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Details

Stereochemistry RACEMIC
Molecular Formula C11H17NO3
Molecular Weight 211.2576
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHOXAMINE

SMILES

COC1=CC=C(OC)C(=C1)[C@@H](O)[C@H](C)N

InChI

InChIKey=WJAJPNHVVFWKKL-CPCISQLKSA-N
InChI=1S/C11H17NO3/c1-7(12)11(13)9-6-8(14-2)4-5-10(9)15-3/h4-7,11,13H,12H2,1-3H3/t7-,11-/m0/s1

HIDE SMILES / InChI

Description

Methoxamine is an alpha-adrenergic agonist that induces prolonged peripheral vasoconstriction, and can also stimulate the release of arginine vasopressin in humans. In clinical trials, methoxamine was found to improve fecal incontinence. It had been marketed by Glaxo-Smith-Kline under the brand name Vasoxyl but has been discontinued. Methoxamine was also found to stimulate the induction of hiPSC-derived hepatoblasts to ALBUMIN+ cells.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.86 null [pKi]
1299.27 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Vasoxyl

Cmax

ValueDoseCo-administeredAnalytePopulation
15.69 ng/mL
10 mg single, rectal
METHOXAMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
178.95 ng × h/mL
10 mg single, rectal
METHOXAMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
6.15 h
10 mg single, rectal
METHOXAMINE plasma
Homo sapiens

Doses

AEs

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Patients suffering fecal incontinence were administered 10 mg of Methoxamine as a slow release suppository into the anal canal.
Route of Administration: Rectal
In Vitro Use Guide
Hepatic differentiation of hiPSC colonies grown on SNL feeder cells occurred in three culture stages over 18 - 21 days concluding with hepatocyte culture medium containing 20 ng/ml recombinant human hepatocyte growth factor and 20 ng/ml recombinant human Oncostatin M for 7 - 8 days. Methoxamine from a commercial compound screen was included in the stage 3 hepatocyte culture media. After 7 days incubation cells were subjected to anti-ALBUMIN immunostaining, and the number and induction rate of ALBUMIN+ cells was examined. Methoxamine was the sole effective compound among the 1,120 tested. The induction rate of hiPSC-derived hepatoblasts into ALBUMIN+ cells in the populations treated with methoxamine was 33.7%. Methoxamine was then titrated against hiPSC-derived hepatoblasts cultures across a range of 0.001 μM to 100 μM and demonstrated a dose-dependent induction activity with the highest efficiency at 1 μM.