Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H28O2 |
Molecular Weight | 324.4565 |
Optical Activity | UNSPECIFIED |
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)[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]
InChI
InChIKey=GCKFUYQCUCGESZ-BPIQYHPVSA-N
InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
DescriptionSources: http://www.drugbank.ca/drugs/DB00294Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021529s004lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00294
Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2009/021529s004lbl.pdf
Etonogestrel, also known as 11-methylenelevonorgestrel and 3-keto-desogestrel, is a steroidal progestin used in hormonal contraceptives, most notably the subdermal implants Nexplanon and Implanon and the vaginal ring NuvaRing. Etonogestrel is a progestin or a synthetic form of the naturally occurring female sex hormone, progesterone. In a woman's normal menstrual cycle, an egg matures and is released from the ovaries (ovulation). The ovary then produces progesterone, preventing the release of further eggs and priming the lining of the womb for a possible pregnancy. If pregnancy occurs, progesterone levels in the body remain high, maintaining the womb lining. If pregnancy does not occur, progesterone levels in the body fall, resulting in a menstrual period. Etonogestrel tricks the body processes into thinking that ovulation has already occurred, by maintaining high levels of the synthetic progesterone. This prevents the release of eggs from the ovaries. Etonogestrel binds to the progesterone and estrogen receptors. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like etonogestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 Sources: http://www.drugbank.ca/drugs/DB00294 |
|||
Target ID: CHEMBL206 Sources: http://www.drugbank.ca/drugs/DB00294 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | IMPLANON Approved UseIMPLANON™ (etonogestrel implant) is indicated for women for the prevention of pregnancy. Launch Date2006 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.59 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30347490 |
75 μg 1 times / day multiple, oral dose: 75 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
ETONOGESTREL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.097 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30347490 |
75 μg 1 times / day multiple, oral dose: 75 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
ETONOGESTREL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
29.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30347490 |
75 μg 1 times / day multiple, oral dose: 75 μg route of administration: Oral experiment type: MULTIPLE co-administered: |
ETONOGESTREL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% |
ETONOGESTREL blood | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Disc. AE: Menstrual irregularity, Emotional lability... AEs leading to discontinuation/dose reduction: Menstrual irregularity (11.1%) Sources: Emotional lability (2.3%) Weight increase (2.3%) Headache (1.6%) Acne (1.3%) Depression (1%) |
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Other AEs: Headache, Vaginitis... Other AEs: Headache (24.9%) Sources: Vaginitis (14.5%) Weight increase (13.7%) Acne (13.5%) Breast pain (12.8%) Abdominal pain (10.9%) Pharyngitis (10.5%) Leukorrhea (9.6%) Influenza-like symptoms (7.6%) Dizziness (7.2%) Dysmenorrhea (7.2%) Back pain (6.8%) Emotional lability (6.5%) Nausea (6.4%) Pain (5.6%) Nervousness (5.6%) Depression (5.5%) Hypersensitivity (5.4%) Injection site pain (5.2%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Depression | 1% Disc. AE |
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Acne | 1.3% Disc. AE |
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Headache | 1.6% Disc. AE |
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Menstrual irregularity | 11.1% Disc. AE |
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Emotional lability | 2.3% Disc. AE |
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Weight increase | 2.3% Disc. AE |
70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Pharyngitis | 10.5% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Abdominal pain | 10.9% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Breast pain | 12.8% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Acne | 13.5% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Weight increase | 13.7% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Vaginitis | 14.5% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Headache | 24.9% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Injection site pain | 5.2% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Hypersensitivity | 5.4% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Depression | 5.5% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Nervousness | 5.6% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Pain | 5.6% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Nausea | 6.4% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Emotional lability | 6.5% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Back pain | 6.8% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Dizziness | 7.2% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Dysmenorrhea | 7.2% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Influenza-like symptoms | 7.6% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Leukorrhea | 9.6% | 70 ug 1 times / day steady, subdermal Recommended Dose: 70 ug, 1 times / day Route: subdermal Route: steady Dose: 70 ug, 1 times / day Sources: |
healthy, adult n = 942 Health Status: healthy Age Group: adult Sex: F Population Size: 942 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-187_NuvaRing_biopharmr_P1.pdf#PAGE=20 Page: (ClinPharm) 20 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-187_NuvaRing_biopharmr_P1.pdf#PAGE=14 Page: (ClinPharm) 14 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-187_NuvaRing_biopharmr_P1.pdf#PAGE=14 Page: (ClinPharm) 14 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-187_NuvaRing_biopharmr_P1.pdf#PAGE=14 Page: (ClinPharm) 14 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-187_NuvaRing_biopharmr_P1.pdf#PAGE=14 Page: (ClinPharm) 14 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-187_NuvaRing_biopharmr_P1.pdf#PAGE=14 Page: (ClinPharm) 14 |
no | |||
yes | yes (co-administration study) Comment: Coadministration of Efavirenz (CYP3A4 inducer) decreased Etonogestrel plasma concentration one week after implant insertion by 84%. Page: 5, 15, (ClinPharm) 14, 25 |
PubMed
Title | Date | PubMed |
---|---|---|
A screening study on the liability of eight different female sex steroids to inhibit CYP2C9, 2C19 and 3A4 activities in human liver microsomes. | 2003 Aug |
|
[A randomized study comparing the efficacy and bleeding pattern of Implanon and Norplant hormonal contraceptive implant]. | 2003 Jul |
|
The impalpable Implanon: a case report. | 2003 Jul |
|
Spontaneous snapping of an Implanon in two halves in situ. | 2003 Oct |
|
[Acne vulgaris in connection with the use of progestagens in a hormonal IUD or a subcutaneous implant]. | 2003 Oct 25 |
|
[Vaginal contraception: new form of administration of hormonal contraception]. | 2003 Oct 25 |
|
Effect of Implanon and Norplant subdermal contraceptive implants on serum lipids--a randomized comparative study. | 2003 Sep |
|
Relative cost effectiveness of Depo-Provera, Implanon, and Mirena in reversible long-term hormonal contraception in the UK. | 2004 |
|
New delivery systems in contraception: vaginal rings. | 2004 Apr |
|
Treatment of endometriotic catamenial haemoptysis with etonogestrel subdermal implant. | 2004 Apr |
|
Pharmacological profile of progestins. | 2004 Apr 15 |
|
Acceptability and side-effects of Implanon in Switzerland: a retrospective study by the Implanon Swiss Study Group. | 2004 Dec |
|
Implanon and medical indemnity: a case study of risk management using the Australian standard. | 2004 Jul 19 |
|
Implanon use in Thai women above the age of 35 years. | 2004 Jun |
|
Experience with Implanon in a northeast London family planning clinic. | 2004 Mar |
|
The combined contraceptive vaginal ring (NuvaRing) and lipid metabolism: a comparative study. | 2004 May |
|
Implanon studies conducted in Indonesia. | 2004 Nov |
|
Depot testosterone with etonogestrel implants result in induction of azoospermia in all men for long-term contraception. | 2004 Nov |
|
A comparative study on the effects of a contraceptive vaginal ring NuvaRing and an oral contraceptive on carbohydrate metabolism and adrenal and thyroid function. | 2004 Sep |
|
[Two patients with a non-palpable, subcutaneously implanted contraceptive]. | 2004 Sep 4 |
|
Absence of pharmacokinetic interactions of the combined contraceptive vaginal ring NuvaRing with oral amoxicillin or doxycycline in two randomised trials. | 2005 |
|
Contraceptive implants. | 2005 Apr |
|
Clinical challenge with Implanon removal: a case report. | 2005 Apr |
|
Unintended pregnancies with the etonogestrel implant (Implanon): a case series from postmarketing experience in Australia. | 2005 Apr |
|
Effect of Implanon on insulin resistance in women with Polycystic Ovary Syndrome. | 2005 Apr |
|
Ultrasound localisation of non-palpable Implanon. | 2005 Apr |
|
A multicenter phase IIb study of a novel combination of intramuscular androgen (testosterone decanoate) and oral progestogen (etonogestrel) for male hormonal contraception. | 2005 Apr |
|
Effects of two types of hormonal contraception--oral versus intravaginal--on the sexual life of women and their partners. | 2005 Apr |
|
Australian women's experience with Implanon. | 2005 Aug |
|
Effect on insulin sensitivity of Implanon vs. GnRH agonist in women with endometriosis. | 2005 Dec |
|
Quantitative analysis of gene regulation by seven clinically relevant progestins suggests a highly similar mechanism of action through progesterone receptors in T47D breast cancer cells. | 2005 Dec |
|
Migration of implanon: two case reports. | 2005 Jan |
|
Treatment of pelvic endometriosis with etonogestrel subdermal implant (Implanon). | 2005 Jan |
|
Self removal of Implanon: a case report. | 2005 Jul |
|
FFPRHC Guidance (July 2005): The use of contraception outside the terms of the product licence. | 2005 Jul |
|
The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. | 2005 Jul |
|
Gateways to clinical trials. | 2005 Jun |
|
One year study of Implanon on the adverse events and discontinuation. | 2005 Mar |
|
Efficacy and safety of a contraceptive vaginal ring (NuvaRing) compared with a combined oral contraceptive: a 1-year randomized trial. | 2005 Mar |
|
[Preliminary results from the OPNI observatory: long-term follow-up of a cohort of women using the progestagen contraceptive implant Implanon]. | 2005 May |
|
Safety and efficacy of Implanon, a single-rod implantable contraceptive containing etonogestrel. | 2005 May |
|
How to remove impalpable Implanon implants. | 2005 Oct |
|
An assessment of the first 3 years' use of Implanon in Luton. | 2005 Oct |
|
[Ectopic pregnancy with etonogestrel contraceptive implant (Implanon): first case]. | 2005 Oct |
|
[Hormonal contraception for males--an option for adolescents?]. | 2005 Oct |
|
Transitory reduction of platelet aggregation with the use of etonogestrel implant in healthy women. | 2005 Sep |
|
Clinical experience and acceptability of the etonogestrel subdermal contraceptive implant. | 2005 Sep |
|
A pilot study to assess the effect of three short-term treatments on frequent and/or prolonged bleeding compared to placebo in women using Implanon. | 2006 Jan |
|
Failure of Implanon contraception in a patient taking carbamazepin for epilepsia. | 2006 Jan |
|
A multicentre study investigating subcutaneous etonogestrel implants with injectable testosterone decanoate as a potential long-acting male contraceptive. | 2006 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/etonogestrel.html
Usual Adult Dose for Contraception
One 68 mg implant inserted subdermally. The implant should not be left in place more than three years.
Route of Administration:
Transdermal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27186136
Etonogestrel (1716 pg/mL) significantly altered antiretroviral uptake across THP-1, BC-3 (CD8+) cell lines, incubated for one hour with tenofovir and emtricitabine to assess uptake except
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000011301
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WHO-ATC |
G03AC08
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NCI_THESAURUS |
C776
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WHO-VATC |
QG03AC08
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LIVERTOX |
388
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NDF-RT |
N0000175602
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1268783
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CHEMBL1531
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1110
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50777
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304GTH6RNH
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14584
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7590
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Etonogestrel
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C47528
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1173268
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258-936-2
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6832
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m5198
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SUB07335MIG
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304GTH6RNH
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DB00294
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54048-10-1
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100000082090
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DTXSID9046782
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ETONOGESTREL
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6917715
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ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)