Oxitriptan

Last updated

Oxitriptan
5-Hydroxy-L-Tryptophan (5-HTP).svg
5-Hydroxy-L-tryptophan-3D-balls.png
Clinical data
Trade names Cincofarm, Levothym, Levotonine, Oxyfan, Serovit, Telesol, Trimag, Tript-OH, Triptum [1]
Other namesOxytryptan; 5-Hydroxytryptophan; L-5-Hydroxytryptophan; 5-Hydroxy-L-tryptophan; L-5-HTP; 5-HTP
Routes of
administration 		Oral [1]
Drug class Serotonin precursor; Serotonin receptor agonist
ATC code
Pharmacokinetic data
Bioavailability 49 ± 19% [1]
With carbidopa: up to 84% [1]
Metabolism Decarboxylation
Metabolites • Serotonin
Elimination half-life Oral: 4.4–7 hours [1]
IV: 2.2–7.4 hours [1]
Identifiers
  • (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
Formula C11H12N2O3
Molar mass 220.228 g·mol−1
3D model (JSmol)
  • C1=CC2=C(C=C1O)C(=CN2)C[C@@H](C(=O)O)N
  • InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1
  • Key:LDCYZAJDBXYCGN-VIFPVBQESA-N

Oxitriptan, also known as L-5-hydroxytryptophan (5-HTP) and sold under various brand names, is a medication and over-the-counter dietary supplement used in the treatment of depression and for other indications. [2] [1] [3] [4] It is taken by mouth. [1]

Contents

Side effects of oxitriptan include appetite loss, nausea, diarrhea, vomiting, and serotonin syndrome. [1] [2] [3] The drug is a centrally permeable monoamine precursor and prodrug of serotonin and hence acts as a serotonin receptor agonist. [2] Chemically, oxitriptan is an amino acid and a tryptamine. [5]

Oxitriptan has been used clinically since at least the 1970s. [1]

Uses

Medical

5-HTP is sold over the counter in the United States, France, Canada, Singapore, the Netherlands, and the United Kingdom as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. It is also marketed in many European countries for the indication of major depression under the trade names Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. [6]

A 2002 review concluded that although the data evaluated suggests that 5-HTP is more effective than placebo in the treatment of depression, the evidence was insufficient to be conclusive due to a lack of clinical data meeting the rigorous standards of the day. [7] More and larger studies using current methodologies are needed to determine if 5-HTP is truly effective in treating depression. [8] [9] In small, controlled trials 5-HTP has also been reported to augment the antidepressant efficacy of the antidepressant clomipramine. [10] [11] [12] A 2020 meta-analysis found oral 5-HTP supplementation had a large effect size on depression symptom severity. However, the included studies were considered relatively weak and the methods and treatment duration varied between the seven studies examined. [13]

Other uses

At high doses, or in combination with carbidopa, 5-HTP has been used to treat obesity (by promoting weight loss). [14] [15]

Use after MDMA

MDMA is an empathogenic-entactogenic and serotonergic psychotropic drug used primarily for recreational, though sometimes also therapeutic, purposes. Among users of MDMA, the serotonergic effects of the drug are often of particular interest and concern: After consuming MDMA, serotonin concentrations are greatly reduced in the brain. 5-HTP is necessary for serotonin production and its concentrations in the brain also decrease after taking MDMA.

Side effects

Potential side effects of 5-HTP include heartburn, stomach pain, nausea, vomiting, diarrhea, drowsiness, sexual problems, vivid dreams or nightmares, and muscle problems. [16] [2] Serotonin syndrome can occur. [2] [3]

Because 5-HTP has not been thoroughly studied in a clinical setting, possible side effects and interactions with other drugs are not well known. According to the US National Library of Medicine, 5-HTP has not been associated with serotonin syndrome or any serious adverse events in humans. [17] Across multiple studies, 5-HTP has also been reported to not cause any noticeable hematological or cardiovascular changes. [18] 5-HTP had also been associated with eosinophilia, but later studies have not found any causal connection. [19]

Interactions

When combined with antidepressants of the MAOI or SSRI class, very high parenteral doses of 5-HTP can cause acute serotonin syndrome in rats. [20] [21] It is unclear if such findings have clinical relevance, as most drugs will cause serious adverse events or death in rodents at very high doses. In humans, 5-HTP has never been clinically associated with serotonin syndrome – although a case report suggests 5-HTP can precipitate mania when added to an MAOI. [22]

When combined with carbidopa (as a treatment for symptoms of Parkinson's disease), 5-HTP causes nausea and vomiting; however this can be alleviated via administration of granisetron. [23] As mentioned below under pharmacology, cases of scleroderma-like illness have been reported in patients using carbidopa and 5-HTP. [24]

Oral 5-HTP results in an increase in urinary 5-HIAA, a serotonin metabolite, indicating that 5-HTP is peripherally metabolized to serotonin, which is then metabolized. This might cause false positive results in tests looking for carcinoid syndrome. [25] [26] Due to the conversion of 5-HTP into serotonin by the liver, there could be a risk of heart valve disease from serotonin's effect on the heart, as based on preclinical findings. [27] [28] However, 5-HTP has not been associated with cardiac toxicity in humans. [19] [18] [17] [29]

It has been suggested that 5-HTP may cause eosinophilia-myalgia syndrome (EMS), a serious condition which results in extreme muscle tenderness, myalgia, and blood abnormalities. However, there is evidence to show that EMS was likely caused by a contaminant in certain 5-HTP supplements. [30]

Pharmacology

The psychoactive action of 5-HTP is derived from its increase in production of serotonin in central nervous system tissue. [31]

Metabolic pathway from tryptophan to serotonin. Trp-5ht-pathway.svg
Metabolic pathway from tryptophan to serotonin.

Research shows that co-administration with carbidopa greatly increases plasma 5-HTP levels. [32] Other studies have indicated the risk of a scleroderma-like condition resulting from the combination of 5-HTP and carbidopa. [33]

After oral administration, 5-HTP is absorbed by the upper intestine. [34] The mode of absorption is not known, but presumably involves active transport via amino acid transporters. 5-HTP is adequately absorbed via oral cavity. [35] With a decarboxylase inhibitor, the bioavailability of 5-HTP can be higher than 50%. [36]

5-HTP is rapidly absorbed with a tmax of ≈1.5 h, and rapidly eliminated with a half-life of ≈1.5 – 2 h. Co-administration of a decarboxylase inhibitor (e.g. carbidopa, benserazide) doubles the half-life of 5-HTP to ≈ 3 – 4 h, [37] [34] and enhances exposure several-fold, depending on the dosing regimen. [34] [38]

5-HTP's short half-life (<2h) [34] may inherently limit its therapeutic potential, [39] as systemic 5-HTP exposure levels will fluctuate substantially even with relatively frequent dosing. Such exposure fluctuations are usually associated with increased adverse event burdens resulting from Cmax (time to maximal systemic concentration) drug spikes, and decreased clinical efficacy resulting from sub-therapeutic exposure for large parts of the day, when taken as a single dose unit or at intervals significantly larger than Cmax. It has been proposed that 5-HTP dosage forms achieving prolonged delivery would be more effective, [39] as has been demonstrated many times with other pharmaceuticals with short durations of action. [40] For example, controlled release oxycodone (OxyContin) or morphine (MS-Contin) are intended to, via novel delivery mechanisms, permit pain relief for up to twelve hours with an active ingredient which only provides relief for 3 to 6 hours. However, the inherent variability amongst different people with respect to drug metabolism makes this task challenging.

Society and culture

Names

Oxitriptan is the generic name of the drug and its INN Tooltip International Nonproprietary Name. [41] [42] [43] Brand names of oxitriptan include Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum. [4] [42]

Regulatory status

There are currently no approved drug products containing 5-HTP approved by the FDA. [44] All available 5-HTP products are nutraceuticals and are as such not regulated or verified for purity, integrity, or clinical efficacy or safety, mandating caution regarding human consumption. [45]

As of 25 August 2020, Hungary added 5-HTP to the controlled psychoactive substances list, prohibiting production, sale, import, storage and use, becoming the first country to do so. [46]

Natural sources

The seeds of the Griffonia simplicifolia , a climbing shrub native to West Africa and Central Africa, are used as an herbal supplement for their 5-HTP content. [47] [48] [49] In one 2010 trial, Griffonia simplicifolia extract appeared to increase satiety in overweight women. [50]

Research

In clinical trials of various design, 5-HTP has also been reported to treat fibromyalgia, [51] myoclonus, [52] migraine, [53] and cerebellar ataxia. [54] However, these clinical findings, as for all therapeutic findings with 5-HTP, are preliminary and need confirmation in larger trials.

Oxitriptan/carbidopa combination

A combination of oxitriptan and carbidopa, oxitriptan/carbidopa, is being developed for the potential treatment of depression.

Slow-release formulation

5-HTP's short half-life is impractical for chronic drug therapy. Research conducted at Duke University in mice have demonstrated that 5-HTP when administered as slow-release appears to gain drug properties. [55] Slow-release delivery attenuates or abolishes the peaks and valleys in 5-HTP exposure during treatment. [56] Slow-release delivery of 5-HTP markedly improved the safety profile of 5-HTP and conferred stable plasma exposure of 5-HTP and strong and sustained enhancement of brain serotonin function. [55] This discovery indicates that 5-HTP slow-release medications represent a new avenue for treatment of brain disorders responsive to serotonergic enhancement.

See also

Related Research Articles

<span class="mw-page-title-main">Monoamine oxidase inhibitor</span> Type of medication

Monoamine oxidase inhibitors (MAOIs) are a class of drugs that inhibit the activity of one or both monoamine oxidase enzymes: monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). They are best known as effective antidepressants, especially for treatment-resistant depression and atypical depression. They are also used to treat panic disorder, social anxiety disorder, Parkinson's disease, and several other disorders.

<span class="mw-page-title-main">Serotonin syndrome</span> Symptoms caused by an excess of serotonin in the central nervous system

Serotonin syndrome (SS) is a group of symptoms that may occur with the use of certain serotonergic medications or drugs. The symptoms can range from mild to severe, and are potentially fatal. Symptoms in mild cases include high blood pressure and a fast heart rate; usually without a fever. Symptoms in moderate cases include high body temperature, agitation, increased reflexes, tremor, sweating, dilated pupils, and diarrhea. In severe cases, body temperature can increase to greater than 41.1 °C (106.0 °F). Complications may include seizures and extensive muscle breakdown.

<span class="mw-page-title-main">Tryptophan</span> Chemical compound

Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromatic beta carbon substituent. Tryptophan is also a precursor to the neurotransmitter serotonin, the hormone melatonin, and vitamin B3 (niacin). It is encoded by the codon UGG.

<span class="mw-page-title-main">Sertraline</span> Antidepressant (SSRI class) medication

Sertraline, sold under the brand name Zoloft among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. The effectiveness of sertraline for depression is similar to that of other antidepressants, and the differences are mostly confined to side effects. Sertraline is better tolerated than the older tricyclic antidepressants. Sertraline is effective for panic disorder, social anxiety disorder, generalized anxiety disorder (GAD), and obsessive–compulsive disorder (OCD). Although approved for post-traumatic stress disorder (PTSD), sertraline leads to only modest improvement in this condition. Sertraline also alleviates the symptoms of premenstrual dysphoric disorder (PMDD) and can be used in sub-therapeutic doses or intermittently for its treatment.

<span class="mw-page-title-main">Citalopram</span> SSRI antidepressant

Citalopram, sold under the brand name Celexa among others, is an antidepressant of the selective serotonin reuptake inhibitor (SSRI) class. It is used to treat major depressive disorder, obsessive compulsive disorder, panic disorder, and social phobia. The antidepressant effects may take one to four weeks to occur. It is typically taken orally. In some European countries, it is sometimes given intravenously to initiate treatment, before switching to the oral route of administration for continuation of treatment. It has also been used intravenously in other parts of the world in some other circumstances.

<span class="mw-page-title-main">Venlafaxine</span> Antidepressant medication

Venlafaxine, sold under the brand name Effexor among others, is an antidepressant medication of the serotonin–norepinephrine reuptake inhibitor (SNRI) class. It is used to treat major depressive disorder, generalized anxiety disorder, panic disorder, and social anxiety disorder. Studies have shown that venlafaxine improves post-traumatic stress disorder (PTSD). It may also be used for chronic pain. It is taken orally. It is also available as the salt venlafaxine besylate in an extended-release formulation.

<span class="mw-page-title-main">Mirtazapine</span> Antidepressant medication

Mirtazapine, sold under the brand name Remeron among others, is an atypical tetracyclic antidepressant, and as such is used primarily to treat depression. Its effects may take up to four weeks but can also manifest as early as one to two weeks. It is often used in cases of depression complicated by anxiety or insomnia. The effectiveness of mirtazapine is comparable to other commonly prescribed antidepressants. It is taken by mouth.

<span class="mw-page-title-main">Serotonin–norepinephrine reuptake inhibitor</span> Class of antidepressant medication

Serotonin–norepinephrine reuptake inhibitors (SNRIs) are a class of antidepressant medications used to treat major depressive disorder (MDD), anxiety disorders, social phobia, chronic neuropathic pain, fibromyalgia syndrome (FMS), and menopausal symptoms. Off-label uses include treatments for attention-deficit hyperactivity disorder (ADHD), obsessive–compulsive disorder (OCD), and migraine prevention. SNRIs are monoamine reuptake inhibitors; specifically, they inhibit the reuptake of serotonin and norepinephrine. These neurotransmitters are thought to play an important role in mood regulation. SNRIs can be contrasted with the selective serotonin reuptake inhibitors (SSRIs) and norepinephrine reuptake inhibitors (NRIs), which act upon single neurotransmitters.

<span class="mw-page-title-main">5-Hydroxytryptophan</span> Chemical compound

5-Hydroxytryptophan (5-HTP), used medically as oxitriptan, is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitter serotonin.

Aromatic <small>L</small>-amino acid decarboxylase Class of enzymes

Aromatic L-amino acid decarboxylase, also known as DOPA decarboxylase (DDC), tryptophan decarboxylase, and 5-hydroxytryptophan decarboxylase, is a lyase enzyme, located in region 7p12.2-p12.1.

<span class="mw-page-title-main">Clomipramine</span> Antidepressant

Clomipramine, sold under the brand name Anafranil among others, is a tricyclic antidepressant (TCA). It is used in the treatment of various conditions, most notably obsessive–compulsive disorder but also many other disorders, including hyperacusis, panic disorder, major depressive disorder, trichotillomania, body dysmorphic disorder and chronic pain. It has also been notably used to treat premature ejaculation and the cataplexy associated with narcolepsy.

<span class="mw-page-title-main">Trazodone</span> Antidepressant medication

Trazodone, sold under many brand names, is an antidepressant medication, used to treat major depressive disorder, anxiety disorders, and insomnia. It is a phenylpiperazine compound of the serotonin antagonist and reuptake inhibitor (SARI) class. The medication is taken orally.

<span class="mw-page-title-main">Tianeptine</span> Atypical antidepressant

Tianeptine, sold under the brand names Stablon, Tatinol, and Coaxil among others, is an atypical tricyclic antidepressant which is used mainly in the treatment of major depressive disorder, although it may also be used to treat anxiety, asthma, and irritable bowel syndrome.

<i>Griffonia simplicifolia</i> Species of legume

Griffonia simplicifolia is a woody climbing shrub native to West Africa and Central Africa. It grows to about 3 m, and bears greenish flowers followed by black pods.

<span class="mw-page-title-main">Tryptophan hydroxylase</span> Class of enzymes

Tryptophan hydroxylase (TPH) is an enzyme (EC 1.14.16.4) involved in the synthesis of the monoamine neurotransmitter serotonin. Tyrosine hydroxylase, phenylalanine hydroxylase, and tryptophan hydroxylase together constitute the family of biopterin-dependent aromatic amino acid hydroxylases. TPH catalyzes the following chemical reaction

Cardiac fibrosis commonly refers to the excess deposition of extracellular matrix in the cardiac muscle, but the term may also refer to an abnormal thickening of the heart valves due to inappropriate proliferation of cardiac fibroblasts. Fibrotic cardiac muscle is stiffer and less compliant and is seen in the progression to heart failure. The description below focuses on a specific mechanism of valvular pathology but there are other causes of valve pathology and fibrosis of the cardiac muscle.

<span class="mw-page-title-main">Vortioxetine</span> Serotonin modulator antidepressant

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<span class="mw-page-title-main">Monoamine precursor</span>

Monoamine precursors are precursors of monoamines and monoamine neurotransmitters in the body. The amino acids L-tryptophan and L-5-hydroxytryptophan are precursors of serotonin and melatonin, while the amino acids L-phenylalanine, L-tyrosine, and L-DOPA (levodopa) are precursors of dopamine, epinephrine (adrenaline), and norepinephrine (noradrenaline).

<span class="mw-page-title-main">Carbidopa/oxitriptan</span> Medication

Carbidopa/oxitriptan, or carbidopa/5-hydroxytryptophan (carbidopa/5-HTP), is a combination of 5-hydroxytryptophan (oxitriptan), a serotonin precursor, and carbidopa, a peripherally selective aromatic L-amino acid decarboxylase inhibitor, which is under development as an antidepressant for the treatment of depressive disorders. As of June 2020, it is in phase 1 clinical trials for this indication.

References

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