Identification

Summary

Testosterone undecanoate is an androgen indicated for testosterone replacement therapy in adult males with primary hypogonadism and hypogonadotropic hypogonadism.

Brand Names
Aveed, Jatenzo, Tlando
Generic Name
Testosterone undecanoate
DrugBank Accession Number
DB13946
Background

Testosterone undecanoate is the ester prodrug of testosterone and has a mid-chain fatty acid at the carbon 17β position.6 It was developed via fatty acid esterification of testosterone in order to achieve orally administer testosterone.2 There are oral and intramuscular formulations available for testosterone undecanoate: both formulations are indicated for testosterone replacement therapy in adult males with hypogonadism.6,7,8

Testosterone is a critical male hormone that is responsible for the normal growth and development of the male sex organs and for the maintenance of secondary sex characteristics. Male hypogonadism, resulting from insufficient testosterone secretion, can result symptoms and signs of testosterone deficiency, such as decreased libido, erectile dysfunction, and loss of muscle and bone mass. Testosterone replacement therapy aims to restore the levels of testosterone, thereby improving symptoms and signs of testosterone deficiency.3,6

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 456.711
Monoisotopic: 456.360345406
Chemical Formula
C30H48O3
Synonyms
  • Testosterone undecanoate
  • Testosterone undeconate
  • Testosterone undecylate
External IDs
  • BAY 86-5037
  • BRN 3176734
  • CLR-610
  • ORG 538
  • ORG-538

Pharmacology

Indication

Testosterone undecanoate is indicated for testosterone replacement therapy in adult males for conditions associated with a deficiency or absence of endogenous testosterone. These conditions include:

  • Congenital or acquired primary hypogonadism: testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome, orchiectomy, Klinefelter’s syndrome, chemotherapy, or toxic damage from alcohol or heavy metals. These men usually have low serum testosterone concentrations and gonadotropins (follicle-stimulating hormone FSH, luteinizing hormone LH) above the normal range.6,7,8
  • Congenital or acquired hypogonadotropic hypogonadism: gonadotropin or luteinizing hormone-releasing hormone (LHRH) deficiency or pituitary-hypothalamic injury from tumors, trauma, or radiation. These men have low testosterone serum concentrations but have gonadotropins in the normal or low range.6,7,8

Testosterone undecanoate is not used to treat age-related hypogonadism.6,7,8

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Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Once in circulation, testosterone undecanoate is cleaved to release testosterone, which mediates a range of biological actions. Testosterone is an endogenous male hormone that plays a key role in male sexual differentiation: it is involved in the regulation of hematopoiesis, body composition, and bone metabolism. As a hormone replacement therapy, testosterone undecanoate is an exogenous source of testosterone in males with hypogonadism. Testosterone therapy aims to improve symptoms and signs of testosterone deficiency including decreased libido, erectile dysfunction, and loss of muscle and bone mass.3

Testosterone has a controlled substance in the US due to the abuse potential by athletes and bodybuilders. The use of testosterone at higher doses than recommended can lead to withdrawal symptoms lasting for weeks or months. Withdrawal symptoms include depressed mood, major depression, fatigue, craving, restlessness, irritability, anorexia, insomnia, decreased libido, and hypogonadotropic hypogonadism.6

Testosterone can cause hirsutism, virilization, deepening of the voice, clitoral enlargement, breast atrophy, male-pattern baldness, and menstrual irregularities when administered to women. The use in adolescents can lead to the premature closure of bony epiphyses with termination of growth and precocious puberty.6

Mechanism of action

Testosterone is a critical male sex hormone that is responsible for the normal growth and development of the male sex organs and the maintenance of secondary sex characteristics, such as the growth and maturation of male sex organs, the development of male hair distribution, vocal cord thickening, and alterations in body musculature and fat distribution. Male hypogonadism, resulting from insufficient testosterone secretion, has two main etiologies: primary hypogonadism is caused by defects in the gonads, whereas secondary hypogonadism is the failure of the hypothalamus (or pituitary) to produce sufficient gonadotropins (FSH and LH).6

In the circulation, testosterone undecanoate is cleaved by endogenous non-specific esterases to release testosterone, the active component of the compound. The undecanoate side chain is pharmacologically inactive.1,6 Testosterone can be further converted by 5α reductase to its more biologically active form, dihydrotestosterone (DHT). The actions of testosterone and DHT are mediated via androgen receptor, which is widely expressed in many tissues, including the bone, muscle, prostate, and adipose tissue. Testosterone binds to androgen receptors with high affinity and regulates target gene transcription involved in the normal growth and development of the male sex organs and the maintenance of secondary sex characteristics.4 Testosterone can cause improved sexual function, increased lean body mass, bone density, erythropoiesis, prostate size, and changes in lipid profiles.3

TargetActionsOrganism
AAndrogen receptor
agonist
Humans
Absorption

Testosterone undecanoate is a lipophilic molecule that is absorbed into the intestinal lymphatic system after oral administration. It is then released into the general blood circulation by the thoracic duct, thereby bypassing the portal circulation and first-pass metabolism in the liver,2,8 unlike endogenous testosterone.3

Following oral administration of 237 mg twice per day in males with hypogonadism, the mean (SD) Cmax was 1008 (581) ng/dL.7 Tmax is about five hours following oral administration.8 Decreased testosterone exposure was observed when administered without food.7,8

Following intramuscular administration of 750 mg testosterone undecanoate, serum testosterone concentrations reached a maximum after a median of seven days (range of four to 42 days), which then slowly declined. The mean (SD) Cmax was about 90.9 (68.8) ng/dL on the fourth day following injection of testosterone undecanoate. Steady-state serum testosterone concentration was achieved with the third injection at 14 weeks. At 42 days following the injection, testosterone undecanoate was nearly undetectable.6

Volume of distribution

There is no information available.

Protein binding

About 40% of circulating testosterone is bound to sex hormone-binding globulin (SHBG) and about 2% of the drug remains unbound to plasma proteins. The rest is loosely bound to albumin and other plasma proteins.6,7

Metabolism

Testosterone undecanoate can be reduced to dihydrotestosterone undecanoate via 5α-reductase.8 In the circulation, the ester bond linking testosterone to the undecanoic acid is cleaved by endogenous non-specific esterases.2,6 Like all fatty acids, the undecanoic side chain undergoes β-oxidation to form acetyl coenzyme A (CoA) and, finally, propionyl CoA.2,7

Testosterone is metabolized to various 17-keto steroids through two different pathways to form major active metabolites, estradiol and dihydrotestosterone (DHT).6

Hover over products below to view reaction partners

Route of elimination

About 90% of a testosterone dose given intramuscularly is excreted in the urine as glucuronic and sulfuric acid-conjugates of testosterone or as metabolites. About 6% of a dose is excreted in the feces, mostly in the unconjugated form. Inactivation of testosterone occurs primarily in the liver.6

Half-life

The elimination half-life of testosterone undecanoate is approximately two hours. Once testosterone is formed from testosterone undecanoate, the half life of testosterone can vary and the reported values in the literature remain inconsistent, ranging from 10 to to 100 minutes.6,8 Testosterone undecanoate in castor oil for intramuscular injection had a half life of 33.9 days, allowing it to maintain serum levels in the normal range for over 6 weeks.[A176954]

Clearance

While there is limited information available, an earlier study reports a metabolic clearance rate of 24.5 mL/min/kg for testosterone following oral administration of 25 mg testosterone and 40 mg testosterone undecanoate in women.5

Adverse Effects
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Toxicity

The oral LD50 is 4000 mg/kg in mice and rats. The subcutaneous LD50 is 2880 mg/kg in mice and rats.9

There is limited information on testosterone undecanoate overdose. There was one report of acute overdose from an approved injectable testosterone product, which resulted in increased serum testosterone levels of up to 11,400 ng/dL with a cerebrovascular accident.6 There was one case of overdose following administration of oral testosterone undecanoate capsules: this patient inadvertently took a 20% higher dose than the maximum recommended dose but did not report any adverse reactions.7 Overdose should be managed with discontinuation of the drug in combination with appropriate symptomatic and supportive care.6

The abuse of anabolic androgenic steroids can result in serious adverse reactions, such as cardiac arrest, myocardial infarction, hypertrophic cardiomyopathy, congestive heart failure, cerebrovascular accident, hepatotoxicity, and psychiatric manifestations, including major depression, mania, paranoia, psychosis, delusions, hallucinations, hostility, and aggression. Men receiving testosterone have experienced transient ischemic attacks, convulsions, hypomania, irritability, dyslipidemias, testicular atrophy, subfertility, and infertility.6

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirAbacavir may decrease the excretion rate of Testosterone undecanoate which could result in a higher serum level.
AbciximabTestosterone undecanoate may increase the anticoagulant activities of Abciximab.
AcarboseTestosterone undecanoate may increase the hypoglycemic activities of Acarbose.
AceclofenacTestosterone undecanoate may increase the hypertensive activities of Aceclofenac.
AcemetacinTestosterone undecanoate may increase the hypertensive activities of Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Testosterone undecanoate is combined with Acenocoumarol.
AcetaminophenAcetaminophen may decrease the excretion rate of Testosterone undecanoate which could result in a higher serum level.
AcetazolamideAcetazolamide may increase the excretion rate of Testosterone undecanoate which could result in a lower serum level and potentially a reduction in efficacy.
AcetohexamideTestosterone undecanoate may increase the hypoglycemic activities of Acetohexamide.
Acetylsalicylic acidTestosterone undecanoate may increase the hypertensive activities of Acetylsalicylic acid.
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Food Interactions
  • Take with food. Food enhances the systemic exposure of testosterone undecanoate administered as oral capsules.

Products

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Active Moieties
NameKindUNIICASInChI Key
Testosteroneprodrug3XMK78S47O58-22-0MUMGGOZAMZWBJJ-DYKIIFRCSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AveedInjection250 mg/1mLIntramuscularEndo Pharmaceuticals Inc.2014-03-05Not applicableUS flag
JatenzoCapsule, liquid filled198 mg/1OralClarus Therapeutics, Inc.2019-08-01Not applicableUS flag
JatenzoCapsule, liquid filled158 mg/1OralClarus Therapeutics, Inc.2019-08-01Not applicableUS flag
JatenzoCapsule, liquid filled237 mg/1OralClarus Therapeutics, Inc.2019-08-01Not applicableUS flag
TlandoCapsule, liquid filled112.5 mg/1OralAntares Pharma, Inc.2022-04-15Not applicableUS flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Androgens and derivatives / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Androgen-skeleton / Androstane-skeleton / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
H16A5VCT9C
CAS number
5949-44-0
InChI Key
UDSFVOAUHKGBEK-CNQKSJKFSA-N
InChI
InChI=1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1
IUPAC Name
(1S,3aS,3bR,9aR,9bS,11aS)-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl undecanoate
SMILES
CCCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

References

General References
  1. Lachance S, Dhingra O, Bernstein J, Gagnon S, Savard C, Pelletier N, Boudreau N, Levesque A: Importance of measuring testosterone in enzyme-inhibited plasma for oral testosterone undecanoate androgen replacement therapy clinical trials. Future Sci OA. 2015 Nov 1;1(4):FSO55. doi: 10.4155/fso.15.55. eCollection 2015 Nov. [Article]
  2. Swerdloff RS, Wang C, White WB, Kaminetsky J, Gittelman MC, Longstreth JA, Dudley RE, Danoff TM: A New Oral Testosterone Undecanoate Formulation Restores Testosterone to Normal Concentrations in Hypogonadal Men. J Clin Endocrinol Metab. 2020 Aug 1;105(8). pii: 5834353. doi: 10.1210/clinem/dgaa238. [Article]
  3. Barbonetti A, D'Andrea S, Francavilla S: Testosterone replacement therapy. Andrology. 2020 Nov;8(6):1551-1566. doi: 10.1111/andr.12774. Epub 2020 Mar 9. [Article]
  4. Davey RA, Grossmann M: Androgen Receptor Structure, Function and Biology: From Bench to Bedside. Clin Biochem Rev. 2016 Feb;37(1):3-15. [Article]
  5. Tauber U, Schroder K, Dusterberg B, Matthes H: Absolute bioavailability of testosterone after oral administration of testosterone-undecanoate and testosterone. Eur J Drug Metab Pharmacokinet. 1986 Apr-Jun;11(2):145-9. [Article]
  6. FDA Approved Drug Products: AVEED (testosterone undecanoate) injection, for intramuscular use CIII [Link]
  7. FDA Approved Drug Products: JATENZO (testosterone undecanoate) capsules, for oral use CIII [Link]
  8. FDA Approved Drug Products: TLANDO (testosterone undecanoate) capsules, for oral use, CIII [Link]
  9. Drug Product Monograph: pms-TESTOSTERONE (testosterone undecanoate) Oral Capsules [Link]
ChemSpider
58664
ChEBI
135741
ChEMBL
CHEMBL2107067
ZINC
ZINC000008214690
Wikipedia
Testosterone_undecanoate

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceTranssexualism1
4CompletedOtherChronic Heart Failure (CHF) / Hypogonadism1
4CompletedPreventionCaloric Restriction / Exercise / Sleep1
4CompletedTreatmentErectile Dysfunction / Hypogonadism1
4CompletedTreatmentHeart Failure2
4CompletedTreatmentObesity / Testicular Hypogonadism / Type 2 Diabetes Mellitus1
4CompletedTreatmentPeyronie's Disease1
4RecruitingOtherBariatric Surgery Candidates / Loss of muscle mass / Testicular Hypogonadism1
4RecruitingPreventionFatty Liver / Overweight/Obesity / Prediabetes/Type2 Diabetes Mellitus / Testicular Hypogonadism1
4RecruitingTreatmentHypogonadism / Idiopathic Hypogonadotropic Hypogonadism / Testicular Hypogonadism1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, liquid filledOral40 mg
CapsuleOral
InjectionIntramuscular250 mg/1mL
Capsule, liquid filledOral158 mg/1
Capsule, liquid filledOral198 mg/1
Capsule, liquid filledOral237 mg/1
Injection, solutionIntramuscular1000 MG/4ML
InjectionIntramuscular
Injection, solutionParenteral
Injection, solutionIntramuscular
SolutionIntramuscular1000.0 mg/4ml
Capsule, liquid filledOral112.5 mg/1
SolutionIntramuscular1000 mg
CapsuleOral40 mg
SolutionIntramuscular250 mg/1ml
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8338395No2012-12-252026-02-27US flag
US7718640No2010-05-182027-03-14US flag
US8241664No2012-08-142029-03-29US flag
US8492369No2013-07-232030-12-20US flag
US8778916No2014-07-152030-04-12US flag
US10543219No2020-01-282030-04-12US flag
US10617696No2020-04-142030-04-12US flag
US11179403No2021-11-232030-04-12US flag
US11179402No2021-11-232026-04-14US flag
US10716794No2010-11-302030-11-30US flag
US9949985No2010-11-302030-11-30US flag
US11304960No2009-01-082029-01-08US flag
US10226473No2010-11-302030-11-30US flag
US9943527No2010-11-302030-11-30US flag
US8865695No2009-01-082029-01-08US flag
US8778922No2009-01-082029-01-08US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility<1 mg/mLhttp://www.abmole.com/literature/testosterone-undecanoate-msds.html
Predicted Properties
PropertyValueSource
Water Solubility7.4e-05 mg/mLALOGPS
logP6.74ALOGPS
logP8.06ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)18.52ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity135.02 m3·mol-1ChemAxon
Polarizability57.8 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Zinc ion binding
Specific Function
Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. [Article]
  2. Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. [Article]
  3. 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. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  5. Davey RA, Grossmann M: Androgen Receptor Structure, Function and Biology: From Bench to Bedside. Clin Biochem Rev. 2016 Feb;37(1):3-15. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. 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. [Article]
  2. Maenpaa J, Hall SD, Ring BJ, Strom SC, Wrighton SA: Human cytochrome P450 3A (CYP3A) mediated midazolam metabolism: the effect of assay conditions and regioselective stimulation by alpha-naphthoflavone, terfenadine and testosterone. Pharmacogenetics. 1998 Apr;8(2):137-55. [Article]
  3. Patki KC, Von Moltke LL, Greenblatt DJ: In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44. [Article]
  4. Flockhart Table of Drug Interactions [Link]
  5. Source [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
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. [Article]
  2. Hoff KM: Interaction of testosterone with monoamineoxidase in mouse brain maturation. Gen Pharmacol. 1977;8(1):55-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 Da
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. doi: 10.1093/toxsci/kfr063. Epub 2011 Apr 6. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Patki KC, Von Moltke LL, Greenblatt DJ: In vitro metabolism of midazolam, triazolam, nifedipine, and testosterone by human liver microsomes and recombinant cytochromes p450: role of cyp3a4 and cyp3a5. Drug Metab Dispos. 2003 Jul;31(7):938-44. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Ohmori S, Fujiki N, Nakasa H, Nakamura H, Ishii I, Itahashi K, Kitada M: Steroid hydroxylation by human fetal CYP3A7 and human NADPH-cytochrome P450 reductase coexpressed in insect cells using baculovirus. Res Commun Mol Pathol Pharmacol. 1998 Apr;100(1):15-28. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Schwarz D, Kisselev P, Schunck WH, Chernogolov A, Boidol W, Cascorbi I, Roots I: Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Watanabe J, Kawajiri K, Sutter TR, Guengerich FP, Gillam EM, Inoue K: Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13. doi: 10.1093/carcin/20.8.1607. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-s...
Gene Name
CYP2A13
Uniprot ID
Q16696
Uniprot Name
Cytochrome P450 2A13
Molecular Weight
56687.095 Da
References
  1. von Weymarn LB, Zhang QY, Ding X, Hollenberg PF: Effects of 8-methoxypsoralen on cytochrome P450 2A13. Carcinogenesis. 2005 Mar;26(3):621-9. doi: 10.1093/carcin/bgh348. Epub 2004 Dec 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  2. Hedrich WD, Hassan HE, Wang H: Insights into CYP2B6-mediated drug-drug interactions. Acta Pharm Sin B. 2016 Sep;6(5):413-425. doi: 10.1016/j.apsb.2016.07.016. Epub 2016 Aug 9. [Article]
  3. Yang TJ, Krausz KW, Shou M, Yang SK, Buters JT, Gonzalez FJ, Gelboin HV: Inhibitory monoclonal antibody to human cytochrome P450 2B6. Biochem Pharmacol. 1998 May 15;55(10):1633-40. doi: 10.1016/s0006-2952(98)00018-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
  2. Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. He N, Edeki T: The inhibitory effects of herbal components on CYP2C9 and CYP3A4 catalytic activities in human liver microsomes. Am J Ther. 2004 May-Jun;11(3):206-12. [Article]
  2. Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [Article]
  3. Zhang JG, Dehal SS, Ho T, Johnson J, Chandler C, Blanchard AP, Clark RJ Jr, Crespi CL, Stresser DM, Wong J: Human cytochrome p450 induction and inhibition potential of clevidipine and its primary metabolite h152/81. Drug Metab Dispos. 2006 May;34(5):734-7. Epub 2006 Feb 24. [Article]
  4. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Monooxygenase activity
Specific Function
Exhibits low testosterone 6-beta-hydroxylase activity.
Gene Name
CYP3A43
Uniprot ID
Q9HB55
Uniprot Name
Cytochrome P450 3A43
Molecular Weight
57669.21 Da
References
  1. Domanski TL, Finta C, Halpert JR, Zaphiropoulos PG: cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450. Mol Pharmacol. 2001 Feb;59(2):386-92. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Electron carrier activity
Specific Function
Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...

Components:
References
  1. FDA Approved Drug Products: TLANDO (testosterone undecanoate) capsules, for oral use, CIII [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Garringer JA, Niyonkuru C, McCullough EH, Loucks T, Dixon CE, Conley YP, Berga S, Wagner AK: Impact of aromatase genetic variation on hormone levels and global outcome after severe TBI. J Neurotrauma. 2013 Aug 15;30(16):1415-25. doi: 10.1089/neu.2012.2565. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
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. [Article]
  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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates sodium-independent multispecific organic anion transport. Transport of prostaglandin E2, prostaglandin F2, tetracycline, bumetanide, estrone sulfate, glutarate, dehydroepiandrosterone sulf...
Gene Name
SLC22A7
Uniprot ID
Q9Y694
Uniprot Name
Solute carrier family 22 member 7
Molecular Weight
60025.025 Da
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
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. [Article]
  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. [Article]
  3. Wessler JD, Grip LT, Mendell J, Giugliano RP: The P-glycoprotein transport system and cardiovascular drugs. J Am Coll Cardiol. 2013 Jun 25;61(25):2495-502. doi: 10.1016/j.jacc.2013.02.058. Epub 2013 Apr 3. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Virus receptor activity
Specific Function
The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
Gene Name
SLC10A1
Uniprot ID
Q14973
Uniprot Name
Sodium/bile acid cotransporter
Molecular Weight
38118.64 Da
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
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. doi: 10.1038/clpt.2009.92. Epub 2009 Jun 17. [Article]
  2. Meetam P, Srimaroeng C, Soodvilai S, Chatsudthipong V: Regulatory role of testosterone in organic cation transport: in vivo and in vitro studies. Biol Pharm Bull. 2009 Jun;32(6):982-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
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. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. He R, Ai L, Zhang D, Wan L, Zheng T, Yin J, Lu H, Lu J, Lu F, Liu F, Jia W: Different effect of testosterone and oestrogen on urinary excretion of metformin via regulating OCTs and MATEs expression in the kidney of mice. J Cell Mol Med. 2016 Dec;20(12):2309-2317. doi: 10.1111/jcmm.12922. Epub 2016 Jul 29. [Article]
  2. Asaka J, Terada T, Okuda M, Katsura T, Inui K: Androgen receptor is responsible for rat organic cation transporter 2 gene regulation but not for rOCT1 and rOCT3. Pharm Res. 2006 Apr;23(4):697-704. doi: 10.1007/s11095-006-9665-2. Epub 2006 Mar 25. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Monovalent cation:proton antiporter activity
Specific Function
Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
Gene Name
SLC47A1
Uniprot ID
Q96FL8
Uniprot Name
Multidrug and toxin extrusion protein 1
Molecular Weight
61921.585 Da
References
  1. He R, Ai L, Zhang D, Wan L, Zheng T, Yin J, Lu H, Lu J, Lu F, Liu F, Jia W: Different effect of testosterone and oestrogen on urinary excretion of metformin via regulating OCTs and MATEs expression in the kidney of mice. J Cell Mol Med. 2016 Dec;20(12):2309-2317. doi: 10.1111/jcmm.12922. Epub 2016 Jul 29. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Sharifi N, Hamada A, Sissung T, Danesi R, Venzon D, Baum C, Gulley JL, Price DK, Dahut WL, Figg WD: A polymorphism in a transporter of testosterone is a determinant of androgen independence in prostate cancer. BJU Int. 2008 Aug 5;102(5):617-21. doi: 10.1111/j.1464-410X.2008.07629.x. Epub 2008 Jun 4. [Article]

Drug created at January 11, 2018 23:11 / Updated at July 01, 2022 12:31