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
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
Molecular Formula | C11H17NO3 |
Molecular Weight | 211.2576 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P35348|||B0ZBD9|||Q6RUJ8 Gene ID: 148.0 Gene Symbol: ADRA1A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7875228 |
4.86 null [pKi] | ||
Target ID: P25100 Gene ID: 146.0 Gene Symbol: ADRA1D Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19493707 |
1299.27 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Vasoxyl Approved UseUnknown Launch Date1981 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
15.69 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24499494/ |
10 mg single, rectal dose: 10 mg route of administration: Rectal experiment type: SINGLE co-administered: |
METHOXAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
178.95 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24499494/ |
10 mg single, rectal dose: 10 mg route of administration: Rectal experiment type: SINGLE co-administered: |
METHOXAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.15 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24499494/ |
10 mg single, rectal dose: 10 mg route of administration: Rectal experiment type: SINGLE co-administered: |
METHOXAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
15 mg single, rectal Recommended |
healthy, 18 - 60 years Health Status: healthy Age Group: 18 - 60 years Sex: M+F Sources: |
DLT: Heart rate decreased... Dose limiting toxicities: Heart rate decreased (8 patients) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Heart rate decreased | 8 patients DLT |
15 mg single, rectal Recommended |
healthy, 18 - 60 years Health Status: healthy Age Group: 18 - 60 years Sex: M+F Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Effect of repeated treatment with reboxetine on the central alpha1-adrenergic system. | 2001 Nov-Dec |
|
Development of a rat model of sexual performance anxiety: effect of behavioural and pharmacological hyperadrenergic stimulation on APO-induced erections. | 2002 Apr |
|
Alpha2-adrenoceptor ligands inhibit alpha1-adrenoceptor-mediated contraction of isolated rat arteries. | 2002 Aug |
|
Bioactivation of nitroglycerin and vasomotor response to nitric oxide are impaired in cirrhotic rat livers. | 2002 Aug |
|
A mitogen-activated protein kinase is involved in the inotropic but not chronotropic actions of adrenoceptor agonists and endothelin-1. | 2002 Aug |
|
Pregnancy and acute baroreflex resetting in conscious rabbits. | 2002 Aug |
|
Chiral separation of methoxamine and lobeline in capillary zone electrophoresis using ethylbenzene-deactivated fused-silica capillary columns and cyclodextrins as buffer additives. | 2002 Aug 1 |
|
Alpha1-adrenoceptor-mediated breakdown of phosphatidylinositol 4,5-bisphosphate inhibits pinacidil-activated ATP-sensitive K+ currents in rat ventricular myocytes. | 2002 Aug 9 |
|
(-)-Cannabidiol antagonizes cannabinoid receptor agonists and noradrenaline in the mouse vas deferens. | 2002 Dec 5 |
|
Dual adrenergic control of in vivo choline levels in the mouse major salivary glands. | 2002 Feb |
|
Existence of functional alpha1A- and alpha1D- but no alpha1B-adrenoceptor subtypes in rat common carotid arteries. | 2002 Feb |
|
Types of adrenoreceptors mediating responses of rabbit gastric muscularis mucosae. | 2002 Feb |
|
Calmodulin inhibitor W-7 unmasks a novel electrocardiographic parameter that predicts initiation of torsade de pointes. | 2002 Feb 12 |
|
Purinergic modulation of vascular sympathetic neurotransmission. | 2002 Jan |
|
Activation of alpha 1-adrenoceptors is not essential for the mediation of ischaemic preconditioning in rat heart. | 2002 Jan-Feb |
|
Norepinephrine elicits beta2-receptor-mediated dilation of isolated human coronary arterioles. | 2002 Jul 30 |
|
Phosphorylation of eNOS initiates excessive NO production in early phases of portal hypertension. | 2002 Jun |
|
Strain-specific patterns of autonomic nervous system activity and heart failure susceptibility in mice. | 2002 Jun |
|
Compression and expansion wavefront travel in canine ascending aortic flow: wave intensity analysis. | 2002 Mar |
|
Effect of repeated treatment with mirtazapine on the central alpha1-adrenergic receptors. | 2002 Mar |
|
Potential anaphylactic shock with abciximab readministration. | 2002 Mar |
|
Use of methoxamine in the resuscitation of epinephrine resistant electromechanical dissociation. | 2002 Mar |
|
Impairment of autoregulation following cortical venous occlusion in the rat. | 2002 Mar |
|
Structural factors increase blood pressure through the interaction of resistance vessel geometry with neurohumoral and local factors: estimates in rabbits with renal cellophane-wrap hypertension with intact effectors and during neurohumoral blockade. | 2002 Mar |
|
Mechanism underlying gamma-aminobutyric acid-induced antihypertensive effect in spontaneously hypertensive rats. | 2002 Mar 1 |
|
Modulation of Na-K-2Cl cotransport by intracellular Cl(-) and protein kinase C-delta in Calu-3 cells. | 2002 May |
|
Effects of chronic administration of L-arginine on vasoactive responses induced by endothelin-1 and its plasma level in streptozotocin-induced diabetic rats. | 2002 Oct |
|
Beta-adrenoceptor-induced inhibition of rat splenocyte proliferation: cytokine gene transcription as the target of action. | 2002 Oct |
|
Use of pharmaceuticals in noninvasive cardiovascular diagnosis. | 2002 Sep-Oct |
|
Effects of halothane and isoflurane on acetylcholine-induced, endothelium-dependent vasodilation in perfused rat mesenteric arterial beds. | 2003 |
|
Vasodilator actions of abnormal-cannabidiol in rat isolated small mesenteric artery. | 2003 Apr |
|
Effects of hypochlorite and hydrogen peroxide on cardiac autonomic receptors and vascular endothelial function. | 2003 Apr |
|
Deficit in nitric oxide production in cirrhotic rat livers is located in the sinusoidal and postsinusoidal areas. | 2003 Apr |
|
Effects of in vivo lipopolysaccharide infusion on vasoconstrictor function of rat isolated mesentery, kidney, and aorta. | 2003 Aug |
|
Evidence for the role of alpha1D- and alpha1A-adrenoceptors in contraction of the rat mesenteric artery. | 2003 Feb |
|
Guanylyl cyclase receptors mediate cardiopulmonary vagal reflex actions of ANP. | 2003 Feb |
|
Functional development of the rat urinary bladder after pre- or postpubertal castration. | 2003 Feb |
|
Stability of actin cytoskeleton and PKC-delta binding to actin regulate NKCC1 function in airway epithelial cells. | 2003 Feb |
|
The effects of volatile anesthetics on nonadrenergic, noncholinergic depressor responses in rats. | 2003 Jan |
|
Cyclooxygenase-derived products modulate the increased intrahepatic resistance of cirrhotic rat livers. | 2003 Jan |
|
Vasoconstrictor responsiveness of tail arteries from endotoxaemic rats. | 2003 Jan 24 |
|
Hormonal influence on expression and functionality of alpha1-adrenoceptor in rat submandibular gland. | 2003 Jan 31 |
|
L-Erythro-methoxamine is more potent than phenylephrine in effecting contraction of internal anal sphincter in vitro. | 2003 Jul |
|
Modulation of intracellular Ca2+ via L-type calcium channels in heart cells by the autoantibody directed against the second extracellular loop of the alpha1-adrenoceptors. | 2003 Mar |
|
Role of the eNOS Glu298Asp variant on the GNB3825T allele dependent determination of alpha-adrenergic coronary constriction. | 2003 May |
|
Cyclooxygenase-1 inhibition corrects endothelial dysfunction in cirrhotic rat livers. | 2003 Oct |
|
Fish Balistes capriscus skin extract-induced relaxation in mesenteric arterial bed of rat. | 2003 Oct |
|
Microvascular mechanisms by which the combretastatin A-4 derivative AC7700 (AVE8062) induces tumour blood flow stasis. | 2003 Oct 6 |
|
Influence of caveolin on constitutively activated recombinant eNOS: insights into eNOS dysfunction in BDL rat liver. | 2003 Sep |
|
Novel form of long-term synaptic depression in rat hippocampus induced by activation of alpha 1 adrenergic receptors. | 2004 Feb |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT00893607
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29196668
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:30:15 GMT 2025
by
admin
on
Mon Mar 31 18:30:15 GMT 2025
|
Record UNII |
HUQ1KC1YLI
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Preferred Name | English | ||
|
Official Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-ATC |
C01CA10
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
||
|
NCI_THESAURUS |
C29709
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
||
|
WHO-VATC |
QC01CA10
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
METHOXAMINE
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
CHEMBL524
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
390-28-3
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
HUQ1KC1YLI
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
6853
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | RxNorm | ||
|
m7328
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | Merck Index | ||
|
688523
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
100000081455
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
209
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
1753
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
483
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
6839
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
SUB08857MIG
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
DTXSID0023290
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
206-867-3
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
C66119
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
D008729
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY | |||
|
DB00723
Created by
admin on Mon Mar 31 18:30:15 GMT 2025 , Edited by admin on Mon Mar 31 18:30:15 GMT 2025
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ENANTIOMER -> RACEMATE |
|
||
|
TARGET -> AGONIST | |||
|
SALT/SOLVATE -> PARENT | |||
|
ENANTIOMER -> RACEMATE |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |