What is the molecular formula of Levonorgestrel?

Levonorgestrel has a molecular formula of C 21 H 28 O 2

What is the InChI Key of Levonorgestrel molecule?

The InChI Key of Levonorgestrel is: WWYNJERNGUHSAO-XUDSTZEESA-N.

What is the molecular weight of Levonorgestrel?

Levonorgestrel presents a molecular weight of 312.446 g/mol.

Levonorgestrel

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Levonorgestrel are summarized together with 3D and 2D structures and relevant physico-chemical properties.

Table of Contents

1. What is Levonorgestrel?
2. 3D Structure
3. Cartesian coordinates
4. 2D Drawing
5. Molecule descriptors
6. Physico-Chemical properties

What is the Levonorgestrel?

The molecule Levonorgestrel presents a molecular formula of C₂₁H₂₈O₂ and its IUPAC name is (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.

Levonorgestrel is a popular contraceptive drug that is used in a wide variety of birth control products. It is a progestin, which is a synthetic form of the hormone progesterone. Levonorgestrel is used in birth control pills, emergency contraception pills, and intrauterine devices (IUDs). It works by preventing ovulation (the release of an egg from the ovary) and by thinning the lining of the uterus (womb), making it less likely for a fertilized egg to implant and grow..

Levonorgestrel is a very effective contraceptive drug. When used correctly, it can prevent pregnancy up to 99% of the time. However, like all contraceptive drugs, it is not 100% effective. The effectiveness of levonorgestrel can be reduced by certain medications, vomiting, and diarrhea..

Levonorgestrel is generally safe for most women to use. However, like all drugs, it can cause side effects. The most common side effects are nausea, vomiting, headache, and dizziness. These side effects are usually mild and go away on their own. More serious side effects are rare, but can include blood clots, stroke, and heart attack..

If you are considering using levonorgestrel as a contraceptive, talk to your healthcare provider about the risks and benefits..

3D structure

Cartesian coordinates

Geometry of Levonorgestrel in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

Levonorgestrel WWYNJERNGUHSAO-XUDSTZEESA-N chemical compound 2D structure molecule svg — Levonorgestrel

Molecule descriptors

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
InChI code	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
InChI Key	WWYNJERNGUHSAO-XUDSTZEESA-N
SMILES	C#C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[C@H]3CC[C@@]21CC

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

(+-)-13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
(+-)-Norgestrel
(+/-)-13-ETHYL-17-HYDROXY-18,19-DINOR-17.ALPHA.-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
(-)-17alpha-Ethynyl-18-methyl-19-nortestosterone
(-)-18,19-Dinor-13beta-ethyl-17beta-hydroxy-4-pregnen-20-yn-3-one
(-)-Levonorgestrel
(-)-Norgestrel
(17?)-13-Ethyl-17-hydroxy-18,19-dinorpregn-4-en-yn-3-one
(1S,2R,10R,11S,14R,15S)-15-ethyl-14-ethynyl-14-hydroxytetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-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
(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)
(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
(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
13-Ethyl-17-alpha-ethynyl-17-beta-hydroxy-4-gonen-3-one
13-Ethyl-17-alpha-ethynylgon-4-en-17-beta-ol-3-one
13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregn-4-en-20-yn-3-one
13-Ethyl-17alpha-ethynyl-17-hydroxygon-4-en-3-one
13-Ethyl-17alpha-ethynylgon-4-en-17beta-ol-3-one
13-beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
13-ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
13-ethyl-17alpha-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one
13beta-Ethyl-17alpha-ethynyl-17beta-hydroxygon-4-en-3-one
13beta-ethyl-17alpha-ethynyl-17-hydroxy-gon-4-en-3-one
13beta-ethyl-17alpha-ethynyl-17beta-hydroxy-gon-4-en-3-one
17-Ethynyl-18-methyl-19-nortestosterone
17-alpha-Ethinyl-13-beta-ethyl-17-beta-hydroxy-4-estren-3-one
17-alpha-Ethynyl-13-ethyl-19-nortestosterone
17-beta-Hydroxy-18-methyl-19-nor-17-alpha-pregn-4-en-20-yn-3-one
17alpha-Ethynyl-13-ethyl-19-nortestosterone
17alpha-Ethynyl-13beta-ethyl-3-oxo-4-estren-17beta-ol
17alpha-Ethynyl-17-hydroxy-18-methylestr-4-en-3-one
17alpha-Ethynyl-18-homo-19-nortestosterone
17alpha-ethynyl-17beta-hydroxy-18a-homoestr-4-en-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-Dinor-17-alpha-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-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-(+-)-
18,19-Dinorpregn-4-en-20-yn-3-one, 13-ethyl-17-hydroxy-, (17alpha)-(-)-
18-Methyl-17-alpha-ethynyl-19-nortestosterone
18-Methylnorethisterone
19-Nortestosterone, 17-ethynyl-18-methyl-
1lhv
3J8Q1747Z2
5W7SIA7YZW
6533-00-2
797-63-7
797L637
AFIRMELLE COMPONENT LEVONORGESTREL
ALESSE COMPONENT LEVONORGESTREL
ALTAVERA COMPONENT LEVONORGESTREL
AMY40476
AVIANE COMPONENT LEVONORGESTREL
BAY 86-5028
BAY86-5028
BCP9000852
BDBM50410522
BIDD:PXR0194
BPBio1_000932
BRN 2391114
BSPBio_000846
C08149
C08153
CCG-100853
CCRIS 6525
CCRIS 9033
CLIMARA PRO COMPONENT LEVONORGESTREL
CRYSELLE COMPONENT NORGESTREL
D-(-)-Norgestrel
D-(-)-Norgestrel (Levonorgestrel)
D-Norgestrel
D00950
D00954
DB00367
DSSTox_CID_16496
DSSTox_GSID_36496
DSSTox_RID_79283
E-Gen-C
ELIFEMME COMPONENT LEVONORGESTREL
ENPRESSE COMPONENT LEVONORGESTREL
FH 122-A
FH-122A
Fallback Solo
Follistrel
GTPL2881
HMS1570K08
HMS2051M08
HMS2090O06
HMS2097K08
HMS2232H06
HMS2232K12
HMS3649J10
HMS3714K08
HMS3886K18
HSDB 3595
HSDB 6483
HY-B0257
IMPLANT WITH LEVONORGESTREL
INTROVALE COMPONENT LEVONORGESTREL
Intrauterine levonorgestrel
Jadelle
KURVELO COMPONENT LEVONORGESTREL
KYLEENA COMPONENT LEVONORGESTREL
Kyleena
L-4455
LESSINA COMPONENT LEVONORGESTREL
LEVLITE COMPONENT LEVONORGESTREL
LEVONEST COMPONENT LEVONORGESTREL
LEVONORGESTREL COMPONENT OF ALESSE
LEVONORGESTREL COMPONENT OF ALTAVERA
LEVONORGESTREL COMPONENT OF CLIMARA PRO
LEVONORGESTREL COMPONENT OF INTROVALE
LEVONORGESTREL COMPONENT OF KYLEENA
LEVONORGESTREL COMPONENT OF LEVLITE
LEVONORGESTREL COMPONENT OF LEVONEST
LEVONORGESTREL COMPONENT OF LOSEASONIQUE
LEVONORGESTREL COMPONENT OF LYBREL
LEVONORGESTREL COMPONENT OF OPCICON ONE-STEP
LEVONORGESTREL COMPONENT OF PREVEN
LEVONORGESTREL COMPONENT OF QUASENSE
LEVONORGESTREL COMPONENT OF SEASONALE
LEVONORGESTREL COMPONENT OF SEASONIQUE
LEVONORGESTREL COMPONENT OF SETLAKIN
LEVONORGESTREL COMPONENT OF TWIRLA
LEVORA COMPONENT LEVONORGESTREL
LMST02030119
LNG
LNG-IUS
LOSEASONIQUE COMPONENT LEVONORGESTREL
LYBREL COMPONENT LEVONORGESTREL
Levlen ED
Levogel
Levonelle
Levonorgestrel
Levonorgestrel (JAN/USP/INN)
Levonorgestrel (Levonelle)
Levonorgestrel implant
Levonorgestrel implants
Levonorgestrel(Levonelle)
Levonorgestrelum
Levonova
Levora-21
Levora-28
Levosert
Liletta
Logynon ED
MARLISSA COMPONENT LEVONORGESTREL
MFCD00199013
MLS000069491
MLS000759484
MLS001074069
MLS001423967
MYZILRA COMPONENT LEVONORGESTREL
Microgest ED
Microgyn
Microgynon 21
Microgynon 28
Microgynon 30 ED
Microgynon CD
Microlut
Microlution
Microluton
Microval
Minivlar 30
Mirena
Monofeme 28
Monovar
N0889
NC00103
NCGC00159349-02
NCGC00159349-03
NCGC00159349-05
NCGC00257283-01
NCGC00260418-01
NORDETTE COMPONENT LEVONORGESTREL
NORGESTREL COMPONENT OF CRYSELLE
NORGESTREL COMPONENT OF OVRAL
NORPLANT
NSC 744007
NSC 757251
NSC 759653
NSC-744007
NSC-757251
NSC744007
Neogest
Neogynon 21
Next choice
NorLevo
Nordet
Nordette 21
Nordette 28
Norgestrel (-)-form
Norgestrel (JP17/USP/INN)
Norgestrel, (-)-
Norgestrel-(-)-D
Norgestrelum
Norplant 2
Norplant II
Norplant System in Plastic Container
OPCICON ONE-STEP COMPONENT LEVONORGESTREL
ORSYTHIA COMPONENT LEVONORGESTREL
OVRAL COMPONENT NORGESTREL
Opera_ID_552
Oral levonorgestrel
Ovoplex 30-150
Ovral-Lo
Ovranette
Ovrette
PLASTIC IUD WITH LEVONORGESTREL
PORTIA COMPONENT LEVONORGESTREL
PREVEN COMPONENT LEVONORGESTREL
Plan B
Plan B One Step
Plan B One-Step
Postinor
Prestwick0_000773
Prestwick1_000773
Prestwick2_000773
Prestwick3_000773
Prestwick_109
Preven
Q416950
QUARTETTE COMPONENT LEVONORGESTREL
QUASENSE COMPONENT LEVONORGESTREL
Rigevidon 21+7
SEASONALE COMPONENT LEVONORGESTREL
SEASONIQUE COMPONENT LEVONORGESTREL
SETLAKIN COMPONENT LEVONORGESTREL
SH 70850
SH 850
SH-70850
SH-850
SMR000059117
SMR000653526
SR-01000759218
SR-01000759218-5
SR-01000946725
SR-01000946725-1
Skyla
Stediril 30
TRIPHASIL COMPONENT LEVONORGESTREL
TRIVORA COMPONENT LEVONORGESTREL
TWIRLA COMPONENT LEVONORGESTREL
Tri-Levlen 21
Triagynon
Triciclor
Trifeme 28
Trigoa
Trinordiol 21
Trinordiol 28
Triphasil 21
Triphasil 28
Triquilar ED
VIENVA COMPONENT LEVONORGESTREL
Wy 3707
Wy-3707
Wy-5104
Z1551429747
[(-)-13-ethyl-17-hydroxy-18,19-dinor-17a-pregn-4-en-20-yn-3-one
[18,(17.alpha.)-(-)-]
[18,19-Dinorpregn-4-en-20-yn-3-one-13-ethyl-17-hydroxy-,(17..)-(-)-]
d(-)-Norgestrel
dl-13-beta-Ethyl-17-alpha-ethynyl-17-beta-hydroxygon-4-en-3-one
dl-13-beta-Ethyl-17-alpha-ethynyl-19-nortestosterone
dl-Norgestrel
norgestrel
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
s1727
s5709

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:

CAS number (Chemical Abstracts Service Registry Number) is a unique identifier is assigned to every chemical compound indexed in the CAS database.
Beilstein: The Beilstein database is a comprehensive source of information on organic chemistry, including information on chemical structures, properties, and reactions. The Beilstein database assigns unique identifiers which can be used to identify compounds in scientific literature and other sources.
ChEBI (Chemical Entities of Biological Interest): ChEBI is a database of small chemical molecules that are of interest in the field of biology.
PubChem CID (Compound Identifier): PubChem is a database of chemical compounds that is maintained by the National Institutes of Health (NIH).
RTECS number (Registry of Toxic Effects of Chemical Substances): The RTECS is a database of information on the toxic effects of chemicals, including information on their structures and properties.
ChEMBL (Compound Bioactivity Data): ChEMBL is a database of bioactivity data for small molecules, including information on their properties and structures.
CompTox Dashboard (Environmental Protection Agency): The CompTox Dashboard is a database of information on the toxicology and environmental effects of chemicals.

ZINC3814395
CAS-797-63-7
UNII-5W7SIA7YZW
UNII-3J8Q1747Z2
AKOS015894913
BRD-K35189033-001-03-0
DTXSID3036496
DTXSID3047477
CHEMBL1389
CHEBI:6443
Tox21_111593
Tox21_202872
Tox21_303658
Tox21_111593_1
EINECS 212-349-8
EINECS 229-433-5
SPBio_002785
SCHEMBL27597

Physico-Chemical properties

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
Molecular formula	C₂₁H₂₈O₂
Molecular weight	312.446
Melting point (ºC)
Boiling point (ºC)
Density (g/cm³)
Molar refractivity	93.43
LogP	3.9
Topological polar surface area	37.3

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (K_ow) data is applied in toxicology and drug research. K_ow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(K_ow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å² are required. Thus, molecules with a polar surface area greater than 140 Å² tend to be poorly permeable to cell membranes.