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
CC(=O)[C@@]1(O)CC[C@H]2[C@@H]3C=C(C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
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
Molecular Formula | C22H30O3 |
Molecular Weight | 342.4718 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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 Date1993 |
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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 Date1993 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1364 ng/mL |
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: UNKNOWN food status: FED |
|
1616 ng/mL |
675 mg single, oral dose: 675 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
187 ng/mL |
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: UNKNOWN food status: FASTED |
|
1044 ng/mL |
675 mg single, oral dose: 675 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN 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 |
|
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 |
|
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 |
|
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18625 ng × h/mL |
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: UNKNOWN food status: FED |
|
17029 ng × h/mL |
675 mg single, oral dose: 675 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: FED |
|
8942 ng × h/mL |
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: UNKNOWN food status: FASTED |
|
11879 ng × h/mL |
675 mg single, oral dose: 675 mg route of administration: Oral experiment type: SINGLE co-administered: |
MEGESTROL ACETATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN 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 |
|
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 |
|
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 |
|
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 |
|
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 Health Status: unhealthy Age Group: 54-68 years Sex: F 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 |
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 |
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 |
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 |
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 Health Status: unhealthy Age Group: 54-68 years Sex: F 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 |
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 |
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 |
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 |
---|---|---|
Systemic treatment of hepatocellular carcinoma. | 2001 |
|
Treatment. Court decision to allow marketing of generic form of weight-loss drug. | 2001 Aug 3 |
|
Serum immunoglobulins, total protein and albumin levels during UniplantR use by Nigerian women. | 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 |
|
Megestrol-induced Cushing syndrome. | 2001 Oct |
|
Management of common symptoms in terminally ill patients: Part I. Fatigue, anorexia, cachexia, nausea and vomiting. | 2001 Sep 1 |
|
Prevention of menstruation with leuprorelin (GnRH agonist) in women undergoing myelosuppressive chemotherapy or radiochemotherapy for hematological malignancies: a pilot study. | 2001 Sep-Oct |
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Efficacy and economics of hormonal therapies for advanced breast cancer. | 2002 |
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The impact of hormonal treatments on quality of life of patients with metastatic breast cancer. | 2002 |
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Estrogen as therapy for breast cancer. | 2002 |
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Existing and emerging endocrine therapies for breast cancer. | 2002 Apr |
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Effects of megestrol acetate on weight gain, body composition, and pulmonary function in patients with cystic fibrosis. | 2002 Apr |
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Fertility-preserving treatment in young patients with endometrial adenocarcinoma. | 2002 Apr 15 |
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Dronabinol versus megestrol acetate versus combination therapy for cancer-associated anorexia: a North Central Cancer Treatment Group study. | 2002 Jan 15 |
|
Variant estrogen receptors and their role in liver disease. | 2002 Jul 31 |
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Effect of megestrol caproate on the reproductive function of laboratory animals. | 2002 Jun |
|
Intramuscular depot medroxyprogesterone versus oral megestrol for the control of postmenopausal hot flashes in breast cancer patients: a randomized study. | 2002 Jun |
|
[Reversal of nomegestrol acetate on multidrug resistance in drug-resistant human breast cancer cell line MCF7/ADR]. | 2002 Mar |
|
Approval summary: letrozole in the treatment of postmenopausal women with advanced breast cancer. | 2002 Mar |
|
Effects of transdermal hormone replacement therapy on levels of soluble P- and E-selectin in postmenopausal healthy women. | 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 |
|
Phase I and pharmacokinetic study of vinblastine and high-dose megestrol acetate. | 2002 Sep |
|
[Antigonadotropic effects of a 19-nor-progesterone derivative: the example of nomegestrol acetate]. | 2003 Jan |
|
Megestrol complications. | 2003 Jan |
|
An overview of nomegestrol acetate selective receptor binding and lack of estrogenic action on hormone-dependent cancer cells. | 2003 Nov |
|
Cancer cachexia. | 2003 Nov 5 |
|
Effect of nomegestrol acetate on human estrogen sulfotransferase activity in the hormone-dependent MCF-7 and T-47D breast cancer cell lines. | 2003 Nov-Dec |
|
Advances in estrogen receptor biology: prospects for improvements in targeted breast cancer therapy. | 2004 |
|
A comparison of the central effects of different progestins used in hormone replacement therapy. | 2004 Aug 20 |
|
Osteoporosis associated with megestrol acetate. | 2004 Dec |
|
[Nome gesrol (lutenyl) induced severe acute hepatitis]. | 2004 Jan |
|
Serum leptin levels and body composition in postmenopausal women: effects of hormone therapy. | 2004 Jul-Aug |
|
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 |
|
Retrospective review of megestrol use for weight loss in an elderly veteran population. | 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 |
|
Hormonal treatment of a recurrent granulosa cell tumor of the ovary: case report and review of the literature. | 2005 Mar |
|
The role of aromatase inhibitors in ameliorating deleterious effects of ovarian stimulation on outcome of infertility treatment. | 2005 Oct 4 |
|
Effects of a single Silastic contraceptive implant containing nomegestrol acetate (Uniplant) on endometrial morphology and ovarian function for 1 year. | 2006 Dec |
|
Durable response of metastatic endometrial carcinoma to treatment with fulvestrant (Faslodex) after prior progestin and anastrozole therapy. | 2006 Feb |
|
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 |
|
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)
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:33:23 GMT 2025
by
admin
on
Mon Mar 31 17:33:23 GMT 2025
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Record UNII |
EA6LD1M70M
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Record Status |
Validated (UNII)
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Record Version |
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Preferred Name | English | ||
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Official Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Common Name | English | ||
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Systematic Name | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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WHO-VATC |
QG03AC05
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WHO-ATC |
G03AC05
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LIVERTOX |
593
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WHO-ATC |
G03FB04
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CFR |
21 CFR 520.1341
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NCI_THESAURUS |
C776
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WHO-VATC |
QG03DB02
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WHO-ATC |
G03FA08
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WHO-ATC |
L02AB01
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WHO-VATC |
QG03FA08
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WHO-ATC |
G03AB01
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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
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NDF-RT |
N0000011301
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WHO-VATC |
QG03FB04
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WHO-ATC |
G03AA04
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WHO-VATC |
QG03AA04
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Code System | Code | Type | Description | ||
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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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DTXSID001009330
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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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222-628-6
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100000081461
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D008535
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PRIMARY |
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PARENT -> IMPURITY |
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Elimination PHARMACOKINETIC PHARMACOKINETIC |
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