Details
Stereochemistry | ACHIRAL |
Molecular Formula | C9H7Cl2N5 |
Molecular Weight | 256.091 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(N)=C(N=N1)C2=C(Cl)C(Cl)=CC=C2
InChI
InChIKey=PYZRQGJRPPTADH-UHFFFAOYSA-N
InChI=1S/C9H7Cl2N5/c10-5-3-1-2-4(6(5)11)7-8(12)14-9(13)16-15-7/h1-3H,(H4,12,13,14,16)
Molecular Formula | C9H7Cl2N5 |
Molecular Weight | 256.091 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Lamotrigine (marketed as Lamictal) is an anticonvulsant drug used in the treatment of epilepsy and bipolar disorder. The precise mechanism(s) by which lamotrigine exerts its anticonvulsant action are unknown. In animal models designed to detect anticonvulsant activity, lamotrigine was effective in preventing seizure spread in the maximum electroshock (MES) and pentylenetetrazol (scMet) tests, and prevented seizures in the visually and electrically evoked after-discharge (EEAD) tests for antiepileptic activity. Lamotrigine also displayed inhibitory properties in the kindling model in rats both during kindling development and in the fully kindled state. The relevance of these models to human epilepsy, however, is not known. One proposed mechanism of action of lamotrigine, the relevance of which remains to be established in humans, involves an effect on sodium channels. In vitro pharmacological studies suggest that lamotrigine inhibits voltage-sensitive sodium channels, thereby stabilizing neuronal membranes and consequently modulating presynaptic transmitter release of excitatory amino acids (e.g., glutamate and aspartate). Effect of Lamotrigine on N-Methyl d-Aspartate-Receptor Mediated Activity Lamotrigine did not inhibit N-methyl d-aspartate (NMDA)-induced depolarizations in rat cortical slices or NMDA-induced cyclic GMP formation in immature rat cerebellum, nor did lamotrigine displace compounds that are either competitive or noncompetitive ligands at this glutamate receptor complex (CNQX, CGS, TCHP). The IC50 for lamotrigine effects on NMDA-induced currents (in the presence of 3 uM of glycine) in cultured hippocampal neurons exceeded 100 uM. The mechanisms by which lamotrigine exerts its therapeutic action in bipolar disorder have not been established. The mechanisms that underpin the passage of lamotrigine at the blood-brain barrier to its site of action in the brain is poorly understood.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22227272
Curator's Comment: The mechanisms that underpin the passage of lamotrigine at the blood-brain barrier to its site of action in the brain is poorly understood.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2331043 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | LAMICTAL Approved UseINDICATIONS & USAGE Lamotrigine is indicated for: Epilepsy—adjunctive therapy in patients aged 2 years and older: · partial-onset seizures. · primary generalized tonic-clonic seizures. · generalized seizures of Lennox-Gastaut syndrome. (1.1) Epilepsy—monotherapy in patients aged 16 years and older: Conversion to monotherapy in patients with partial-onset seizures who are receiving treatment with carbamazepine, phenytoin, phenobarbital, primidone, or valproate as the single AED. (1.1) Bipolar disorder: Maintenance treatment of bipolar I disorder to delay the time to occurrence of mood episodes in patients treated for acute mood episodes with standard therapy. (1.2) Limitations of Use: Treatment of acute manic or mixed episodes is not recommended. Effectiveness of lamotrigine in the acute treatment of mood episodes has not been established. 1.1 Epilepsy Adjunctive Therapy Lamotrigine is indicated as adjunctive therapy for the following seizure types in patients aged 2 years and older: · partial-onset seizures. · primary generalized tonic-clonic (PGTC) seizures. · generalized seizures of Lennox-Gastaut syndrome. Monotherapy Lamotrigine is indicated for conversion to monotherapy in adults (aged 16 years and older) with partial-onset seizures who are receiving treatment with carbamazepine, phenytoin, phenobarbital, primidone, or valproate as the single antiepileptic drug (AED). Safety and effectiveness of lamotrigine have not been established (1) as initial monotherapy; (2) for conversion to monotherapy from AEDs other than carbamazepine, phenytoin, phenobarbital, primidone, or valproate; or (3) for simultaneous conversion to monotherapy from 2 or more concomitant AEDs. 1.2 Bipolar Disorder Lamotrigine is indicated for the maintenance treatment of bipolar I disorder to delay the time to occurrence of mood episodes (depression, mania, hypomania, mixed episodes) in adults in patients treated for acute mood episodes with standard therapy [see Clinical Studies (14.1) Launch Date7.8848642E11 |
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Primary | LAMICTAL Approved UseINDICATIONS & USAGE Lamotrigine is indicated for: Epilepsy—adjunctive therapy in patients aged 2 years and older: · partial-onset seizures. · primary generalized tonic-clonic seizures. · generalized seizures of Lennox-Gastaut syndrome. (1.1) Epilepsy—monotherapy in patients aged 16 years and older: Conversion to monotherapy in patients with partial-onset seizures who are receiving treatment with carbamazepine, phenytoin, phenobarbital, primidone, or valproate as the single AED. (1.1) Bipolar disorder: Maintenance treatment of bipolar I disorder to delay the time to occurrence of mood episodes in patients treated for acute mood episodes with standard therapy. (1.2) Limitations of Use: Treatment of acute manic or mixed episodes is not recommended. Effectiveness of lamotrigine in the acute treatment of mood episodes has not been established. 1.1 Epilepsy Adjunctive Therapy Lamotrigine is indicated as adjunctive therapy for the following seizure types in patients aged 2 years and older: · partial-onset seizures. · primary generalized tonic-clonic (PGTC) seizures. · generalized seizures of Lennox-Gastaut syndrome. Monotherapy Lamotrigine is indicated for conversion to monotherapy in adults (aged 16 years and older) with partial-onset seizures who are receiving treatment with carbamazepine, phenytoin, phenobarbital, primidone, or valproate as the single antiepileptic drug (AED). Safety and effectiveness of lamotrigine have not been established (1) as initial monotherapy; (2) for conversion to monotherapy from AEDs other than carbamazepine, phenytoin, phenobarbital, primidone, or valproate; or (3) for simultaneous conversion to monotherapy from 2 or more concomitant AEDs. 1.2 Bipolar Disorder Lamotrigine is indicated for the maintenance treatment of bipolar I disorder to delay the time to occurrence of mood episodes (depression, mania, hypomania, mixed episodes) in adults in patients treated for acute mood episodes with standard therapy [see Clinical Studies (14.1) Launch Date7.8848642E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4900 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20047572 |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2518 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00835263 |
200 mg single, oral dose: 200 mg route of administration: oral experiment type: single co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: age: sex: food status: Fed |
|
2912.04 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00834561 |
200 mg single, oral dose: 200 mg route of administration: oral experiment type: single co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: age: sex: food status: Fasted |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
73723 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20047572 |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
113029.409999999 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00835263 |
200 mg single, oral dose: 200 mg route of administration: oral experiment type: single co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: age: sex: food status: Fed |
|
120080.26 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00834561 |
200 mg single, oral dose: 200 mg route of administration: oral experiment type: single co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: age: sex: food status: Fasted |
|
131594.33 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00835263 |
200 mg single, oral dose: 200 mg route of administration: oral experiment type: single co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: age: sex: food status: Fed |
|
139995.13 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT00834561 |
200 mg single, oral dose: 200 mg route of administration: oral experiment type: single co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: age: sex: food status: Fasted |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
22.6 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/20047572 |
150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
LAMOTRIGINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% |
LAMOTRIGINE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >133 uM] | ||||
no | ||||
no | ||||
weak | ||||
weak | ||||
weak | ||||
weak | yes (co-administration study) Comment: Coadministration of Lamotrigine decreased Valproate steady-state concentration by 25%. |
|||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/020241s058,020764s051,022251s022lbl.pdf#page=35 Page: 35-36, 52 |
yes [IC50 53.8 uM] | |||
yes | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (PMDA) 31, 39-40, (PMDA_K100) 50 |
major | yes (co-administration study) Comment: Coadministration of Valproic acid (UGT inducer) decreased Lamotrigine CL/F by about 50%. Page: (PMDA) 31, 39-40, (PMDA_K100) 50 |
||
Page: (PMDA) 31, 39-40, (PMDA_K100) 50 |
minor | yes (co-administration study) Comment: Coadministration of Valproic acid (UGT inducer) decreased Lamotrigine CL/F by about 50%. Page: (PMDA) 31, 39-40, (PMDA_K100) 50 |
||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
Page: (PMDA) 31, (PMDA_K100) 50-51 |
no [IC50 >100 uM] | |||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
Page: (PMDA) 31, (PMDA_K100) 50 |
no | |||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: (PMDA_H100) 34 |
PubMed
Title | Date | PubMed |
---|---|---|
Adding lamotrigine to valproate: incidence of rash and other adverse effects. Postmarketing Antiepileptic Drug Survey (PADS) Group. | 1999 Aug |
|
Lamotrigine as prophylaxis against steroid-induced mania. | 1999 Oct |
|
Acute hepatitis after lamotrigine administration. | 2000 Sep |
|
Adverse effects of antiepileptic drugs on bone structure: epidemiology, mechanisms and therapeutic implications. | 2001 |
|
Effects of antiepileptic drugs on cognition. | 2001 |
|
Incompleteness of lamotrigine data. | 2001 |
|
Lamotrigine therapy for autistic disorder: a randomized, double-blind, placebo-controlled trial. | 2001 Apr |
|
Case reports. | 2001 Apr |
|
Effect of divalproex-lamotrigine combination therapy in frontal lobe seizures. | 2001 Aug |
|
A comparison of monotherapy with lamotrigine or carbamazepine in patients with newly diagnosed partial epilepsy. | 2001 Aug |
|
Adverse event monitoring in lamotrigine patients: a pharmacoepidemiologic study in the United Kingdom. | 2001 Feb |
|
The effect of lamotrigine on epileptiform discharges in young patients with drug-resistant epilepsy. | 2001 Feb |
|
Evaluating the tolerability of the newer mood stabilizers. | 2001 Jan |
|
Progress report on new antiepileptic drugs: a summary of the Fifth Eilat Conference (EILAT V). | 2001 Jan |
|
Weight change associated with valproate and lamotrigine monotherapy in patients with epilepsy. | 2001 Jan 23 |
|
Seizures, hormones and sexuality. | 2001 Jul |
|
The role of new antiepileptic drugs. | 2001 Jul |
|
Antiepileptic drug utilization: a Danish prescription database analysis. | 2001 Jul |
|
Lamotrigine in two cases of Rett syndrome. | 2001 Jul |
|
Teratogenic effects of lamotrigine on rat fetal brain: a morphometric study. | 2001 Jun |
|
Oxcarbazepine in focal epilepsy and hepatic porphyria: a case report. | 2001 Jun |
|
Preclinical evaluation of CHF3381 as a novel antiepileptic agent. | 2001 Jun |
|
Neurophysiological evaluation of vigilance in epileptic patients on monotherapy with lamotrigine. | 2001 Jun |
|
Single-dose pharmacokinetics of lamotrigine in children: influence of age and antiepileptic comedication. | 2001 Jun |
|
[SUNCT syndrome sensitive to lamotrigine]. | 2001 Jun 30 |
|
Absence epilepsy with fast rhythmic discharges during sleep: an intermediary form of generalized epilepsy? | 2001 Mar |
|
On the association between valproate and polycystic ovary syndrome. | 2001 Mar |
|
New generation anti-epileptics for facial pain and headache. | 2001 Mar |
|
Influence of retigabine on the anticonvulsant activity of some antiepileptic drugs against audiogenic seizures in DBA/2 mice. | 2001 Mar |
|
Anticonvulsant lamotrigine administered on reperfusion fails to improve experimental stroke outcomes. | 2001 Mar |
|
Influence of cirrhosis on lamotrigine pharmacokinetics. | 2001 May |
|
Lamotrigine: a review of clinical studies in bipolar disorders. | 2001 May |
|
Modulation of K+-evoked [3H]-noradrenaline release from rat and human brain slices by gabapentin: involvement of KATP channels. | 2001 May |
|
Mechanisms influencing stimulus-response properties of the human corticospinal system. | 2001 May |
|
A comparison of the effects of lamotrigine on neuroma-induced action potential firing and normal behaviour in rat: implications for establishing a pre-clinical 'therapeutic index'. | 2001 May 18 |
|
Exacerbation of juvenile myoclonic epilepsy with lamotrigine. | 2001 May 22 |
|
Differential cognitive and behavioral effects of carbamazepine and lamotrigine. | 2001 May 8 |
|
Pharmacologic management of epilepsy in the elderly. | 2001 May-Jun |
Patents
Sample Use Guides
Epilepsy—Conversion From Adjunctive Therapy to Monotherapy:
The recommended maintenance dose of LAMICTAL (lamotrigine) as monotherapy is 500 mg/day given in 2 divided doses.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16129425
In vitro, lamotrigine inhibited rat brain A-type of monoamine oxidase (MAO) activities with Ki values (MAO-A, 15 uM; MAO-B, 18 uM) potentially within the therapeutic range for this drug. The effects of lamotrigine on the MAO-A activities of rat brain and human liver preparations were almost identical suggesting minimal species or tissue variation
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:46:45 UTC 2023
by
admin
on
Wed Jul 05 22:46:45 UTC 2023
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Record UNII |
U3H27498KS
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000175753
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NDF-RT |
N0000175751
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FDA ORPHAN DRUG |
91695
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WHO-ATC |
N03AX09
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WHO-VATC |
QN03AX09
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NCI_THESAURUS |
C264
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NDF-RT |
N0000008486
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LIVERTOX |
NBK548562
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3878
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U3H27498KS
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281-901-8
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X-44
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5638
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2622
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1540
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1356756
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84057-84-1
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28439
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7526
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C38703
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DTXSID2023195
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SUB08393MIG
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Lamotrigine
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C047781
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759171
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6367
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100000092282
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M6673
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DB00555
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LAMOTRIGINE
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U3H27498KS
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CHEMBL741
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
|
||
|
TARGET -> INHIBITOR |
Binds to inactivated state and prevents activation
|
||
|
BINDER->LIGAND |
BINDING
|
||
|
TARGET -> INHIBITOR |
Binds to inactivated state and prevents activation
|
||
|
TARGET -> INHIBITOR |
Binds to inactivated state and prevents activation
|
||
|
TARGET -> INHIBITOR |
Binds to inactivated state and prevents activation
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
10% of dose
MINOR
URINE
|
||
|
METABOLITE -> PARENT |
URINE
|
||
|
METABOLITE -> PARENT |
0-5% of dose
URINE
|
||
|
METABOLITE -> PARENT |
trace amount
|
||
|
METABOLITE -> PARENT |
80-90% of dose
MAJOR
URINE
|
||
|
METABOLITE INACTIVE -> PARENT |
MAJOR
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.3
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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