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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10ClN3O3
Molecular Weight 315.711
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Clonazepam

SMILES

[O-][N+](=O)C1=CC=C2NC(=O)CN=C(C3=CC=CC=C3Cl)C2=C1

InChI

InChIKey=DGBIGWXXNGSACT-UHFFFAOYSA-N
InChI=1S/C15H10ClN3O3/c16-12-4-2-1-3-10(12)15-11-7-9(19(21)22)5-6-13(11)18-14(20)8-17-15/h1-7H,8H2,(H,18,20)

HIDE SMILES / InChI
Clonazepam, a benzodiazepine, is used primarily as an anticonvulsant in the treatment of absence seizures, petit mal variant seizures (Lennox-Gastaut syndrome), akinetic and myoclonic seizures, and nocturnal myoclonus. Klonopin is the brand name for Clonazepam, an anxiolytic and anticonvulsant. The precise mechanism by which clonazepam exerts its antiseizure and antipanic effects is unknown, although it is believed to be related to its ability to enhance the activity of gamma aminobutyric acid (GABA), the major inhibitory neurotransmitter in the central nervous system. Allosteric interactions between central benzodiazepine receptors and gamma-aminobutyric acid (GABA) receptors potentiate the effects of GABA. As GABA is an inhibitory neurotransmitter, this results in increased inhibition of the ascending reticular activating system. Benzodiazepines, in this way, block the cortical and limbic arousal that occurs following stimulation of the reticular pathways.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
KLONOPIN

Approved Use

INDICATIONS & USAGE Seizure Disorders: Clonazepam tablets, USP are useful alone or as an adjunct in the treatment of the Lennox-Gastaut syndrome (petit mal variant), akinetic and . In patients with absence seizures (petit mal) who have failed to respond to succinimides, clonazepam may be useful. In some studies, up to 30% of patients have shown a loss of anticonvulsant activity, often within 3 months of administration. In some cases, dosage adjustment may reestablish efficacy. Panic Disorder: Clonazepam tablets, USP are indicated for the treatment of panic disorder, with or without agoraphobia, as defined in DSM-IV. Panic disorder is characterized by the occurrence of unexpected panic attacks and associated concern about having additional attacks, worry about the implications or consequences of the attacks, and/or a significant change in behavior related to the attacks. The efficacy of clonazepam was established in two 6- to 9-week trials in panic disorder patients whose diagnoses corresponded to the DSM-IIIR category of panic disorder. Panic disorder (DSM-IV) is characterized by recurrent unexpected panic attacks, ie, a discrete period of intense fear or discomfort in which four (or more) of the following symptoms develop abruptly and reach a peak within 10 minutes: (1) palpitations, pounding heart or accelerated heart rate; (2) sweating; (3) trembling or shaking; (4) sensations of shortness of breath or smothering; (5) feeling of choking; (6) chest pain or discomfort; (7) nausea or abdominal distress; (8) feeling dizzy, unsteady, lightheaded or faint; (9) derealization (feelings of unreality) or depersonalization (being detached from oneself); (10) fear of losing control; (11) fear of dying; (12) paresthesias (numbness or tingling sensations); (13) chills or hot flushes. The effectiveness of clonazepam in long-term use, that is, for more than 9 weeks, has not been systematically studied in controlled clinical trials. The physician who elects to use clonazepam for extended periods should periodically reevaluate the long-term usefulness of the drug for the individual patient.

Launch Date

1975
Primary
KLONOPIN

Approved Use

INDICATIONS & USAGE Seizure Disorders: Clonazepam tablets, USP are useful alone or as an adjunct in the treatment of the Lennox-Gastaut syndrome (petit mal variant), akinetic and . In patients with absence seizures (petit mal) who have failed to respond to succinimides, clonazepam may be useful. In some studies, up to 30% of patients have shown a loss of anticonvulsant activity, often within 3 months of administration. In some cases, dosage adjustment may reestablish efficacy. Panic Disorder: Clonazepam tablets, USP are indicated for the treatment of panic disorder, with or without agoraphobia, as defined in DSM-IV. Panic disorder is characterized by the occurrence of unexpected panic attacks and associated concern about having additional attacks, worry about the implications or consequences of the attacks, and/or a significant change in behavior related to the attacks. The efficacy of clonazepam was established in two 6- to 9-week trials in panic disorder patients whose diagnoses corresponded to the DSM-IIIR category of panic disorder. Panic disorder (DSM-IV) is characterized by recurrent unexpected panic attacks, ie, a discrete period of intense fear or discomfort in which four (or more) of the following symptoms develop abruptly and reach a peak within 10 minutes: (1) palpitations, pounding heart or accelerated heart rate; (2) sweating; (3) trembling or shaking; (4) sensations of shortness of breath or smothering; (5) feeling of choking; (6) chest pain or discomfort; (7) nausea or abdominal distress; (8) feeling dizzy, unsteady, lightheaded or faint; (9) derealization (feelings of unreality) or depersonalization (being detached from oneself); (10) fear of losing control; (11) fear of dying; (12) paresthesias (numbness or tingling sensations); (13) chills or hot flushes. The effectiveness of clonazepam in long-term use, that is, for more than 9 weeks, has not been systematically studied in controlled clinical trials. The physician who elects to use clonazepam for extended periods should periodically reevaluate the long-term usefulness of the drug for the individual patient.

Launch Date

1975
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.3 ng/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLONAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3 ng/mL
0.5 mg 3 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLONAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
102 ng × h/mL
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLONAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
339 ng × h/mL
0.5 mg 3 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLONAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
40 h
0.5 mg 3 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLONAZEPAM plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
15%
0.5 mg single, oral
dose: 0.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CLONAZEPAM plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 mg single, intramuscular
Dose: 2 mg
Route: intramuscular
Route: single
Dose: 2 mg
Sources:
healthy, 30 years (range: 23–50 years)
Health Status: healthy
Age Group: 30 years (range: 23–50 years)
Sex: M+F
Sources:
2 mg single, intravenous
Dose: 2 mg
Route: intravenous
Route: single
Dose: 2 mg
Sources:
healthy, 30 years (range: 23–50 years)
Health Status: healthy
Age Group: 30 years (range: 23–50 years)
Sex: M+F
Sources:
2 mg single, oral
Dose: 2 mg
Route: oral
Route: single
Dose: 2 mg
Sources:
healthy, 30 years (range: 23–50 years)
Health Status: healthy
Age Group: 30 years (range: 23–50 years)
Sex: M+F
Sources:
1.5 mg 1 times / day multiple, oral
Recommended
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
unhealthy
Disc. AE: Somnolence, Depression...
AEs leading to
discontinuation/dose reduction:
Somnolence (7%)
Depression (4%)
Nervousness (1%)
Dizziness (1%)
Ataxia (1%)
Intellectual disability (1%)
Sources:
6 mg 1 times / day steady, oral
Studied dose
Dose: 6 mg, 1 times / day
Route: oral
Route: steady
Dose: 6 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
AEs

AEs

AESignificanceDosePopulation
Ataxia 1%
Disc. AE
1.5 mg 1 times / day multiple, oral
Recommended
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
unhealthy
Dizziness 1%
Disc. AE
1.5 mg 1 times / day multiple, oral
Recommended
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
unhealthy
Intellectual disability 1%
Disc. AE
1.5 mg 1 times / day multiple, oral
Recommended
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
unhealthy
Nervousness 1%
Disc. AE
1.5 mg 1 times / day multiple, oral
Recommended
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
unhealthy
Depression 4%
Disc. AE
1.5 mg 1 times / day multiple, oral
Recommended
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
unhealthy
Somnolence 7%
Disc. AE
1.5 mg 1 times / day multiple, oral
Recommended
Dose: 1.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 1.5 mg, 1 times / day
Sources:
unhealthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
yes
yes
yes (pharmacogenomic study)
Comment: The statistical analysis displayed significant association between the patients’ CYP3A4 expression and the stable plasma concentrations of clonazepam normalized by the dose and the patient’s bodyweight.
PubMed

PubMed

TitleDatePubMed
Pharmacological options for the treatment of Tourette's disorder.
2001
Psychiatric disorders associated with Cushing's syndrome. Epidemiology, pathophysiology and treatment.
2001
LSD-induced Hallucinogen Persisting Perception Disorder treated with clonazepam: two case reports.
2001
Insomnia and fronto-basal tumor: a case report.
2001
Role of clonazepam in the treatment of idiopathic downbeat nystagmus.
2001 Aug
Benzodiazepines protect against ethanol-induced gastric mucosal damage in vitro.
2001 Aug
Carbamazepine treatment of corticosteroid-induced mood disorder.
2001 Aug
Nonconvulsive status epilepticus associated with cephalosporins in patients with renal failure.
2001 Aug
Smoking and panic disorder.
2001 Aug
Gamma irradiation effects on stability of poly(lactide-co-glycolide) microspheres containing clonazepam.
2001 Aug 10
[Primary orthostatic tremor: slow harmonic component as responsible of inestability].
2001 Aug-Sep
Pharmacoepidemiologic investigation of a clonazepam-carbamazepine interaction by mixed effect modeling using routine clinical pharmacokinetic data in Japanese patients.
2001 Dec
Pharmacological characterization of the 6 Hz psychomotor seizure model of partial epilepsy.
2001 Dec
Direct LC analysis of five benzodiazepines in human urine and plasma using an ADS restricted access extraction column.
2001 Dec
Roles for mitochondrial and reverse mode Na+/Ca2+ exchange and the plasmalemma Ca2+ ATPase in post-tetanic potentiation at crayfish neuromuscular junctions.
2001 Dec 15
Sleep disorders.
2001 Feb
Case report: unexplained syncope explained.
2001 Jul
Infantile status epilepticus in Tunisia. Clinical, etiological and prognostic aspects.
2001 Jul
Involuntary movements in infantile cobalamin deficiency appearing after treatment.
2001 Jul
[Piracetam in the treatment of a patient with idiopathic cortical myoclonus].
2001 Jul 16-31
A 28-year-old woman with panic disorder.
2001 Jul 25
Spectrofluorimetric determination of vigabatrin and gabapentin in dosage forms and spiked plasma samples through derivatization with 4-chloro-7-nitrobenzo-2-oxa-1,3-diazole.
2001 Jul-Aug
Burning mouth syndrome after taking clonazepam.
2001 Jul-Aug
Interaction of GYKI 52466, a selective non-competitive antagonist of AMPA/kainate receptors, with conventional antiepileptic drugs in amygdala-kindled seizures in rats.
2001 Mar-Apr
Stiff leg syndrome: case report.
2001 Nov
Fast orthostatic tremor in Parkinson's disease mimicking primary orthostatic tremor.
2001 Nov
Selective, high-resolution fluorescence imaging of mitochondrial Ca2+ concentration.
2001 Nov
West syndrome: the Philippine experience.
2001 Nov
Kinetic and pharmacological properties of GABA(A) receptors in single thalamic neurons and GABA(A) subunit expression.
2001 Nov
Increased [Mg2+]o reduces Ca2+ influx and disruption of mitochondrial membrane potential during reoxygenation.
2001 Nov
Successful use of methadone in the treatment of chronic neuropathic pain arising from burn injuries: a case-study.
2001 Nov
Determination of benzodiazepines in human hair by on-line high-performance liquid chromatography using a restricted access extraction column.
2001 Nov 15
Population pharmacokinetic analysis resulting in a tool for dose individualization of busulphan in bone marrow transplantation recipients.
2001 Oct
Influence of age and comedication on steady-state clonazepam serum level-dose ratios in Japanese epileptic patients.
2001 Oct
Diazepam inhibits HIV-1 Tat-induced migration of human microglia.
2001 Oct
2-Arylpyrazolo[1,5-a]pyrimidin-3-yl acetamides. New potent and selective peripheral benzodiazepine receptor ligands.
2001 Oct
Effect of clonazepam treatment on antipsychotic drug-induced Meige syndrome and changes in plasma levels of GABA, HVA, and MHPG during treatment.
2001 Oct
A successful clonazepam treatment without tolerance in a patient with spontaneous oral dyskinesia.
2001 Oct
Nutritional parameters modify muricidal behavior of male Wistar rats: preventive effects of amino acids and 4' Cl diazepam.
2001 Oct 26
Evaluation of in vitro percutaneous absorption of lorazepam and clonazepam from hydro-alcoholic gel formulations.
2001 Oct 9
[Involuntary movement disorders as first manifestation of systemic lupus erythematosus: case report].
2001 Sep
[Efficacy of anticonvulsants on acute encephalitis with refractory, repetitive partial seizures (AERRPS)].
2001 Sep
Topiramate as a mood stabilizer.
2001 Sep
Hyperekplexia in neonates.
2001 Sep
Evaluation of polymeric nanoparticles composed of cholic acid and methoxy poly(ethylene glycol).
2001 Sep 11
Effect of midazolam on interleukin-6 mRNA expression in human peripheral blood mononuclear cells in the absence of lipopolysaccharide.
2001 Sep 21
[Treatment and long-term follow-up of post-anoxic myoclonus].
2001 Sep 23
Burning mouth syndrome.
2001 Summer
Effects of commonly used benzodiazepines on the fetus, the neonate, and the nursing infant.
2002 Jan
Spectrofluorimetric determination of vigabatrin and gabapentin in urine and dosage forms through derivatization with fluorescamine.
2002 Jan 1
Patents

Sample Use Guides

Seizure Disorders: Adults: The initial dose for adults with seizure disorders should not exceed 1.5 mg/day divided into three doses. Dosage may be increased in increments of 0.5 to 1 mg every 3 days until seizures are adequately controlled or until side effects preclude any further increase. Maintenance dosage must be individualized for each patient depending upon response. Maximum recommended daily dose is 20 mg. Clonazepam is available as a tablet or an orally disintegrating tablet (wafer). The tablets should be administered with water by swallowing the tablet whole. The orally disintegrating tablet should be administered as follows: After opening the pouch, peel back the foil on the blister. Do not push tablet through foil. Immediately upon opening the blister, using dry hands, remove the tablet and place it in the mouth. Tablet disintegration occurs rapidly in saliva so it can be easily swallowed with or without water.
Route of Administration: Oral
Clonazepam (100 nM) increased inhibitory postsynaptic current (IPSC) decay time constants in rat thalamic nuclei-the reticular nucleus (nRt) (from 44.3 to 77.9 ms, P < 0.01) but not in the ventrobasal (VB) complex..
Name Type Language
Clonazepam
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   VANDF   WHO-DD  
USAN   INN  
Official Name English
Clonazepam CIV
USP-RS  
Preferred Name English
NSC-179913
Code English
Clonazepam [JAN]
Common Name English
RIVOTRIL
Brand Name English
RO-5-4023
Code English
Clonazepam [MART.]
Common Name English
RIVATRIL
Brand Name English
RO5-4023
Code English
2H-1,4-Benzodiazepin-2-one, 5-(2-chlorophenyl)-1,3-dihydro-7-nitro-
Systematic Name English
Clonazepam [WHO-DD]
Common Name English
Clonazepam [ORANGE BOOK]
Common Name English
5-(o-Chlorophenyl)-1,3-dihydro-7-nitro-2H-1,4-benzodiazepin-2-one
Systematic Name English
Clonazepam [MI]
Common Name English
KLONOPIN
Brand Name English
Clonazepam [EP MONOGRAPH]
Common Name English
RO-54023
Code English
Clonazepam [INN]
Common Name English
RAVOTRIL
Brand Name English
Clonazepam [VANDF]
Common Name English
Clonazepam CIV [USP-RS]
Common Name English
Clonazepam [HSDB]
Common Name English
Clonazepam [USAN]
Common Name English
Clonazepam [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175694
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
WHO-VATC QN03AE01
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
NCI_THESAURUS C264
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
FDA ORPHAN DRUG 243507
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
WHO-ATC N03AE01
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
NDF-RT N0000007542
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
NCI_THESAURUS C1012
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
DEA NO. 2737
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
LIVERTOX NBK548030
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
FDA ORPHAN DRUG 82794
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
Code System Code Type Description
PUBCHEM
2802
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
WIKIPEDIA
CLONAZEPAM
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
SMS_ID
100000084528
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
RXCUI
2598
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY RxNorm
DRUG CENTRAL
703
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
NSC
179913
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
LACTMED
Clonazepam
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
DAILYMED
5PE9FDE8GB
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
DRUG BANK
DB01068
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
CAS
1622-61-3
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
MESH
D002998
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
RS_ITEM_NUM
1140305
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PRIMARY
CHEBI
3756
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
MERCK INDEX
m3649
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
216-596-2
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
EPA CompTox
DTXSID1022845
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
INN
2765
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PRIMARY
NCI_THESAURUS
C28935
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
FDA UNII
5PE9FDE8GB
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
EVMPD
SUB06728MIG
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
ChEMBL
CHEMBL452
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
HSDB
3265
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY
IUPHAR
6963
Created by admin on Wed Apr 02 08:32:11 GMT 2025 , Edited by admin on Wed Apr 02 08:32:11 GMT 2025
PRIMARY