Details
Stereochemistry | ACHIRAL |
Molecular Formula | C21H26ClN3OS.2C4H4O4 |
Molecular Weight | 636.113 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O.OCCN1CCN(CCCN2C3=C(SC4=C2C=C(Cl)C=C4)C=CC=C3)CC1
InChI
InChIKey=HYYMPXVEPSKZOU-SPIKMXEPSA-N
InChI=1S/C21H26ClN3OS.2C4H4O4/c22-17-6-7-21-19(16-17)25(18-4-1-2-5-20(18)27-21)9-3-8-23-10-12-24(13-11-23)14-15-26;2*5-3(6)1-2-4(7)8/h1-2,4-7,16,26H,3,8-15H2;2*1-2H,(H,5,6)(H,7,8)/b;2*2-1-
Molecular Formula | C4H4O4 |
Molecular Weight | 116.0722 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
Molecular Formula | C21H26ClN3OS |
Molecular Weight | 403.969 |
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 Date5.873472E11 |
|||
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 Date5.873472E11 |
|||
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 Date5.873472E11 |
|||
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 Date5.9512318E11 |
|||
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 Date5.9512318E11 |
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 |
|
Specific therapeutic actions of acetophenazine, perphenazine, and benzquinamide in newly admitted schizophrenic patients. | 1967 Mar-Apr |
|
Dystonic reaction to perphenazine. | 1969 Aug 9 |
|
Iatrogenic epilepsy due to antidepressant drugs. | 1969 Oct 11 |
|
The mechanism of the potentiating effect of antidepressant drugs on the protective influenc oe of diphenhydramine in experimental catatonia. The role of histamine. | 1974 |
|
[Psychometric effects of perphenacine below the "neuroleptic threshold" (author's transl)]. | 1975 Dec |
|
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 |
|
Metoclopramide and dystonic reactions in Sardinians. | 1979 Jun 23 |
|
Toxic psychosis with cimetidine. | 1979 May |
|
Plasma levels of perphenazine (Trilafon) related to development of extrapyramidal side effects. | 1981 |
|
Tricyclic antidepressants and alcoholic blackouts. | 1981 Jun |
|
Dose-response relationships of perphenazine in the treatment of acute psychoses. | 1982 |
|
Cerebellar syndrome following neuroleptic induced heat stroke. | 1983 Feb |
|
Effect of different neuroleptics in tardive dyskinesia and parkinsonism. A video-controlled multicenter study with chlorprothixene, perphenazine, haloperidol and haloperidol + biperiden. Nordic Dyskinesia Study Group. | 1986 |
|
A case of progressive hemichorea responsive to high-dose reserpine. | 1986 Mar |
|
D1/D2 dopamine and N-methyl-D-aspartate (NMDA) receptor participation in experimental catalepsy in rats. | 1992 |
|
Association of plasma homovanillic acid with behavioral symptoms in patients diagnosed with dementia: a preliminary report. | 1997 Dec 1 |
|
Olanzapine use in women with antipsychotic-induced hyperprolactinemia. | 1998 Oct |
|
Perphenazine-induced hiccups. | 1999 Mar |
|
Antipsychotic-induced extrapyramidal syndromes. Risperidone compared with low- and high-potency conventional antipsychotic drugs. | 2001 Jul |
|
Role of adenosine in drug-induced catatonia in mice. | 2002 Aug |
|
Drug-induced toxic myocarditis. | 2003 |
|
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition. | 2003 Jun |
|
H1-histamine receptor affinity predicts short-term weight gain for typical and atypical antipsychotic drugs. | 2003 Mar |
|
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 |
|
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 |
|
Nerve growth factor mRNA expression in the regenerating antler tip of red deer (Cervus elaphus). | 2007 Jan 10 |
|
Clinical characteristics and psychopathological profile of patients with vulvodynia: an observational and descriptive study. | 2008 |
|
Pharmacologic profiling of human and rat cytochrome P450 1A1 and 1A2 induction and competition. | 2008 Dec |
|
Identification of selected therapeutic agents as inhibitors of carboxylesterase 1: potential sources of metabolic drug interactions. | 2010 Apr 11 |
|
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle. | 2010 Feb 23 |
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
Sat Dec 16 01:26:50 UTC 2023
by
admin
on
Sat Dec 16 01:26:50 UTC 2023
|
Record UNII |
7K96LZ09JI
|
Record Status |
Validated (UNII)
|
Record Version |
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-
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3534-08-5
Created by
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6444477
Created by
admin on Sat Dec 16 01:26:51 UTC 2023 , Edited by admin on Sat Dec 16 01:26:51 UTC 2023
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100000085679
Created by
admin on Sat Dec 16 01:26:51 UTC 2023 , Edited by admin on Sat Dec 16 01:26:51 UTC 2023
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7K96LZ09JI
Created by
admin on Sat Dec 16 01:26:51 UTC 2023 , Edited by admin on Sat Dec 16 01:26:51 UTC 2023
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SUB03718MIG
Created by
admin on Sat Dec 16 01:26:51 UTC 2023 , Edited by admin on Sat Dec 16 01:26:51 UTC 2023
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PRIMARY | |||
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CHEMBL567
Created by
admin on Sat Dec 16 01:26:51 UTC 2023 , Edited by admin on Sat Dec 16 01:26:51 UTC 2023
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34912
Created by
admin on Sat Dec 16 01:26:51 UTC 2023 , Edited by admin on Sat Dec 16 01:26:51 UTC 2023
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5352-90-9
Created by
admin on Sat Dec 16 01:26:51 UTC 2023 , Edited by admin on Sat Dec 16 01:26:51 UTC 2023
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NON-SPECIFIC STOICHIOMETRY |
Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |