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
CC[C@]12CC(=C)[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(O)C#C
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
| Molecular Formula | C22H28O2 |
| Molecular Weight | 324.4565 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 Health Status: healthy Age Group: adult Sex: F 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 pilot study to assess the effect of three short-term treatments on frequent and/or prolonged bleeding compared to placebo in women using Implanon. | 2006-01 |
|
| Failure of Implanon contraception in a patient taking carbamazepin for epilepsia. | 2006-01 |
|
| A multicentre study investigating subcutaneous etonogestrel implants with injectable testosterone decanoate as a potential long-acting male contraceptive. | 2006-01 |
|
| Effect on insulin sensitivity of Implanon vs. GnRH agonist in women with endometriosis. | 2005-12 |
|
| 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. | 2005-12 |
|
| How to remove impalpable Implanon implants. | 2005-10 |
|
| An assessment of the first 3 years' use of Implanon in Luton. | 2005-10 |
|
| [Ectopic pregnancy with etonogestrel contraceptive implant (Implanon): first case]. | 2005-10 |
|
| [Hormonal contraception for males--an option for adolescents?]. | 2005-10 |
|
| Transitory reduction of platelet aggregation with the use of etonogestrel implant in healthy women. | 2005-09 |
|
| Clinical experience and acceptability of the etonogestrel subdermal contraceptive implant. | 2005-09 |
|
| Australian women's experience with Implanon. | 2005-08 |
|
| Self removal of Implanon: a case report. | 2005-07 |
|
| FFPRHC Guidance (July 2005): The use of contraception outside the terms of the product licence. | 2005-07 |
|
| The role of CYP2C and CYP3A in the disposition of 3-keto-desogestrel after administration of desogestrel. | 2005-07 |
|
| Gateways to clinical trials. | 2005-06 |
|
| [Preliminary results from the OPNI observatory: long-term follow-up of a cohort of women using the progestagen contraceptive implant Implanon]. | 2005-05 |
|
| Safety and efficacy of Implanon, a single-rod implantable contraceptive containing etonogestrel. | 2005-05 |
|
| Contraceptive implants. | 2005-04 |
|
| Clinical challenge with Implanon removal: a case report. | 2005-04 |
|
| Unintended pregnancies with the etonogestrel implant (Implanon): a case series from postmarketing experience in Australia. | 2005-04 |
|
| Effect of Implanon on insulin resistance in women with Polycystic Ovary Syndrome. | 2005-04 |
|
| Ultrasound localisation of non-palpable Implanon. | 2005-04 |
|
| A multicenter phase IIb study of a novel combination of intramuscular androgen (testosterone decanoate) and oral progestogen (etonogestrel) for male hormonal contraception. | 2005-04 |
|
| Effects of two types of hormonal contraception--oral versus intravaginal--on the sexual life of women and their partners. | 2005-04 |
|
| One year study of Implanon on the adverse events and discontinuation. | 2005-03 |
|
| Efficacy and safety of a contraceptive vaginal ring (NuvaRing) compared with a combined oral contraceptive: a 1-year randomized trial. | 2005-03 |
|
| Migration of implanon: two case reports. | 2005-01 |
|
| Treatment of pelvic endometriosis with etonogestrel subdermal implant (Implanon). | 2005-01 |
|
| Absence of pharmacokinetic interactions of the combined contraceptive vaginal ring NuvaRing with oral amoxicillin or doxycycline in two randomised trials. | 2005 |
|
| Acceptability and side-effects of Implanon in Switzerland: a retrospective study by the Implanon Swiss Study Group. | 2004-12 |
|
| Implanon studies conducted in Indonesia. | 2004-11 |
|
| Effect of etonogestrel subdermal contraceptive implant (Implanon) on liver function tests -- a randomized comparative study with Norplant implants. | 2004-11 |
|
| Depot testosterone with etonogestrel implants result in induction of azoospermia in all men for long-term contraception. | 2004-11 |
|
| [Two patients with a non-palpable, subcutaneously implanted contraceptive]. | 2004-09-04 |
|
| [The progestagen-containing implant (Implanon); who is responsible for what?]. | 2004-09-04 |
|
| A comparative study on the effects of a contraceptive vaginal ring NuvaRing and an oral contraceptive on carbohydrate metabolism and adrenal and thyroid function. | 2004-09 |
|
| [Acceptability of the etonogestrel-containing contraceptive implant (Implanon)]. | 2004-09 |
|
| Implanon and medical indemnity: a case study of risk management using the Australian standard. | 2004-07-19 |
|
| Implanon use in Thai women above the age of 35 years. | 2004-06 |
|
| The combined contraceptive vaginal ring (NuvaRing) and lipid metabolism: a comparative study. | 2004-05 |
|
| Pharmacological profile of progestins. | 2004-04-15 |
|
| New delivery systems in contraception: vaginal rings. | 2004-04 |
|
| Implanon audit. | 2004-04 |
|
| Treatment of endometriotic catamenial haemoptysis with etonogestrel subdermal implant. | 2004-04 |
|
| Experience with Implanon in a northeast London family planning clinic. | 2004-03 |
|
| The combined contraceptive vaginal ring, NuvaRing, and tampon co-usage. | 2004-03 |
|
| The contraceptive vaginal ring, NuvaRing, and antimycotic co-medication. | 2004-02 |
|
| Relative cost effectiveness of Depo-Provera, Implanon, and Mirena in reversible long-term hormonal contraception in the UK. | 2004 |
|
| Vaginal rings for menopausal symptom relief. | 2004 |
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
| Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 09:43:28 GMT 2025
by
admin
on
Wed Apr 02 09:43:28 GMT 2025
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| Record UNII |
304GTH6RNH
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| Record Status |
Validated (UNII)
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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 |
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