Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C11H17NO3 |
| Molecular Weight | 211.2576 |
| Optical Activity | UNSPECIFIED |
| 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) |
4.86 null [pKi] | ||
Target ID: P25100 Gene ID: 146.0 Gene Symbol: ADRA1D Target Organism: Homo sapiens (Human) |
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 |
|---|---|---|
| Cyclosporin A: effects on the secretory process and noradrenergic activity in the submandibular gland of the rat. | 2001 |
|
| Nitric oxide modulates acetylcholine-induced vasodilatation in the hepatic arterial vasculature of the dual-perfused rat liver. | 2001 Apr |
|
| Erection and NO override the vasoconstrictive effect of alpha-adrenergic stimulation in the rat penile vasculature. | 2001 Aug |
|
| Antihypertensive drugs induce structural remodeling of the penile vasculature. | 2001 Aug |
|
| Vasoconstrictors in erectile physiology. | 2001 Dec |
|
| Alpha-1A adrenoceptors modulate potentiation of spinal nociceptive pathways in the rat spinal cord in vitro. | 2001 Dec |
|
| Role of tyrosine kinase activity in alpha-adrenergic inhibition of the beta-adrenergically regulated L-type Ca(2+) current in guinea-pig ventricular myocytes. | 2001 Dec 15 |
|
| Effect of high extracellular Ca(2+) levels in spontaneously hypertensive rat aorta. | 2001 Dec 7 |
|
| Noradrenaline stimulates 5-hydroxytryptamine release from mouse ileal tissues via alpha(2)-adrenoceptors. | 2001 Dec 7 |
|
| Assessment of the pro-arrhythmic potential of anti-arrhythmic drugs: an experimental approach. | 2001 Jan |
|
| d,l-sotalol enhances baroreflex sensitivity in conscious rats surviving acute myocardial infarction. | 2001 Jul |
|
| Phe-308 and Phe-312 in transmembrane domain 7 are major sites of alpha 1-adrenergic receptor antagonist binding. Imidazoline agonists bind like antagonists. | 2001 Jul 6 |
|
| Increased heme oxygenase activity in splanchnic organs from portal hypertensive rats: role in modulating mesenteric vascular reactivity. | 2001 Jun |
|
| Regional haemodynamic responses to the cannabinoid agonist, WIN 55212-2, in conscious, normotensive rats, and in hypertensive, transgenic rats. | 2001 Jun |
|
| The influence of phosphodiesterase inhibitor, rolipram, on hemodynamics in lipopolysaccharide-treated rats. | 2001 Mar |
|
| Female gender is a risk factor for drug-induced long QT and cardiac arrhythmias in an in vivo rabbit model. | 2001 May |
|
| Adrenergic nerves mediate acetylcholine-induced endothelium-independent vasodilation in the rat mesenteric resistance artery. | 2001 May 11 |
|
| Hypoxia alters the sensitivity of the L-type Ca(2+) channel to alpha-adrenergic receptor stimulation in the presence of beta-adrenergic receptor stimulation. | 2001 May 25 |
|
| Use of methoxamine in the resuscitation of epinephrine-resistant electromechanical dissociation. | 2001 Nov |
|
| Stimulation of alpha1-adrenoceptors inhibits memory consolidation in the chick. | 2001 Oct |
|
| The noradrenergic inhibition of an apamin-sensitive, small-conductance Ca2+-activated K+ channel in hypothalamic gamma-aminobutyric acid neurons: pharmacology, estrogen sensitivity, and relevance to the control of the reproductive axis. | 2001 Oct |
|
| Effect of Rho-kinase inhibition on vasoconstriction in the penile circulation. | 2001 Sep |
|
| Abrogation of alpha-adrenergic vasoactivity in chronically inflamed rat knee joints. | 2001 Sep |
|
| [Priapism secondary to chronic myeloid leukemia: value of initial treatment with cavernous lavage plus adjuvant methoxamine]. | 2002 Apr |
|
| Development of a rat model of sexual performance anxiety: effect of behavioural and pharmacological hyperadrenergic stimulation on APO-induced erections. | 2002 Apr |
|
| Bioactivation of nitroglycerin and vasomotor response to nitric oxide are impaired in cirrhotic rat livers. | 2002 Aug |
|
| Existence of functional alpha1A- and alpha1D- but no alpha1B-adrenoceptor subtypes in rat common carotid arteries. | 2002 Feb |
|
| Interaction of nitric oxide with calcium in the mesenteric bed of bile duct-ligated rats. | 2002 Jan |
|
| Functional cerebral hyperemia is unaffected by isovolemic hemodilution. | 2002 Jan |
|
| Mechanism underlying gamma-aminobutyric acid-induced antihypertensive effect in spontaneously hypertensive rats. | 2002 Mar 1 |
|
| Effects of halothane and isoflurane on acetylcholine-induced, endothelium-dependent vasodilation in perfused rat mesenteric arterial beds. | 2003 |
|
| L-Erythro-methoxamine is more potent than phenylephrine in effecting contraction of internal anal sphincter in vitro. | 2003 Jul |
|
| 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
Patients suffering fecal incontinence were administered 10 mg of Methoxamine as a slow release suppository into the anal canal.
Route of Administration:
Rectal
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
Wed Apr 02 21:23:41 GMT 2025
by
admin
on
Wed Apr 02 21:23:41 GMT 2025
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| Record UNII |
HG4D84VF66
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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13699-29-1
Created by
admin on Wed Apr 02 21:23:41 GMT 2025 , Edited by admin on Wed Apr 02 21:23:41 GMT 2025
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HG4D84VF66
Created by
admin on Wed Apr 02 21:23:41 GMT 2025 , Edited by admin on Wed Apr 02 21:23:41 GMT 2025
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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RACEMATE -> ENANTIOMER |
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