General
Preferred name
ETONOGESTREL
Synonyms
IMPLANON ()
Nexplanon ()
3-Oxodesogestrel ()
3-keto-Desogestrel ()
NuvaRing-etonogestrel ()
Implanon, Nexplanon, 3-Oxodesogestrel, 3-keto-Desogestrel ()
Implanon ()
ORG-3236 ()
ORG 3236 ()
Etonogestrel ()
Etonogestrel ()
P&D ID
PD010119
CAS
54048-10-1
Tags
natural product
drug
available
Approved by
FDA
First approval
2001
Drug Status
investigational
approved
Drug indication
Progestin
Contraception
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
METABOLISM Etonogestrel is highly metabolized in the liver by the action of the cytochrome isoenzyme 3A4 mainly by the presence of hydroxylation, sulfate conjugation and glucuronide conjugation reactions.[L5695]
ROE The elimination of etonogestrel and its metabolites is mainly done renally.[L5695]
PHARMACODYNAMICS Etonogestrel attains its therapeutic effect inhibiting fertility by impairing the release of the luteinizing hormone which is one of the most important reproductive hormones for ovulation. As well, etonogestrel is known to increase the viscosity of the cervical mucus hindering the passage of the spermatozoa and altering the lining in the uterus to prevent the implantation of the fertilized eggs in the endometrium.[L5695] In clinical trials, etonogestrel was implanted and reported to avoid 100% of pregnancies over a three year period. When the implant was removed, normal periods were reinstalled within 90 days in 91% of the individuals. Fertility was established quickly with 20 reported pregnancies within 3 months of implant removal.[L5695] The implants of etonogestrel release 40 mcg of etonogestrel daily and they usually provide a continuous contraception effect for 3 years. When the implant is administered, the failure rate is reported to be 0.1%. Some non-contraceptive effects are improved dysmenorrhea.[T502] All data of etonogestrel comes from patients between 80-130% of the body mass.
MOA Etonogestrel binds with high affinity to the progesterone and estrogen receptors in the target organs.[L5695] From the target organs, they include the female reproductive tract, mammary gland, hypothalamus, and pituitary. Once bound, this drug changes the synthesis of different proteins which in order decreases the level of gonadotropin-releasing hormone and the luteinizing hormone.[L5701]
INDICATION Etonogestrel is administered in subdermal implants as long-acting reversible contraception. It is known to be effective in postpartum insertion including breastfeeding women.[A175990] Etonogestrel is part of the long-acting contraceptive implants that prevent pregnancy. The implant's effect can remain for 5 years.[L5698]
TOXICITY The reported LD50 of oral etonogestrel in the rat is reported to be higher than 2000 mg/kg.[MSDS] Overdosage can only happen when more than one implant is inserted. In cases of overdose, removal of the implant is recommended.[FDA label] There aren't reports relating etonogestrel with carcinogenesis, mutagenesis or impaired fertility.[FDA label]
ABSORPTION Vaginal administration of etonogestrel is known to be significantly absorbed through the vaginal epithelium but it does not increase the levels of etonogestrel in the urine. On the other hand, oral administration is absorbed in the GI tract and it goes through the first-pass metabolism.[A37184] When etonogestrel is administered subdermally it is absorbed rapidly into the bloodstream and it presents a bioavailability of 82%.[T55] It is reported that the implant releases around 60 mcg per day in the first 3 months and then decreases steady reaching a concentration of 30 mcg at the end of year 2.[A175993]
HALF-LIFE The elimination half-life of etonogestrel is reported to be of 25 hours which indicates a reversible contraceptive effect.[L5695]
INDICATION Etonogestrel is administered in subdermal implants as long-acting reversible contraception. It is known to be effective in postpartum insertion including breastfeeding women.[A175990]; ; Etonogestrel is part of the long-acting contraceptive implants that prevent pregnancy. The implant's effect can remain for 5 years.[L5698]
TOXICITY The reported LD50 of oral etonogestrel in the rat is reported to be higher than 2000 mg/kg.[MSDS] Overdosage can only happen when more than one implant is inserted. In cases of overdose, removal of the implant is recommended.[FDA label]; ; There aren't reports relating etonogestrel with carcinogenesis, mutagenesis or impaired fertility.[FDA label]
ABSORPTION Vaginal administration of etonogestrel is known to be significantly absorbed through the vaginal epithelium but it does not increase the levels of etonogestrel in the urine. On the other hand, oral administration is absorbed in the GI tract and it goes through the first-pass metabolism.[A37184]; ; When etonogestrel is administered subdermally it is absorbed rapidly into the bloodstream and it presents a bioavailability of 82%.[T55] It is reported that the implant releases around 60 mcg per day in the first 3 months and then decreases steady reaching a concentration of 30 mcg at the end of year 2.[A175993]
DESCRIPTION Etonogestrel is the active metabolite of the inactive prodrug desogestrel. (GtoPdb)
PHARMACODYNAMICS Etonogestrel attains its therapeutic effect inhibiting fertility by impairing the release of the luteinizing hormone which is one of the most important reproductive hormones for ovulation. As well, etonogestrel is known to increase the viscosity of the cervical mucus hindering the passage of the spermatozoa and altering the lining in the uterus to prevent the implantation of the fertilized eggs in the endometrium.[L5695]; ; In clinical trials, etonogestrel was implanted and reported to avoid 100% of pregnancies over a three year period. When the implant was removed, normal periods were reinstalled within 90 days in 91% of the individuals. Fertility was established quickly with 20 reported pregnancies within 3 months of implant removal.[L5695]; ; The implants of etonogestrel release 40 mcg of etonogestrel daily and they usually provide a continuous contraception effect for 3 years. When the implant is administered, the failure rate is reported to be 0.1%. Some non-contraceptive effects are improved dysmenorrhea.[T502] All data of etonogestrel comes from patients between 80-130% of the body mass.
Compound Sets
18
Cayman Chemical Bioactives
21062
ChEMBL Approved Drugs
CHEMBL1531
ChEMBL Drugs
CHEMBL1531
Drug Repurposing Hub
DrugBank
DB00294
DrugBank Approved Drugs
DB00294
DrugCentral
1110
DrugCentral Approved Drugs
1110
DrugMAP
DMKA8J4
DrugMAP Approved Drugs
DMKA8J4
Guide to Pharmacology
7590
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL1531
Natural product-based probes and drugs
NCATS Inxight Approved Drugs
304GTH6RNH
NPC Screening Collection
ReFrame library
Selleckchem Bioactive Compound Library
etonogestrel
TargetMol Bioactive Compound Library
T2567
External IDs
35
Properties
(calculated by RDKit )
Molecular Weight
324.21
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
1
Ring Count
4
Aromatic Ring Count
0
cLogP
4.05
TPSA
37.3
Fraction CSP3
0.68
Chiral centers
6.0
Largest ring
6.0
QED
0.58
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Endocrinology/Hormones
Target
ER
ESR1, PGR
Estrogen/progestogen Receptor
Indication
contraceptive
MOA
Progesterone receptor agonist
Biosynthetic Origin
Terpenoid (Steroid)
Therapeutic Indication
Contraception
Therapeutic Class
Hormone Therapy
Contraceptive Agents
Source data