U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C21H28O2
Molecular Weight 312.4458
Optical Activity ( + / - )
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORGESTREL

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(CC)CC[C@]3([H])[C@@]4([H])CCC(=O)C=C4CC[C@@]23[H]

InChI

InChIKey=WWYNJERNGUHSAO-XUDSTZEESA-N
InChI=1S/C21H28O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h2,13,16-19,23H,3,5-12H2,1H3/t16-,17+,18+,19-,20-,21-/m0/s1

HIDE SMILES / InChI

Molecular Formula C21H28O2
Molecular Weight 312.4458
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

Norgestrel is synthetic steroidal progestin that is used in combination with ethinyl estradiol for oral contraception. Norgestrel is composed of a racemic mixture of two stereoisomers, dextronorgestrel and levonorgestrel. However, only the levorotary enantiomer (levonorgestrel) is biologically active. Norgestrel (and more specifically the active stereoisomer levonorgestrel) binds to the progesterone and estrogen receptors within the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Once bound to the receptor, progestins like levonorgestrel will slow the frequency of release of gonadotropin releasing hormone (GnRH) from the hypothalamus and blunt the pre-ovulatory LH (luteinizing hormone) surge. Loss of the LH surge inhibits ovulation and thereby prevents pregnancy. Norgestrel in combination with ethinyl estradiol is indicated for the prevention of pregnancy in women who elect to use this product as a method of contraception.

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
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
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
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
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
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: Page: p.10
healthy, 16-45
n = 1714
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 16-45
Sex: F
Population Size: 1714
Sources: Page: p.10
Disc. AE: Bleeding...
AEs leading to
discontinuation/dose reduction:
Bleeding (1.5%)
Sources: Page: p.10
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: Page: p.2
healthy, 27.3 ± 5.7
n = 1700
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 27.3 ± 5.7
Sex: F
Population Size: 1700
Sources: Page: p.2
Disc. AE: Menstrual irregularity, Amenorrhea...
AEs leading to
discontinuation/dose reduction:
Menstrual irregularity (0.7%)
Amenorrhea (0.06%)
Sources: Page: p.2
90 ug 1 times / day multiple, oral
Recommended
Dose: 90 ug, 1 times / day
Route: oral
Route: multiple
Dose: 90 ug, 1 times / day
Co-administed with::
ethinyl estradiol, p.o(20 ug; q.d; 1 year)
Sources: Page: p.507
healthy, 27.6±6.7
n = 323
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 27.6±6.7
Sex: F
Population Size: 323
Sources: Page: p.507
Disc. AE: Metrorrhagia, Bleeding vaginal...
AEs leading to
discontinuation/dose reduction:
Metrorrhagia (8.7%)
Bleeding vaginal (3.7%)
Sources: Page: p.507
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: Page: p.10
healthy, 16-45
n = 1714
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 16-45
Sex: F
Population Size: 1714
Sources: Page: p.10
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: Page: p.2
healthy, 27.3 ± 5.7
n = 1700
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 27.3 ± 5.7
Sex: F
Population Size: 1700
Sources: Page: p.2
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: Page: p.2
healthy, 27.3 ± 5.7
n = 1700
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 27.3 ± 5.7
Sex: F
Population Size: 1700
Sources: Page: p.2
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
Co-administed with::
ethinyl estradiol, p.o(20 ug; q.d; 1 year)
Sources: Page: p.507
healthy, 27.6±6.7
n = 323
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 27.6±6.7
Sex: F
Population Size: 323
Sources: Page: p.507
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
Co-administed with::
ethinyl estradiol, p.o(20 ug; q.d; 1 year)
Sources: Page: p.507
healthy, 27.6±6.7
n = 323
Health Status: healthy
Condition: Prevention of pregnancy
Age Group: 27.6±6.7
Sex: F
Population Size: 323
Sources: Page: p.507
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
Superficial endometrial vascular fragility in Norplant users and in women with ovulatory dysfunctional uterine bleeding.
2000 Jul
Post-marketing surveillance of Norplant((R)) contraceptive implants: II. Non-reproductive health(1).
2001 Apr
Non-protein bound dienogest in serum and salivary dienogest in women taking the oral contraceptives Certostat and Valette.
2001 Apr
Preclinical profiles of progestins used in formulations of oral contraceptives and hormone replacement therapy.
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
Fluoroscopically guided Norplant removal.
2001 Feb
Intrauterine contraception--what now and what next?
2001 Jan
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
A village would be nice but...it takes a long-acting contraceptive to prevent repeat adolescent pregnancies.
2001 Jul
Evaluation of genotoxic potential of synthetic progestins-norethindrone and norgestrel in human lymphocytes in vitro.
2001 Jul 25
Weight change and adverse event incidence with a low-dose oral contraceptive: two randomized, placebo-controlled trials.
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
Clinical recommendations for oxcarbazepine.
2001 Mar
Implanon contraceptive implants: effects on carbohydrate metabolism.
2001 Mar
The effects of peri-ovulatory administration of levonorgestrel on the menstrual cycle.
2001 Mar
Mechanism of action of hormonal preparations used for emergency contraception: a review of the literature.
2001 Mar
Use of a levonorgestrel-releasing intrauterine device in the treatment of rectovaginal endometriosis.
2001 Mar
Contraception in the adolescent: an update.
2001 Mar
Norplant and other implantable contraceptives.
2001 Mar
Progestin regulation of galanin and prolactin gene expression in oestrogen-induced pituitary tumours.
2001 Mar
Determination of steroid sex hormones and related synthetic compounds considered as endocrine disrupters in water by fully automated on-line solid-phase extraction-liquid chromatography-diode array detection.
2001 Mar 16
Estimation of hormone replacement therapy influence on serum galanin level in postmenopausal women.
2001 Sep
Patents

Sample Use Guides

Mirena contains 52 mg of levonorgestrel (LNG). Initially, LNG is released at a rate of approximately 20 mcg/day. This rate decreases progressively to half that value after 5 years. Mirena must be removed by the end of the fifth year and can be replaced at the time of removal with a new Mirena if continued contraceptive protection is desired.
Route of Administration: Vaginal
5 × 10(-5) mol/L Levonorgestrel (LNG) revealed a time-dependent inhibition of cell proliferation and an increase of apoptosis in both human endometrial stromal cells (HESCs) and glandular cells (HEGCs). Furthermore, these cells demonstrated a significant Gap Junctional Intercellular Communication (GJIC) enhancement upon treatment with 5 × 10(-5) mol/L for 48 hours. The effects of LNG were most noticeable in HESCs rather than in HEGCs.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:26:36 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:36 GMT 2023
Record UNII
3J8Q1747Z2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORGESTREL
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
NORGESTREL COMPONENT OF OVRAL
Common Name English
norgestrel [INN]
Common Name English
NORGESTREL [HSDB]
Common Name English
NORGESTREL [USP-RS]
Common Name English
WY-3707
Code English
SH-70850
Code English
Norgestrel [WHO-DD]
Common Name English
OVRAL COMPONENT NORGESTREL
Common Name English
NORGESTREL [USAN]
Common Name English
FH-122A
Code English
NORGESTREL [EP MONOGRAPH]
Common Name English
NORGESTREL [JAN]
Common Name English
18,19-DINORPREGN-4-EN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-, (17.ALPHA.)-(±)-
Common Name English
NORGESTREL [USP MONOGRAPH]
Common Name English
NORGESTREL [MI]
Common Name English
(±)-13-ETHYL-17-HYDROXY-18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-3-ONE
Common Name English
NORGESTREL [ORANGE BOOK]
Common Name English
CRYSELLE COMPONENT NORGESTREL
Common Name English
DL-NORGESTREL
Common Name English
SH-850
Code English
NORGESTREL [MART.]
Common Name English
NSC-757251
Code English
NORGESTREL COMPONENT OF CRYSELLE
Common Name English
NORGESTREL [VANDF]
Common Name English
OVRETTE
Brand Name English
Classification Tree Code System Code
WHO-VATC QG03FA10
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
WHO-VATC QG03FB01
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
WHO-VATC QG03AA06
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
WHO-ATC G03FA10
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
WHO-ATC G03AA06
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
LIVERTOX 699
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
WHO-ATC G03FB01
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
Code System Code Type Description
PUBCHEM
13109
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
MERCK INDEX
m8063
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
NORGESTREL
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
CHEBI
7630
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
RS_ITEM_NUM
1472000
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
EVMPD
SUB09371MIG
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
MESH
D009644
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
SMS_ID
100000092602
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
INN
2157
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
CAS
6533-00-2
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
NCI_THESAURUS
C703
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
DRUG BANK
DB09389
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
HSDB
3595
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
DAILYMED
3J8Q1747Z2
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
FDA UNII
3J8Q1747Z2
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
NSC
757251
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107797
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
RXCUI
7518
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
229-433-5
Created by admin on Fri Dec 15 15:26:36 GMT 2023 , Edited by admin on Fri Dec 15 15:26:36 GMT 2023
PRIMARY
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