You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameTestosterone
Accession NumberDB00624  (APRD00433)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Testosterone is a steroid sex hormone found in both men and women. In men, testosterone is produced primarily by the Leydig (interstitial) cells of the testes when stimulated by luteinizing hormone (LH). It functions to stimulate spermatogenesis, promote physical and functional maturation of spermatozoa, maintain accessory organs of the male reproductive tract, support development of secondary sexual characteristics, stimulate growth and metabolism throughout the body and influence brain development by stimulating sexual behaviors and sexual drive. In women, testosterone is produced by the ovaries (25%), adrenals (25%) and via peripheral conversion from androstenedione (50%). Testerone in women functions to maintain libido and general wellbeing. Testosterone exerts a negative feedback mechanism on pituitary release of LH and follicle-stimulating hormone (FSH). Testosterone may be further converted to dihydrotestosterone or estradiol depending on the tissue.

Structure
Thumb
Synonyms
SynonymLanguageCode
17beta-hydroxy-4-androsten-3-oneNot AvailableNot Available
17beta-Hydroxy-4-androsten-3-oneNot AvailableNot Available
4-Androsten-17beta-ol-3-oneNot AvailableNot Available
4-androsten-17β-ol-3-oneNot AvailableNot Available
AndrodermNot AvailableNot Available
Depo-TestadiolNot AvailableIS
MertestateNot AvailableIS
Synandrol FNot AvailableIS
TestosteronGermanINN
TestosteronaSpanishINN
TestostéroneFrenchINN
TestosteronumLatinINN
TestoxylNot AvailableIS
TestrylNot AvailableIS
VirosteroneNot AvailableIS
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Axironsolution30 mg/1.5mLtopicalEli Lilly and Company2010-12-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalAbb Vie Inc.2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalAbb Vie Inc.2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel16.2 mg/gtransdermalAbb Vie Inc.2011-04-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalAbb Vie Inc.2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Vogelxogel50 mg/5gtopicalUpsher Smith Laboratories, Inc.2014-06-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Vogelxogel, metered12.5 mg/1.25gtopicalUpsher Smith Laboratories, Inc.2014-06-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosteronegel, metered10 mg/.5gtopicalQualitest Pharmaceuticals2014-08-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosteronegel50 mg/5gtopicalUpsher Smith Laboratories, Inc.2014-06-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosteronegel, metered50 mg/5gtopicalUpsher Smith Laboratories, Inc.2014-06-16Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testimgel50 mg/5gtopicalStat Rx USA2002-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalRebel Distributors Corp.2003-06-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testimgel50 mg/5gtransdermalLake Erie Medical DBA Quality Care Products LLC2002-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Natesto nasal gelgel, metered5.5 mg/.122gnasalTrimel Pharmaceuticals Corporation2015-01-30Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosteronegel12.5 mg/1.25gtopicalPerrigo New York Inc2014-12-27Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testimgel50 mg/5gtransdermalA S Medication Solutions Llc2002-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel16.2 mg/gtransdermalA S Medication Solutions Llc2011-04-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Strianttablet30 mgbuccalActient Pharmaceuticals LLC2003-06-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androdermpatch2 mg/dtransdermalActavis Pharma, Inc.1995-09-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androdermpatch4 mg/dtransdermalActavis Pharma, Inc.1995-09-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalA S Medication Solutions Llc2011-03-14Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testimgel50 mg/5gtransdermalA S Medication Solutions Llc2002-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel16.2 mg/gtransdermalA S Medication Solutions Llc2011-04-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalPhysicians Total Care, Inc.2003-05-15Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalPhysicians Total Care, Inc.2003-06-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testimgel50 mg/5gtransdermalPhysicians Total Care, Inc.2004-01-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Androgelgel10 mg/gtransdermalPhysicians Total Care, Inc.2007-08-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Axironsolution30 mg/1.5mLtopicalPhysicians Total Care, Inc.2013-09-06Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Strianttablet30 mgbuccalColumbia Laboratories, Inc.2003-06-19Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Fortestagel, metered10 mg/.5gtopicalEndo Pharmaceuticals Inc.2010-12-29Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testimgel50 mg/5gtransdermalAuxilium Pharmaceuticals, Inc.2002-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosterone Gelgel50 mg/5gtransdermalPrasco Laboratories2014-06-09Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Delatestrylinjection, solution200 mg/mLintramuscularEndo Pharmaceuticals Solutions Inc.1953-12-24Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Aveedinjection250 mg/mLintramuscularEndo Pharmaceuticals Solutions Inc.2014-03-05Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Depo-testosteroneinjection, solution100 mg/mLintramuscularPharmacia and Upjohn Company2014-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution200 mg/mLintramuscularPharmacia and Upjohn Company2014-07-01Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution100 mg/mLintramuscularPharmacia and Upjohn Company1979-07-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution200 mg/mLintramuscularPharmacia and Upjohn Company1979-07-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution200 mg/mLintramuscularPharmacia and Upjohn Company2014-03-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosterone Enanthateinjection, solution200 mg/mLintramuscularWest ward Pharmaceutical Corp2012-09-18Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosterone Enanthateinjection200 mg/mLintramuscularPaddock Laboratories, Inc.2007-08-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testosterone Enanthateinjection, solution200 mg/mLintramuscularWatson Laboratories, Inc.2011-05-04Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testopelpellet75 mgsubcutaneousSlate Pharma2009-07-21Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution100 mg/mLintramuscularA S Medication Solutions Llc1979-07-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution200 mg/mLintramuscularA S Medication Solutions Llc1979-07-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution100 mg/mLintramuscularA S Medication Solutions Llc1979-07-25Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Depo-testosteroneinjection, solution200 mg/mLintramuscularPhysicians Total Care, Inc.1994-07-12Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Testopelpellet75 mgsubcutaneousAuxilium Pharmaceuticals, Inc.2014-10-31Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Over the Counter ProductsNot Available
International Brands
NameCompany
AndriolMerck
Andronate 100Not Available
Andronate 200Not Available
AndropatchGlaxoSmithKline
Andropository 200Not Available
Andryl 200Not Available
Bio-T-GelBioSante Pharmaceuticals, Inc. and Teva Pharmaceuticals USA, Inc.
IntrinsaProcter & Gamble
LivensaProcter & Gamble
NebidoBayer
SustanonOrganon
Testamone 100Not Available
Testaqua IMNot Available
TestodermNot Available
Testoderm TTSNot Available
TestogelBayer
TestolinNot Available
TestopatchPierre Fabre
Testopel PelletsNot Available
Testrin-P.ANot Available
Testro AQNot Available
VirormoneNordic Pharma
Brand mixtures
Brand NameIngredients
ClimacteronEstradiol Benzoate + Estradiol Dienanthate + Testosterone Enanthate Benzilic Acid Hydrazone
Neo Pause InjectionEstradiol Valerate + Testosterone Enanthate
Salts
Name/CASStructureProperties
Testosterone Enanthate
ThumbNot applicableDBSALT001030
Testosterone Heptanoate
ThumbNot applicableDBSALT001031
Testosterone Propionate
ThumbNot applicableDBSALT001032
Testosterone Undecanoate
ThumbNot applicableDBSALT001033
Categories
CAS number58-22-0
WeightAverage: 288.4244
Monoisotopic: 288.20893014
Chemical FormulaC19H28O2
InChI KeyMUMGGOZAMZWBJJ-DYKIIFRCSA-N
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
IUPAC Name
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationTo be used as hormone replacement or substitution of diminished or absent endogenous testosterone. Use in males: For management of congenital or acquired hypogonadism, hypogonadism associated with HIV infection, and male climacteric (andopause). Use in females: For palliative treatment of androgen-responsive, advanced, inoperable, metastatis (skeletal) carcinoma of the breast in women who are 1-5 years postmenopausal; testosterone esters may be used in combination with estrogens in the management of moderate to severe vasomotor symptoms associated with menopause in women who do not respond to adequately to estrogen therapy alone.
PharmacodynamicsTestosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.
Mechanism of actionThe effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
AbsorptionApproximately 10% of the testosterone dose applied on the skin surface is absorbed into systemic circulation
Volume of distributionNot Available
Protein binding40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
Metabolism

Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).

SubstrateEnzymesProduct
Testosterone
6-beta-hydroxytestosteroneDetails
Testosterone
EstradiolDetails
Testosterone
Not Available
Testosterone sulfateDetails
Testosterone
DihydrotestosteroneDetails
Testosterone
Not Available
Testosterone glucuronideDetails
Testosterone
Not Available
5-alpha-Dihydrotestosterone glucuronideDetails
Testosterone
Not Available
5a-Dihydrotestosterone sulfateDetails
Testosterone
Not Available
17-Hydroxyandrostane-3-glucuronideDetails
Route of eliminationAbout 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form.
Half life10-100 minutes
ClearanceNot Available
ToxicitySide effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Androgen and Estrogen MetabolismMetabolicSMP00068
Aromatase deficiencyDiseaseSMP00565
17-Beta Hydroxysteroid Dehydrogenase III DeficiencyDiseaseSMP00356
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.973
Caco-2 permeable+0.8984
P-glycoprotein substrateSubstrate0.6498
P-glycoprotein inhibitor IInhibitor0.5489
P-glycoprotein inhibitor IINon-inhibitor0.8923
Renal organic cation transporterNon-inhibitor0.7324
CYP450 2C9 substrateNon-substrate0.8167
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7739
CYP450 1A2 substrateNon-inhibitor0.9005
CYP450 2C9 substrateNon-inhibitor0.95
CYP450 2D6 substrateNon-inhibitor0.9452
CYP450 2C19 substrateNon-inhibitor0.6668
CYP450 3A4 substrateNon-inhibitor0.8812
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8683
Ames testNon AMES toxic0.9382
CarcinogenicityNon-carcinogens0.9483
BiodegradationNot ready biodegradable0.9174
Rat acute toxicity1.6259 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8938
hERG inhibition (predictor II)Non-inhibitor0.7163
Pharmacoeconomics
Manufacturers
  • Heather drug co inc
  • Valeant pharmaceuticals international
  • Schering corp sub schering plough corp
  • Novartis pharmaceuticals corp
  • Impax laboratories inc
  • Eli lilly and co
  • Purepac pharmaceutical co
  • Private formulations inc
  • Tablicaps inc
  • Usl pharma inc
  • Inwood laboratories inc sub forest laboratories inc
  • Kv pharmaceutical co
  • Lannett co inc
  • Parke davis div warner lambert co
  • Watson laboratories inc
  • West ward pharmaceutical corp
  • Alza corp
  • Unimed pharmaceuticals inc
  • Auxilium pharmaceuticals
  • Par pharmaceutical
  • Watson laboratories
  • Slate pharmaceuticals inc
  • Columbia laboratories inc
  • Pharmacia and upjohn co
  • Bedford laboratories div ben venue laboratories inc
  • Paddock laboratories inc
  • Sandoz canada inc
  • Synerx pharma llc
  • Endo pharmaceutical solutions inc
  • Solvay Pharmaceuticals, Inc.
Packagers
Dosage forms
FormRouteStrength
Geltopical12.5 mg/1.25g
Geltopical50 mg/5g
Geltransdermal10 mg/g
Geltransdermal16.2 mg/g
Geltransdermal50 mg/5g
Gel, meterednasal5.5 mg/.122g
Gel, meteredtopical10 mg/.5g
Gel, meteredtopical12.5 mg/1.25g
Gel, meteredtopical50 mg/5g
Injectionintramuscular200 mg/mL
Injectionintramuscular250 mg/mL
Injection, solutionintramuscular100 mg/mL
Injection, solutionintramuscular200 mg/mL
Patchtransdermal2 mg/d
Patchtransdermal4 mg/d
Pelletsubcutaneous75 mg
Solutiontopical30 mg/1.5mL
Tabletbuccal30 mg
Prices
Unit descriptionCostUnit
AndroGel Pump 1% Gel (1 Box Contains Two 75 gm Bottles)290.63USD box
Androderm 60 2.5 mg/24hr Patches 1 Box = 60 Patches278.56USD box
Androderm 30 5 mg/24hr Patches 1 Box = 30 Patches277.53USD box
AndroGel (each Box Contains Thirty - 50 mg/5 gm Packets) 150 gm Box274.58USD box
AndroGel (each Box Contains Thirty - 25 mg/2.5 gm Packets) 75 gm Box270.61USD box
Delatestryl 200 mg/ml Oil 5ml Vial93.98USD vial
Testosterone Cypionate 200 mg/ml Oil 10ml Vial88.99USD vial
Testosterone Cypionate 100 mg/ml Oil 10ml Vial57.99USD vial
Depo-Testosterone 200 mg/ml Oil 1ml Vial34.99USD vial
Testosterone cypionate powd32.74USD g
Testosterone Cypionate 200 mg/ml Oil 1ml Vial28.99USD vial
Depo-testosterone 200 mg/ml28.63USD ml
Testopel 75 mg pellets27.5USD pellet
Testosterone cyp 200 mg/ml23.18USD ml
Delatestryl 200 mg/ml vial19.86USD ml
Testred 10 mg capsule17.6USD capsule
Testosterone enan 200 mg/ml16.99USD ml
Testosterone Enanthate 200 mg/ml Oil16.66USD ml
Depo-Testosterone 200 mg/ml Oil13.23USD ml
Android 10 mg capsule11.91USD capsule
Delatestryl 200 mg/ml10.75USD ml
Testim 1% Gel 5 gm Tube10.08USD tube
Androderm 5 mg/24hr patch10.06USD patch
Methyltestosterone powder8.54USD g
Depo-Testosterone 100 mg/ml Oil7.87USD ml
Depo-testosterone 100 mg/ml vial7.67USD ml
Testosterone powder6.25USD g
Testosterone propionate powder6.25USD g
Testosterone cyp 100 mg/ml5.91USD ml
Androderm 2.5 mg/24hr patch5.03USD patch
Methitest 10 mg tablet4.84USD tablet
Striant 30 mg Miscellaneous4.32USD ea
Striant 30 mg mucoadhesive4.31USD each
Depo-Testosterone Cypionate 100 mg/ml2.98USD ml
Testim 1%(50 mg) gel2.47USD g
Testosterone Cypionate 100 mg/ml2.23USD ml
Androgel 1% gel pump1.92USD g
First-testosterone mc 2% cr0.91USD g
First 2% testosterone oint0.88USD g
First-Testosterone 2% Ointment0.86USD gm
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada13325701994-10-182011-10-18
Canada23668562006-05-162020-03-27
United States51529971993-12-112010-12-11
United States73209682005-01-182025-01-18
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point155 °CPhysProp
water solubility23.4 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP3.32HANSCH,C ET AL. (1995)
Caco2 permeability-4.34ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.0333 mg/mLALOGPS
logP2.99ALOGPS
logP3.37ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity84.43 m3·mol-1ChemAxon
Polarizability34.02 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (13.5 KB)
SpectraGC-MSMS/MSMS1D NMR2D NMR
References
Synthesis Reference

Merle G. Wovcha, Frederick J. Antosz, John M. Beaton, Alfred B. Garcia, Leo A. Kominek, “Process for preparing 9.alpha.-OH testosterone.” U.S. Patent US4221868, issued November, 1977.

US4221868
General Reference
  1. Freeman ER, Bloom DA, McGuire EJ: A brief history of testosterone. J Urol. 2001 Feb;165(2):371-3. Pubmed
  2. Hoberman JM, Yesalis CE: The history of synthetic testosterone. Sci Am. 1995 Feb;272(2):76-81. Pubmed
  3. Contraceptive efficacy of testosterone-induced azoospermia in normal men. World Health Organization Task Force on methods for the regulation of male fertility. Lancet. 1990 Oct 20;336(8721):955-9. Pubmed
  4. Dean JD, Carnegie C, Rodzvilla J, Smith T: Long-term effects of testim® 1% testosterone gel in hypogonadal men. Rev Urol. 2004;6 Suppl 6:S22-9. Pubmed
External Links
ATC CodesG03BA03
AHFS Codes
  • 68:08.00
PDB EntriesNot Available
FDA labelDownload (738 KB)
MSDSDownload (49.6 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolThe androgen, Testosterone, may incrase the anticoagulant effect of the Vitamin K antagonist, Acenocoumarol. Monitor for changes in the therapeutic effect of Acenocoumarol if Testosterone is initiated, discontinued or dose changed.
AnisindioneThe androgen may increase the anticoagulant effect of anisindione.
CyclosporineThe androgen, Testosterone, may increase the hepatotoxicity of Cyclosporine. Testosterone may also elevate serum concentrations of Cyclosporine. Consider alternate therapy or monitor for signs of renal and hepatic toxicity.
DicoumarolThe androgen may increase the anticoagulant effect of dicumarol.
DocetaxelTestosterone may increase the serum levels and toxicity of docetaxel.
WarfarinTestosterone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if testosterone is initiated, discontinued or dose changed.
Food InteractionsNot Available

Targets

1. Androgen receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Androgen receptor P10275 Details

References:

  1. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. Pubmed
  2. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. Pubmed
  3. Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. Pubmed
  4. Maudsley S, Davidson L, Pawson AJ, Freestone SH, Lopez de Maturana R, Thomson AA, Millar RP: Gonadotropin-releasing hormone functionally antagonizes testosterone activation of the human androgen receptor in prostate cells through focal adhesion complexes involving Hic-5. Neuroendocrinology. 2006;84(5):285-300. Epub 2007 Jan 4. Pubmed
  5. Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor inducer

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. © Tianyi Zhang, Yongxin Zhu, and Chandrani Gunaratna. Simultaneous Determination of Metabolites from Multiple Cytochrome P450 Probe Substrates by Gradient Liquid Chromatography with UV Detection. Source
  3. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  4. Zhang T, Zhu Y, Gunaratna C: Rapid and quantitative determination of metabolites from multiple cytochrome P450 probe substrates by gradient liquid chromatography-electrospray ionization-ion trap mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 25;780(2):371-9. Pubmed

2. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

References:

  1. Sjoberg RL, Ducci F, Barr CS, Newman TK, Dell’osso L, Virkkunen M, Goldman D: A non-additive interaction of a functional MAO-A VNTR and testosterone predicts antisocial behavior. Neuropsychopharmacology. 2008 Jan;33(2):425-30. Epub 2007 Apr 11. Pubmed
  2. Hoff KM: Interaction of testosterone with monoamineoxidase in mouse brain maturation. Gen Pharmacol. 1977;8(1):55-7. Pubmed

4. Cholesterol side-chain cleavage enzyme, mitochondrial

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cholesterol side-chain cleavage enzyme, mitochondrial P05108 Details

References:

  1. Kostic TS, Stojkov NJ, Bjelic MM, Mihajlovic AI, Janjic MM, Andric SA: Pharmacological doses of testosterone upregulated androgen receptor and 3-Beta-hydroxysteroid dehydrogenase/delta-5-delta-4 isomerase and impaired leydig cells steroidogenesis in adult rats. Toxicol Sci. 2011 Jun;121(2):397-407. Epub 2011 Apr 6. Pubmed

5. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 3A7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A7 P24462 Details

References:

  1. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 1B1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 1B1 Q16678 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

9. Cytochrome P450 2A13

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2A13 Q16696 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

10. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inducer

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

11. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

12. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

13. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

14. Cytochrome P450 3A43

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A43 Q9HB55 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. Pubmed

2. Sex hormone-binding globulin

Kind: protein

Organism: Human

Pharmacological action: no

Actions: other/unknown

Components

Name UniProt ID Details
Sex hormone-binding globulin P04278 Details

References:

  1. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. Pubmed

Transporters

1. Solute carrier organic anion transporter family member 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor inducer

Components

Name UniProt ID Details
Solute carrier organic anion transporter family member 1A2 P46721 Details

References:

  1. Lu R, Kanai N, Bao Y, Wolkoff AW, Schuster VL: Regulation of renal oatp mRNA expression by testosterone. Am J Physiol. 1996 Feb;270(2 Pt 2):F332-7. Pubmed
  2. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. Pubmed
  3. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. Pubmed

2. Solute carrier family 22 member 8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Solute carrier family 22 member 8 Q8TCC7 Details

References:

  1. Kobayashi Y, Hirokawa N, Ohshiro N, Sekine T, Sasaki T, Tokuyama S, Endou H, Yamamoto T: Differential gene expression of organic anion transporters in male and female rats. Biochem Biophys Res Commun. 2002 Jan 11;290(1):482-7. Pubmed

3. Solute carrier family 22 member 7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inducer

Components

Name UniProt ID Details
Solute carrier family 22 member 7 Q9Y694 Details

References:

  1. Kobayashi Y, Hirokawa N, Ohshiro N, Sekine T, Sasaki T, Tokuyama S, Endou H, Yamamoto T: Differential gene expression of organic anion transporters in male and female rats. Biochem Biophys Res Commun. 2002 Jan 11;290(1):482-7. Pubmed

4. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

References:

  1. Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. Pubmed

5. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Katoh M, Nakajima M, Yamazaki H, Yokoi T: Inhibitory effects of CYP3A4 substrates and their metabolites on P-glycoprotein-mediated transport. Eur J Pharm Sci. 2001 Feb;12(4):505-13. Pubmed
  2. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. Pubmed

6. Sodium/bile acid cotransporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium/bile acid cotransporter Q14973 Details

References:

  1. Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. Pubmed

7. Solute carrier family 22 member 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 3 O75751 Details

References:

  1. Tzvetkov MV, Vormfelde SV, Balen D, Meineke I, Schmidt T, Sehrt D, Sabolic I, Koepsell H, Brockmoller J: The effects of genetic polymorphisms in the organic cation transporters OCT1, OCT2, and OCT3 on the renal clearance of metformin. Clin Pharmacol Ther. 2009 Sep;86(3):299-306. Epub 2009 Jun 17. Pubmed

8. Solute carrier family 22 member 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

References:

  1. Tzvetkov MV, Vormfelde SV, Balen D, Meineke I, Schmidt T, Sehrt D, Sabolic I, Koepsell H, Brockmoller J: The effects of genetic polymorphisms in the organic cation transporters OCT1, OCT2, and OCT3 on the renal clearance of metformin. Clin Pharmacol Ther. 2009 Sep;86(3):299-306. Epub 2009 Jun 17. Pubmed

9. ATP-binding cassette sub-family G member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
ATP-binding cassette sub-family G member 2 Q9UNQ0 Details

References:

  1. Janvilisri T, Venter H, Shahi S, Reuter G, Balakrishnan L, van Veen HW: Sterol transport by the human breast cancer resistance protein (ABCG2) expressed in Lactococcus lactis. J Biol Chem. 2003 Jun 6;278(23):20645-51. Epub 2003 Mar 28. Pubmed

Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on February 11, 2014 11:24