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Levonorgestrel

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Identification
Molecular formula
C21H28O2
CAS number
797-63-7
IUPAC name
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
State
State

Levonorgestrel is a solid at room temperature. The crystalline nature is typical for steroids, which are often used in solid formulations such as tablets.

Melting point (Celsius)
205.00
Melting point (Kelvin)
478.20
Boiling point (Celsius)
388.50
Boiling point (Kelvin)
661.70
General information
Molecular weight
312.45g/mol
Molar mass
312.4460g/mol
Density
1.1250g/cm3
Appearence

Levonorgestrel appears as a white to off-white crystalline powder. It is usually odorless and has a slightly bitter taste. The compound is commonly used in contraceptive formulations and is handled in a pharmaceutical-grade environment.

Comment on solubility

Solubility of (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

The solubility of (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one can be influenced by several factors, including its structural characteristics and the nature of its substituents. The compound’s complex structure, which includes multiple chiral centers and hydroxy groups, contributes to its solubility behavior in different solvents.

Key considerations include:

  • Polarity: The presence of hydroxy (-OH) groups typically enhances solubility in polar solvents such as water. However, the overall hydrophobic nature of the compound due to its elongated hydrocarbon chains may limit this solubility.
  • Hydrogen Bonding: Hydroxy groups can participate in hydrogen bonding, which may increase solubility in aqueous solutions but may also lead to the compound being poorly soluble in non-polar solvents.
  • Temperature: Like many organic compounds, solubility is temperature-dependent. Increased temperatures often enhance solubility due to the greater kinetic energy that assists in overcoming intermolecular forces.

In summary, while the hydroxy substituent in the compound may suggest some level of solubility in water, the overall hydrophobic characteristics imparted by the extensive carbon framework suggest a tendency towards higher solubility in organic solvents. Therefore, the compound is likely to exhibit:

  • Fair solubility in polar solvents
  • Better solubility in non-polar organic solvents

Understanding the solubility profile of this compound is crucial for its effective use in chemical applications and formulations.

Interesting facts

Interesting Facts About (8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

This compound is an intriguing member of the class of steroids, specifically categorized under synthetic derivatives. It possesses unique structural features that contribute to its biological activities and applications in pharmacology.

Key Highlights

  • Biological Activity: Compounds with such complex structures often exhibit interesting biological properties, including hormonal activity, which can influence metabolic pathways.
  • Synthetic Pathways: The synthesis of this compound involves intricate techniques, showcasing the ingenuity of organic chemistry. The use of ethynyl groups often leads to enhanced potency and selectivity in biological systems.
  • Pharmaceutical Applications: As a steroid derivative, it may be investigated for therapeutic potentials such as anti-inflammatory or anabolic properties, akin to other steroids in its category.
  • Chirality: The numerous chiral centers in its structure (as indicated by the R and S configurations) contribute to its stereoisomerism, which can significantly affect its chemical behavior and interaction with biological systems.

As a chemical scientist or a chemistry student, one might explore the implications of such structural complexity. Understanding the subtle interplay between structure and function is critical in drug design and development. As noted by chemist Marie Curie, "Nothing in life is to be feared, it is only to be understood." This compound represents a fascinating case study where chemistry meets biology.

Moreover, the exploration of **steroid derivatives** opens a Pandora's box of research opportunities, from potential therapeutic candidates to understanding endocrine disruptors in environmental studies. With our evolving knowledge of pharmacodynamics and pharmacokinetics, compounds like this continue to be essential in advancing modern medicinal chemistry.

Synonyms
norgestrel
6533-00-2
Norgestrelum
Methylnorethindrone
Ld norgestrel
3J8Q1747Z2
OVRAL COMPONENT NORGESTREL
FH-122A
alpha-Norgestrel
CRYSELLE COMPONENT NORGESTREL
SH-850
SH-70850
NORGESTREL (MART.)
NORGESTREL [MART.]
NORGESTREL (USP-RS)
NORGESTREL [USP-RS]
NORGESTREL (EP MONOGRAPH)
NORGESTREL [EP MONOGRAPH]
NORGESTREL (USP MONOGRAPH)
NORGESTREL [USP MONOGRAPH]
DL Norgestrel
NSC-757251
18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-(+-)-
OPILL
(+-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
CHEBI:50901
NORGESTREL COMPONENT OF OVRAL
NORGESTREL COMPONENT OF CRYSELLE
229-433-5
(17alpha)-dl-13-ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
dl-13-ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
Levonorgestrel
797-63-7
D-Norgestrel
Mirena
Levonova
Microval
Postinor
Plan B
NORPLANT
Jadelle
dl-Norgestrel
D-(-)-Norgestrel
Follistrel
18-Methylnorethisterone
Levonorgestrelum
Ovrette
d(-)-Norgestrel
Levonelle
(-)-Norgestrel
Neogest
Levonorgestrelum [INN-Latin]
Liletta
Fallback Solo
Monovar
Wy-5104
Norgestrel-(-)-D
Wy-3707
17-Ethynyl-18-methyl-19-nortestosterone
17alpha-Ethynyl-18-homo-19-nortestosterone
18-Methyl-17-alpha-ethynyl-19-nortestosterone
13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one
17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one
17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol
13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one
BAY86-5028
Norgestrel, (-)-
Norgestrel (-)-form
Norplant 2
13beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
Microlution
Ovranette
Triagynon
Triciclor
MFCD00199013
Microgyn
Microlut
5W7SIA7YZW
Nordet
Trigoa
Wy 3707
17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one
NSC-744007
Microgynon CD
Microgest ED
Norplant II
(-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
Logynon ED
Ovral-Lo
Levlen ED
Microgynon 21
Microgynon 28
Trinordiol 21
Trinordiol 28
MLS000069491
CHEBI:6443
Minivlar 30
Monofeme 28
Neogynon 21
Nordette 21
Nordette 28
Stediril 30
Trifeme 28
DTXSID3036496
DTXSID3047477
Preven
Levora-21
Levora-28
Microgynon 30 ED
Tri-Levlen 21
17-alpha-Ethynyl-13-ethyl-19-nortestosterone
Rigevidon 21+7
FH 122-A
NorLevo
13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
SH 850
Triquilar ED
LD norgestrel [French]
Triphasil 21
Triphasil 28
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
SH 70850
NCGC00159349-02
Norgestrelum [INN-Latin]
13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
SMR000059117
Levonorgestrel implants
E-Gen-C
Norgestrel [Progestins]
Ovoplex 30-150
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
DTXCID1016496
Microluton
Levogel
Levosert
Skyla
13-ethyl-17alpha-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
Next choice
D-(-)-Norgestrel beta-D-Glucuronide
Norplant System in Plastic Container
Plan B One Step
Plan B One-Step
Norplant (TN)
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one
rel-(8R,9S,10R,13S,14S,17R)-13-Ethyl-17-ethynyl-17-hydroxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one
Ovrette (TN)
Mirena (TN)
CCRIS 6525
CCRIS 9033
Levonorgestrel (Levonelle)
HSDB 3595
HSDB 6483
LNG-IUS
(+/-)-NORGESTREL
17alpha-Ethynyl-13-ethyl-19-nortestosterone
EINECS 212-349-8
EINECS 229-433-5
UNII-5W7SIA7YZW
17-Ethynyl-18-methyl-19-nortestosterone;Levonorgestrel
BRN 2391114
13-Ethyl-17alpha-ethynylgon-4-en-17beta-ol-3-one
18,19-Dinor-4-pregnen-20-yn-3-one
Kyleena
dl-13-beta-Ethyl-17-alpha-ethynyl-19-nortestosterone
19-Nortestosterone, 17-ethynyl-18-methyl-
Levonorgestrel (JAN/USP/INN)
UNII-3J8Q1747Z2
1lhv
17-Ethynyl-18-methyl-19-nortestosterone Glucuronide; Levonorgestrel Glucuronide;
Oral levonorgestrel
CAS-797-63-7
LNG
Prestwick_109
(-)-Levonorgestrel
Levonorgestrel [USAN:USP:INN:BAN]
Levonorgestrel implant
Skyla (TN)
Norgestrel [USAN:USP:INN:BAN:JAN]
BAY 86-5028
NORGESTREL [MI]
Opera_ID_552
Levonorgestrel(Levonelle)
NORGESTREL [INN]
NORGESTREL [JAN]
dl-13-beta-Ethyl-17-alpha-ethynyl-17-beta-hydroxygon-4-en-3-one
Prestwick0_000773
Prestwick1_000773
Prestwick2_000773
Prestwick3_000773
Levonorgestrel (Standard)
NORGESTREL [HSDB]
NORGESTREL [USAN]
Intrauterine levonorgestrel
17-beta-Hydroxy-18-methyl-19-nor-17-alpha-pregn-4-en-20-yn-3-one
17alpha-Ethynyl-18-homo-19-nor-testosterone
NORGESTREL [VANDF]
(-)-Norgestrel, 98%
18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-(-)-
CHEMBL1389
LEVONORGESTREL [INN]
LEVONORGESTREL [JAN]
NORGESTREL [WHO-DD]
BIDD:PXR0194
SCHEMBL27597
BSPBio_000846
LEVONORGESTREL [HSDB]
LEVONORGESTREL [USAN]
MLS000759484
MLS001074069
MLS001423967
LEVONORGESTREL [VANDF]
SPBio_002785
LEVONORGESTREL [MART.]
13-Ethyl-17alpha-ethynyl-17-hydroxygon-4-en-3-one
BPBio1_000932
GTPL2881
Norgestrel (JP17/USP/INN)
LEVONORGESTREL [USP-RS]
LEVONORGESTREL [WHO-DD]
LEVONORGESTREL [WHO-IP]
NORGESTREL [ORANGE BOOK]
HY-B0257R
17alpha-ethynyl-17beta-hydroxy-18a-homoestr-4-en-3-one
IMPLANT WITH LEVONORGESTREL
DTXCID401079284
HMS1570K08
HMS2051M08
HMS2090O06
HMS2097K08
HMS2232H06
HMS2232K12
HMS3649J10
HMS3714K08
HMS3886K18
HY-B0257
NORGESTREL (-)-FORM [MI]
LEVONORGESTREL [ORANGE BOOK]
Tox21_111593
Tox21_202872
Tox21_303623
Tox21_303658
BDBM50410522
LEVONORGESTREL [EP MONOGRAPH]
LEVONORGESTREL [USP IMPURITY]
LMST02030119
NSC744007
s1727
s5709
ALESSE COMPONENT LEVONORGESTREL
AVIANE COMPONENT LEVONORGESTREL
D(-)-Norgestrel, analytical standard
LEVONORGESTREL [USP MONOGRAPH]
LEVORA COMPONENT LEVONORGESTREL
LYBREL COMPONENT LEVONORGESTREL
PORTIA COMPONENT LEVONORGESTREL
PREVEN COMPONENT LEVONORGESTREL
TWIRLA COMPONENT LEVONORGESTREL
VIENVA COMPONENT LEVONORGESTREL
18,19-Dinor-17-alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-
AKOS015894913
KURVELO COMPONENT LEVONORGESTREL
KYLEENA COMPONENT LEVONORGESTREL
LESSINA COMPONENT LEVONORGESTREL
LEVLITE COMPONENT LEVONORGESTREL
MYZILRA COMPONENT LEVONORGESTREL
PLASTIC IUD WITH LEVONORGESTREL
Tox21_111593_1
TRIVORA COMPONENT LEVONORGESTREL
BCP9000852
CCG-100853
DB00367
FN26454
FN26455
Levonorgestrel for system suitability 1
Levonorgestrel for system suitability 2
LEVONORGESTRELUM [WHO-IP LATIN]
NC00103
NSC 744007
NSC 757251
NSC 759653
18,19-Dinor-17-alpha-pregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (+-)-
ALTAVERA COMPONENT LEVONORGESTREL
D-(-)-Norgestrel - Bio-X trade mark
ELIFEMME COMPONENT LEVONORGESTREL
ENPRESSE COMPONENT LEVONORGESTREL
LEVONEST COMPONENT LEVONORGESTREL
MARLISSA COMPONENT LEVONORGESTREL
NORDETTE COMPONENT LEVONORGESTREL
ORSYTHIA COMPONENT LEVONORGESTREL
QUASENSE COMPONENT LEVONORGESTREL
SETLAKIN COMPONENT LEVONORGESTREL
[18,(17.alpha.)-(-)-]
AFIRMELLE COMPONENT LEVONORGESTREL
INTROVALE COMPONENT LEVONORGESTREL
NCGC00159349-03
NCGC00159349-05
NCGC00256735-01
NCGC00257283-01
NCGC00260418-01
QUARTETTE COMPONENT LEVONORGESTREL
SEASONALE COMPONENT LEVONORGESTREL
TRIPHASIL COMPONENT LEVONORGESTREL
BN300105
SEASONIQUE COMPONENT LEVONORGESTREL
SMR000653526
CAS-6533-00-2
CLIMARA PRO COMPONENT LEVONORGESTREL
LOSEASONIQUE COMPONENT LEVONORGESTREL
N0889
NORGESTIMATE IMPURITY B [EP IMPURITY]
NS00002177
NS00067059
Levonorgestrel 100 microg/mL in Acetonitrile
C08149
C08153
D00950
D00954
EN300-122613
OPCICON ONE-STEP COMPONENT LEVONORGESTREL
Q416950
SR-01000759218
SR-01000946725
(-)-17alpha-Ethynyl-18-methyl-19-nortestosterone
SR-01000759218-5
SR-01000946725-1
BRD-K35189033-001-03-0
BRD-K35189033-001-26-1
13-ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
Z1544404028
13beta-ethyl-17alpha-ethynyl-17-hydroxy-gon-4-en-3-one
13beta-ethyl-17alpha-ethynyl-17beta-hydroxy-gon-4-en-3-one
Levonorgestrel, British Pharmacopoeia (BP) Reference Standard
Levonorgestrel, European Pharmacopoeia (EP) Reference Standard
18,19-Dinor-13beta-ethyl-17beta-hydroxy-4-pregnen-20-yn-3-one
Levonorgestrel, United States Pharmacopeia (USP) Reference Standard
(-)-18,19-Dinor-13beta-ethyl-17beta-hydroxy-4-pregnen-20-yn-3-one
(17alpha)-dl-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3- one
[(-)-13-ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one
dl-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20- yn-3-one
(+/-)-13-ETHYL-17-HYDROXY-18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-3-ONE
(+/-)-13-ETHYL-17-HYDROXY-18,19-DINOR-17alpha-PREGN-4-EN-20-YN-3-ONE
(-)-13-ETHYL-17-HYDROXY-18,19-DINOR-17.ALPHA.-PREGN-4-EN-20-YN-3-ONE
18,19-DINORPREGN-4-EN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-, (17.ALPHA.)-(+/-)-
18,19-DINORPREGN-4-EN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-, (17.ALPHA.)-(-)-
18,19-DINORPREGN-4-EN-20-YN-3-ONE, 13-ETHYL-17-HYDROXY-, (17alpha)-(+/-)-
Levonorgestrel for system suitability 2, European Pharmacopoeia (EP) Reference Standard
Levonorgestrel, Pharmaceutical Secondary Standard; Certified Reference Material
(17a)-(+/-)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one;(+/-)-13-Ethyl-17a-ethynyl-17-hydroxygon-4-en-3-one
(1R,3aS,3bR,9aR,9bS,11aS)-11a-ethyl-1-ethynyl-1-hydroxy-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy- 1,2,6,7,8,9,10,11,12,13,14,15,16, 17- tetradecahydrocyclopenta[a] phenanthren-3-one
(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (non-preferred name)