Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H10N4 |
| Molecular Weight | 138.1704 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CCN2N=NN=C2CC1
InChI
InChIKey=CWRVKFFCRWGWCS-UHFFFAOYSA-N
InChI=1S/C6H10N4/c1-2-4-6-7-8-9-10(6)5-3-1/h1-5H2
| Molecular Formula | C6H10N4 |
| Molecular Weight | 138.1704 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Pentetrazol (pentylenetetrazole, BTD-001) is a pharmaceutical agent that displays activity as a central nervous system and respiratory stimulant. It is considered a non-competitive gamma-aminobutyric acid (GABA) antagonist. Pentetrazol (pentylenetetrazole) has been used experimentally to study seizure phenomenon and to identify pharmaceuticals that may control seizure susceptibility. GABA is thought to play a role in promoting sleep and its function is believed to be elevated in idiopathic hypersomnia. By blocking GABA’s function, pentetrazol (pentylenetetrazole, BTD-001) is expected to reduce excessive daytime sleepiness.
CNS Activity
Originator
Approval Year
Doses
| Dose | Population | Adverse events |
|---|---|---|
32 mg 3 times / day multiple, oral Recommended Dose: 32 mg, 3 times / day Route: oral Route: multiple Dose: 32 mg, 3 times / day Sources: |
unhealthy, 1-7 n = 23 Health Status: unhealthy Condition: mental deficiency due to Mongolism Age Group: 1-7 Sex: M+F Population Size: 23 Sources: |
Other AEs: Convulsive seizure, Weight gain... Other AEs: Convulsive seizure (1 patient) Sources: Weight gain (16 patients) |
130 mg 3 times / day multiple, oral Recommended Dose: 130 mg, 3 times / day Route: oral Route: multiple Dose: 130 mg, 3 times / day Sources: |
unhealthy, 4-11 n = 26 Health Status: unhealthy Condition: mental deficiency Age Group: 4-11 Sex: M+F Population Size: 26 Sources: |
Other AEs: Convulsive seizure, Weight gain... Other AEs: Convulsive seizure (1 patient) Sources: Weight gain (21 patient) Weight loss (4 patients) |
97 mg 3 times / day multiple, oral Recommended Dose: 97 mg, 3 times / day Route: oral Route: multiple Dose: 97 mg, 3 times / day Sources: |
unhealthy, 5-17 n = 72 Health Status: unhealthy Condition: mental deficiency Age Group: 5-17 Sex: F Population Size: 72 Sources: |
Disc. AE: Behavior disorder... AEs leading to discontinuation/dose reduction: Behavior disorder (3 patients) Sources: |
200 mg 4 times / day multiple, oral Recommended Dose: 200 mg, 4 times / day Route: oral Route: multiple Dose: 200 mg, 4 times / day Sources: |
unhealthy, 65-82 n = 10 Health Status: unhealthy Condition: memory impairment Age Group: 65-82 Sex: M+F Population Size: 10 Sources: |
Other AEs: Weight loss... |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, 65-93 n = 19 Health Status: unhealthy Condition: psychiatric disorder Age Group: 65-93 Sex: M+F Population Size: 19 Sources: |
Disc. AE: Dizziness, Drowsiness... AEs leading to discontinuation/dose reduction: Dizziness (2 patients) Sources: Drowsiness (1 patient) Nausea (1 patient) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Convulsive seizure | 1 patient | 32 mg 3 times / day multiple, oral Recommended Dose: 32 mg, 3 times / day Route: oral Route: multiple Dose: 32 mg, 3 times / day Sources: |
unhealthy, 1-7 n = 23 Health Status: unhealthy Condition: mental deficiency due to Mongolism Age Group: 1-7 Sex: M+F Population Size: 23 Sources: |
| Weight gain | 16 patients | 32 mg 3 times / day multiple, oral Recommended Dose: 32 mg, 3 times / day Route: oral Route: multiple Dose: 32 mg, 3 times / day Sources: |
unhealthy, 1-7 n = 23 Health Status: unhealthy Condition: mental deficiency due to Mongolism Age Group: 1-7 Sex: M+F Population Size: 23 Sources: |
| Convulsive seizure | 1 patient | 130 mg 3 times / day multiple, oral Recommended Dose: 130 mg, 3 times / day Route: oral Route: multiple Dose: 130 mg, 3 times / day Sources: |
unhealthy, 4-11 n = 26 Health Status: unhealthy Condition: mental deficiency Age Group: 4-11 Sex: M+F Population Size: 26 Sources: |
| Weight gain | 21 patient | 130 mg 3 times / day multiple, oral Recommended Dose: 130 mg, 3 times / day Route: oral Route: multiple Dose: 130 mg, 3 times / day Sources: |
unhealthy, 4-11 n = 26 Health Status: unhealthy Condition: mental deficiency Age Group: 4-11 Sex: M+F Population Size: 26 Sources: |
| Weight loss | 4 patients | 130 mg 3 times / day multiple, oral Recommended Dose: 130 mg, 3 times / day Route: oral Route: multiple Dose: 130 mg, 3 times / day Sources: |
unhealthy, 4-11 n = 26 Health Status: unhealthy Condition: mental deficiency Age Group: 4-11 Sex: M+F Population Size: 26 Sources: |
| Behavior disorder | 3 patients Disc. AE |
97 mg 3 times / day multiple, oral Recommended Dose: 97 mg, 3 times / day Route: oral Route: multiple Dose: 97 mg, 3 times / day Sources: |
unhealthy, 5-17 n = 72 Health Status: unhealthy Condition: mental deficiency Age Group: 5-17 Sex: F Population Size: 72 Sources: |
| Weight loss | 9 patients | 200 mg 4 times / day multiple, oral Recommended Dose: 200 mg, 4 times / day Route: oral Route: multiple Dose: 200 mg, 4 times / day Sources: |
unhealthy, 65-82 n = 10 Health Status: unhealthy Condition: memory impairment Age Group: 65-82 Sex: M+F Population Size: 10 Sources: |
| Drowsiness | 1 patient Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, 65-93 n = 19 Health Status: unhealthy Condition: psychiatric disorder Age Group: 65-93 Sex: M+F Population Size: 19 Sources: |
| Nausea | 1 patient Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, 65-93 n = 19 Health Status: unhealthy Condition: psychiatric disorder Age Group: 65-93 Sex: M+F Population Size: 19 Sources: |
| Dizziness | 2 patients Disc. AE |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, 65-93 n = 19 Health Status: unhealthy Condition: psychiatric disorder Age Group: 65-93 Sex: M+F Population Size: 19 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Levetiracetam: the preclinical profile of a new class of antiepileptic drugs? | 2001 |
|
| Effects of ketoconazole on oestrus cycle and convulsant action of pentylenetetrazol in mice. | 2001 Dec |
|
| KJ Smith, M Theal, A Mulji. Pericarditis presenting and treated as an acute anterospetal myocardial infarction. Can J Cardiol 2001;17(7):815-817. | 2001 Dec |
|
| Stimulation of gene expression of NeuroD-related factor in the mouse brain following pentylenetetrazol-induced seizures. | 2001 Dec 30 |
|
| Neurobehavioural study of subchronic administration of oxydemeton-methyl (insecticide and acaricide) in rats. | 2001 Jul |
|
| Comparison of the anticonvulsant efficacies and neurotoxic effects of valproic acid, phenytoin, and the ketogenic diet. | 2001 Oct |
|
| Myectomy for hypertrophic obstructive cardiomyopathy after failed alcohol septal ablation: Clinicopathological correlations. Can J Cardiol 2001;17:197-202. | 2001 Oct |
|
| Low doses of AMPA exert anticonvulsant effects on pentylenetetrazol-kindled seizures. | 2001 Oct-Nov |
|
| Morphological alterations of neurons and astrocytes and changes in emotional behavior in pentylenetetrazol-kindled rats. | 2001 Oct-Nov |
|
| Decreased susceptibility to pentylenetetrazol-induced seizures after low-frequency transcranial magnetic stimulation in rats. | 2001 Sep 14 |
|
| Effects of angiotensin III and angiotensin IV on pentylenetetrazol seizure susceptibility (threshold and kindling): interaction with adenosine A(1) receptors. | 2001 Sep 15 |
|
| Re: Morales, FJ, Montemayor T, Martínez A. Shuttle versus six-minute walk test in the prediction of outcome in chronic heart failure. Int J Cardiol 2000;76: 101-105. | 2001 Sep-Oct |
|
| Behavior and physiology of mice lacking the GABAA-receptor delta subunit. | 2002 |
|
| Effects of NG-nitro-L-arginine methyl ester, 7-nitro indazole, and agmatine on pentylenetetrazol-induced discriminative stimulus in Long-Evans rats. | 2002 Apr |
|
| Proconvulsant effects of high doses of venlafaxine in pentylenetetrazole-convulsive rats. | 2002 Apr |
|
| 2-Chloroadenosine, a preferential agonist of adenosine A1 receptors, enhances the anticonvulsant activity of carbamazepine and clonazepam in mice. | 2002 Apr |
|
| Seizure-mediated accumulation of the beta subunit of Ca2+/calmodulin-dependent protein kinase II in nuclei of mouse brain cells. | 2002 Apr 12 |
|
| Anxiolytic and anticonvulsive activity of Sesbania grandiflora leaves in experimental animals. | 2002 Aug |
|
| GABA-A receptor complex and memory processes. | 2002 Aug |
|
| Synthesis and anticonvulsant activity of enaminones. 4. Investigations on isoxazole derivatives. | 2002 Aug |
|
| Anticonvulsant profile and teratogenicity of N-methyl-tetramethylcyclopropyl carboxamide: a new antiepileptic drug. | 2002 Feb |
|
| Is glutamine beneficial in ischemic heart disease? | 2002 Feb |
|
| [A novel model of perfused rat brain with intact nervous system]. | 2002 Jan |
|
| The effects of callosal agenesis on the susceptibility to seizures elicited by pentylenetetrazol in BALB/cCF mice. | 2002 Jan-Feb |
|
| Increase of nucleotidase activities in rat blood serum after a single convulsive injection of pentylenetetrazol. | 2002 Jul |
|
| Anticonvulsant profile and mechanism of action of propranolol and its two enantiomers. | 2002 Jul |
|
| Anticonvulsive activity of Butea monosperma flowers in laboratory animals. | 2002 Jul |
|
| The discriminative stimulus effects of pentylenetetrazol as a model of anxiety: recent developments. | 2002 Jun |
|
| Possible anxiolytic effects of ivermectin in rats. | 2002 Jun |
|
| Do preclinical seizure models preselect certain adverse effects of antiepileptic drugs. | 2002 Jun |
|
| Anticonvulsant and sedative effects of Salvadora persica L. stem extracts. | 2002 Jun |
|
| Pentylenetetrazol-induced recurrent seizures in rat pups: time course on spatial learning and long-term effects. | 2002 Jun |
|
| GABA(A)-benzodiazepine receptor complex sensitivity in 5-HT(1A) receptor knockout mice on a 129/Sv background. | 2002 Jun 28 |
|
| Effects of antisense glutamic acid decarboxylase oligodeoxynucleotide on epileptic rats induced by pentylenetetrazol. | 2002 Mar |
|
| Effects of lorazepam treatment for multiple ethanol withdrawals in mice. | 2002 Mar |
|
| Selectivity of the protective effects of dihydropyridine calcium channel antagonists against the ethanol withdrawal syndrome. | 2002 Mar 15 |
|
| Anxiogenic properties of Ptychopetalum olacoides Benth. (Marapuama). | 2002 May |
|
| Changes of cortical epileptic afterdischarges under the influence of convulsant drugs. | 2002 May |
|
| Nitric oxide (NO) and convulsions induced by pentylenetetrazol. | 2002 May |
|
| Cardiovascular protection by alcohol and polyphenols: role of nitric oxide. | 2002 May |
|
| The effects of ACTH and adrenocorticosteroids on seizure susceptibility in 15-day-old male rats. | 2002 May |
|
| GABAA-benzodiazepine receptor complex ligands and stress-induced hyperthermia in singly housed mice. | 2002 May |
|
| Stress-induced deoxycorticosterone-derived neurosteroids modulate GABA(A) receptor function and seizure susceptibility. | 2002 May 1 |
|
| Congenic mapping of alcohol and pentobarbital withdrawal liability loci to a <1 centimorgan interval of murine chromosome 4: identification of Mpdz as a candidate gene. | 2002 May 1 |
|
| Developmental lead exposure differentially alters the susceptibility to chemoconvulsants in rats. | 2002 May 1 |
|
| Neonatal toluene exposure selectively alters sensitivity to different chemoconvulsant drugs in juvenile rats. | 2002 Nov |
|
| Effects of pentylenetetrazol-induced kindling of seizures on rat emotional behavior and brain monoaminergic systems. | 2002 Nov |
|
| Effect of CGP39551 administration on the kindling of ethanol-withdrawal seizures. | 2002 Sep |
|
| Lithium and KB-R7943 effects on mechanics and energetics of rat heart muscle. | 2002 Sep |
|
| Single mutation (A162H) in human cardiac troponin I corrects acid pH sensitivity of Ca2+-regulated actomyosin S1 ATPase. | 2002 Sep 20 |
Sample Use Guides
In rat alpha1/beta2/gamma2 gamma-aminobutyric acid (GABA) type A receptors, pentetrazol inhibited GABA-activated Cl(-) current in a concentration-dependent, voltage-independent manner, with an IC50 of 0.62 +/- 0.13 mM. The mechanism of inhibition appeared competitive with respect to GABA in both rat and human alpha1/beta2/gamma2 receptors. Varying subunit configuration (change or lack of alpha subunit isoform or lack of gamma2 subunit) had modest effects on pentetrazol-induced inhibition, as evidenced by comparable IC50 values (0.6-2.2 mM) in all receptor configurations tested. Using a one-site model for pentetrazol interaction with alpha1/beta2/gamma2 receptors, the association rate (k(+1)) was found to be 1.14 x 10^3 M(-1)s(-1) and the dissociation rate (k(-1)) was 0.476 s(-1), producing a functional Kd of 0.418 mM.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:02:06 UTC 2023
by
admin
on
Fri Dec 15 16:02:06 UTC 2023
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| Record UNII |
WM5Z385K7T
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| Record Status |
Validated (UNII)
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| Record Version |
|
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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EU-Orphan Drug |
EU/3/15/1569
Created by
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FDA ORPHAN DRUG |
558716
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WHO-VATC |
QR07AB53
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WHO-ATC |
R07AB03
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FDA ORPHAN DRUG |
488815
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WHO-ATC |
R07AB53
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WHO-VATC |
QR07AB03
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NCI_THESAURUS |
C47795
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admin on Fri Dec 15 16:02:06 UTC 2023 , Edited by admin on Fri Dec 15 16:02:06 UTC 2023
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3428
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D010433
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m8524
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PENTYLENETETRAZOL
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5917
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WM5Z385K7T
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66489
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DTXSID7041091
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SUB09690MIG
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54-95-5
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DB13415
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100000082492
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CHEMBL116943
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C81054
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34910
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200-219-3
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8015
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410
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5729
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