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Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/17107221 | http://adisinsight.springer.com/drugs/800013168

Norelgestromin, the progestin, is the active metabolite of norgestimate and is structurally related to 19-nortestosterone. Norgestimate and norelgestromin mimic the physiologic effects of progesterone at the progesterone receptor. Johnson & Johnson developed an adhesive female contraceptive patch that contains ethinylestradiol (0.75mg) and the progestogen norelgestromin (6mg). his product is a combination contraceptive acting via the inhibition gonadotropins. Its primary mechanism of action involves the suppression of ovulation, including changes in the cervical mucus and endometrium. The patch delivers a continuous flow of hormones through the skin and into the bloodstream. The contraceptive patch is available in countries worldwide.

Originator

Approval Year

2001
194
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
ORTHO EVRA

Approved Use

ORTHO EVRA® is indicated for the prevention of pregnancy in women who elect to use a transdermal patch as a method of contraception.

Launch Date

2001
Preventing
Approved
8429
XULANE

Approved Use

Xulane is indicated for the prevention of pregnancy in women who elect to use a transdermal patch as a method of contraception.

Launch Date

2014
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
987 pg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/31935382
6 mg 1 times / day steady-state, transdermal
dose: 6 mg
route of administration: Transdermal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 NORELGESTROMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
156702 pg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/31935382
6 mg 1 times / day steady-state, transdermal
dose: 6 mg
route of administration: Transdermal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 NORELGESTROMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
27.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/31935382
6 mg 1 times / day steady-state, transdermal
dose: 6 mg
route of administration: Transdermal
experiment type: STEADY-STATE
co-administered: ETHINYL ESTRADIOL
ETHINYL ESTRADIOL
 NORELGESTROMIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
3%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
NORELGESTROMIN serum
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
150 ug 1 times / day multiple, transdermal
Recommended
Dose: 150 ug, 1 times / day
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / day
Co-administed with::
ethinyl estradiol, transdermal(20 ug/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
healthy, 28.7
n = 1672
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 28.7
Sex: F
Population Size: 1672
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
Disc. AE: Application site reaction, Nausea...
AEs leading to
discontinuation/dose reduction:
Application site reaction (1.9%)
Nausea (1.8%)
Emotional lability (1.5%)
Headache (1.1%)
Breast discomfort (1%)
Menorrhagia (serious, 0.06%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
6 mg 1 times / week multiple, transdermal
Recommended
Dose: 6 mg, 1 times / week
Route: transdermal
Route: multiple
Dose: 6 mg, 1 times / week
Co-administed with::
ethinyl estradiol, transdermal(0.75 mg/week)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
Page: p.1
healthy
Health Status: healthy
Condition: Pregnancy prevention
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
Page: p.1
Disc. AE: Cardiovascular risk, Venous thromboembolism...
AEs leading to
discontinuation/dose reduction:
Cardiovascular risk (serious)
Venous thromboembolism
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Breast discomfort 1%
Disc. AE
150 ug 1 times / day multiple, transdermal
Recommended
Dose: 150 ug, 1 times / day
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / day
Co-administed with::
ethinyl estradiol, transdermal(20 ug/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
healthy, 28.7
n = 1672
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 28.7
Sex: F
Population Size: 1672
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
Headache 1.1%
Disc. AE
150 ug 1 times / day multiple, transdermal
Recommended
Dose: 150 ug, 1 times / day
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / day
Co-administed with::
ethinyl estradiol, transdermal(20 ug/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
healthy, 28.7
n = 1672
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 28.7
Sex: F
Population Size: 1672
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
Emotional lability 1.5%
Disc. AE
150 ug 1 times / day multiple, transdermal
Recommended
Dose: 150 ug, 1 times / day
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / day
Co-administed with::
ethinyl estradiol, transdermal(20 ug/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
healthy, 28.7
n = 1672
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 28.7
Sex: F
Population Size: 1672
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
Nausea 1.8%
Disc. AE
150 ug 1 times / day multiple, transdermal
Recommended
Dose: 150 ug, 1 times / day
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / day
Co-administed with::
ethinyl estradiol, transdermal(20 ug/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
healthy, 28.7
n = 1672
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 28.7
Sex: F
Population Size: 1672
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
Application site reaction 1.9%
Disc. AE
150 ug 1 times / day multiple, transdermal
Recommended
Dose: 150 ug, 1 times / day
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / day
Co-administed with::
ethinyl estradiol, transdermal(20 ug/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
healthy, 28.7
n = 1672
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 28.7
Sex: F
Population Size: 1672
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
Menorrhagia serious, 0.06%
Disc. AE
150 ug 1 times / day multiple, transdermal
Recommended
Dose: 150 ug, 1 times / day
Route: transdermal
Route: multiple
Dose: 150 ug, 1 times / day
Co-administed with::
ethinyl estradiol, transdermal(20 ug/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
healthy, 28.7
n = 1672
Health Status: healthy
Condition: Pregnancy prevention
Age Group: 28.7
Sex: F
Population Size: 1672
Sources:
https://pubmed.ncbi.nlm.nih.gov/11704172
Page: p.803
Venous thromboembolism Disc. AE
6 mg 1 times / week multiple, transdermal
Recommended
Dose: 6 mg, 1 times / week
Route: transdermal
Route: multiple
Dose: 6 mg, 1 times / week
Co-administed with::
ethinyl estradiol, transdermal(0.75 mg/week)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
Page: p.1
healthy
Health Status: healthy
Condition: Pregnancy prevention
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
Page: p.1
Cardiovascular risk serious
Disc. AE
6 mg 1 times / week multiple, transdermal
Recommended
Dose: 6 mg, 1 times / week
Route: transdermal
Route: multiple
Dose: 6 mg, 1 times / week
Co-administed with::
ethinyl estradiol, transdermal(0.75 mg/week)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
Page: p.1
healthy
Health Status: healthy
Condition: Pregnancy prevention
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021180s043lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1737
substrate
1037
substrate
1217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2B6
664

UGT1A1
418

CYP1A2
1054

CYP2C19
991

CYP3A5
395

CYP2C8
693
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A5
395
 inconclusive
CYP1A2
1054
 no
CYP2C19
991
 no
CYP2C8
693
 no
CYP2D6
1217
 no
CYP2B6
664
 yes
CYP2C9
1037
 yes
UGT1A1
418
 yes
CYP3A4
1737
 yes
yes (co-administration study)
Comment: compounds that inhibit or induce CYP3A4 such as cobicistat, LPR/RTV combination, RTV/ATV combination and EFZ significantly altered the exposure and PK of NGMN (Vogler et al., 2010; Polina German, 2011; Sevinsky et al., 2011; Zhang et al., 2011). A fixed dose combination ofelvitegravir/cobicistat/emtricitabine/tenofovir disoproxil fumarate increased NGMN’s exposure by greater than 2-fold which is consistent with cobicistat’s irreversible CYP3A4 inhibition properties (Polina German, 2011).
Page: -
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00DB4K
AK Scientific
3046AH
AbovChem LLC
HY-G0018
BLD Pharm
BD123562
BOC Sciences
53016-31-2
Chem Scene
CS-4097
Compound Cloud
9568628
Hangzhou Yuhao Chemical Technology
RT17183
Lab Network
LN01341588
MedChem Express
HY-G0018
MolPort
MolPort-005-943-875
MuseChem
R007958
Toronto Research Chemicals
D288700
Toronto Research Chemicals
D288716
Toronto Research Chemicals
D288721
ZINC
ZINC000256433946
http://zinc15.docking.org/substances/ZINC000256433946
ZINC
ZINC000256433948
http://zinc15.docking.org/substances/ZINC000256433948
ZINC
ZINC000256433952
http://zinc15.docking.org/substances/ZINC000256433952
ZINC
ZINC000263584040
http://zinc15.docking.org/substances/ZINC000263584040
ZINC
ZINC000642895275
http://zinc15.docking.org/substances/ZINC000642895275
eMolecules
110009154
eMolecules
195169519
eMolecules
195316203
eMolecules
300997082
mcule
MCULE-1335660483
PubMed

PubMed

TitleDatePubMed
Antiandrogenic activity of norgestimate in a human androgen-dependent stable-transfected cell line.
2007 Apr
Patents

Patents

7393964
1
WO2007035940A2
1

Sample Use Guides

In Vivo Use Guide
Transdermal system: 150 mcg/day norelgestromin and 35 mcg/day ethinyl estradiol.
Route of Administration: Transdermal
In Vitro Use Guide
After 24h incubation of physiological concentrations of estrone sulfate 5 nM the inhibitory effect of norelgestromin (NGMN) (a metabolite of norgestimate) at concentrations of 5 nM, 0.5 uM and 50 uM was 43, 74 and 97%, respectively, in T-47D cells; 25, 57 and 96 respectively, in MCF-7 cells. Comparative studies using medroxyprogesterone acetate (MPA) showed that this progestin also has an inhibitory effect on sulfatase activity, but significantly less intense than that of NGMN. The inhibition for MPA at concentrations of 5 nM, 0.5 uM and 50 uM was 31, 47 and 61, respectively, for T-47D cells; 6, 20 and 63, respectively, for MCF-7 cells.
Substance Class Mixture
Created
by admin
on Sat Dec 16 18:57:43 GMT 2023
Edited
by admin
on Sat Dec 16 18:57:43 GMT 2023
Record UNII
R0TAY3X631
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NORELGESTROMIN
EMA EPAR   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
norelgestromin [INN]
Common Name English
DEACETYLNORGESTIMATE
USP-RS  
Common Name English
NORELGESTROMIN [USP-RS]
Common Name English
NORELGESTROMIN [MI]
Common Name English
13-ETHYL-17-HYDROXY-18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-3-ONE OXIME.
Common Name English
NORELGESTROMIN [USP MONOGRAPH]
Common Name English
NORELGESTROMIN [MART.]
Common Name English
Norelgestromin [WHO-DD]
Common Name English
DEACETYLNORGESTIMATE [USP-RS]
Common Name English
MIXTURE OF NORELGESTROMIN (E)-AND (Z)-ISOMERS HAVING A RATIO OF (E)-TO (Z)-ISOMER BETWEEN 1.3 AND 1.6
Common Name English
NORELGESTROMIN [VANDF]
Common Name English
RWJ-10553
Code English
XULANE COMPONENT NORELGESTROMIN
Brand Name English
NORELGESTROMIN [ORANGE BOOK]
Common Name English
NORELGESTROMIN [USAN]
Common Name English
NORELGESTROMIN [EMA EPAR]
Common Name English
18,19-DINORPREGN-4-EN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-, OXIME, (17.ALPHA.)-
Common Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS EVRA (AUTHORIZED: CONTRACEPTION)
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
WHO-ATC G03AA13
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
LIVERTOX 695
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
WHO-VATC QG03AA13
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
NDF-RT N0000175602
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
NDF-RT N0000011301
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
NCI_THESAURUS C776
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
Code System Code Type Description
SMS_ID
100000092089
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
MERCK INDEX
m8053
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
1959
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
DRUG BANK
DB06713
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
FDA UNII
R0TAY3X631
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
INN
7939
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
EVMPD
SUB20476
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
RS_ITEM_NUM
1468454
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
ALTERNATIVE
RS_ITEM_NUM
1471958
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
MESH
C449219
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
WIKIPEDIA
NORELGESTROMIN
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
MESH
C511292
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
DAILYMED
R0TAY3X631
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
RXCUI
326374
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY RxNorm
NCI_THESAURUS
C66243
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
USAN
KK-83
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
CAS
53016-31-2
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID9046788
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
PUBCHEM
62930
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200807
Created by admin on Sat Dec 16 18:57:43 GMT 2023 , Edited by admin on Sat Dec 16 18:57:43 GMT 2023
PRIMARY
All of the following components must be present:
Structure of NORELGESTROMIN, (E)-
Structure of NORELGESTROMIN, (Z)-
Related Record Type Details
Structure of LEVONORGESTREL
METABOLITE ACTIVE -> PARENT
Related Record Type Details
NORGESTIMATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of NORGESTREL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
NORELGESTROMIN
ACTIVE MOIETY
Definition References
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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