Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C22H30O |
Molecular Weight | 310.473 |
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])CCCC=C4CC[C@@]23[H]
InChI
InChIKey=RPLCPCMSCLEKRS-BPIQYHPVSA-N
InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
Molecular Formula | C22H30O |
Molecular Weight | 310.473 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL208 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | DESOGEN Approved UseDesogen (desogestrel and ethinyl estradiol) Tablets are indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception. Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.69 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2147817/ |
0.15 mg 1 times / day steady-state, oral dose: 0.15 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ETONOGESTREL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
5840 pg/mL |
0.15 mg 1 times / day steady-state, oral dose: 0.15 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ETHINYL ESTRADIOL |
ETONOGESTREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
|
2805 pg/mL |
0.15 mg single, oral dose: 0.15 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL |
ETONOGESTREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
35.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2147817/ |
0.15 mg 1 times / day steady-state, oral dose: 0.15 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ETONOGESTREL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
|
52299 pg × h/mL |
0.15 mg 1 times / day steady-state, oral dose: 0.15 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ETHINYL ESTRADIOL |
ETONOGESTREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
|
33858 pg × h/mL |
0.15 mg single, oral dose: 0.15 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL |
ETONOGESTREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
23.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2147817/ |
0.15 mg 1 times / day steady-state, oral dose: 0.15 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
ETONOGESTREL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2% |
0.15 mg 1 times / day steady-state, oral dose: 0.15 mg route of administration: Oral experiment type: STEADY-STATE co-administered: ETHINYL ESTRADIOL |
ETONOGESTREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
|
2% |
0.15 mg single, oral dose: 0.15 mg route of administration: Oral experiment type: SINGLE co-administered: ETHINYL ESTRADIOL |
ETONOGESTREL plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: FEMALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
150 ug 1 times / day steady, oral Recommended Dose: 150 ug, 1 times / day Route: oral Route: steady Dose: 150 ug, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: |
healthy, mean 24.6 years n = 221 Health Status: healthy Age Group: mean 24.6 years Sex: F Population Size: 221 Sources: |
Disc. AE: Headache, Depression... AEs leading to discontinuation/dose reduction: Headache (> 0.45) Sources: Depression (> 0.45) Menorrhagia (> 0.45) Skin disorder (> 0.45) Emotional lability (> 0.45) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Depression | > 0.45 Disc. AE |
150 ug 1 times / day steady, oral Recommended Dose: 150 ug, 1 times / day Route: oral Route: steady Dose: 150 ug, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: |
healthy, mean 24.6 years n = 221 Health Status: healthy Age Group: mean 24.6 years Sex: F Population Size: 221 Sources: |
Emotional lability | > 0.45 Disc. AE |
150 ug 1 times / day steady, oral Recommended Dose: 150 ug, 1 times / day Route: oral Route: steady Dose: 150 ug, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: |
healthy, mean 24.6 years n = 221 Health Status: healthy Age Group: mean 24.6 years Sex: F Population Size: 221 Sources: |
Headache | > 0.45 Disc. AE |
150 ug 1 times / day steady, oral Recommended Dose: 150 ug, 1 times / day Route: oral Route: steady Dose: 150 ug, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: |
healthy, mean 24.6 years n = 221 Health Status: healthy Age Group: mean 24.6 years Sex: F Population Size: 221 Sources: |
Menorrhagia | > 0.45 Disc. AE |
150 ug 1 times / day steady, oral Recommended Dose: 150 ug, 1 times / day Route: oral Route: steady Dose: 150 ug, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: |
healthy, mean 24.6 years n = 221 Health Status: healthy Age Group: mean 24.6 years Sex: F Population Size: 221 Sources: |
Skin disorder | > 0.45 Disc. AE |
150 ug 1 times / day steady, oral Recommended Dose: 150 ug, 1 times / day Route: oral Route: steady Dose: 150 ug, 1 times / day Co-administed with:: ethinylestradiol(20 mug) Sources: |
healthy, mean 24.6 years n = 221 Health Status: healthy Age Group: mean 24.6 years Sex: F Population Size: 221 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | ||||
yes | ||||
yes | yes (co-administration study) Comment: Subjects received a 10-day pretreatment with an oral contraceptive, containing 30 microg ethinyl estradiol (INN, ethinylestradiol) and 150 microg desogestrel, and the bupropion dose was given 1 hour after the last hormone dose. The bupropion, hydroxybupropion, and hydrobupropion plasma concentrations were determined for up to 72 hours. Sources: https://pubmed.ncbi.nlm.nih.gov/14534519/ |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
major | no (co-administration study) Comment: administration of fluconazole has no effect on desogestrel PK |
|||
minor | ||||
no | ||||
no | ||||
yes | yes (co-administration study) Comment: Pretreatment with itraconazole for 4 days significantly increased the area under the plasma concentration-time curve (AUC) of 3-keto-desogestrel by 72.4% |
PubMed
Title | Date | PubMed |
---|---|---|
Risk of venous thromboembolism from oral contraceptives containing gestodene and desogestrel versus levonorgestrel: a meta-analysis and formal sensitivity analysis. | 2001 Aug |
|
Third-generation progestogen type influences hemostatic changes caused by oral contraceptives in Brazilian women. | 2001 Dec |
|
Contraceptive vaginal rings. | 2001 Dec |
|
Transdermal contraception. | 2001 Dec |
|
Oral contraceptives and the risk of myocardial infarction. | 2001 Dec 20 |
|
Sex steroids used in hormonal treatment increase vascular procoagulant activity by inducing thrombin receptor (PAR-1) expression: role of the glucocorticoid receptor. | 2001 Dec 4 |
|
Nonpalpable ultrasonographically not detectable Implanon rods can be localized by magnetic resonance imaging. | 2001 Jun |
|
Effect of second and third generation oral contraceptives on lipid metabolism in the absence or presence of the factor V Leiden mutation. | 2001 Nov |
|
The effects of two progestogen-only pills containing either desogestrel (75 microg/day) or levonorgestrel (30 microg/day) on lipid metabolism. | 2001 Nov |
|
Excretion and metabolism of desogestrel in healthy postmenopausal women. | 2001 Nov |
|
A novel male contraceptive pill-patch combination: oral desogestrel and transdermal testosterone in the suppression of spermatogenesis in normal men. | 2001 Nov |
|
Medical management of dysfunctional uterine bleeding. | 2001 Nov |
|
A prospective study evidencing rhinomanometric and olfactometric outcomes in women taking oral contraceptives. | 2001 Nov |
|
The effect of hormone replacement therapy on serum homocysteine levels in perimenopausal women: a randomized controlled trial. | 2001 Oct |
|
A prospective, controlled study of the effects of hormonal contraception on bone mineral density. | 2001 Oct |
|
[Hormonal contraception and thromboembolic disease--pathophysiologic findings and practical recommendations]. | 2001 Sep |
|
[New gestagens--advantages and disadvantages]. | 2001 Sep |
|
Suppression of spermatogenesis by etonogestrel implants with depot testosterone: potential for long-acting male contraception. | 2002 Aug |
|
Editor's reply. | 2002 Dec |
|
Implanon. | 2002 Dec |
|
Randomized controlled study of the influence of two low estrogen dose oral contraceptives containing gestodene or desogestrel on carbohydrate metabolism. | 2002 Dec |
|
Primary dysmenorrhea treatment with a desogestrel-containing low-dose oral contraceptive. | 2002 Dec |
|
Serum concentrations of markers of type I collagen metabolism in women taking monophasic oral contraceptives. | 2002 Feb |
|
Effects of second and third generation oral contraceptives and their respective progestagens on the coagulation system in the absence or presence of the factor V Leiden mutation. | 2002 Feb |
|
Reduction of aromatic steroidal A rings by lithium in ethyl amine. | 2002 Feb |
|
Base promoted air oxidation of 13beta-ethyl-11-methylenegon-4-en-17-one. | 2002 Feb |
|
Female hormones and thrombosis. | 2002 Feb 1 |
|
Implantable contraceptives for women. | 2002 Jan |
|
Different effects of oral contraceptives containing levonorgestrel or desogestrel on plasma lipoproteins and coagulation factor VII. | 2002 Jan |
|
Cyproterone acetate versus a continuous monophasic oral contraceptive in the treatment of recurrent pelvic pain after conservative surgery for symptomatic endometriosis. | 2002 Jan |
|
Triphasic oral contraceptives: review and comparison of various regimens. | 2002 Jan |
|
[Changed routines in connection with first prescription of oral contraceptives. Lower risk of venous thromboembolism with levonorgestrel preparations]. | 2002 Jan 10 |
|
[Third generation oral contraceptives and risk of venous thrombosis]. | 2002 Jan 14 |
|
Effect of desogestrel on blood-lipid in relation to its biological activities. | 2002 Jan-Feb |
|
Clinical risk factors for venous thromboembolus in users of the combined oral contraceptive pill. | 2002 Jun |
|
Can changes in sex hormone binding globulin predict the risk of venous thromboembolism with combined oral contraceptive pills? | 2002 Jun |
|
Oral desogestrel with testosterone pellets induces consistent suppression of spermatogenesis to azoospermia in both Caucasian and Chinese men. | 2002 Jun |
|
Contraceptives and cerebral thrombosis: a five-year national case-control study. | 2002 Mar |
|
Long-acting progestogen contraceptives. | 2002 May |
|
Androgen and lipid profiles in adolescents with polycystic ovary syndrome who were treated with two forms of combined oral contraceptives. | 2002 May |
|
Investigation of hormonal male contraception in African men: suppression of spermatogenesis by oral desogestrel with depot testosterone. | 2002 Nov |
|
Persistent vaginal bleeding in a patient with a broken Implanon. | 2002 Oct |
|
An assessment of the use of Implanon in three community services. | 2002 Oct |
|
Bleeding problems and progestogen-only contraception. | 2002 Oct |
|
Contraception failure and wrongful birth claims. | 2002 Oct |
|
Implanon. The new alternative. | 2002 Oct |
|
Ultrasonographic features of the endometrium and the ovaries in women on etonogestrel implant. | 2002 Oct |
|
Sonographic imaging in progestin users and future directions. | 2002 Oct |
|
Improving cycle control in progestogen-only contraceptive pill users by intermittent treatment with a new anti-progestogen. | 2002 Oct |
|
Auditory brainstem response in premenopausal women taking oral contraceptives. | 2003 Jan |
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:46:54 GMT 2023
by
admin
on
Fri Dec 15 15:46:54 GMT 2023
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Record UNII |
81K9V7M3A3
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Record Status |
Validated (UNII)
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Record Version |
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-
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Classification Tree | Code System | Code | ||
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WHO-ATC |
G03AA09
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NDF-RT |
N0000011301
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NDF-RT |
N0000175602
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WHO-VATC |
QG03FB10
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WHO-VATC |
QG03AC09
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LIVERTOX |
285
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WHO-VATC |
QG03AB05
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WHO-ATC |
G03FB10
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WHO-ATC |
G03AC09
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WHO-ATC |
G03AB05
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NCI_THESAURUS |
C776
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WHO-VATC |
QG03AA09
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Code System | Code | Type | Description | ||
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m4198
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PRIMARY | Merck Index | ||
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1173235
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PRIMARY | |||
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Desogestrel
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3593
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7065
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4384
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54024-22-5
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DESOGESTREL
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818
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81K9V7M3A3
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CHEMBL1533
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C47476
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D017135
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DB00304
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258-929-4
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81K9V7M3A3
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DTXSID6022898
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4453
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22656
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100000083191
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SUB07003MIG
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CC-14
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40973
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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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BINDER->LIGAND |
BINDING
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Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PRODRUG | |||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE INACTIVE -> PARENT | |||
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METABOLITE ACTIVE -> PARENT |
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METABOLITE INACTIVE -> PARENT |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.5
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 1.8
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |