Details
Stereochemistry | ACHIRAL |
Molecular Formula | C19H24N2 |
Molecular Weight | 280.4073 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN(C)CCCN1C2=C(CCC3=C1C=CC=C3)C=CC=C2
InChI
InChIKey=BCGWQEUPMDMJNV-UHFFFAOYSA-N
InChI=1S/C19H24N2/c1-20(2)14-7-15-21-18-10-5-3-8-16(18)12-13-17-9-4-6-11-19(17)21/h3-6,8-11H,7,12-15H2,1-2H3
Molecular Formula | C19H24N2 |
Molecular Weight | 280.4073 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.drugbank.ca/drugs/DB00458Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/087846s028,087844s027,087845s027lbl.pdf
Sources: https://www.drugbank.ca/drugs/DB00458
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/087846s028,087844s027,087845s027lbl.pdf
Imipramine is a tricyclic antidepressant with general pharmacological properties similar to those of structurally related tricyclic antidepressant drugs such as amitriptyline and doxepin. A tertiary amine, imipramine inhibits the reuptake of serotonin more so than most secondary amine tricyclics, meaning that it blocks the reuptake of neurotransmitters serotonin and noradrenaline almost equally. With chronic use, imipramine also down-regulates cerebral cortical β-adrenergic receptors and sensitizes post-synaptic sertonergic receptors, which also contributes to increased serotonergic transmission. It takes approximately 2 - 4 weeks for antidepressants effects to occur. The onset of action may be longer, up to 8 weeks, in some individuals. It is also effective in migraine prophylaxis, but not in abortion of acute migraine attack. Imipramine works by inhibiting the neuronal reuptake of the neurotransmitters norepinephrine and serotonin. It binds the sodium-dependent serotonin transporter and sodium-dependent norepinephrine transporter preventing or reducing the reuptake of norepinephrine and serotonin by nerve cells. Depression has been linked to a lack of stimulation of the post-synaptic neuron by norepinephrine and serotonin. Slowing the reuptake of these neurotransmitters increases their concentration in the synaptic cleft, which is thought to contribute to relieving symptoms of depression. In addition to acutely inhibiting neurotransmitter re-uptake, imipramine causes down-regulation of cerebral cortical beta-adrenergic receptors and sensitization of post-synaptic serotonergic receptors with chronic use. This leads to enhanced serotonergic transmission. Used for relief of symptoms of depression and as temporary adjunctive therapy in reducing enuresis in children aged 6 years and older. May also be used to manage panic disorders, with or without agoraphobia, as a second line agent in ADHD, management of eating disorders, for short-term management of acute depressive episodes in bipolar disorder and schizophrenia, and for symptomatic treatment of postherpetic neuralgia.
CNS Activity
Sources: https://www.drugs.com/pro/imipramine.html
Curator's Comment: CNS active and penetrant http://onlinelibrary.wiley.com/doi/10.1016/S0009-9236(03)90534-0/abstract;jsessionid=0501D49064CCA6E885143C367F1535B3.f02t02
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25930134
Curator's Comment: Roland Kuhn, Swiss psychiatrist, discovered the therapeutic affect of imipramine in depression in 1957 http://www.cinp.org/wp-content/uploads/2015/06/history1.pdf
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P27169 Gene ID: 5444.0 Gene Symbol: PON1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/23001316 |
|||
Target ID: CHEMBL222 Sources: https://www.drugbank.ca/drugs/DB00458 |
12.0 nM [Ki] | ||
Target ID: CHEMBL228 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18983139 |
3.2 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Tofranil Approved UseTofranil is used for:
Treating depression. It is also used in some children to help reduce bedwetting. It may also be used for other conditions as determined by your doctor. Launch Date4.5394559E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
107 μg/L |
130 mg 1 times / day steady-state, oral dose: 130 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Desipramine |
IMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
24.5 ng/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
427 ng × h/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12 h |
130 mg 1 times / day steady-state, oral dose: 130 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Desipramine |
IMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
21.1 h |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
IMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22% |
130 mg 1 times / day steady-state, oral dose: 130 mg route of administration: Oral experiment type: STEADY-STATE co-administered: Desipramine |
IMIPRAMINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
200 mg/day 1 times / day steady, oral Dose: 200 mg/day, 1 times / day Route: oral Route: steady Dose: 200 mg/day, 1 times / day Sources: |
unhealthy, 18-70 years n = 82 Health Status: unhealthy Condition: major depression | melancholia Age Group: 18-70 years Population Size: 82 Sources: |
Disc. AE: Nausea... AEs leading to discontinuation/dose reduction: Nausea (1 patient) Sources: |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Disc. AE: Sleep disturbance, Urinary tract signs and symptoms NEC... AEs leading to discontinuation/dose reduction: Sleep disturbance (3 patients) Sources: Urinary tract signs and symptoms NEC (2 patients) Palpitations (2 patients) Anxiety (1 patient) Dry mouth (1 patient) Dizziness (3 patients) Flushing (1 patient) Constipation (1 patient) |
75 mg/day 1 times / day steady, oral (starting) Recommended Dose: 75 mg/day, 1 times / day Route: oral Route: steady Dose: 75 mg/day, 1 times / day Sources: |
unhealthy, < 24 years Health Status: unhealthy Condition: depression Age Group: < 24 years Sources: |
Disc. AE: Suicidal ideation... AEs leading to discontinuation/dose reduction: Suicidal ideation (grade 5) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 1 patient Disc. AE |
200 mg/day 1 times / day steady, oral Dose: 200 mg/day, 1 times / day Route: oral Route: steady Dose: 200 mg/day, 1 times / day Sources: |
unhealthy, 18-70 years n = 82 Health Status: unhealthy Condition: major depression | melancholia Age Group: 18-70 years Population Size: 82 Sources: |
Anxiety | 1 patient Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Constipation | 1 patient Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Dry mouth | 1 patient Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Flushing | 1 patient Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Palpitations | 2 patients Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Urinary tract signs and symptoms NEC | 2 patients Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Dizziness | 3 patients Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Sleep disturbance | 3 patients Disc. AE |
25 mg/day 1 times / day steady, oral Dose: 25 mg/day, 1 times / day Route: oral Route: steady Dose: 25 mg/day, 1 times / day Sources: |
unhealthy, 42.6 ± 12.4 years n = 59 Health Status: unhealthy Condition: irritable bowel syndrome Age Group: 42.6 ± 12.4 years Sex: M+F Population Size: 59 Sources: |
Suicidal ideation | grade 5 Disc. AE |
75 mg/day 1 times / day steady, oral (starting) Recommended Dose: 75 mg/day, 1 times / day Route: oral Route: steady Dose: 75 mg/day, 1 times / day Sources: |
unhealthy, < 24 years Health Status: unhealthy Condition: depression Age Group: < 24 years Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 6 uM] | ||||
yes [Ki 182.9 uM] | ||||
yes [Ki 42 uM] | ||||
yes [Ki 42 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Imipramine dosage in children: a comment on "imipramine and electrocardiographic abnormalities in hyperactive children". | 1975 May |
|
Imipramine and electrocardiographic abnormalities in hyperactive children. | 1975 May |
|
On the anticataleptic action of cyproheptadine. | 1976 Aug |
|
Biphasic effects of imipramine in experimental models of epilepsy. | 1976 Jun |
|
Imipramine-induced syndrome of inappropriate antidiuretic hormone secretion. | 1991 Dec |
|
Pediatric cardiovascular effects of imipramine and desipramine. | 1991 Jan |
|
Painful ejaculation associated with antidepressants in four patients. | 1991 Nov |
|
The antidepressants imipramine, clomipramine, and citalopram induce apoptosis in human acute myeloid leukemia HL-60 cells via caspase-3 activation. | 1999 |
|
The effect of therapeutic drugs and other pharmacologic agents on activity of porphobilinogen deaminase, the enzyme that is deficient in intermittent acute porphyria. | 1999 |
|
Reboxetine versus imipramine in the treatment of elderly patients with depressive disorders: a double-blind randomised trial. | 1999 Oct |
|
Gabapentin therapy for cocaine cravings. | 2000 Dec |
|
Sudden death of a child treated with imipramine. Case study. | 2000 Winter |
|
The use of short-form quality of life questionnaires to measure the impact of imipramine on women with urge incontinence. | 2001 |
|
Differential inhibition and inactivation of human CYP1 enzymes by trans-resveratrol: evidence for mechanism-based inactivation of CYP1A2. | 2001 Dec |
|
Pharmacokinetics of imipramine in narcoleptic horses. | 2001 May |
|
Adverse pulmonary vascular effects of high dose tricyclic antidepressants: acute and chronic animal studies. | 2002 Aug |
|
N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. | 2003 Nov |
|
[Hypnotherapy in the treatment of refractory nocturnal enuresis]. | 2004 Feb 19 |
|
[Effect of acute melipramine administration on motor activity and defensive conditioned reflexes of passive and active avoidance in rats]. | 2004 Nov-Dec |
|
Mechanism of block of hEag1 K+ channels by imipramine and astemizole. | 2004 Oct |
|
Improved pharmacodynamics of timolol maleate from a mucoadhesive niosomal ophthalmic drug delivery system. | 2005 Feb 16 |
|
[Influence of chronic melipramine administration abolition on locomotion and defensive conditioned reflexes in passive and active avoidance in rats]. | 2005 Jan-Feb |
|
Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
|
QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine. | 2005 Mar |
|
Serotonin (5HT), fluoxetine, imipramine and dopamine target distinct 5HT receptor signaling to modulate Caenorhabditis elegans egg-laying behavior. | 2005 Mar |
|
Exacerbation of harmaline-induced tremor by imipramine. | 2005 May |
|
UDP-glucuronosyltransferase 1A4 polymorphisms in a Japanese population and kinetics of clozapine glucuronidation. | 2005 May |
|
[Treatment of anxiety syndrome. A systematic literature review. Summary and conclusions by the SBU]. | 2005 Nov 21-27 |
|
The role of serendipity in drug discovery. | 2006 |
|
[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 |
|
Histone deacetylase 5 epigenetically controls behavioral adaptations to chronic emotional stimuli. | 2007 Nov 8 |
|
D-161, a novel pyran-based triple monoamine transporter blocker: behavioral pharmacological evidence for antidepressant-like action. | 2008 Jul 28 |
|
Sub-chronic administration of rimonabant causes loss of antidepressive activity and decreases doublecortin immunoreactivity in the mouse hippocampus. | 2009 Dec 25 |
|
Possible role of trazodone and imipramine in sleep deprivation-induced anxiety-like behavior and oxidative damage in mice. | 2009 Jul-Aug |
|
Neurogenesis-dependent and -independent effects of fluoxetine in an animal model of anxiety/depression. | 2009 May 28 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/pro/imipramine.html
Usual Adult Dose for Depression
Tablets:
Initial dose: 100 mg orally per day
Maintenance dose: 100 to 200 mg orally per day (If no response after 2 weeks, increase to 250 to 300 mg per day)
Maximum dose: 300 mg orally per day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23001316
The inhibition percentage of human PON1 for imipramine was 15.6% at 100 ug/L after incubation for 1 h). At 350 ug/L, the inhibition percentage for imipramine 19.2% after 1 h and 20.2% after 2 h.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 16:36:55 UTC 2022
by
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on
Fri Dec 16 16:36:55 UTC 2022
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Record UNII |
OGG85SX4E4
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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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WHO-VATC |
QN06AA02
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LIVERTOX |
NBK547884
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WHO-ATC |
N06AA02
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NCI_THESAURUS |
C94727
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NDF-RT |
N0000175752
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1427
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C62039
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793
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OGG85SX4E4
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D007099
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SUB08152MIG
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200-042-1
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Imipramine
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169866
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DTXSID1043881
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3696
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CHEMBL11
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M6232
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5691
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IMIPRAMINE
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DB00458
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50-49-7
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47499
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
Metabolizing reaction by CYP2D6: 2-Hydroxylation
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METABOLIC ENZYME -> SUBSTRATE |
|
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METABOLIC ENZYME -> SUBSTRATE |
10%-20% OF TOTAL METABOLISM
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BINDING PROTEIN->LIGAND | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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BINDER->LIGAND |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE ACTIVE -> PARENT |
Imipramine has activities at both the serotonin and norepeinephrine transporters with greater affinity for the serotonin transporter while desipramine and 2-hydroxydesipramine have greater affinities for the norepinephrine transporter (Owens et al., 1997).
|
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METABOLITE ACTIVE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |