Details
Stereochemistry | ACHIRAL |
Molecular Formula | C31H44ClN3O2S |
Molecular Weight | 558.218 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCC(=O)OCCN1CCN(CCCN2C3=C(SC4=C2C=C(Cl)C=C4)C=CC=C3)CC1
InChI
InChIKey=WAVWONFNDBPAGA-UHFFFAOYSA-N
InChI=1S/C31H44ClN3O2S/c1-2-3-4-5-6-7-8-14-31(36)37-24-23-34-21-19-33(20-22-34)17-11-18-35-27-12-9-10-13-29(27)38-30-16-15-26(32)25-28(30)35/h9-10,12-13,15-16,25H,2-8,11,14,17-24H2,1H3
Molecular Formula | C31H44ClN3O2S |
Molecular Weight | 558.218 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Perphenazine is a relatively high potency phenothiazine that blocks dopamine 2 receptors predominantly, but also may possess antagonist actions at histamine 1 and cholinergic M1 and alpha 1 adrenergic receptors in the vomiting center leading to reduced nausea and vomiting. The drug was approved by FDA for the treatment of schizophrenia and control of severe nausea and vomiting (either alone or in combination with amitriptyline hydrochloride). Perphenazine is extensively hepatic to metabolites via sulfoxidation, hydroxylation, dealkylation, and glucuronidation; primarily metabolized by CYP2D6 to N-dealkylated perphenazine, perphenazine sulfoxide, and 7-hydroxyperphenazine (active metabolite with 70% of the activity of perphenazine) and excreted in the urine and feces.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) Sources: http://apm.amegroups.com/article/view/1039/1266 |
0.16 nM [Ki] | ||
Target ID: P35367 Gene ID: 3269.0 Gene Symbol: HRH1 Target Organism: Homo sapiens (Human) Sources: http://apm.amegroups.com/article/view/1039/1266 |
8.0 nM [Kd] | ||
Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: http://apm.amegroups.com/article/view/1039/1266 |
1.5 µM [Kd] | ||
Target ID: CHEMBL2094251 Sources: http://apm.amegroups.com/article/view/1039/1266 |
10.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | PERPHENAZINE Approved UsePerphenazine is indicated for use in the treatment of schizophrenia and for the control of severe nausea and vomiting in adults. Launch Date1988 |
|||
Preventing | PERPHENAZINE Approved UsePerphenazine is indicated for use in the treatment of schizophrenia and for the control of severe nausea and vomiting in adults. Launch Date1988 |
|||
Primary | PERPHENAZINE Approved UsePerphenazine is indicated for use in the treatment of schizophrenia and for the control of severe nausea and vomiting in adults. Launch Date1988 |
|||
Primary | PERPHENAZINE AND AMITRIPTYLINE HYDROCHLORIDE Approved UsePerphenazine and amitriptyline hydrochloride tablets are recommended for treatment of (1) patients with moderate to severe anxiety and/or agitation and depressed mood, (2) patients with depression in whom anxiety and/or agitation are severe, and (3) patients with depression and anxiety in association with chronic physical disease. In many of these patients, anxiety masks the depressive state so that, although therapy with a tranquilizer appears to be indicated, the administration of a tranquilizer alone will not be adequate. Launch Date1988 |
|||
Primary | PERPHENAZINE AND AMITRIPTYLINE HYDROCHLORIDE Approved UsePerphenazine and amitriptyline hydrochloride tablets are recommended for treatment of (1) patients with moderate to severe anxiety and/or agitation and depressed mood, (2) patients with depression in whom anxiety and/or agitation are severe, and (3) patients with depression and anxiety in association with chronic physical disease. In many of these patients, anxiety masks the depressive state so that, although therapy with a tranquilizer appears to be indicated, the administration of a tranquilizer alone will not be adequate. Launch Date1988 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
509 pg/mL |
4 mg 3 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
7-HYDROXYPERPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
0.546 ng/mL |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
984 pg/mL |
4 mg 3 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PERPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.673 ng × h/mL |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.8 h |
4 mg 3 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
7-HYDROXYPERPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
9.12 h |
16 mg single, oral dose: 16 mg route of administration: Oral experiment type: SINGLE co-administered: |
PERPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
12 h |
4 mg 3 times / day steady-state, oral dose: 4 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
PERPHENAZINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9% |
unknown, unknown |
PERPHENAZINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
0.93 g single, oral Overdose Dose: 0.93 g Route: oral Route: single Dose: 0.93 g Co-administed with:: maprotiline, p.o(5.6 g; single) Sources: Page: p.2627, 2631triazolam, p.o(14 mg; single) salicylate |
unhealthy, 42 n = 1 Health Status: unhealthy Condition: Depression Age Group: 42 Sex: M Population Size: 1 Sources: Page: p.2627, 2631 |
Disc. AE: QT interval prolonged, Hypothermia... AEs leading to discontinuation/dose reduction: QT interval prolonged Sources: Page: p.2627, 2631Hypothermia Loss of consciousness PR interval prolonged QRS prolonged |
200 mg single, oral Overdose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: Page: p.104 |
unhealthy, 48 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 48 Sex: F Population Size: 1 Sources: Page: p.104 |
Disc. AE: Coma, Hypothermia... AEs leading to discontinuation/dose reduction: Coma Sources: Page: p.104Hypothermia Tachycardia Miosis |
30 mg 1 times / day multiple, intramuscular (total daily dose) Recommended Dose: 30 mg, 1 times / day Route: intramuscular Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.3 |
Disc. AE: Tardive dyskinesia... AEs leading to discontinuation/dose reduction: Tardive dyskinesia Sources: Page: p.3 |
30 mg 1 times / day multiple, intramuscular (total daily dose) Recommended Dose: 30 mg, 1 times / day Route: intramuscular Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.4 |
Disc. AE: Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Neuroleptic malignant syndrome Sources: Page: p.4 |
64 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 64 mg, 1 times / day Route: oral Route: multiple Dose: 64 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.3 |
Disc. AE: Tardive dyskinesia... AEs leading to discontinuation/dose reduction: Tardive dyskinesia Sources: Page: p.3 |
64 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 64 mg, 1 times / day Route: oral Route: multiple Dose: 64 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.4 |
Disc. AE: Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Neuroleptic malignant syndrome Sources: Page: p.4 |
20 mg single, intramuscular Studied dose Dose: 20 mg Route: intramuscular Route: single Dose: 20 mg Sources: |
unhealthy n = 1 Health Status: unhealthy Condition: Schizophrenia Population Size: 1 Sources: |
Disc. AE: Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Neuroleptic malignant syndrome Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypothermia | Disc. AE | 0.93 g single, oral Overdose Dose: 0.93 g Route: oral Route: single Dose: 0.93 g Co-administed with:: maprotiline, p.o(5.6 g; single) Sources: Page: p.2627, 2631triazolam, p.o(14 mg; single) salicylate |
unhealthy, 42 n = 1 Health Status: unhealthy Condition: Depression Age Group: 42 Sex: M Population Size: 1 Sources: Page: p.2627, 2631 |
Loss of consciousness | Disc. AE | 0.93 g single, oral Overdose Dose: 0.93 g Route: oral Route: single Dose: 0.93 g Co-administed with:: maprotiline, p.o(5.6 g; single) Sources: Page: p.2627, 2631triazolam, p.o(14 mg; single) salicylate |
unhealthy, 42 n = 1 Health Status: unhealthy Condition: Depression Age Group: 42 Sex: M Population Size: 1 Sources: Page: p.2627, 2631 |
PR interval prolonged | Disc. AE | 0.93 g single, oral Overdose Dose: 0.93 g Route: oral Route: single Dose: 0.93 g Co-administed with:: maprotiline, p.o(5.6 g; single) Sources: Page: p.2627, 2631triazolam, p.o(14 mg; single) salicylate |
unhealthy, 42 n = 1 Health Status: unhealthy Condition: Depression Age Group: 42 Sex: M Population Size: 1 Sources: Page: p.2627, 2631 |
QRS prolonged | Disc. AE | 0.93 g single, oral Overdose Dose: 0.93 g Route: oral Route: single Dose: 0.93 g Co-administed with:: maprotiline, p.o(5.6 g; single) Sources: Page: p.2627, 2631triazolam, p.o(14 mg; single) salicylate |
unhealthy, 42 n = 1 Health Status: unhealthy Condition: Depression Age Group: 42 Sex: M Population Size: 1 Sources: Page: p.2627, 2631 |
QT interval prolonged | Disc. AE | 0.93 g single, oral Overdose Dose: 0.93 g Route: oral Route: single Dose: 0.93 g Co-administed with:: maprotiline, p.o(5.6 g; single) Sources: Page: p.2627, 2631triazolam, p.o(14 mg; single) salicylate |
unhealthy, 42 n = 1 Health Status: unhealthy Condition: Depression Age Group: 42 Sex: M Population Size: 1 Sources: Page: p.2627, 2631 |
Coma | Disc. AE | 200 mg single, oral Overdose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: Page: p.104 |
unhealthy, 48 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 48 Sex: F Population Size: 1 Sources: Page: p.104 |
Hypothermia | Disc. AE | 200 mg single, oral Overdose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: Page: p.104 |
unhealthy, 48 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 48 Sex: F Population Size: 1 Sources: Page: p.104 |
Miosis | Disc. AE | 200 mg single, oral Overdose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: Page: p.104 |
unhealthy, 48 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 48 Sex: F Population Size: 1 Sources: Page: p.104 |
Tachycardia | Disc. AE | 200 mg single, oral Overdose Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: Page: p.104 |
unhealthy, 48 n = 1 Health Status: unhealthy Condition: Schizophrenia Age Group: 48 Sex: F Population Size: 1 Sources: Page: p.104 |
Tardive dyskinesia | Disc. AE | 30 mg 1 times / day multiple, intramuscular (total daily dose) Recommended Dose: 30 mg, 1 times / day Route: intramuscular Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.3 |
Neuroleptic malignant syndrome | Disc. AE | 30 mg 1 times / day multiple, intramuscular (total daily dose) Recommended Dose: 30 mg, 1 times / day Route: intramuscular Route: multiple Dose: 30 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.4 |
Tardive dyskinesia | Disc. AE | 64 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 64 mg, 1 times / day Route: oral Route: multiple Dose: 64 mg, 1 times / day Sources: Page: p.3 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.3 |
Neuroleptic malignant syndrome | Disc. AE | 64 mg 1 times / day multiple, oral (total daily dose) Recommended Dose: 64 mg, 1 times / day Route: oral Route: multiple Dose: 64 mg, 1 times / day Sources: Page: p.4 |
unhealthy Health Status: unhealthy Condition: Schizophrenia Sources: Page: p.4 |
Neuroleptic malignant syndrome | Disc. AE | 20 mg single, intramuscular Studied dose Dose: 20 mg Route: intramuscular Route: single Dose: 20 mg Sources: |
unhealthy n = 1 Health Status: unhealthy Condition: Schizophrenia Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/10460810/ Page: abstract |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10460810/ Page: abstract |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10460810/ Page: abstract |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10460810/ Page: abstract |
yes [IC50 1.5 uM] | |||
Page: abstract |
yes [IC50 38.2 uM] | |||
Sources: https://dmd.aspetjournals.org/content/44/3/378.short Page: 42.0 |
yes [IC50 66.2 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/10460810/ Page: abstract |
yes [Ki 65.1 uM] | |||
Sources: https://iv.iiarjournals.org/content/23/6/943.short Page: 945.0 |
yes | |||
Page: 962.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 961.0 |
yes | |||
Page: 510.0 |
yes | |||
Page: 961.0 |
yes | |||
Page: 961.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 1033.0 |
||||
Page: abstract |
PubMed
Title | Date | PubMed |
---|---|---|
The bucco-linguo-masticatory syndrome as a side-effect of neuroleptics therapy. | 1967 |
|
Side-effects of phenothiazines. | 1967 Apr 1 |
|
Phenothiazines in early labour. | 1967 Feb 11 |
|
Drug-induced extrapyramidal symptoms: their incidence and treatment. | 1967 Jan |
|
Oculogyric crises due to phenothiazines. | 1967 Jul 22 |
|
Specific therapeutic actions of acetophenazine, perphenazine, and benzquinamide in newly admitted schizophrenic patients. | 1967 Mar-Apr |
|
Phenothiazines and diabetes in hospitalized women. | 1968 Jan |
|
Dystonic reaction to perphenazine. | 1969 Aug 9 |
|
Iatrogenic epilepsy due to antidepressant drugs. | 1969 Oct 11 |
|
Idiosyncratic responses to phenothiazines. | 1972 Jan 22 |
|
Letter: Side-effects of perphenazine. | 1975 Jun 21 |
|
Drug-induced dystonia. | 1975 May |
|
Tetany, tetanus or drug reaction? A case report. | 1976 Jul |
|
Asymptomatic idiopathic syndrome of prolonged Q-T interval in a 45-year-old woman. Ventricular tachyarrhythmias precipitated by hypokalemia and therapy with amitriptyline and prephenazine. | 1977 Feb |
|
Drug-induced anaphylaxis, convulsions, deafness, and extrapyramidal symptoms. | 1977 Mar 12 |
|
Electrophysiologic studies of perphenazine and protriptyline in a patient with psychotropic drug-induced ventricular fibrillation. | 1979 Aug |
|
Seven cases of somnambulism induced by drugs. | 1979 Jul |
|
Metoclopramide and dystonic reactions in Sardinians. | 1979 Jun 23 |
|
Prolactin and the small intestine. Effect of hyperprolactinaemia on mucosal structure in the rat. | 1981 Jul |
|
Sigma opiates and certain antipsychotic drugs mutually inhibit (+)-[3H] SKF 10,047 and [3H]haloperidol binding in guinea pig brain membranes. | 1984 Sep |
|
Pharmacology in vivo of the phenylindan derivative, Lu 19-005, a new potent inhibitor of dopamine, noradrenaline and 5-hydroxytryptamine uptake in rat brain. | 1985 Apr |
|
GABAergic, dopaminergic and cholinergic interactions in perphenazine-induced catatonia in rats. | 1985 Dec |
|
Tourette-like syndrome following low dose short-term neuroleptic treatment. | 1986 May |
|
Neuroleptic malignant syndrome during perphenazine treatment. | 1987 Mar |
|
The relationship between blood perphenazine levels, early resolution of psychotic symptoms, and side effects. | 1990 Aug |
|
Neurologic approach to drug-induced movement disorders: a study of 125 patients. | 1990 May |
|
Induction of mania by risperidone resistant to mood stabilizers. | 1997 Feb |
|
Perphenazine-induced hiccups. | 1999 Mar |
|
[Diabetes mellitus after treatment with clozapine]. | 2000 Feb 26 |
|
Role of adenosine in drug-induced catatonia in mice. | 2002 Aug |
|
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition. | 2003 Jun |
|
Survey on schizophrenia treatment in Mexico: perception and antipsychotic prescription patterns. | 2004 Apr 27 |
|
An unexpected increase of troponin I after perphenazine depot injection. | 2004 Feb |
|
Induction of the rabbit syndrome following coadministration of paroxetine, perphenazine, and amitriptyline. | 2004 Nov-Dec |
|
PASS assisted search and evaluation of some azetidin-2-ones as C.N.S. active agents. | 2005 Aug 3 |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
Stable expression of constitutively activated mutant h5HT6 and h5HT7 serotonin receptors: inverse agonist activity of antipsychotic drugs. | 2005 May |
|
[Trazodone for the treatment of behavioral and psychological symptoms of dementia (BPSD) in Alzheimer's disease: a retrospective study focused on the aggression and negativism in caregiving situations]. | 2006 Jun |
|
Aripiprazole for treatment-resistant schizophrenia: results of a multicenter, randomized, double-blind, comparison study versus perphenazine. | 2007 Feb |
|
Permanent lithium-induced cerebellar toxicity: three cases and review of literature. | 2007 Mar 15 |
|
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
|
[Consumption of inappropriate psychotropic drugs in residential homes for the elderly: comparative study between 2001 and 2006]. | 2008 Mar-Apr |
|
A mutual prodrug ester of GABA and perphenazine exhibits antischizophrenic efficacy with diminished extrapyramidal effects. | 2008 May 8 |
|
BL-1020: a novel antipsychotic drug with GABAergic activity and low catalepsy, is efficacious in a rat model of schizophrenia. | 2009 Jan |
|
Identification of selected therapeutic agents as inhibitors of carboxylesterase 1: potential sources of metabolic drug interactions. | 2010 Apr 11 |
|
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2. | 2011 Jul 14 |
|
Antitubercular pharmacodynamics of phenothiazines. | 2013 Apr |
Patents
Sample Use Guides
Moderately disturbed nonhospitalized patients with schizophrenia: 4 to 8 mg t.i.d. initially; reduce as soon as possible to minimum effective dosage. Hospitalized patients with schizophrenia: 8 to 16 mg b.i.d. to q.i.d.; avoid dosages in excess of 64 mg daily. Severe nausea and vomiting in adults: 8 to 16 mg daily in divided doses; 24 mg occasionally may be necessary; early dosage reduction is desirable.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12043843
Perphenazine (10-100 microM) was administered, either alone or combined with dopamine, to primary mouse neuronal or intact brain culture and to a human neuroblastoma (NB) cell line (SK-N-SH). Cell viability (measured by neutral red and alamar blue), DNA fragmentation (flow cytometry-NB) were determined. Neuroblastoma: perphenazine decreased viability by 87%.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 22:11:15 GMT 2023
by
admin
on
Fri Dec 15 22:11:15 GMT 2023
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Record UNII |
RHE0987NHE
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Record Status |
Validated (UNII)
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Record Version |
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Common Name | English | ||
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SUB03716MIG
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C047342
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262-615-2
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DTXSID00210006
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RHE0987NHE
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61120-81-8
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100000085678
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62873
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