Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H26N2O3.C4H6O6 |
| Molecular Weight | 504.5296 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 7 / 7 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@H]([C@@H](O)C(O)=O)C(O)=O.[H][C@@]12CC[C@H](O)[C@@H](C(=O)OC)[C@@]1([H])C[C@]3([H])N(CCC4=C3NC5=C4C=CC=C5)C2
InChI
InChIKey=HMEXTTWSBUBIOL-URXSSEHMSA-N
InChI=1S/C21H26N2O3.C4H6O6/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24;5-1(3(7)8)2(6)4(9)10/h2-5,12,15,17-19,22,24H,6-11H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t12-,15-,17-,18-,19-;1-,2-/m01/s1
Corynanthine is one of the two diastereomers of yohimbine (the other is alpha-yohimbine). Corynanthine is an antagonist of the alpha-1, alpha-2A and alpha-2C adrenergic receptors showing greater selectivity for the alpha-1 adrenergic receptor. Corynanthine was tested as the active ingredient of eye drops in a small clinical trial for Ocular hypertension where formulations of 2% and 5% demonstrated relief of symptoms.
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) |
562.0 nM [Kd] | ||
Target ID: P08913 Gene ID: 150.0 Gene Symbol: ADRA2A Target Organism: Homo sapiens (Human) |
5.1 null [pKd] | ||
Target ID: P22086 Gene ID: 24175.0 Gene Symbol: Adra2c Target Organism: Rattus norvegicus (Rat) |
232.0 nM [Kd] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The effect of adrenergic compounds on neurogenic dural vasodilatation. | 2001 Jul 13 |
|
| Basolateral adrenoceptor activation mediates noradrenaline-induced Cl- secretion in M-1 mouse cortical collecting duct cells. | 2002 Dec |
|
| Influence of prazosin and clonidine on morphine analgesia, tolerance and withdrawal in mice. | 2003 Jan 24 |
|
| Pharmacological characterization of unique prazosin-binding sites in human kidney. | 2003 Jul |
|
| Ocular hypotensive effects of melatonin receptor agonists in the rabbit: further evidence for an MT3 receptor. | 2003 Mar |
|
| Small molecules targeting severe acute respiratory syndrome human coronavirus. | 2004 Jul 6 |
|
| Inhibition of perforant path input to the CA1 region by serotonin and noradrenaline. | 2005 Aug |
|
| Histamine receptors that influence blockage of the normal human nasal airway. | 2005 Mar |
|
| Presynaptic alpha1 adrenergic receptors differentially regulate synaptic glutamate and GABA release to hypothalamic presympathetic neurons. | 2006 Feb |
|
| Stimulation of an alpha1-adrenergic receptor downregulates ecto-5' nucleotidase activity on the apical membrane of RPE cells. | 2006 Sep |
|
| Purinergic signalling in the subretinal space: a role in the communication between the retina and the RPE. | 2008 Jun |
|
| Significance of the adrenergic system in the regulation of vasopressin secretion in rat neurohypophyseal tissue cultures. | 2008 Jun 5 |
|
| [Studies on predict of absorption of corynanthine, yohimbine, ajmalicine and ajmaline across human intestinal epithelial by using human Caco-2 cells monolayers]. | 2008 Oct |
|
| [Effect of the endogenous catecholamines synthesized by lymphocytes on T cell proliferation]. | 2009 Feb |
|
| Modulation of natural killer cell function by alpha-adrenoreceptor-coupled signalling. | 2010 |
|
| Inhibitory effect of galanin on adrenaline- and noradrenaline-induced increased oxytocin secretion in rat neurohypophyseal cell cultures. | 2010 Sep |
Sample Use Guides
10 symmetrically ocular hypertensive patients were treated with a single drop of 1%, 2% and 5% corynanthine solution. The 1% solution showed no effect while the 2% solution reduced IOP for at least 8 hours and the 5% solution showed a significant reduction in IOP in both eyes.
Route of Administration:
Topical
The binding constants obtained for 26 compounds (including, corynanthine) were determined by the 3-curve approach. Of these compounds WB4101, corynanthine, rauwolscine, yohimbine, ARC 239 and prazosin were found to be clearly alpha2C-selective; their electivites ranging from 16 to 30 fold (Kd for corynanthine = 232 nM). Radioligand binding was performed in 150 uL of 1 mM EDTA, 100 uM Gpp(NH)p (guanyl-5'-yl-imido-diphos-phate), 140 mM NaCl, 33 mM Tris-Cl, pH 7.5 with [3H]-MK912 and drugs for 1 h at 25°C and then filtering and washing on Whatman GF/C filters.
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274278
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24721101
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92634-48-5
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NON-SPECIFIC STOICHIOMETRY | |||
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63989-78-6
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DTXSID90981713
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7359P0A2QF
Created by
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PRIMARY |
ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
