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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H19NO5
Molecular Weight 233.2616
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HOPANTENIC ACID

SMILES

CC(C)(CO)[C@@H](O)C(=O)NCCCC(O)=O

InChI

InChIKey=SBBDHANTMHIRGW-QMMMGPOBSA-N
InChI=1S/C10H19NO5/c1-10(2,6-12)8(15)9(16)11-5-3-4-7(13)14/h8,12,15H,3-6H2,1-2H3,(H,11,16)(H,13,14)/t8-/m0/s1

HIDE SMILES / InChI

Molecular Formula C10H19NO5
Molecular Weight 233.2616
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Hopantenic acid (homopantothenic acid) is a central nervous system depressant. Formulated as the calcium salt, it is used as a pharmaceutical drug in the Russian Federation under the brand name Pantogam. In Russia it is widely used to treat a variety of neurological, psychological and psychiatric conditions. The drug has been on the pharmaceutical market since 1979 and has been proven to be safe even for children from 3 years old upwards. Hopantenic acid is a natural forming substance, has some of the lowest side effects and considered to be very safe. Use Pantogam to treat a wide variety of cognitive and nervous system disorders with combined sedative and mild stimulant effect. Hopantenic acid is not approved for use in Europe or the United States. GABA receptor agonist.

Originator

Curator's Comment: Hopantenic acid that was firstly synthesized in Japan in the beginning of 1950s

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PANTOGAM

Approved Use

USES Improves Mental and Physical Ability Become More Calm Erradicate Mood Swings Treat Epilepsy in Both Adults and Children Reduce Hyperactivity in Children Treat Attention Deficit Disorders Treat Nerve Ticks
Primary
PANTOGAM

Approved Use

Indications • congitive affections due to organic impairments of the brain (including consequences of neuro-infections and craniocerebral traumas) and neurotic disturbances; • schizophrenia with a cerebral organic insufficiency ; • • cerebrovascular insufficiency due to aterosclerotic changes of the brain; • extrapyramid hyper-kinesises (myoclonus epilepsy, Huntingtone's chorea, hepato-lenticular degeneration, Parkinson's disease etc.), for treatment of the extrapyramid syndrome due to a neuroleptics use; • epilepsy with deceleration of psychic processes and a decrease of a cognitive productivity (in combination with anti-convulsive drugs); • psycho-emotional overloads, a decrease of the mental and physical workability, for an improvement of an attention concentration and memorization; • neurogenous disturbances of urination (pollakiuria, imperative feelings of urination, imperative urinary incontinence, enuresis); • children with a perinatal encephalopathy; mental retardation of a different severity (including that with behavioral disturbances); psychology state affections in children, like a common psychic development retardation, specific speech disturbances, motoric functions and combined states; hyperkinetic disturbances, including a hyperactivity syndrome with an attention deficiency; neurosis-like states (stammering (preferably a clonic form), tics).
Primary
PANTOGAM

Approved Use

Indications • congitive affections due to organic impairments of the brain (including consequences of neuro-infections and craniocerebral traumas) and neurotic disturbances; • schizophrenia with a cerebral organic insufficiency ; • • cerebrovascular insufficiency due to aterosclerotic changes of the brain; • extrapyramid hyper-kinesises (myoclonus epilepsy, Huntingtone's chorea, hepato-lenticular degeneration, Parkinson's disease etc.), for treatment of the extrapyramid syndrome due to a neuroleptics use; • epilepsy with deceleration of psychic processes and a decrease of a cognitive productivity (in combination with anti-convulsive drugs); • psycho-emotional overloads, a decrease of the mental and physical workability, for an improvement of an attention concentration and memorization; • neurogenous disturbances of urination (pollakiuria, imperative feelings of urination, imperative urinary incontinence, enuresis); • children with a perinatal encephalopathy; mental retardation of a different severity (including that with behavioral disturbances); psychology state affections in children, like a common psychic development retardation, specific speech disturbances, motoric functions and combined states; hyperkinetic disturbances, including a hyperactivity syndrome with an attention deficiency; neurosis-like states (stammering (preferably a clonic form), tics).
Primary
PANTOGAM

Approved Use

Indications • congitive affections due to organic impairments of the brain (including consequences of neuro-infections and craniocerebral traumas) and neurotic disturbances; • schizophrenia with a cerebral organic insufficiency ; • • cerebrovascular insufficiency due to aterosclerotic changes of the brain; • extrapyramid hyper-kinesises (myoclonus epilepsy, Huntingtone's chorea, hepato-lenticular degeneration, Parkinson's disease etc.), for treatment of the extrapyramid syndrome due to a neuroleptics use; • epilepsy with deceleration of psychic processes and a decrease of a cognitive productivity (in combination with anti-convulsive drugs); • psycho-emotional overloads, a decrease of the mental and physical workability, for an improvement of an attention concentration and memorization; • neurogenous disturbances of urination (pollakiuria, imperative feelings of urination, imperative urinary incontinence, enuresis); • children with a perinatal encephalopathy; mental retardation of a different severity (including that with behavioral disturbances); psychology state affections in children, like a common psychic development retardation, specific speech disturbances, motoric functions and combined states; hyperkinetic disturbances, including a hyperactivity syndrome with an attention deficiency; neurosis-like states (stammering (preferably a clonic form), tics).
PubMed

PubMed

TitleDatePubMed
Intracranial self-stimulation and locomotor traces as indicators for evaluating the homopantothenic acid.
1993 Dec
Chemical knockout of pantothenate kinase reveals the metabolic and genetic program responsible for hepatic coenzyme A homeostasis.
2007 Mar
Patents

Patents

Sample Use Guides

In Vivo Use Guide
To be taken orally 15-30 minutes after breakfast and lunch. Can be taken by children from 3 years old upwards. For adults: Single dose 250-1000 mg, daily dose 1500-3000 mg. For children: Single dose 250-500 mg, daily dose 750-2000 mg. Course of treatment is 1-4 months, sometimes 6 months. A break of 3-6 months is required between courses of treatment.
Route of Administration: Oral
In Vitro Use Guide
Hopantenic acid inhibits the absorption of [14C]-GABA (0.2 uM) by the rat brain cortex slices (3 mm) incubated in calcium-free medium. The effect of Hopantenic acid manifests at its low concentrations (10(-6) M).
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:10:06 GMT 2023
Edited
by admin
on Fri Dec 15 16:10:06 GMT 2023
Record UNII
H473MVB16U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HOPANTENIC ACID
INN   MI   WHO-DD  
INN  
Official Name English
4-(((2R)-2,4-DIHYDROXY-3,3-DIMETHYL-1-OXOBUTYL)AMINO)BUTANOIC ACID
Systematic Name English
PANTOCALCIN
Brand Name English
hopantenic acid [INN]
Common Name English
HOPANTENIC ACID [MI]
Common Name English
D-HOMOPANTOTHENIC ACID
Common Name English
D-(+)-4-(2,4-DIHYDROXY-3,3-DIMETHYLBUTYRAMIDO)BUTYRIC ACID
Common Name English
Hopantenic acid [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
Code System Code Type Description
DRUG CENTRAL
3280
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
WIKIPEDIA
HOPANTENIC ACID
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
PUBCHEM
28281
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
EVMPD
SUB08055MIG
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
DRUG BANK
DB14044
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110783
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
INN
2649
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
SMS_ID
100000083987
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
NCI_THESAURUS
C83808
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
CAS
18679-90-8
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
FDA UNII
H473MVB16U
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID6048331
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
MESH
C016030
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY
MERCK INDEX
m6053
Created by admin on Fri Dec 15 16:10:06 GMT 2023 , Edited by admin on Fri Dec 15 16:10:06 GMT 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
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ACTIVE MOIETY