TESTOSTERONE

Search structure
Trade Names:
Synonyms:
Status: Approved (1972)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G03BA03
UNII: 3XMK78S47O

Structure
InChI Key MUMGGOZAMZWBJJ-DYKIIFRCSA-N
Smile C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43C)[C@@H]1CC[C@@H]2O
InChI
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H28O2
Molecular Weight 288.43
AlogP 3.88
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 0.0
Polar Surface Area 37.3
Molecular species NEUTRAL
Aromatic Rings 0.0
Heavy Atoms 21.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.32 - EXP
Henry's Law Constant 3.53E-09 atm-m3/mole EST
Atmospheric OH Rate Constant 1.07E-10 cm3/molecule-sec EST
Melting Point 155 deg C EXP
Water Solubility 23.4 mg/L EXP
Vapor Pressure 2.23E-08 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
AGONIST Androgen Receptor agonist Wikipedia FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 19 Cytochrome P450 family 19A Cytochrome P450 19A1
- - - 600 -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 10000 - - 4-103
Enzyme Cytochrome P450 Cytochrome P450 family 51 Cytochrome P450 family 51A Cytochrome P450 51A1
- 50000 - - -
Enzyme Isomerase
- - - 7760 -
Enzyme Oxidoreductase
- 1900 - - 8
Ion channel Voltage-gated ion channel Voltage-gated calcium channel
- 34-38 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 22
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Steroid-like ligand receptor
18300 - - - -
Membrane receptor
18300 - - 1200 -
Secreted protein
- 14 1 191 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 3
- 30000 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 3 Nuclear hormone receptor subfamily 3 group C Nuclear hormone receptor subfamily 3 group C member 4
1-3 3-30 - 1-5 0-100
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 33-80
Unclassified protein
- 96800 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypogonadism 4 D007006 ClinicalTrials
Infertility 3 D007246 ClinicalTrials
Sexual Dysfunction, Physiological 3 D012735 ClinicalTrials
Renal Insufficiency, Chronic 3 D051436 ClinicalTrials
Disorders of Sex Development 3 D012734 ClinicalTrials
Neoplasms 3 D009369 ClinicalTrials
Hip Fractures 3 D006620 ClinicalTrials
Metabolic Syndrome 3 D024821 ClinicalTrials
Coronary Disease 3 D003327 ClinicalTrials
Erectile Dysfunction 3 D007172 ClinicalTrials
Acquired Immunodeficiency Syndrome 2 D000163 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Anorexia Nervosa 2 D000856 ClinicalTrials
Menopause 2 D008593 ClinicalTrials
Muscular Diseases 2 D009135 ClinicalTrials
Obesity 2 D009765 ClinicalTrials
Dwarfism 2 D004392 ClinicalTrials
Sarcopenia 2 D055948 ClinicalTrials
Multiple Sclerosis 2 D009103 ClinicalTrials
Heart Failure 2 D006333 ClinicalTrials
Testicular Neoplasms 2 D013736 ClinicalTrials
Spinal Cord Injuries 2 D013119 ClinicalTrials
Hereditary Breast and Ovarian Cancer Syndrome 2 D061325 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Kallmann Syndrome 1 D017436 ClinicalTrials
Aging 1 D000375 ClinicalTrials
Penile Induration 1 D010411 ClinicalTrials
Cerebral Arterial Diseases 0 D002539 ClinicalTrials
Insulin Resistance 0 D007333 ClinicalTrials
Polycystic Ovary Syndrome 0 D011085 ClinicalTrials
Dyspareunia 0 D004414 ClinicalTrials

Related Entries

MCS

Scaffolds

UKNOWN
UKNOWN
UKNOWN

Side Effects from Label

Side effects Relative Frequency (%) Labels
Skin and subcutaneous tissue disorders Pruritus 39.0
General disorders and administration site conditions Application site pruritus 37.0
General disorders and administration site conditions Application site pruritus 17.0
General disorders and administration site conditions Application site reaction 16.1
Skin and subcutaneous tissue disorders Blister 12.0
Skin and subcutaneous tissue disorders Dermatitis bullous 12.0
Injury, poisoning and procedural complications Thermal burn 12.0
Reproductive system and breast disorders Prostatomegaly 11.7
Investigations Prostatic specific antigen increased 11.1
Investigations Laboratory test abnormal 9.3
Investigations Laboratory test abnormal 9.26
Gastrointestinal disorders Stomatitis 9.2
Skin and subcutaneous tissue disorders Acne 8.0
General disorders and administration site conditions Application site irritation 8.0
Skin and subcutaneous tissue disorders Erythema 8.0
General disorders and administration site conditions Application site erythema 7.0
General disorders and administration site conditions Application site irritation 7.0
Investigations Haematocrit increased 7.0
General disorders and administration site conditions Application site vesicles 6.0
Musculoskeletal and connective tissue disorders Back pain 6.0
Nervous system disorders Headache 6.0
Investigations Laboratory test abnormal 6.0
General disorders and administration site conditions Application site reaction 5.6
General disorders and administration site conditions Application site reaction 5.56
Skin and subcutaneous tissue disorders Acne 5.23
General disorders and administration site conditions Application site erythema 5.0
General disorders and administration site conditions Application site reaction 5.0
Nervous system disorders Headache 5.0
Investigations Laboratory test abnormal 5.0
Reproductive system and breast disorders Prostatic disorder 5.0
Investigations Haemoglobin increased 4.6
General disorders and administration site conditions Injection site pain 4.6
Investigations Prostatic specific antigen increased 4.6
General disorders and administration site conditions Injection site pain 4.58
Investigations Prostatic specific antigen increased 4.58
Investigations Haematocrit increased 4.3
Investigations Prostatic specific antigen increased 4.3
General disorders and administration site conditions Application site erythema 4.1
Gastrointestinal disorders Dysgeusia 4.1
General disorders and administration site conditions Application site reaction 4.0
Immune system disorders Dermatitis contact 4.0
Gastrointestinal disorders Diarrhoea 4.0
Investigations Haematocrit increased 4.0
Nervous system disorders Headache 4.0
Investigations Prostatic specific antigen increased 4.0
Gastrointestinal disorders Vomiting 4.0
Investigations Haematocrit increased 3.9
Investigations Haemoglobin increased 3.7
Investigations Prostatic specific antigen increased 3.5
Skin and subcutaneous tissue disorders Acne 3.1
Nervous system disorders Headache 3.1
Skin and subcutaneous tissue disorders Acne 3.09
Skin and subcutaneous tissue disorders Acne 3.0
Psychiatric disorders Affect lability 3.0
General disorders and administration site conditions Application site burn 3.0
General disorders and administration site conditions Application site erythema 3.0
General disorders and administration site conditions Application site induration 3.0
General disorders and administration site conditions Application site pain 3.0
General disorders and administration site conditions Application site reaction 3.0
General disorders and administration site conditions Asthenia 3.0
Skin and subcutaneous tissue disorders Blister 3.0
Reproductive system and breast disorders Breast pain 3.0
Psychiatric disorders Depression 3.0
Skin and subcutaneous tissue disorders Dermatitis bullous 3.0
Gastrointestinal disorders Diarrhoea 3.0
Psychiatric disorders Disturbance in sexual arousal 3.0
Endocrine disorders Gynaecomastia 3.0
Nervous system disorders Headache 3.0
Vascular disorders Hypertension 3.0
General disorders and administration site conditions Induration 3.0
Investigations Laboratory test abnormal 3.0
Psychiatric disorders Libido decreased 3.0
Psychiatric disorders Mood swings 3.0
Psychiatric disorders Nervousness 3.0
Reproductive system and breast disorders Prostatic disorder 3.0
Psychiatric disorders Tension 3.0
Reproductive system and breast disorders Testicular disorder 3.0
Gastrointestinal disorders Vomiting 3.0
Endocrine disorders Hypogonadism 2.61
Investigations Oestradiol increased 2.61
Endocrine disorders Hypogonadism 2.6
Investigations Oestradiol increased 2.6
Psychiatric disorders Affect lability 2.56
Psychiatric disorders Mood swings 2.56
Blood and lymphatic system disorders Anaemia 2.5
General disorders and administration site conditions Application site erythema 2.5
Endocrine disorders Gynaecomastia 2.5
Blood and lymphatic system disorders Anaemia 2.47
Endocrine disorders Gynaecomastia 2.47
General disorders and administration site conditions Application site erythema 2.3
Immune system disorders Dermatitis contact 2.14
Investigations Haemoglobin increased 2.14
Vascular disorders Hypertension 2.14
General disorders and administration site conditions Application site erythema
Skin and subcutaneous tissue disorders Dermatitis 2.0
Psychiatric disorders Disturbance in sexual arousal 2.0
Gastrointestinal disorders Dysgeusia 2.0
Gastrointestinal disorders Gastrointestinal haemorrhage 2.0
Gastrointestinal disorders Gingival oedema 2.0
Gastrointestinal disorders Gingival swelling 2.0
Investigations Haemoglobin increased 2.0
Psychiatric disorders Libido decreased 2.0
Investigations Prostatic specific antigen increased 2.0
Skin and subcutaneous tissue disorders Pruritus 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Psychiatric disorders Affect lability 1.96
General disorders and administration site conditions Asthenia 1.96
General disorders and administration site conditions Fatigue 1.96
Investigations Haemoglobin increased 1.96
Nervous system disorders Insomnia 1.96
General disorders and administration site conditions Irritability 1.96
Psychiatric disorders Mood swings 1.96
Skin and subcutaneous tissue disorders Dry skin 1.9
Skin and subcutaneous tissue disorders Pruritus 1.9
Reproductive system and breast disorders Testicular disorder 1.9
Skin and subcutaneous tissue disorders Dry skin 1.85
Skin and subcutaneous tissue disorders Pruritus 1.85
Reproductive system and breast disorders Testicular disorder 1.85
General disorders and administration site conditions Application site rash 1.8
General disorders and administration site conditions Application site rash 1.7
Skin and subcutaneous tissue disorders Acne 1.5
Skin and subcutaneous tissue disorders Acne 1.4
Psychiatric disorders Aggression 1.31
Reproductive system and breast disorders Ejaculation disorder 1.31
Investigations Haematocrit increased 1.31
General disorders and administration site conditions Hyperhidrosis 1.31
General disorders and administration site conditions Injection site erythema 1.31
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Prostate cancer 1.31
Reproductive system and breast disorders Prostate induration 1.31
Investigations Weight increased 1.31
Reproductive system and breast disorders Benign prostatic hyperplasia 1.3
Vascular disorders Hypertension 1.3
Investigations Red blood cell count increased 1.3
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Prostate cancer 1.23
General disorders and administration site conditions Application site erythema 1.2
General disorders and administration site conditions Application site irritation 1.2
Reproductive system and breast disorders Benign prostatic hyperplasia 1.2
Nervous system disorders Headache 1.2
Vascular disorders Hypertension 1.2
Nervous system disorders Insomnia 1.2
Neoplasms benign, malignant and unspecified (incl cysts and polyps) Prostate cancer 1.2
Investigations Red blood cell count increased 1.2
Skin and subcutaneous tissue disorders Acne 1.0
Psychiatric disorders Affect lability 1.0
Skin and subcutaneous tissue disorders Alopecia 1.0
General disorders and administration site conditions Application site reaction 1.0
General disorders and administration site conditions Asthenia 1.0
Reproductive system and breast disorders Benign prostatic hyperplasia
Reproductive system and breast disorders Benign prostatic hyperplasia 1.0
Investigations Blood pressure diastolic decreased 1.0
Investigations Blood pressure increased 1.0
Reproductive system and breast disorders Breast pain 1.0
Psychiatric disorders Depression 1.0
Psychiatric disorders Disturbance in sexual arousal 1.0
Endocrine disorders Gynaecomastia 1.0
Investigations Haemoglobin increased 1.0
Nervous system disorders Headache 1.0
General disorders and administration site conditions Hot flush 1.0
Nervous system disorders Insomnia 1.0
Eye disorders Lacrimation increased 1.0
Psychiatric disorders Libido decreased 1.0
Reproductive system and breast disorders Menopausal symptoms 1.0
Psychiatric disorders Mood swings 1.0
Psychiatric disorders Nervousness 1.0
Investigations Prostatic specific antigen increased 1.0
Reproductive system and breast disorders Spontaneous penile erection 1.0
Psychiatric disorders Tension 1.0
General disorders and administration site conditions Application site reaction 0.7
Investigations Haematocrit increased 0.7
Skin and subcutaneous tissue disorders Acne 0.5
General disorders and administration site conditions Application site irritation 0.5
General disorders and administration site conditions Application site rash 0.5
General disorders and administration site conditions Application site reaction 0.5
Nervous system disorders Headache 0.5
Reproductive system and breast disorders Benign prostatic hyperplasia 0.2
Investigations Haemoglobin increased 0.2
Vascular disorders Hypertension 0.2
Investigations Red blood cell count increased 0.2

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Vascular disorders
18.84
General disorders and administration site conditions
12.33
Cardiac disorders
9.71
Psychiatric disorders
9.11
Investigations
8.08
Nervous system disorders
8.08
Injury, poisoning and procedural complications
6.89
Skin and subcutaneous tissue disorders
4.84
Respiratory, thoracic and mediastinal disorders
4.57
Social circumstances
3.6
Reproductive system and breast disorders
2.92
Musculoskeletal and connective tissue disorders
2.86

Cross References

Resources Reference
CAS NUMBER 58-22-0
ChEBI 17347
ChEMBL CHEMBL386630
DrugBank DB00624
DrugCentral 2607
EPA CompTox DTXSID8022371
FDA SRS 3XMK78S47O
Guide to Pharmacology 2858
KEGG C00535
PDB TES
PharmGKB PA451627
PubChem 6013
SureChEMBL SCHEMBL8452
ZINC ZINC000118912393
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