U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C10H8F2N4O
Molecular Weight 238.1935
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RUFINAMIDE

SMILES

NC(=O)C1=CN(CC2=C(F)C=CC=C2F)N=N1

InChI

InChIKey=POGQSBRIGCQNEG-UHFFFAOYSA-N
InChI=1S/C10H8F2N4O/c11-7-2-1-3-8(12)6(7)4-16-5-9(10(13)17)14-15-16/h1-3,5H,4H2,(H2,13,17)

HIDE SMILES / InChI

Molecular Formula C10H8F2N4O
Molecular Weight 238.1935
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.rxlist.com/banzel-drug.htm https://www.drugs.com/mtm/rufinamide.html

Rufinamide is an anti-epileptic drug that is FDA approved for the treatment of lennox-gastaut syndrome (LGS). The principal mechanism of action of rufinamide is modulation of the activity of sodium channels and, in particular, prolongation of the inactive state of the channel. Hormonal contraceptives may be less effective with rufinamide. Patients on valproate should begin at a rufinamide dose lower than 10 mg/kg per day (pediatric patients) or 400 mg per day (adults). Common adverse reactions include headache, dizziness, fatigue, somnolence, and nausea.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
BANZEL

Approved Use

I NDICATIONS AND USAGE BANZEL is indicated for adjunctive treatment of seizures associated with Lennox-Gastaut Syndrome in pediatric patients 1 year of age and older and in adults. BANZEL is indicated for adjunctive treatment of seizures associated with Lennox-Gastaut Syndrome (LGS) in pediatric patients 1 year of age and older, and in adults (1)

Launch Date

2008
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
3.8 μg/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RUFINAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
70.3 μg × h/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RUFINAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7.2 h
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
RUFINAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
10 h
200 mg 2 times / day unknown, oral
dose: 200 mg
route of administration: Oral
experiment type: UNKNOWN
co-administered:
RUFINAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
66%
200 mg 2 times / day unknown, oral
dose: 200 mg
route of administration: Oral
experiment type: UNKNOWN
co-administered:
RUFINAMIDE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
3600 mg 2 times / day multiple, oral
MTD
Dose: 3600 mg, 2 times / day
Route: oral
Route: multiple
Dose: 3600 mg, 2 times / day
Sources: Page: p.1125, p.1139
healthy
n = 15
Health Status: healthy
Population Size: 15
Sources: Page: p.1125, p.1139
Sources: Page: p.1125, p.1139
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.1
Other AEs: Depression worsened, Suicidal behavior...
Other AEs:
Depression worsened
Suicidal behavior (serious)
Leukopenia (serious)
Mood change
Central nervous system disorder NOS
Hypersensitivity reaction
Sources: Page: p.1
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.4
Disc. AE: Fatigue...
Other AEs: QT shortened...
AEs leading to
discontinuation/dose reduction:
Fatigue (1-2)
Other AEs:
QT shortened (serious)
Sources: Page: p.4
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.7
Disc. AE: Convulsion, Rash...
AEs leading to
discontinuation/dose reduction:
Convulsion (2%)
Rash (2%)
Sources: Page: p.7
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.8
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.8
Disc. AE: Vomiting, Dizziness...
AEs leading to
discontinuation/dose reduction:
Vomiting (1%)
Dizziness (3%)
Headache (2%)
Nausea (1%)
Ataxia (1%)
Sources: Page: p.8
AEs

AEs

AESignificanceDosePopulation
Central nervous system disorder NOS
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.1
Depression worsened
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.1
Hypersensitivity reaction
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.1
Mood change
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.1
Leukopenia serious
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.1
Suicidal behavior serious
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.1
Fatigue 1-2
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.4
QT shortened serious
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.4
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.4
Convulsion 2%
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.7
Rash 2%
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.7
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.7
Ataxia 1%
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.8
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.8
Nausea 1%
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.8
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.8
Vomiting 1%
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.8
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.8
Headache 2%
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.8
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.8
Dizziness 3%
Disc. AE
22.5 mg/kg 2 times / day multiple, oral
Studied dose
Dose: 22.5 mg/kg, 2 times / day
Route: oral
Route: multiple
Dose: 22.5 mg/kg, 2 times / day
Sources: Page: p.8
unhealthy
Health Status: unhealthy
Condition: Lennox-Gastaut Syndrome
Sources: Page: p.8
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as perpetrator​

Drug as perpetrator​

Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Rufinamide: a double-blind, placebo-controlled proof of principle trial in patients with epilepsy.
2001 Feb
Progress report on new antiepileptic drugs: a summary of the Fifth Eilat Conference (EILAT V).
2001 Jan
Gateways to clinical trials.
2006 Jul-Aug
New antiepileptic drugs that are second generation to existing antiepileptic drugs.
2006 Jun
Diverse mechanisms of antiepileptic drugs in the development pipeline.
2006 Jun
Gateways to clinical trials.
2006 Sep
Rufinamide.
2007 Jan
Progress report on new antiepileptic drugs: a summary of the Eigth Eilat Conference (EILAT VIII).
2007 Jan
Physicochemical characterization of solid dispersions of three antiepileptic drugs prepared by solvent evaporation method.
2007 May
Pregabalin for the management of partial epilepsy.
2008 Dec
Treatment of Lennox-Gastaut syndrome: overview and recent findings.
2008 Dec
The anticonvulsant profile of rufinamide (CGP 33101) in rodent seizure models.
2008 Jul
Rufinamide for generalized seizures associated with Lennox-Gastaut syndrome.
2008 May 20
Onset of action and seizure control in Lennox-Gaustaut syndrome: focus on rufinamide.
2009 Apr
Safety and tolerability of rufinamide in children with epilepsy: a pooled analysis of 7 clinical studies.
2009 Dec
Product: Banzel.
2009 Feb
Minimizing AED adverse effects: improving quality of life in the interictal state in epilepsy care.
2009 Jun
Transitional polytherapy: tricks of the trade for monotherapy to monotherapy AED conversions.
2009 Jun
Antiepileptic drug monotherapy: the initial approach in epilepsy management.
2009 Jun
Rufinamide (Banzel) for epilepsy.
2009 Mar 9
Third-generation antiepileptic drugs: mechanisms of action, pharmacokinetics and interactions.
2009 Mar-Apr
Treatment of Lennox-Gastaut Syndrome (LGS).
2009 Nov
The possible antianxiety and mood-stabilizing effects of rufinamide.
2010
Recent advances in adjunctive therapy for epilepsy: focus on sodium channel blockers as third-generation antiepileptic drugs.
2010 Apr
Gateways to clinical trials.
2010 Apr
Rufinamide: a new antiepileptic medication for the treatment of seizures associated with lennox-gastaut syndrome.
2010 Apr
First European long-term experience with the orphan drug rufinamide in childhood-onset refractory epilepsy.
2010 Apr
"Epileptic encephalopathy" of infancy and childhood: electro-clinical pictures and recent understandings.
2010 Dec
A 24-week multicenter, randomized, double-blind, parallel-group, dose-ranging study of rufinamide in adults and adolescents with inadequately controlled partial seizures.
2010 Feb
Simultaneous HPLC-UV analysis of rufinamide, zonisamide, lamotrigine, oxcarbazepine monohydroxy derivative and felbamate in deproteinized plasma of patients with epilepsy.
2010 Feb 1
Rufinamide: a novel broad-spectrum antiepileptic drug.
2010 Jan
Drug-induced QT interval shortening: potential harbinger of proarrhythmia and regulatory perspectives.
2010 Jan
New antiepileptic drugs: lacosamide, rufinamide, and vigabatrin.
2010 Jul
Update on anticonvulsant drugs.
2010 Jul
Rufinamide: a new antiepileptic drug treatment for Lennox-Gastaut syndrome.
2010 Jun
Gateways to clinical trials.
2010 Mar
Severe constipation associated with the use of rufinamide (Banzel) in an adolescent.
2010 May
[Antiepileptic drugs in North America].
2010 May
Rufinamide in children and adults with Lennox-Gastaut syndrome: first Italian multicenter experience.
2010 Nov
Expression, regulation and function of phosphofructo-kinase/fructose-biphosphatases (PFKFBs) in glucocorticoid-induced apoptosis of acute lymphoblastic leukemia cells.
2010 Nov 23
Treating Lennox-Gastaut syndrome in epileptic pediatric patients with third-generation rufinamide.
2010 Oct 5
Experience with rufinamide in a pediatric population: a single center's experience.
2010 Sep
Emerging drugs for partial onset seizures.
2010 Sep
Adjunctive rufinamide in Lennox-Gastaut syndrome: a long-term, open-label extension study.
2010 Sep
Patents

Sample Use Guides

Starting daily dose: 400-800 mg per day in two equally divided doses. Increase by 400-800 mg every other day until a maximum dose of 3200 mg per day, in two divided doses, is reached.
Route of Administration: Oral
In vitro studies with human liver microsomes using con-centrations of rufinamide in the range of 10–300 µmol/L(2.4–72 µg/ml) found no significant inhibition of any ofeight major human CYP isozymes—CYP1A2, CYP2A6,CYP2C9, CYP2C19, CYP2D6, CYP2E1, CYP3A4/5, andCYP4A9/11.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:38:26 GMT 2023
Edited
by admin
on Fri Dec 15 15:38:26 GMT 2023
Record UNII
WFW942PR79
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RUFINAMIDE
DASH   EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
1-(2,6-Difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide
Systematic Name English
1H-1,2,3-TRIAZOLE-4-CARBOXAMIDE, 1-((2,6-DIFLUOROPHENYL)METHYL)-
Systematic Name English
RUFINAMIDE [ORANGE BOOK]
Common Name English
RUFINAMIDE [JAN]
Common Name English
INOVELON
Brand Name English
RUFINAMIDE [MART.]
Common Name English
RUF 331
Code English
RUFINAMIDE [EMA EPAR]
Common Name English
CGP 33101
Code English
E-2080
Code English
Rufinamide [WHO-DD]
Common Name English
CGP-33101
Code English
RUFINAMIDE [VANDF]
Common Name English
RUFINAMIDE [USP MONOGRAPH]
Common Name English
RUF-331
Code English
60231/4
Code English
RUFINAMIDE [MI]
Common Name English
E2080
Code English
RUFINAMIDE [USP-RS]
Common Name English
RUFINAMIDE [USAN]
Common Name English
rufinamide [INN]
Common Name English
BANZEL
Brand Name English
Classification Tree Code System Code
WHO-ATC N03AF03
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
NCI_THESAURUS C264
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
WHO-VATC QN03AF03
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
LIVERTOX NBK548457
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
EU-Orphan Drug EU/3/04/240
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
EMA ASSESSMENT REPORTS INOVELON (AUTHORIZED: EPILEPSY)
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
FDA ORPHAN DRUG 193504
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
Code System Code Type Description
MESH
C079703
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
INN
7387
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
WIKIPEDIA
RUFINAMIDE
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
CAS
106308-44-5
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
FDA UNII
WFW942PR79
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
PUBCHEM
129228
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
IUPHAR
7470
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
EVMPD
SUB10403MIG
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
DAILYMED
WFW942PR79
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL1201754
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
RXCUI
69036
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY RxNorm
LACTMED
Rufinamide
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
SMS_ID
100000089186
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
MERCK INDEX
m9696
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY Merck Index
RS_ITEM_NUM
1606401
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
NCI_THESAURUS
C75167
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
USAN
SS-30
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
DRUG BANK
DB06201
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID1046506
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
DRUG CENTRAL
3534
Created by admin on Fri Dec 15 15:38:27 GMT 2023 , Edited by admin on Fri Dec 15 15:38:27 GMT 2023
PRIMARY
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