Hopantenic acid

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Hopantenic acid
Stereo, skeletal formula of hopantenic acid
Hopantenic acid ball-and-stick.png
Identifiers
CAS number 18679-90-8 YesY, 17097-76-6 (Calcium salt) YesY
PubChem 28281
ChemSpider 26309 YesY
KEGG D08042 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H19NO5
Molar mass 233.26 g mol−1
Related compounds
Related alkanoic acids
Related compounds Panthenol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Hopantenic acid (homopantothenic acid) is a central nervous system drug. Formulated as the calcium salt, it is used in the Russian Federation for a variety of neurological, psychological and psychiatric conditions and sold as Pantogam (Russian: Пантогам).[1]

Pantogam was introduced in 1979. A newer version, Pantogam Active was introduced in 2008. Original Pantogam was only D-isomer Hopantenic Acid. The new Pantogam Active formulation has equal D & L (Dextrorotation and Levorotation) isomers. It is claimed Pantogam Active has greater nootropic, anxiolytic, anticonvulsant and antidepressant effect than the prior version.[2]

Clinical Trials

Randomized double-blind, placebo-controlled study to determine efficacy and tolerability of pantogam activ as an add-on drug in patients with partial epilepsy was conducted. 20 patients received pantogam activ, 20 patients - placebo. Good tolerability and no adverse event were detected in the dose of 1800 mg/d. The reduction in the frequency of epileptic seizures was achieved in 72.1% in the group receiving pantogam activ and in 16.7% in the group placebo. Significant improvement in long-term memory and manifestations of anxiety were found in patients using pantogam activ. Quality of life in scale QOLIE-31 improved after taking pantogam and did not change after placebo.[3]

35 patients with organic brain lesions caused by secondary brain harmful factors (group 1) and 33 patients with organic brain diseases of vascular genesis (group 2) were studied. Mean age of patients was 45.5 ±2.3 years. Asthenic, cerebroasthenic, psychoorganic syndromes in the combination with dissomnic, psychoautonomous, depressive, hypochondriac disorders predominated in the clinical picture of patients. Pantogam was prescribed in dose 1.0 g 3 times daily during 45 days. The effect of the drug on cognitive and mental disorders was found. The drug was most effective in patients of group 1. Pantogam was well-tolerated.[4]

The efficacy of the nootropic drug Pantogam in the treatment of hyperkinetic disorders in children aged 6-12 years was analyzed. The results of the randomized placebo-controlled trial demonstrated the decrease of major symptoms of hyperkinetic disorders (inattention, hyperactivity, impulsivity), comorbid mental and behavior disorders, the improvement of cognitive functions in the group of children treated with Pantogam during 6 weeks and the absence of significant changes in the placebo group. It was concluded that Pantogam is effective in the treatment of hyperkinetic disorders in children. [5]

The Manufacturers Instructions For Use advise the following: [6]

Pharmacotherapeutic group of drug: Nootropic Agent.

Pharmacodynamic. Pantogam range of actions is related to the presence in its structure of gamma-aminobutyric acid. The mechanism of action is due to a direct effect on Pantogam GABA-B-receptor-channel complex. The drug has neuroprotective and anticonvulsant effects. Pantogam increases brain resistance to hypoxia and the effects of toxic substances, stimulates anabolic processes in neurons that combines moderate sedation with a mild stimulating effect, reduces the excitability of the motor activates the mental and physical performance. Enhances GABA metabolism in chronic alcohol intoxication and after ethanol withdrawal. Able to inhibit acetylation reaction involved in the mechanisms of inactivation, procaine (novocaine), and sulfonamides, thereby achieving prolongation of the action of the latter. Causes inhibition of pathologically elevated cystic reflex and detrusor tone.

Pharmacokinetics . Pantogam is rapidly absorbed from the gastrointestinal tract permeates through the blood-brain barrier, the largest concentrations are in the liver, kidneys, the stomach wall and into the skin. The drug is not metabolized and is excreted unchanged in 48 hours: 67.5% of the dose - the urine, 28.5% - in the feces.

Indications

  • Cognitive impairment in organic lesions of the brain (including the effects and neuroinfections traumatic brain injury) and neurotic disorders;
  • Schizophrenia with organic cerebral insufficiency;
  • Cerebrovascular disease caused by atherosclerotic changes of cerebral vessels;
  • Extrapyramidal disorders (myoclonus, epilepsy, Huntington's chorea, hepatolenticular degeneration, Parkinson's disease, etc.), as well as for the treatment and prevention of extrapyramidal syndrome (hyperkinetic and akinetic) caused by taking antipsychotics;
  • Epilepsy with mental retardation processes in the complex therapy with anticonvulsants;
  • Psycho-emotional overload, decreased mental and physical activity, to improve concentration and memory;
  • Neurogenic bladder disorders (pollakiuria, urgency, imperative urinary incontinence, enuresis);
  • Children with perinatal encephalopathy, mental retardation of varying severity, developmental delay (mental, verbal, motor, or a combination thereof), with various forms of cerebral palsy, with hyperkinetic disorders ( syndrome, attention deficit hyperactivity disorder), neurosis-like states (stuttering, mostly clonic form; ticks.) The drug is used in children older than 3 years. In an earlier age is recommended to take the drug in the form of a syrup.

Chemistry[edit]

Hopantenic acid is a homolog of pantothenic acid. While pantothenic acid is the amide of D-pantoate and β-alanine, hopantenic acid is the amide of D-pantoate and γ-aminobutyric acid (GABA). This change leads to an additional CH2 in the molecule.[7]

References[edit]

  1. ^ Pantogam, drugs.com
  2. ^ http://pantogam.ru
  3. ^ PMID 21350425
  4. ^ PMID 21183912
  5. ^ PMID 21311483
  6. ^ http://pantogam.ru/preparaty/pantogam-tabletki-instrukcija
  7. ^ Kopelevich, V. M.; Evdokimova, G. S. Marieva T. D., Shmuilovich, L. M. (1971). "Synthesis of D-homopantothenic acid". Pharmaceutical Chemistry Journal 5 (9): 534–536. doi:10.1007/BF00771659. 

External links[edit]