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 Date1.15300801E12 |
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 |
---|---|---|
Implanon: when is the ideal time to insert? | 2001 Jul |
|
Suppression of spermatogenesis by etonogestrel implants with depot testosterone: potential for long-acting male contraception. | 2002 Aug |
|
High acceptability and satisfaction with NuvaRing use. | 2002 Dec |
|
Contraceptive efficacy and tolerability with a novel combined contraceptive vaginal ring, NuvaRing. | 2002 Dec |
|
Complete and robust ovulation inhibition with NuvaRing. | 2002 Dec |
|
Investigation of a novel preparation of testosterone decanoate in men: pharmacokinetics and spermatogenic suppression with etonogestrel implants. | 2002 Nov |
|
An assessment of the use of Implanon in three community services. | 2002 Oct |
|
Efficacy, cycle control, and user acceptability of a novel combined contraceptive vaginal ring. | 2002 Sep |
|
Risks and benefits, advantages and disadvantages of levonorgestrel-releasing contraceptive implants. | 2003 |
|
The combined contraceptive ring NuvaRing and spermicide co-medication. | 2003 Apr |
|
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 |
|
Interaction of St John's wort with low-dose oral contraceptive therapy: a randomized controlled trial. | 2003 Dec |
|
The effect of progesterone and synthetic progestins on serum- and estradiol-stimulated proliferation of human breast cancer cells. | 2003 Feb |
|
The impalpable Implanon: a case report. | 2003 Jul |
|
Etonogestrel implant use is not related to hypercoagulable changes in anticoagulant system. | 2003 Mar |
|
Implanon: user views in the first year across three family planning services in the Trent Region, UK. | 2003 Mar |
|
Use of progestins in male contraception. | 2003 Nov |
|
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 |
|
Vaginal rings for menopausal symptom relief. | 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 |
|
The contraceptive vaginal ring, NuvaRing, and antimycotic co-medication. | 2004 Feb |
|
Experience with Implanon in a northeast London family planning clinic. | 2004 Mar |
|
The combined contraceptive vaginal ring, NuvaRing, and tampon co-usage. | 2004 Mar |
|
The combined contraceptive vaginal ring (NuvaRing) and lipid metabolism: a comparative study. | 2004 May |
|
Implanon studies conducted in Indonesia. | 2004 Nov |
|
Effect of etonogestrel subdermal contraceptive implant (Implanon) on liver function tests -- a randomized comparative study with Norplant implants. | 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 |
|
[Acceptability of the etonogestrel-containing contraceptive implant (Implanon)]. | 2004 Sep |
|
[The progestagen-containing implant (Implanon); who is responsible for what?]. | 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 |
|
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 |
|
Australian women's experience with Implanon. | 2005 Aug |
|
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 |
|
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 |
|
Gateways to clinical trials. | 2005 Jun |
|
One year study of Implanon on the adverse events and discontinuation. | 2005 Mar |
|
An assessment of the first 3 years' use of Implanon in Luton. | 2005 Oct |
|
[Hormonal contraception for males--an option for adolescents?]. | 2005 Oct |
|
Clinical experience and acceptability of the etonogestrel subdermal contraceptive implant. | 2005 Sep |
|
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
Created by
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WHO-ATC |
G03AC08
Created by
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NCI_THESAURUS |
C776
Created by
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WHO-VATC |
QG03AC08
Created by
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LIVERTOX |
388
Created by
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NDF-RT |
N0000175602
Created by
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1268783
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PRIMARY | |||
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CHEMBL1531
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PRIMARY | |||
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1110
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50777
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304GTH6RNH
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PRIMARY | |||
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14584
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PRIMARY | RxNorm | ||
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7590
Created by
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Etonogestrel
Created by
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C47528
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1173268
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ALTERNATIVE | |||
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258-936-2
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6832
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M5198
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PRIMARY | Merck Index | ||
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SUB07335MIG
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304GTH6RNH
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PRIMARY | |||
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DB00294
Created by
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54048-10-1
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DTXSID9046782
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ETONOGESTREL
Created by
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6917715
Created by
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PRIMARY |
ACTIVE MOIETY
PARENT (METABOLITE ACTIVE)