LEVONORGESTREL

Search structure
Trade Names:
Synonyms:
Status: Approved (1982)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G03AC03
UNII: 5W7SIA7YZW

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

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H28O2
Molecular Weight 312.45
AlogP 3.88
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 1.0
Polar Surface Area 37.3
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 23.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Progesterone receptor agonist PubMed Wikipedia
Primary Target
Progesterone receptor

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Dysmenorrhea 3 D004412 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Endometrial Hyperplasia 3 D004714 ClinicalTrials
Endometriosis 3 D004715 ClinicalTrials
Hemorrhage 3 D006470 ClinicalTrials
Bone Diseases, Metabolic 3 D001851 ClinicalTrials
Anorexia Nervosa 3 D000856 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Adenomyosis 2 D062788 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Pain 2 D010146 ClinicalTrials
Non-alcoholic Fatty Liver Disease 1 D065626 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 1 D015451 ClinicalTrials
Diabetes Mellitus, Type 2 1 D003924 ClinicalTrials
Hepatitis C, Chronic 1 D019698 ClinicalTrials
Neoplasms 1 D009369 ClinicalTrials
Hepatitis B, Chronic 1 D019694 ClinicalTrials

Related Entries

MCS

Scaffolds

UNKNOWN
Mixture
Mixture
Mixture

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Nausea 50.5
Gastrointestinal disorders Nausea 49.3
Gastrointestinal disorders Nausea 46.5
General disorders and administration site conditions Asthenia 36.8
General disorders and administration site conditions Fatigue 36.8
General disorders and administration site conditions Asthenia 31.0
General disorders and administration site conditions Fatigue 31.0
Investigations Haemoglobin 31.0
Vascular disorders Haemorrhage 31.0
Investigations Haemoglobin 30.9
Vascular disorders Haemorrhage 30.9
General disorders and administration site conditions Asthenia 28.5
General disorders and administration site conditions Fatigue 28.5
Reproductive system and breast disorders Menorrhagia 25.9
Endocrine disorders Amenorrhoea 23.9
General disorders and administration site conditions Asthenia 23.9
General disorders and administration site conditions Fatigue 23.9
Cardiac disorders Dizziness 23.1
Gastrointestinal disorders Nausea 23.1
Gastrointestinal disorders Nausea 23.0
Gastrointestinal disorders Vomiting 22.4
Gastrointestinal disorders Nausea 21.1
Gastrointestinal disorders Abdominal pain 20.9
Gastrointestinal disorders Gastrointestinal pain 20.9
Reproductive system and breast disorders Breast tenderness 20.8
Reproductive system and breast disorders Menometrorrhagia 20.5
Reproductive system and breast disorders Breast disorder 20.2
Nervous system disorders Headache 20.2
Infections and infestations Vulvovaginitis 20.2
Gastrointestinal disorders Vomiting 19.9
General disorders and administration site conditions Asthenia 19.0
General disorders and administration site conditions Fatigue 19.0
Gastrointestinal disorders Pelvic pain 18.9
Gastrointestinal disorders Vomiting 18.8
Cardiac disorders Dizziness 18.6
Cardiac disorders Dizziness 18.5
Gastrointestinal disorders Abdominal pain 18.0
Gastrointestinal disorders Gastrointestinal pain 18.0
Gastrointestinal disorders Abdominal pain 17.6
Gastrointestinal disorders Gastrointestinal pain 17.6
General disorders and administration site conditions Asthenia 17.0
General disorders and administration site conditions Fatigue 17.0
Nervous system disorders Headache 17.0
General disorders and administration site conditions Asthenia 16.9
General disorders and administration site conditions Fatigue 16.9
Nervous system disorders Headache 16.8
Cardiac disorders Dizziness 16.6
Gastrointestinal disorders Nausea 16.1
Reproductive system and breast disorders Breast tenderness 15.9
Skin and subcutaneous tissue disorders Seborrhoeic dermatitis 15.0
Reproductive system and breast disorders Breast tenderness 14.7
Gastrointestinal disorders Nausea 14.5
Gastrointestinal disorders Abdominal pain lower 14.4
Gastrointestinal disorders Abdominal pain 14.3
Gastrointestinal disorders Gastrointestinal pain 14.3
Gastrointestinal disorders Nausea 14.0
Endocrine disorders Amenorrhoea 13.9
Gastrointestinal disorders Nausea 13.7
Investigations Haemoglobin 13.6
Vascular disorders Haemorrhage 13.6
Reproductive system and breast disorders Menorrhagia 13.4
Gastrointestinal disorders Abdominal pain lower 13.3
General disorders and administration site conditions Asthenia 13.3
Cardiac disorders Dizziness 13.3
General disorders and administration site conditions Fatigue 13.3
General disorders and administration site conditions Asthenia 13.2
General disorders and administration site conditions Fatigue 13.2
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Ovarian cyst 13.2
Gastrointestinal disorders Abdominal pain lower 13.0
General disorders and administration site conditions Asthenia 13.0
General disorders and administration site conditions Fatigue 13.0
Endocrine disorders Oligomenorrhoea 12.8
Gastrointestinal disorders Pelvic pain 12.8
Nervous system disorders Headache 12.4
Gastrointestinal disorders Nausea 12.4
Nervous system disorders Nervous system disorder 12.4
Reproductive system and breast disorders Breast tenderness 12.3
Reproductive system and breast disorders Breast tenderness 12.1
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Ovarian cyst 12.0
Investigations Haemoglobin 11.8
Vascular disorders Haemorrhage 11.8
Nervous system disorders Headache 11.3
Cardiac disorders Dizziness 11.2
Reproductive system and breast disorders Breast tenderness 11.0
Cardiac disorders Dizziness 11.0
Reproductive system and breast disorders Breast tenderness 10.8
Reproductive system and breast disorders Breast tenderness 10.7
Nervous system disorders Headache 10.3
Cardiac disorders Dizziness 10.0
Nervous system disorders Headache 10.0
Endocrine disorders Amenorrhoea 9.8
Cardiac disorders Dizziness 9.6
Reproductive system and breast disorders Menometrorrhagia 9.6
Cardiac disorders Dizziness 9.57
Endocrine disorders Oligomenorrhoea 9.5
Nervous system disorders Headache 9.44
Cardiac disorders Dizziness 9.15
General disorders and administration site conditions Discomfort 8.6
Reproductive system and breast disorders Dysmenorrhoea 8.6
Reproductive system and breast disorders Breast tenderness 8.35
Reproductive system and breast disorders Breast tenderness 8.2
Reproductive system and breast disorders Breast tenderness 8.19
General disorders and administration site conditions Asthenia 8.0
General disorders and administration site conditions Fatigue 8.0
Investigations Haemoglobin 7.8
Vascular disorders Haemorrhage 7.8
Nervous system disorders Migraine 7.7
Gastrointestinal disorders Diarrhoea 6.54
Psychiatric disorders Affect lability 6.4
Psychiatric disorders Mood swings 6.4
Reproductive system and breast disorders Menorrhagia 6.3
Gastrointestinal disorders Vomiting 5.63
Nervous system disorders Headache 5.6
Gastrointestinal disorders Vomiting 5.6
Gastrointestinal disorders Nausea 5.5
Gastrointestinal disorders Diarrhoea 5.02
Gastrointestinal disorders Diarrhoea 5.0
Reproductive system and breast disorders Polymenorrhoea 5.0
Product issues Device expulsion 4.9
General disorders and administration site conditions Pain 4.9
Reproductive system and breast disorders Vaginal discharge 4.9
Gastrointestinal disorders Vomiting 4.76
Reproductive system and breast disorders Menorrhagia 4.5
Reproductive system and breast disorders Metrorrhagia 4.3
Reproductive system and breast disorders Vaginal haemorrhage 4.25
Gastrointestinal disorders Diarrhoea 3.84
Cardiac disorders Dizziness 3.7
Reproductive system and breast disorders Vaginal haemorrhage 3.41
Product issues Device expulsion 3.2
Gastrointestinal disorders Diarrhoea 3.2
Endocrine disorders Hypomenorrhoea 2.9
Skin and subcutaneous tissue disorders Seborrhoeic dermatitis 2.9
Reproductive system and breast disorders Polymenorrhoea 2.7
Gastrointestinal disorders Vomiting 2.68
Gastrointestinal disorders Abdominal pain 2.5
Gastrointestinal disorders Gastrointestinal pain 2.5
Investigations Haemoglobin 2.14
Vascular disorders Haemorrhage 2.14
Musculoskeletal and connective tissue disorders Muscle spasms 2.0
Gastrointestinal disorders Pelvic pain 1.8
Investigations Haemoglobin 1.73
Vascular disorders Haemorrhage 1.73
Reproductive system and breast disorders Menorrhagia 1.6
Endocrine disorders Hypomenorrhoea 1.5
Gastrointestinal disorders Vomiting 1.38
Reproductive system and breast disorders Vaginal haemorrhage 1.23
Gastrointestinal disorders Vomiting 1.2
Infections and infestations Influenza 1.02
Reproductive system and breast disorders Vaginal haemorrhage 1.02
Infections and infestations Influenza 0.919

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Reproductive system and breast disorders
18.74
Product issues
12.05
General disorders and administration site conditions
11.56
Injury, poisoning and procedural complications
10.23
Gastrointestinal disorders
8.23
Psychiatric disorders
7.14
Vascular disorders
6.9
Nervous system disorders
4.67
Endocrine disorders
4.26
Pregnancy, puerperium and perinatal conditions
3.0

Cross References

Resources Reference
CAS NUMBER 797-63-7
ChEBI 6443
ChEMBL CHEMBL1389
DrugBank DB00367
DrugCentral 1572
EPA CompTox DTXSID3036496
FDA SRS 5W7SIA7YZW
Human Metabolome Database HMDB0014511
Guide to Pharmacology 2881
KEGG C08153
PDB NOG
PharmGKB PA450656
PubChem 13109
SureChEMBL SCHEMBL27597
ZINC ZINC000003814395
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