecular Weight 209.2483
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.62 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Minoxidil
Primary
ROGAINE

Cmax

ValueDoseCo-administeredAnalytePopulation
2.13 ng/mL
50 mg 2 times / day multiple, topical
MINOXIDIL plasma
Homo sapiens
37.2 ng/mL
10 mg single, oral
MINOXIDIL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
18.71 ng × h/mL
50 mg 2 times / day multiple, topical
MINOXIDIL plasma
Homo sapiens
55.1 ng × h/mL
10 mg single, oral
MINOXIDIL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.27 h
10 mg single, oral
MINOXIDIL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
100%
MINOXIDIL plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
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
Minoxidil (0.1-100 uM) increased deer hair follicle growth
Substance Class Chemical
Record UNII
5965120SH1
Record Status Validated (UNII)
Record Version