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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H30O3
Molecular Weight 354.4825
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEVONORGESTREL ACETATE

SMILES

CC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@H]34)[C@@H]1CC[C@@]2(OC(C)=O)C#C

InChI

InChIKey=YDQDJLTYVZAOQX-GOMYTPFNSA-N
InChI=1S/C23H30O3/c1-4-22-12-10-19-18-9-7-17(25)14-16(18)6-8-20(19)21(22)11-13-23(22,5-2)26-15(3)24/h2,14,18-21H,4,6-13H2,1,3H3/t18-,19+,20+,21-,22-,23-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H30O3
Molecular Weight 354.4825
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25698840

Levonorgestrel (LNG) is a synthetic progestational hormone with actions similar to those of progesterone and about twice as potent as its racemic or (+-)-isomer (norgestrel). It is used for contraception, control of menstrual disorders, and treatment of endometriosis. It is usually supplied in a racemic mixture (Norgestrel, 6533-00-2). Only the levonorgestrel isomer is active. Within an Intrauterine device (IUD), sold as Mirena among others, it is effective for long term prevention of pregnancy. The local mechanism by which continuously released LNG enhances contraceptive effectiveness of Mirena has not been conclusively demonstrated. Studies of Mirena and similar LNG IUS prototypes have suggested several mechanisms that prevent pregnancy: thickening of cervical mucus preventing passage of sperm into the uterus, inhibition of sperm capacitation or survival, and alteration of the endometrium. Mirena has mainly local progestogenic effects in the uterine cavity. The high local levels of levonorgestrel lead to morphological changes including stromal pseudodecidualization, glandular atrophy, a leukocytic infiltration and a decrease in glandular and stromal mitoses. Ovulation is inhibited in some women using Mirena. In a 1-year study, approximately 45% of menstrual cycles were ovulatory, and in another study after 4 years, 75% of cycles were ovulatory. There has been much debate regarding levonorgestrel emergency contraception's (LNG-EC's) method of action since 1999 when the Food and Drug Administration first approved its use. Proponents of LNG-EC have argued that they have moral certitude that LNG-EC works via a non-abortifacient mechanism of action, and claim that all the major scientific and medical data consistently support this hypothesis. However, newer medical data serve to undermine the consistency of the non-abortifacient hypothesis and instead support the hypothesis that preovulatory administration of LNG-EC has significant potential to work via abortion. The implications of the newer data have important ramifications for medical personnel, patients, and both Catholic and non-Catholic emergency room protocols. In the future, technology such as the use of early pregnancy factor may have the potential to quantify how frequently preovulatory LNG-EC works via abortion. The latest scientific and medical evidence now demonstrates that levonorgestrel emergency contraception theoretically works via abortion quite often. The implications of the newer data have important ramifications for medical personnel, patients, and both Catholic and non-Catholic emergency room rape protocols.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
MIRENA

Approved Use

Mirena 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 Date

2000
Primary
MIRENA

Approved Use

Mirena 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 Date

2000
Preventing
OVRETTE

Approved Use

Progestin-only oral contraceptives are indicated for the prevention of pregnancy.

Launch Date

1973
Preventing
ELINEST

Approved Use

Oral contraceptives are indicated for the prevention of pregnancy in women who elect to use oral contraceptives as a method of contraception.

Launch Date

2012
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.11 ng/mL
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
16.2 ng/mL
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
123.1 ng × h/mL
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
360.1 ng × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
24.4 h
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
29.7 h
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
Doses

Doses

DosePopulationAdverse 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:
healthy, 16-45
Health Status: healthy
Age Group: 16-45
Sex: F
Sources:
Disc. AE: Bleeding...
AEs leading to
discontinuation/dose reduction:
Bleeding (1.5%)
Sources:
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:
healthy, 27.3 ± 5.7
Health Status: healthy
Age Group: 27.3 ± 5.7
Sex: F
Sources:
Disc. AE: Menstrual irregularity, Amenorrhea...
AEs leading to
discontinuation/dose reduction:
Menstrual irregularity (0.7%)
Amenorrhea (0.06%)
Sources:
90 ug 1 times / day multiple, oral
Recommended
Dose: 90 ug, 1 times / day
Route: oral
Route: multiple
Dose: 90 ug, 1 times / day
Sources:
healthy, 27.6±6.7
Health Status: healthy
Age Group: 27.6±6.7
Sex: F
Sources:
Disc. AE: Metrorrhagia, Bleeding vaginal...
AEs leading to
discontinuation/dose reduction:
Metrorrhagia (8.7%)
Bleeding vaginal (3.7%)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
healthy, 16-45
Health Status: healthy
Age Group: 16-45
Sex: F
Sources:
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:
healthy, 27.3 ± 5.7
Health Status: healthy
Age Group: 27.3 ± 5.7
Sex: F
Sources:
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:
healthy, 27.3 ± 5.7
Health Status: healthy
Age Group: 27.3 ± 5.7
Sex: F
Sources:
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
Sources:
healthy, 27.6±6.7
Health Status: healthy
Age Group: 27.6±6.7
Sex: F
Sources:
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
Sources:
healthy, 27.6±6.7
Health Status: healthy
Age Group: 27.6±6.7
Sex: F
Sources:
OverviewDrug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
likely
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >133 uM]
no [IC50 >250 uM]
no [IC50 >250 uM]
no [IC50 >250 uM]
no [IC50 >250 uM]
no [IC50 >250 uM]
no [IC50 >250 uM]
yes [IC50 13.6 uM]
yes
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Rat uterine complement C3 expression as a model for progesterone receptor modulators: characterization of the new progestin trimegestone.
2001 Aug
Influence of two low-dose oral contraceptives on pulsatile gonadotropin secretion.
2001 Aug
Etonogestrel implant (Implanon) for contraception.
2001 Aug
Combined oral hormone replacement therapy formulations.
2001 Aug
Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy.
2001 Aug
Over-the-counter advice for genital problems: the role of the community pharmacist.
2001 Aug
Treatment of menorrhagia with the levonorgestrel intrauterine system versus endometrial resection.
2001 Aug
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
[Hormonal contraception with gestagens].
2001 Aug 20
Fine structure of prolactin cell of female albino rat as affected by some antifertility drugs--a comparative electron microscopic study.
2001 Feb
A prospective study of the effects of oral contraceptives on sexuality and well-being and their relationship to discontinuation.
2001 Jul
Levonorgestrel concentrations during 7 years of continuous use of Jadelle contraceptive implants.
2001 Jul
Use of Norplant implants in the immediate postpartum period among asymptomatic HIV-1-positive mothers.
2001 Jul
Young women requesting emergency contraception are, despite contraceptive counseling, a high risk group for new unintended pregnancies.
2001 Jul
Levonorgestrel-only emergency contraception: real-world tolerance and efficacy.
2001 Jul
Effects of two low-dose oral contraceptives containing ethinylestradiol and either desogestrel or levonorgestrel on serum lipids and lipoproteins with particular regard to LDL size.
2001 Jul
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
Norgestimate. From the laboratory to three clinical indications.
2001 Jul
The management of menorrhagia--SMART study (Satisfaction with Mirena and Ablation: a Randomised Trial).
2001 Jul
Levonorgestrel-releasing (20mcg/day) intrauterine systems (Mirena) compared with other methods of reversible contraceptives.
2001 Jul
A village would be nice but...it takes a long-acting contraceptive to prevent repeat adolescent pregnancies.
2001 Jul
Third generation oral contraceptives and risk of venous thrombosis: meta-analysis.
2001 Jul 21
Evaluation of genotoxic potential of synthetic progestins-norethindrone and norgestrel in human lymphocytes in vitro.
2001 Jul 25
The roles of estrogen and progestin in producing deciduosarcoma and other lesions in the rabbit.
2001 Jul-Aug
The development and regression of deciduosarcomas and other lesions caused by estrogens and progestins in rabbits.
2001 Jul-Aug
Weight change and adverse event incidence with a low-dose oral contraceptive: two randomized, placebo-controlled trials.
2001 Jun
Comparison of a novel norgestimate/ethinyl estradiol oral contraceptive (Ortho Tri-Cyclen Lo) with the oral contraceptive Loestrin Fe 1/20.
2001 Jun
Treatment of menorrhagia with a novel 'frameless' intrauterine levonorgestrel-releasing drug delivery system: a pilot study.
2001 Jun
The effects of two progrestogen-only pills containing either desogestrel (75 microgram/day) or levonorgestrel (30 microgram/day) on carbohydrate metabolism and adrenal and thyroid function.
2001 Jun
The need for more active promotion of emergency contraception.
2001 Jun
Hormonal and barrier methods of contraception, oncogenic human papillomaviruses, and cervical squamous intraepithelial lesion development.
2001 Jun
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
Treatment of menorrhagia.
2001 Jun 9
Postmarketing surveillance study of Norplant in developing countries.
2001 Jun 9
Clinical recommendations for oxcarbazepine.
2001 Mar
[Contraception with depot gestagens].
2001 May
The effect of hormone replacement therapy on serum homocysteine levels in perimenopausal women: a randomized controlled trial.
2001 Oct
Effects of natural products and nutraceuticals on steroid hormone-regulated gene expression.
2001 Oct
Effects of the levonorgestrel-releasing intrauterine system on proliferation and apoptosis in the endometrium.
2001 Oct
[Low-dose oral contraception and bone density].
2001 Sep
[Postcoital emergency contraception].
2001 Sep
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women.
2001 Sep
Levonorgestrel-releasing IUD and breast cancer.
2001 Sep
Determination of circular dichroism and ultraviolet spectral parameters of norgestimate- and other Delta(4)-3-ketosteroid oxime isomers via normal phase HPLC method.
2001 Sep
Validity of radioimmunological methods for determining free testosterone in serum.
2001 Sep
Endometrial expression of glycodelin in women with levonorgestrel-releasing subdermal implants.
2001 Sep
A randomized, controlled trial of a low-dose contraceptive containing 20 microg of ethinyl estradiol and 100 microg of levonorgestrel for acne treatment.
2001 Sep
Contraceptive dispensing and selection in school-based health centers.
2001 Sep
Assessment of the oestrogenic activity of the contraceptive progestin levonorgestrel and its non-phenolic metabolites.
2001 Sep 14
Effect of hormone replacement therapy on lipids in perimenopausal and early postmenopausal women.
2001 Sep 28
Patents

Sample Use Guides

In Vivo Use Guide
OVRETTE tablets (0.075 mg norgestrel) are available in packages of 6 PILPAK dispensers with 28 tablets each as follows: NDC 0008-0062-01, yellow, round tablet marked "WYETH" on one side and "62" on reverse side. To achieve maximum contraceptive effectiveness, OVRETTE must be taken exactly as directed. One tablet is taken every day, at the same time. Administration is continuous, with no interruption between pill packs.
Route of Administration: Oral
In Vitro Use Guide
Norgestrel stimulated MCF-7 cell proliferation at a concentration of 10(-8) M.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:26:17 GMT 2025
Edited
by admin
on Mon Mar 31 18:26:17 GMT 2025
Record UNII
VF642934XZ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
18,19-DINORPREGN-4-EN-20-YN-3-ONE, 17-(ACETYLOXY)-13-ETHYL-, (17.ALPHA.)-
Preferred Name English
LEVONORGESTREL ACETATE
WHO-DD  
Common Name English
NORGESTIMATE IMPURITY A [EP IMPURITY]
Common Name English
13.BETA.-ETHYL-3-OXO-18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-17-YL ACETATE
Systematic Name English
LEVONORGESTREL 17-ACETATE
Common Name English
NORGESTIMATE RELATED COMPOUND A [USP IMPURITY]
Common Name English
(17.ALPHA.)-17-(ACETYLOXY)-13-ETHYL-18,19-DINORPREGN-4-EN-20-YN-3-ONE
Systematic Name English
NORGESTIMATE RELATED COMPOUND A [USP-RS]
Common Name English
Levonorgestrel acetate [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
Code System Code Type Description
CAS
13732-69-9
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
NCI_THESAURUS
C77014
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
PUBCHEM
62954
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
WIKIPEDIA
Levonorgestrel acetate
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
FDA UNII
VF642934XZ
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
SMS_ID
300000034879
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
RS_ITEM_NUM
1471925
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID301314299
Created by admin on Mon Mar 31 18:26:17 GMT 2025 , Edited by admin on Mon Mar 31 18:26:17 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY