Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H30O3 |
Molecular Weight | 342.4718 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])C=C(C)C4=CC(=O)CC[C@]34C
InChI
InChIKey=VXIMPSPISRVBPZ-NWUMPJBXSA-N
InChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-,17+,18+,20-,21+,22+/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=23395103
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/?term=23395103
Megestrol acetate is a progestational hormone used most commonly as the acetate ester. As the acetate, it is more potent than progesterone both as a progestagen and as an ovulation inhibitor. It has also been used in the palliative treatment of breast cancer. MEGACE Oral Suspension is indicated for the treatment of anorexia, cachexia, or an unexplained, significant weight loss in patients with a diagnosis of acquired immunodeficiency syndrome (AIDS). The precise mechanism by which megestrol acetate produces effects in anorexia and cachexia is unknown at the present time. But its progestin antitumour activity may involve suppression of luteinizing hormone by inhibition of pituitary function. Studies also suggest that the megestrol's weight gain effect is related to its appetite-stimulant or metabolic effects rather than its glucocorticoid-like effects or the production of edema. It has also been suggested that megestrol may alter metabolic pathyways via interferences with the production or action of mediators such as cachectin, a hormone that inhibits adipocyte lipogenic enzymes. The major route of drug elimination in humans is urine. When radiolabeled megestrol acetate was administered to humans in doses of 4 to 90 mg, the urinary excretion within 10 days ranged from 56.5% to 78.4% (mean 66.4%) and fecal excretion ranged from 7.7% to 30.3% (mean 19.8%). The total recovered radioactivity varied between 83.1% and 94.7% (mean 86.2%). Megestrol acetate metabolites which were identified in urine constituted 5% to 8% of the dose administered. Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces. Plasma steady-state pharmacokinetics of megestrol acetate were evaluated in 10 adult, cachectic male patients with acquired immunodeficiency syndrome (AIDS) and an involuntary weight loss greater than 10% of baseline. Patients received single oral doses of 800 mg/day of MEGACE Oral Suspension for 21 days. Plasma concentration data obtained on day 21 were evaluated for up to 48 hours past the last dose.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15086241 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | MEGACE Approved UseMegestrol acetate oral suspension is indicated for the treatment of anorexia, cachexia, or an unexplained, significant weight loss in patients with a diagnosis of acquired immunodeficiency syndrome (AIDS). Launch Date7.4761922E11 |
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Palliative | MEGACE Approved UseMegestrol acetate oral suspension is indicated for the treatment of anorexia, cachexia, or an unexplained, significant weight loss in patients with a diagnosis of acquired immunodeficiency syndrome (AIDS). Launch Date7.4761922E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
753 ng/mL |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
490 ng/mL |
750 mg 1 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
1133 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
625 mg single, oral dose: 625 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1618 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
625 mg single, oral dose: 625 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
1364 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
187 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10476 ng × h/mL |
800 mg 1 times / day steady-state, oral dose: 800 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
6779 ng × h/mL |
750 mg 1 times / day steady-state, oral dose: 750 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
12095 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
625 mg single, oral dose: 625 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
16268 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
625 mg single, oral dose: 625 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
18625 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
8942 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
33.68 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
625 mg single, oral dose: 625 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
39.75 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
625 mg single, oral dose: 625 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
32.84 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED |
|
31.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/19774117/ |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
400 mg 2 times / day multiple, oral Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy, 54-68 years n = 2 Health Status: unhealthy Age Group: 54-68 years Sex: F Population Size: 2 Sources: |
Disc. AE: Osteoporosis... AEs leading to discontinuation/dose reduction: Osteoporosis (2 patients) Sources: |
625 mg 1 times / day multiple, oral Recommended Dose: 625 mg, 1 times / day Route: oral Route: multiple Dose: 625 mg, 1 times / day Sources: |
unhealthy, 65 years n = 1 Health Status: unhealthy Age Group: 65 years Sex: M Population Size: 1 Sources: |
Disc. AE: Adrenal insufficiency... AEs leading to discontinuation/dose reduction: Adrenal insufficiency (1 patient) Sources: |
40 mg 2 times / day multiple, oral Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: |
unhealthy, 85 years n = 1 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 85 years Sex: F Population Size: 1 Sources: |
Disc. AE: Deep vein thrombosis... AEs leading to discontinuation/dose reduction: Deep vein thrombosis (1 patient) Sources: |
400 mg 2 times / day multiple, oral Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy, 86 years n = 1 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 86 years Sex: F Population Size: 1 Sources: |
Disc. AE: Deep vein thrombosis... AEs leading to discontinuation/dose reduction: Deep vein thrombosis (1 patient) Sources: |
1600 mg 1 times / day multiple, oral Highest studied dose Dose: 1600 mg, 1 times / day Route: oral Route: multiple Dose: 1600 mg, 1 times / day Sources: |
unhealthy Health Status: unhealthy Condition: advanced breast cancer Sex: F Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Osteoporosis | 2 patients Disc. AE |
400 mg 2 times / day multiple, oral Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy, 54-68 years n = 2 Health Status: unhealthy Age Group: 54-68 years Sex: F Population Size: 2 Sources: |
Adrenal insufficiency | 1 patient Disc. AE |
625 mg 1 times / day multiple, oral Recommended Dose: 625 mg, 1 times / day Route: oral Route: multiple Dose: 625 mg, 1 times / day Sources: |
unhealthy, 65 years n = 1 Health Status: unhealthy Age Group: 65 years Sex: M Population Size: 1 Sources: |
Deep vein thrombosis | 1 patient Disc. AE |
40 mg 2 times / day multiple, oral Dose: 40 mg, 2 times / day Route: oral Route: multiple Dose: 40 mg, 2 times / day Sources: |
unhealthy, 85 years n = 1 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 85 years Sex: F Population Size: 1 Sources: |
Deep vein thrombosis | 1 patient Disc. AE |
400 mg 2 times / day multiple, oral Dose: 400 mg, 2 times / day Route: oral Route: multiple Dose: 400 mg, 2 times / day Sources: |
unhealthy, 86 years n = 1 Health Status: unhealthy Condition: Alzheimer's disease Age Group: 86 years Sex: F Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
no | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Reversal effects of nomegestrol acetate on multidrug resistance in adriamycin-resistant MCF7 breast cancer cell line. | 2001 |
|
A comparison of megestrol acetate, nandrolone decanoate and dietary counselling for HIV associated weight loss. | 2001 Aug |
|
Implant contraception. | 2001 Dec |
|
Inhibitory effect of nomegestrol acetate on steroidogenesis of cultured granulosa cells from rat ovary in vitro. | 2001 Jan |
|
Megestrol treatment in patients with hepatocellular carcinoma. | 2001 Nov 16 |
|
Effects of different types of hormone replacement therapy on mammographic density. | 2001 Nov 30 |
|
The impact of hormonal treatments on quality of life of patients with metastatic breast cancer. | 2002 |
|
Estrogen as therapy for breast cancer. | 2002 |
|
Tamoxifen resistant and refractory breast cancer: the value of aromatase inhibitors. | 2002 |
|
Fertility-preserving treatment in young patients with endometrial adenocarcinoma. | 2002 Apr 15 |
|
Effect of megestrol caproate on the reproductive function of laboratory animals. | 2002 Jun |
|
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer. | 2002 Mar |
|
[Low-grade sarcoma of the endometrial stroma: late recurrence with ureteral and bladder involvement]. | 2002 Oct |
|
Discovery of molecular mechanisms of neuroprotection using cell-based bioassays and oligonucleotide arrays. | 2002 Oct 29 |
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Should aromatase inhibitors replace tamoxifen? | 2003 Aug |
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Acute effects of megestrol on the hypothalamic-pituitary-adrenal axis. | 2003 Dec |
|
[Comparison of changes in biochemical markers of bone turnover after 6 months of hormone replacement therapy with either transdermal 17 beta-estradiol or equine conjugated estrogen plus nomegestrol acetate]. | 2003 May |
|
Cancer cachexia. | 2003 Nov 5 |
|
Advances in estrogen receptor biology: prospects for improvements in targeted breast cancer therapy. | 2004 |
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Osteoporosis associated with megestrol acetate. | 2004 Dec |
|
Therapy for unresectable hepatocellular carcinoma: review of the randomized clinical trials-II: systemic and local non-embolization-based therapies in unresectable and advanced hepatocellular carcinoma. | 2004 Jun |
|
Cost utility and budget impact of third-generation aromatase inhibitors for advanced breast cancer: a literature-based model analysis of costs in the Italian National Health Service. | 2004 Sep |
|
Clinical utility of serum HER2/neu in monitoring and prediction of progression-free survival in metastatic breast cancer patients treated with trastuzumab-based therapies. | 2005 |
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The science of megestrol acetate delivery: potential to improve outcomes in cachexia. | 2005 |
|
Retrospective review of megestrol use for weight loss in an elderly veteran population. | 2005 Apr |
|
Effects of the combined treatment with thalidomide, megestrol and interleukine-2 in cirrhotic patients with advanced hepatocellular carcinoma. A pilot study. | 2005 Apr |
|
Treatment with inhibitors of angiogenesis in advanced hepatocellular carcinoma: a new tool in our hands or simply a hope? | 2005 Apr |
|
[Actions of a 19-norprogesterone derivative on mammary gland: nomegestrol acetate]. | 2005 Feb |
|
Effect of nomegestrol acetate on estrogen biosynthesis and transformation in MCF-7 and T47-D breast cancer cells. | 2005 Jan |
|
Control of sulfatase activity by nomegestrol acetate in normal and cancerous human breast tissues. | 2005 Jul-Aug |
|
Nomegestrol acetate may enhance the skeletal effects of estradiol on biochemical markers of bone turnover in menopausal women after a 12-week treatment period. | 2005 Jun |
|
Pregnancy following intracytoplasmic sperm injection and preimplantation genetic diagnosis after the conservative management of endometrial cancer. | 2005 Jun |
|
Antigenotoxic effects of ascorbic acid against megestrol acetate-induced genotoxicity in mice. | 2005 Mar |
|
Hormonal treatment of a recurrent granulosa cell tumor of the ovary: case report and review of the literature. | 2005 Mar |
|
Phase II study of sequential hormonal therapy with anastrozole/exemestane in advanced and metastatic breast cancer. | 2005 May 9 |
|
[Isolation and identification of two new epimer from the mother liquid of megestrol acetate]. | 2005 Sep |
|
Review of cost-effectiveness analyses in hormonal therapies in advanced breast cancer. | 2005 Sep |
|
Megestrol attenuates the hormonal response to CCK-4-induced panic attacks. | 2006 |
|
Hepatocellular carcinoma--Pathological complete response to oral capecitabine, megestrol and thalidomide. | 2006 |
|
Effects of a single Silastic contraceptive implant containing nomegestrol acetate (Uniplant) on endometrial morphology and ovarian function for 1 year. | 2006 Dec |
|
Effects of estrogen, raloxifene, and hormone replacement therapy on serum C-reactive protein and homocysteine levels. | 2006 Feb 20 |
|
Short-term progestin treatments prevent estrous induction by a GnRH agonist implant in anestrous bitches. | 2006 Jan 20 |
|
Orchiectomy or androgen receptor blockade attenuates baroreflex-mediated bradycardia in conscious rats. | 2006 Jan 23 |
|
A successful live birth through in vitro fertilization program after conservative treatment of FIGO grade I endometrial cancer. | 2006 Jun |
|
Characterization of related impurities in megestrol acetate. | 2006 Jun 16 |
|
Cyclic progestin administration increases energy expenditure and decreases body fat mass in perimenopausal women. | 2006 Mar-Apr |
|
New progestagens for contraceptive use. | 2006 Mar-Apr |
|
Activation of nitric oxide synthesis in human endothelial cells using nomegestrol acetate. | 2006 Oct |
|
Testosterone supplementation of megestrol therapy does not enhance lean tissue accrual in men with human immunodeficiency virus-associated weight loss: a randomized, double-blind, placebo-controlled, multicenter trial. | 2007 Feb |
|
Longitudinal evaluation of serum leptin and bone mineral density in early postmenopausal women. | 2007 May-Jun |
Patents
Sample Use Guides
Oral Suspension is 800 mg/day (20 mL/day).
In clinical trials evaluating different dose schedules, daily doses of 400 and 800 mg/day.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15297426
Megestrol acetate was shown to inhibit the growth of HepG2 cells in vitro in dose- and time-dependent manners with an IC (50) of 260 uM (24-h incubation)
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QG03AC05
Created by
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WHO-ATC |
G03AC05
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LIVERTOX |
593
Created by
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WHO-ATC |
G03FB04
Created by
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CFR |
21 CFR 520.1341
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NCI_THESAURUS |
C776
Created by
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WHO-VATC |
QG03DB02
Created by
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WHO-ATC |
G03FA08
Created by
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WHO-ATC |
L02AB01
Created by
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WHO-VATC |
QG03FA08
Created by
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WHO-ATC |
G03AB01
Created by
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WHO-VATC |
QG03AB01
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NDF-RT |
N0000175602
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WHO-ATC |
G03DB02
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WHO-VATC |
QL02AB01
Created by
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NDF-RT |
N0000011301
Created by
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WHO-VATC |
QG03FB04
Created by
admin on Wed Jul 05 22:30:20 UTC 2023 , Edited by admin on Wed Jul 05 22:30:20 UTC 2023
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WHO-ATC |
G03AA04
Created by
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WHO-VATC |
QG03AA04
Created by
admin on Wed Jul 05 22:30:20 UTC 2023 , Edited by admin on Wed Jul 05 22:30:20 UTC 2023
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EA6LD1M70M
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1529
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C630
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6722
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6703
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3233
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EA6LD1M70M
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CHEMBL1201139
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MEGESTROL
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3562-63-8
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SUB08712MIG
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19090
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DTXSID00100933
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222-628-6
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100000081461
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D008535
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ACTIVE MOIETY