Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H28O2 |
Molecular Weight | 312.4458 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]
InChI
InChIKey=WWYNJERNGUHSAO-XUDSTZEESA-N
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1
Molecular Formula | C21H28O2 |
Molecular Weight | 312.4458 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021225s031lbl.pdfhttps://www.drugbank.ca/drugs/DB09389 | https://www.drugs.com/drp/norgestrel.html | https://www.ncbi.nlm.nih.gov/pubmed/8136310Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25698840
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021225s031lbl.pdfhttps://www.drugbank.ca/drugs/DB09389 | https://www.drugs.com/drp/norgestrel.html | https://www.ncbi.nlm.nih.gov/pubmed/8136310
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/25698840
Norgestrel is synthetic steroidal progestin that is used in combination with ethinyl estradiol for oral contraception. Norgestrel is composed of a racemic mixture of two stereoisomers, dextronorgestrel and levonorgestrel. However, only the levorotary enantiomer (levonorgestrel) is biologically active. Norgestrel (and more specifically the active stereoisomer levonorgestrel) binds to the progesterone and estrogen receptors within the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. Loss of the LH surge inhibits ovulation and thereby prevents pregnancy. Norgestrel in combination with ethinyl estradiol is indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL208 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3139361 |
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Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3139361 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | MIRENA Approved UseMirena is indicated for intrauterine contraception for up to 5 years. Mirena is also indicated for the treatment of heavy menstrual bleeding in women who choose to use intrauterine contraception as their method of contraception. Mirena is recommended for women who have had at least one child. The system should be replaced after 5 years if continued use is desired. Launch Date2000 |
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Primary | MIRENA Approved UseMirena is indicated for intrauterine contraception for up to 5 years. Mirena is also indicated for the treatment of heavy menstrual bleeding in women who choose to use intrauterine contraception as their method of contraception. Mirena is recommended for women who have had at least one child. The system should be replaced after 5 years if continued use is desired. Launch Date2000 |
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Sources: https://www.drugs.com/drp/norgestrel.html |
Preventing | OVRETTE Approved UseProgestin-only oral contraceptives are indicated for the prevention of pregnancy. Launch Date1973 |
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Sources: https://www.drugs.com/pro/elinest.html |
Preventing | ELINEST Approved UseOral contraceptives are indicated for the prevention of pregnancy in women who elect to use oral contraceptives as a method of contraception. Launch Date2012 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
16.2 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30703352 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
14.11 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12169384 |
0.75 mg single, oral dose: 0.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
360.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30703352 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
123.1 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12169384 |
0.75 mg single, oral dose: 0.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29.7 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/30703352 |
1.5 mg single, oral dose: 1.5 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL blood | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
|
24.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/12169384 |
0.75 mg single, oral dose: 0.75 mg route of administration: Oral experiment type: SINGLE co-administered: |
LEVONORGESTREL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: Page: p.10 |
healthy, 16-45 n = 1714 Health Status: healthy Condition: Prevention of pregnancy Age Group: 16-45 Sex: F Population Size: 1714 Sources: Page: p.10 |
Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (1.5%) Sources: Page: p.10 |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: Page: p.2 |
healthy, 27.3 ± 5.7 n = 1700 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.3 ± 5.7 Sex: F Population Size: 1700 Sources: Page: p.2 |
Disc. AE: Menstrual irregularity, Amenorrhea... AEs leading to discontinuation/dose reduction: Menstrual irregularity (0.7%) Sources: Page: p.2Amenorrhea (0.06%) |
90 ug 1 times / day multiple, oral Recommended Dose: 90 ug, 1 times / day Route: oral Route: multiple Dose: 90 ug, 1 times / day Co-administed with:: ethinyl estradiol, p.o(20 ug; q.d; 1 year) Sources: Page: p.507 |
healthy, 27.6±6.7 n = 323 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.6±6.7 Sex: F Population Size: 323 Sources: Page: p.507 |
Disc. AE: Metrorrhagia, Bleeding vaginal... AEs leading to discontinuation/dose reduction: Metrorrhagia (8.7%) Sources: Page: p.507Bleeding vaginal (3.7%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bleeding | 1.5% Disc. AE |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: Page: p.10 |
healthy, 16-45 n = 1714 Health Status: healthy Condition: Prevention of pregnancy Age Group: 16-45 Sex: F Population Size: 1714 Sources: Page: p.10 |
Amenorrhea | 0.06% Disc. AE |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: Page: p.2 |
healthy, 27.3 ± 5.7 n = 1700 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.3 ± 5.7 Sex: F Population Size: 1700 Sources: Page: p.2 |
Menstrual irregularity | 0.7% Disc. AE |
20 ug 1 times / day multiple, intrauterine Recommended Dose: 20 ug, 1 times / day Route: intrauterine Route: multiple Dose: 20 ug, 1 times / day Sources: Page: p.2 |
healthy, 27.3 ± 5.7 n = 1700 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.3 ± 5.7 Sex: F Population Size: 1700 Sources: Page: p.2 |
Bleeding vaginal | 3.7% Disc. AE |
90 ug 1 times / day multiple, oral Recommended Dose: 90 ug, 1 times / day Route: oral Route: multiple Dose: 90 ug, 1 times / day Co-administed with:: ethinyl estradiol, p.o(20 ug; q.d; 1 year) Sources: Page: p.507 |
healthy, 27.6±6.7 n = 323 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.6±6.7 Sex: F Population Size: 323 Sources: Page: p.507 |
Metrorrhagia | 8.7% Disc. AE |
90 ug 1 times / day multiple, oral Recommended Dose: 90 ug, 1 times / day Route: oral Route: multiple Dose: 90 ug, 1 times / day Co-administed with:: ethinyl estradiol, p.o(20 ug; q.d; 1 year) Sources: Page: p.507 |
healthy, 27.6±6.7 n = 323 Health Status: healthy Condition: Prevention of pregnancy Age Group: 27.6±6.7 Sex: F Population Size: 323 Sources: Page: p.507 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
likely | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
likely | |||
major | yes (co-administration study) Comment: Concomitant administration of efavirenz (moderate CYP3A inducer) has been found to reduce plasma levels of levonorgestrel (AUC) by around 50%. Page: (ClinPharm) 16-17 |
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Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
minor | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/203159Orig1s000ClinPharmR.pdf#page=17 Page: (ClinPharm) 17 |
unlikely |
PubMed
Title | Date | PubMed |
---|---|---|
Superficial endometrial vascular fragility in Norplant users and in women with ovulatory dysfunctional uterine bleeding. | 2000 Jul |
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Post-marketing surveillance of Norplant((R)) contraceptive implants: II. Non-reproductive health(1). | 2001 Apr |
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Non-protein bound dienogest in serum and salivary dienogest in women taking the oral contraceptives Certostat and Valette. | 2001 Apr |
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Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy. | 2001 Aug |
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Treatment of menorrhagia with the levonorgestrel intrauterine system versus endometrial resection. | 2001 Aug |
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The relation of oxidized LDL autoantibodies and long-term hormone replacement therapy to ultrasonographically assessed atherosclerotic plaque quantity and severity in postmenopausal women. | 2001 Aug |
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[Hormonal contraception with gestagens]. | 2001 Aug 20 |
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Fine structure of prolactin cell of female albino rat as affected by some antifertility drugs--a comparative electron microscopic study. | 2001 Feb |
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Fluoroscopically guided Norplant removal. | 2001 Feb |
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Intrauterine contraception--what now and what next? | 2001 Jan |
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Multicenter, comparative study of cycle control, efficacy and tolerability of two low-dose oral contraceptives containing 20 microg ethinylestradiol/100 microg levonorgestrel and 20 microg ethinylestradiol/500 microg norethisterone. | 2001 Jul |
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Norgestimate. From the laboratory to three clinical indications. | 2001 Jul |
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The management of menorrhagia--SMART study (Satisfaction with Mirena and Ablation: a Randomised Trial). | 2001 Jul |
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A village would be nice but...it takes a long-acting contraceptive to prevent repeat adolescent pregnancies. | 2001 Jul |
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Evaluation of genotoxic potential of synthetic progestins-norethindrone and norgestrel in human lymphocytes in vitro. | 2001 Jul 25 |
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Weight change and adverse event incidence with a low-dose oral contraceptive: two randomized, placebo-controlled trials. | 2001 Jun |
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The need for more active promotion of emergency contraception. | 2001 Jun |
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Hormonal and barrier methods of contraception, oncogenic human papillomaviruses, and cervical squamous intraepithelial lesion development. | 2001 Jun |
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Protein S levels are lower in women receiving desogestrel-containing combined oral contraceptives (COCs) than in women receiving levonorgestrel-containing COCs at steady state and on cross-over. | 2001 Jun |
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Treatment of menorrhagia. | 2001 Jun 9 |
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Clinical recommendations for oxcarbazepine. | 2001 Mar |
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Implanon contraceptive implants: effects on carbohydrate metabolism. | 2001 Mar |
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The effects of peri-ovulatory administration of levonorgestrel on the menstrual cycle. | 2001 Mar |
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Mechanism of action of hormonal preparations used for emergency contraception: a review of the literature. | 2001 Mar |
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Use of a levonorgestrel-releasing intrauterine device in the treatment of rectovaginal endometriosis. | 2001 Mar |
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Contraception in the adolescent: an update. | 2001 Mar |
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Norplant and other implantable contraceptives. | 2001 Mar |
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Progestin regulation of galanin and prolactin gene expression in oestrogen-induced pituitary tumours. | 2001 Mar |
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Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction-liquid chromatography-diode array detection. | 2001 Mar 16 |
|
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women. | 2001 Sep |
Sample Use Guides
Mirena contains 52 mg of levonorgestrel (LNG). Initially, LNG is released at a rate of approximately 20 mcg/day. This rate decreases progressively to half that value after 5 years. Mirena must be removed by the end of the fifth year and can be replaced at the time of removal with a new Mirena if continued contraceptive protection is desired.
Route of Administration:
Vaginal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26161412
5 × 10(-5) mol/L Levonorgestrel (LNG) revealed a time-dependent inhibition of cell proliferation and an increase of apoptosis in both human endometrial stromal cells (HESCs) and glandular cells (HEGCs). Furthermore, these cells demonstrated a significant Gap Junctional Intercellular Communication (GJIC) enhancement upon treatment with 5 × 10(-5) mol/L for 48 hours. The effects of LNG were most noticeable in HESCs rather than in HEGCs.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:26:36 GMT 2023
by
admin
on
Fri Dec 15 15:26:36 GMT 2023
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Record UNII |
3J8Q1747Z2
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QG03FA10
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WHO-VATC |
QG03FB01
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WHO-VATC |
QG03AA06
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NCI_THESAURUS |
C776
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WHO-ATC |
G03FA10
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WHO-ATC |
G03AA06
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LIVERTOX |
699
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WHO-ATC |
G03FB01
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13109
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m8063
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NORGESTREL
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7630
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1472000
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SUB09371MIG
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D009644
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100000092602
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2157
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6533-00-2
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C703
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DB09389
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3595
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3J8Q1747Z2
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3J8Q1747Z2
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757251
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CHEMBL2107797
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7518
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PRIMARY | RxNorm | ||
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229-433-5
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Related Record | Type | Details | ||
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ENANTIOMER -> RACEMATE |
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ENANTIOMER -> RACEMATE |
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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PARENT -> METABOLITE ACTIVE |
URINE
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METABOLITE -> PARENT |
URINE
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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Related Record | Type | Details | ||
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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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