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

Details

Stereochemistry ACHIRAL
Molecular Formula C17H11N5
Molecular Weight 285.3034
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LETROZOLE

SMILES

c1cc(ccc1C#N)C(c2ccc(cc2)C#N)n3cncn3

InChI

InChIKey=HPJKCIUCZWXJDR-UHFFFAOYSA-N
InChI=1S/C17H11N5/c18-9-13-1-5-15(6-2-13)17(22-12-20-11-21-22)16-7-3-14(10-19)4-8-16/h1-8,11-12,17H

HIDE SMILES / InChI

Molecular Formula C17H11N5
Molecular Weight 285.3034
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: https://www.ncbi.nlm.nih.gov/pubmed/?term=17912632

Letrozole (trade name Femara), a nonsteroidal aromatase inhibitor. Femara is indicated for the adjuvant treatment of postmenopausal women with hormone receptor positive early breast cancer. Also is indicated for the extended adjuvant treatment of early breast cancer in postmenopausal women, who have received 5 years of adjuvant tamoxifen therapy. Femara has to be used for first-line treatment of postmenopausal women with hormone receptor positive or unknown, locally advanced or metastatic breast cancer and for the treatment of advanced breast cancer in postmenopausal women with disease progression following antiestrogen therapy. Treatment of breast cancer thought to be hormonally responsive (i.e., estrogen and/or progesterone receptor positive or receptor unknown) has included a variety of efforts to decrease estrogen levels (ovariectomy, adrenalectomy, hypophysectomy) or inhibit estrogen effects (antiestrogens and progestational agents). These interventions lead to decreased tumor mass or delayed progression of tumor growth in some women. In postmenopausal women, estrogens are mainly derived from the action of the aromatase enzyme, which converts adrenal androgens (primarily androstenedione and testosterone) to estrone and estradiol. The suppression of estrogen biosynthesis in peripheral tissues and in the cancer tissue itself can therefore be achieved by specifically inhibiting the aromatase enzyme. Letrozole inhibits the conversion of androgens to estrogens. Letrozole selectively inhibits gonadal steroidogenesis but has no significant effect on adrenal mineralocorticoid or glucocorticoid synthesis. Letrozole inhibits the aromatase enzyme by competitively binding to the heme of the cytochrome P450 subunit of the enzyme, resulting in a reduction of estrogen biosynthesis in all tissues. Treatment of women with letrozole significantly lowers serum estrone, estradiol and estrone sulfate and has not been shown to significantly affect adrenal corticosteroid synthesis, aldosterone synthesis, or synthesis of thyroid hormones. Letrozole is rapidly and completely absorbed from the gastrointestinal tract and absorption is not affected by food. Metabolism to a pharmacologically inactive carbinol metabolite (4,4'¬ methanol-bisbenzonitrile) and renal excretion of the glucuronide conjugate of this metabolite is the major pathway of letrozole clearance. In human microsomes with specific CYP isozyme activity, CYP3A4 metabolized letrozole to the carbinol metabolite while CYP2A6 formed both this metabolite and its ketone analog. In human liver microsomes, letrozole strongly inhibited CYP2A6 and moderately inhibited CYP2C19. The most common side effects are sweating, hot flashes, arthralgia (joint pain), and fatigue

Originator

Curator's Comment:: # Novartis

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
7.26999999999999957 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
FEMARA

Approved Use

1.1 Adjuvant Treatment of Early Breast Cancer Letrozole tablets are indicated for the adjuvant treatment of postmenopausal women with hormone receptor positive early breast cancer. 1.2 Extended Adjuvant Treatment of Early Breast Cancer Letrozole tablets are indicated for the extended adjuvant treatment of early breast cancer in postmenopausal women, who have received 5 years of adjuvant tamoxifen therapy. The effectiveness of letrozole tablets in extended adjuvant treatment of early breast cancer is based on an analysis of disease-free survival in patients treated with letrozole tablets for a median of 60 months [see Clinical Studies (14.2, 14.3)

Launch Date

869788800000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
128 nM
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LETROZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.26 μM × h
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LETROZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
41.9 h
2.5 mg single, oral
dose: 2.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LETROZOLE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
30 mg 1 times / day single, oral
Highest studied dose
Dose: 30 mg, 1 times / day
Route: oral
Route: single
Dose: 30 mg, 1 times / day
Sources:
healthy, Mean age 28.4 years
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 63.6 years
Health Status: unhealthy
Age Group: Mean age 63.6 years
Sex: F
Sources:
Other AEs: Bilirubin abnormal, Aspartate aminotransferase abnormal...
Other AEs:
Bilirubin abnormal (grade 3, 5%)
Aspartate aminotransferase abnormal (grade 3, 3%)
ALT increased (grade 3, 3%)
Gamma-glutamyltransferase increased (grade 3, 6%)
Sources:
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 66 years
Health Status: unhealthy
Age Group: Mean age 66 years
Sex: F
Sources:
Disc. AE: Hypercalcemia, Cerebrovascular accident...
Other AEs: Bilirubin abnormal, Aspartate aminotransferase abnormal...
AEs leading to
discontinuation/dose reduction:
Hypercalcemia
Cerebrovascular accident
Other AEs:
Bilirubin abnormal (grade 3, 3%)
Aspartate aminotransferase abnormal (grade 3, 4%)
ALT increased (grade 3, 1%)
Gamma-glutamyltransferase increased (grade 3, 9%)
Sources:
10 mg 1 times / day multiple, oral
Highest studied dose
Dose: 10 mg, 1 times / day
Route: oral
Route: multiple
Dose: 10 mg, 1 times / day
Sources:
unhealthy, Mean age 71.6 years
62.5 mg 1 times / day single, oral
Studied dose
Dose: 62.5 mg, 1 times / day
Route: oral
Route: single
Dose: 62.5 mg, 1 times / day
Sources:
unknown
AEs

AEs

AESignificanceDosePopulation
ALT increased grade 3, 3%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 63.6 years
Health Status: unhealthy
Age Group: Mean age 63.6 years
Sex: F
Sources:
Aspartate aminotransferase abnormal grade 3, 3%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 63.6 years
Health Status: unhealthy
Age Group: Mean age 63.6 years
Sex: F
Sources:
Bilirubin abnormal grade 3, 5%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 63.6 years
Health Status: unhealthy
Age Group: Mean age 63.6 years
Sex: F
Sources:
Gamma-glutamyltransferase increased grade 3, 6%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 63.6 years
Health Status: unhealthy
Age Group: Mean age 63.6 years
Sex: F
Sources:
Cerebrovascular accident Disc. AE
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 66 years
Health Status: unhealthy
Age Group: Mean age 66 years
Sex: F
Sources:
Hypercalcemia Disc. AE
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 66 years
Health Status: unhealthy
Age Group: Mean age 66 years
Sex: F
Sources:
ALT increased grade 3, 1%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 66 years
Health Status: unhealthy
Age Group: Mean age 66 years
Sex: F
Sources:
Bilirubin abnormal grade 3, 3%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 66 years
Health Status: unhealthy
Age Group: Mean age 66 years
Sex: F
Sources:
Aspartate aminotransferase abnormal grade 3, 4%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 66 years
Health Status: unhealthy
Age Group: Mean age 66 years
Sex: F
Sources:
Gamma-glutamyltransferase increased grade 3, 9%
2.5 mg 1 times / day multiple, oral
Recommended
Dose: 2.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 2.5 mg, 1 times / day
Sources:
unhealthy, Mean age 66 years
Health Status: unhealthy
Age Group: Mean age 66 years
Sex: F
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
yes
yes (co-administration study)
Comment: The effect of a 400 mg b.i.d treatment with cimetidine for 7 days on the letrozole pharmacokinetics after a single 2.5-mg dose was investigated in 16 healthy subjects [Protocol 004], A slight but statistically significant decrease in systemic exposure and an increase in Cmax were observed when letrozole was administered together with cimetidine (table below).
Page: 4
yes
yes (co-administration study)
Comment: The effect of a 400 mg b.i.d treatment with cimetidine for 7 days on the letrozole pharmacokinetics after a single 2.5-mg dose was investigated in 16 healthy subjects [Protocol 004], A slight but statistically significant decrease in systemic exposure and an increase in Cmax were observed when letrozole was administered together with cimetidine (table below).
Page: 4
PubMed

PubMed

TitleDatePubMed
Aromatase inhibitors.
2001
Treatment of delayed male puberty: efficacy of aromatase inhibition.
2001
Third-generation aromatase inhibitors in the treatment of advanced breast cancer.
2001
[Neoadjuvant use of the aromatase inhibitor letrozole in uterine cancer: endocrine and clinical effects].
2001
Letrozole as primary medical therapy for locally advanced and large operable breast cancer.
2001 Apr
Flare and tumor lysis syndrome with atypical features after letrozole therapy in advanced breast cancer. A case report.
2001 Apr-Jun
Exemestane: new preparation. No tangible advance in metastatic breast cancer after tamoxifen failure.
2001 Aug
Nonsteroidal and steroidal aromatase inhibitors in breast cancer.
2001 Aug
Endometrial stromal sarcoma: objective response to letrozole.
2001 Aug
Promising results for Arimidex and Femara.
2001 Dec
Preliminary data from ongoing adjuvant aromatase inhibitor trials.
2001 Dec
Neoadjuvant endocrine therapy for breast cancer: medical perspectives.
2001 Dec
Adjuvant trials of aromatase inhibitors: determining the future landscape of adjuvant endocrine therapy.
2001 Dec
Biological and clinical effects of aromatase inhibitors in neoadjuvant therapy.
2001 Dec
Local endocrine effects of aromatase inhibitors within the breast.
2001 Dec
Comparative clinical pharmacology and pharmacokinetic interactions of aromatase inhibitors.
2001 Dec
Aromatase and COX-2 expression in human breast cancers.
2001 Dec
Aromatase overexpression transgenic mice model: cell type specific expression and use of letrozole to abrogate mammary hyperplasia without affecting normal physiology.
2001 Dec
High dehydroepiandrosterone-sulfate predicts breast cancer progression during new aromatase inhibitor therapy and stimulates breast cancer cell growth in tissue culture: a renewed role for adrenalectomy.
2001 Dec
False shortening of time to progression in letrozole 2.5-mg dose?
2001 Dec 1
Letrozole in second-line therapy of advanced breast cancer: more questions than answers.
2001 Dec 1
New breast cancer drug.
2001 Dec 24
Effect of age and single versus multiple dose pharmacokinetics of letrozole (Femara) in breast cancer patients.
2001 Jul
[Endocrine therapy for advanced or recurrent breast cancer].
2001 Jul
Huge response to letrozole in inoperable T4 breast cancer: a case report.
2001 Jul-Aug
Formestane, a steroidal aromatase inhibitor after failure of non-steroidal aromatase inhibitors (anastrozole and letrozole): is a clinical benefit still achievable?
2001 Nov
Preoperative treatment of postmenopausal breast cancer patients with letrozole: A randomized double-blind multicenter study.
2001 Nov
Role of anti-aromatase agents in postmenopausal advanced breast cancer.
2001 Oct
Inhibition of P450 aromatase enhances gonadotropin secretion in early and midpubertal boys: evidence for a pituitary site of action of endogenous E.
2001 Oct
Developmental maturation of primate placental trophoblast: placental cytosolic and secretory phospholipase A2 expression after estrogen suppression of baboons.
2001 Oct
Aromatase inhibitors: treatment of advanced breast cancer.
2001 Oct 1
Aromatase inhibitors and inactivators in breast cancer.
2001 Oct 20
Advances in aromatase inhibition: clinical efficacy and tolerability in the treatment of breast cancer.
2001 Sep
Letrozole is more effective neoadjuvant endocrine therapy than tamoxifen for ErbB-1- and/or ErbB-2-positive, estrogen receptor-positive primary breast cancer: evidence from a phase III randomized trial.
2001 Sep 15
Use of ErbB-1 and ErbB-2 to select endocrine therapy for breast cancer: will it play in Peoria?
2001 Sep 15
Sex reversal and aromatase in the European pond turtle: treatment with letrozole after the thermosensitive period for sex determination.
2001 Sep 15
Estrogen as therapy for breast cancer.
2002
[The role of aromatase inhibitors in the treatment of breast neoplasms. An evaluation of clinical efficacy and the tolerability profile].
2002 Apr
[CGS 20267 (Letrozole), a new aromatase inhibitor: early phase II study for postmenopausal women with advanced breast cancer].
2002 Apr
New breast cancer drugs expand treatment options.
2002 Apr
Current status and future innovations of hormonal agents, chemotherapy and investigational agents in endometrial cancer.
2002 Feb
Superior efficacy of letrozole versus tamoxifen as first-line therapy.
2002 Feb 1
Role of low levels of endogenous estrogen in regulation of bone resorption in late postmenopausal women.
2002 Jan
[Growth rate can be manipulated. Estrogen production in pubertal boys can be blocked by an aromatase inhibitor].
2002 Jan 17
[Aromatase inhibitors of the 3rd generation. What can the "pill against breast cancer" really do?].
2002 Jan 31
Genetic or enzymatic disruption of aromatase inhibits the growth of ectopic uterine tissue.
2002 Jul
Endocrine and clinical endpoints of exemestane as neoadjuvant therapy.
2002 Mar-Apr
Anti-aromatase agents in the treatment and prevention of breast cancer.
2002 Mar-Apr
[CGS20267 (Letrozole), a new aromatase inhibitor: late phase II study for postmenopausal women with advanced or recurrent breast cancer (no. 1)--investigation of recommended clinical dose CGS20267 Study Group].
2002 May
Letrozole in the treatment of breast cancer.
2002 May
Patents

Sample Use Guides

The recommended dose of Femara (letrozole) is one 2.5 mg tablet administered once a day, without regard to meals.
Route of Administration: Oral
After treatment of cells with letrozole (10 nM) for 24 and 48 h, significant inhibition of matrix metalloproteinases (MMP) levels was obtained. Furthermore, concurrent treatment of MCF-7, human epithelial breast cancer cells with 17-beta-estradiol in the presence of letrozole significantly suppressed the estradiol-induced stimulation of MMP levels. Letrozole is a potent in vitro inhibitor of cell proliferation and of type IV collagenases expressed by estrogen receptor (ER)-positive MCF-7 cells and may be of value for suppressing breast tumor growth and invasiveness.
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:00:50 UTC 2021
Edited
by admin
on Fri Jun 25 21:00:50 UTC 2021
Record UNII
7LKK855W8I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LETROZOLE
EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
CGS 20267
Code English
4,4'-(1H-1,2,4-TRIAZOL-1-YLMETHYLENE)DIBENZONITRILE
Systematic Name English
LETROZOLE [ORANGE BOOK]
Common Name English
LETROZOLE [USP MONOGRAPH]
Common Name English
LETROZOLE [EP]
Common Name English
LETROZOLE [USAN]
Common Name English
FEMARA
Brand Name English
CGS-20267
Code English
LETROZOLE COMPONENT OF KISQALI FEMARA CO-PACK
Brand Name English
KISQALI FEMARA CO-PACK COMPONENT LETROZOLE
Brand Name English
LETROZOLE [MART.]
Common Name English
LETROZOLE [USP-RS]
Common Name English
LETROZOLE [MI]
Common Name English
LETROZOLE [JAN]
Common Name English
LETROZOLE [EP MONOGRAPH]
Common Name English
BENZONITRILE, 4,4'-(1H-1,2,4-TRIAZOL-1-YLMETHYLENE)BIS-
Systematic Name English
NSC-759652
Code English
LETROZOLE [INN]
Common Name English
LETROZOLE [HSDB]
Common Name English
LETROZOLE [WHO-DD]
Common Name English
Classification Tree Code System Code
LIVERTOX 546
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
WHO-VATC QL02BG04
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
NDF-RT N0000175563
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
WHO-ATC L02BG04
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
NDF-RT N0000175080
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
NCI_THESAURUS C2018
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
Code System Code Type Description
USP_CATALOG
1356971
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY USP-RS
MERCK INDEX
M6772
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1444
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
NCI_THESAURUS
C1527
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
RXCUI
72965
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY RxNorm
IUPHAR
5209
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
DRUG CENTRAL
1556
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
DRUG BANK
DB01006
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
CAS
112809-51-5
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
MESH
C067431
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
FDA UNII
7LKK855W8I
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
EPA CompTox
112809-51-5
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
WIKIPEDIA
LETROZOLE
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
HSDB
7461
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
PUBCHEM
3902
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
EVMPD
SUB08444MIG
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
LACTMED
Letrozole
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
INN
7118
Created by admin on Fri Jun 25 21:00:50 UTC 2021 , Edited by admin on Fri Jun 25 21:00:50 UTC 2021
PRIMARY
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