Testosterone cypionate

Summary

Testosterone cypionate is an androgen used to treat low or absent testosterone.

Brand Names

Depo-testosterone

Generic Name
Testosterone cypionate
DrugBank Accession Number
DB13943
Background

Testosterone cypionate is a synthetic derivative of testosterone in the form of an oil-soluble 17 (beta)-cyclopentylpropionate ester. Its benefit compared to other testosterone derivatives is the slow rate of release after injection and longer half-life. It was developed by the company Pharmacia and Upjohn and FDA approved on July 25, 1979.

Type
Small Molecule
Groups
Approved
Structure

Thumb

Image

Weight
Average: 412.614
Monoisotopic: 412.297745148
Chemical Formula
C27H40O3
Synonyms
  • testosterone 17β-cyclopentanepropionate
  • testosterone 17β-cyclopentylpropionate
  • testosterone 17β-cypionate
  • Testosterone cipionate
  • Testosterone cyclopentanepropionate
  • Testosterone cyclopentylpropionate
  • Testosterone cypionate
Indication

Testosterone cypionate is used in males that present conditions derived from a deficiency or absence of endogenous testosterone. These conditions are 1) primary hypogonadism, defined as the testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome or orchidectomy; and 2) hypogonadotropic hypogonadism characterized by idiopathic gonadotropin, LHRH deficiency or pituitary-hypothalamic injury from tumors, trauma or radiation.6

Pharmacology

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Associated Conditions
  • Hypergonadotropic Hypogonadism
  • Hypogonadotrophic Hypogonadism
Contraindications & Blackbox Warnings

Contraindications

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Pharmacodynamics

Administration of ester derivatives of testosterone as testosterone cypionate generates an increase in serum testosterone to levels reaching 400% from the baseline within 24 hours of administration. These androgen levels remain elevated for 3-5 days after initial administration.3 The continuous variation in plasma testosterone after intramuscular administration of testosterone cypionate results in fluctuations in mood and libido as well as some local inflammation.4

Mechanism of action

The 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 5-alpha-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5-alpha-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.2

Target Actions Organism
AAndrogen receptor

agonist

 Humans
UEstrogen receptor alpha Not Available Humans
UMineralocorticoid receptor Not Available Humans
Absorption

Testosterone cypionate is an esterified anabolic which allows it to present a greater degree of solubility in fats and thus, the release and absorption occur in a slow rate compare to homologous molecules.5 Intramuscular administration of 200 mg of testosterone cypionate produced a mean supratherapeutic Cmax of 1122 ng/dl which occurred 4-5 days post-injection. After the fifth day, the levels of testosterone cypionate in plasma went down reaching an average of 400 ng/dl.4

Volume of distribution

The volume of distribution following intravenous administration of testosterone is of approximately 1 L/kg.7

Protein binding

Testosterone cypionate, following conversion into testosterone, is approximately 98% protein-bound to sex hormone-binding globulin in plasma.5

Metabolism

To start its activity, testosterone cypionate has to be processed by enzymes in the bloodstream. These enzymes will break the bond between the cypionate ester moiety and the testosterone. Once separated, testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT). Testosterone is metabolized to DHT by steroid 5α-reductase in skin, liver and urogenital tract. In reproductive tissues DHT is further metabolized to androstanediol.6

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Route of elimination

About 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.6

Half-life

The half-life of testosterone cypionate is one of the longest, being approximately of 8 days.5

Clearance

Testosterone cypionate presents a lower clearance rate after intramuscular administration compared to other analogs of testosterone.

Adverse Effects

Adverseeffects

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Toxicity

Preclinical studies with testosterone implants induced cervical-uterine tumors in mice which metastasized in some cases. Some reports indicate that administration of testosterone cypionate in females can augment the susceptibility to hepatoma as well as increase the number of tumors. Clinical studies have reported cases of hepatocellular carcinoma in long-term high-dose therapy.6

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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.

  • Approved
  • Vet approved
  • Nutraceutical
  • Illicit
  • Withdrawn
  • Investigational
  • Experimental
  • All Drugs
Drug Interaction

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interactions in your software
Abacavir Abacavir may decrease the excretion rate of Testosterone cypionate which could result in a higher serum level.
Abametapir The serum concentration of Testosterone cypionate can be increased when it is combined with Abametapir.
Abatacept The metabolism of Testosterone cypionate can be increased when combined with Abatacept.
Abciximab Testosterone cypionate may increase the anticoagulant activities of Abciximab.
Abemaciclib Abemaciclib may decrease the excretion rate of Testosterone cypionate which could result in a higher serum level.
Abiraterone The metabolism of Testosterone cypionate can be decreased when combined with Abiraterone.
Acalabrutinib The metabolism of Testosterone cypionate can be decreased when combined with Acalabrutinib.
Acamprosate The excretion of Acamprosate can be increased when combined with Testosterone cypionate.
Acarbose Testosterone cypionate may increase the hypoglycemic activities of Acarbose.
Aceclofenac Aceclofenac may decrease the excretion rate of Testosterone cypionate which could result in a higher serum level.
Food Interactions
No interactions found.

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Active Moieties
Name Kind UNII CAS InChI Key
Testosterone prodrug 3XMK78S47O 58-22-0 MUMGGOZAMZWBJJ-DYKIIFRCSA-N
Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Testosterone Cypionate Solution 200 mg/1mL Intramuscular Qualgen Llc 2021-01-02 Not applicable US flag
Testosterone Cypionate Injection 200 mg/1mL Intramuscular; Subcutaneous ASP Cares 2019-04-24 Not applicable US flag
Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image
Depo-Testosterone Injection, solution 200 mg/1mL Intramuscular Pharmacia and Upjohn Company LLC 1979-07-25 Not applicable US flag
Depo-Testosterone Injection, solution 200 mg/1mL Intramuscular Pharmacia and Upjohn Company LLC 2014-03-31 2020-02-29 US flag
Depo-Testosterone Injection, solution 100 mg/1mL Intramuscular Pharmacia and Upjohn Company LLC 2014-07-01 Not applicable US flag
Depo-Testosterone Injection, solution 100 mg/1mL Intramuscular A S Medication Solutions 1979-07-25 Not applicable US flag
Depo-Testosterone Injection, solution 100 mg/1mL Intramuscular Pharmacia and Upjohn Company LLC 1979-07-25 Not applicable US flag
Depo-Testosterone Injection, solution 200 mg/1mL Intramuscular A S Medication Solutions 1979-07-25 Not applicable US flag
Depo-Testosterone Injection, solution 100 mg/1mL Intramuscular A-S Medication Solutions 1979-07-25 2019-03-31 US flag
Depo-Testosterone Injection, solution 200 mg/1mL Intramuscular Pharmacia and Upjohn Company LLC 2014-07-01 Not applicable US flag
Depo-Testosterone Injection, solution 200 mg/1mL Intramuscular Physicians Total Care, Inc. 1994-07-12 Not applicable US flag
Testosterone Cypionate Injection 200 mg/1mL Intramuscular Proficient Rx LP 2012-05-01 Not applicable US flag
Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image
Testone CIK Testosterone cypionate (200 mg/1mL) + Isopropyl alcohol (0.7 mL/1mL) Intramuscular; Topical Asclemed Usa, Inc. 2007-12-21 Not applicable US flag
Testosterone Cypionate Testosterone cypionate (200 mg/1mL) Injection Intramuscular; Subcutaneous ASP Cares 2019-04-24 Not applicable US flag
Testosterone Cypionate Testosterone cypionate (200 mg/1mL) Solution Intramuscular Qualgen Llc 2021-01-02 Not applicable US flag
Drug Categories
  • Anabolic Agents
  • Androgens
  • Androstanes
  • Androstenes
  • Androstenols
  • BCRP/ABCG2 Substrates
  • Cytochrome P-450 CYP2B6 Substrates
  • Cytochrome P-450 CYP2C19 Substrates
  • Cytochrome P-450 CYP2C8 Substrates
  • Cytochrome P-450 CYP2C9 Substrates
  • Cytochrome P-450 CYP3A Inducers
  • Cytochrome P-450 CYP3A Inhibitors
  • Cytochrome P-450 CYP3A Substrates
  • Cytochrome P-450 CYP3A4 Inducers
  • Cytochrome P-450 CYP3A4 Inducers (strength unknown)
  • Cytochrome P-450 CYP3A4 Inhibitors
  • Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
  • Cytochrome P-450 CYP3A4 Substrates
  • Cytochrome P-450 CYP3A5 Substrates
  • Cytochrome P-450 CYP3A7 Substrates
  • Cytochrome P-450 Enzyme Inducers
  • Cytochrome P-450 Enzyme Inhibitors
  • Cytochrome P-450 Substrates
  • Delayed-Action Preparations
  • Drugs that are Mainly Renally Excreted
  • Fused-Ring Compounds
  • Gonadal Hormones
  • Gonadal Steroid Hormones
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • OAT3/SLC22A8 Inducers
  • P-glycoprotein inhibitors
  • Steroids
  • Testosterone and derivatives
  • Testosterone Congeners
  • Thyroxine-binding globulin inhibitors
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
sterol ester (CHEBI:9463) / C19 steroids (androgens) and derivatives (C08156) / C19 steroids (androgens) and derivatives (LMST02020074)
Affected organisms
  • Humans and other mammals
UNII
M0XW1UBI14
CAS number
58-20-8
InChI Key
HPFVBGJFAYZEBE-ZLQWOROUSA-N
InChI

InChI=1S/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/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 3-cyclopentylpropanoate

SMILES

[H][C@@]12CC[C@H](OC(=O)CCC3CCCC3)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

General References
  1. Freeman ER, Bloom DA, McGuire EJ: A brief history of testosterone. J Urol. 2001 Feb;165(2):371-3. [Article]
  2. Hoberman JM, Yesalis CE: The history of synthetic testosterone. Sci Am. 1995 Feb;272(2):76-81. [Article]
  3. Weinbauer GF, Jackwerth B, Yoon YD, Behre HM, Yeung CH, Nieschlag E: Pharmacokinetics and pharmacodynamics of testosterone enanthate and dihydrotestosterone enanthate in non-human primates. Acta Endocrinol (Copenh). 1990 Apr;122(4):432-42. [Article]
  4. Shoskes JJ, Wilson MK, Spinner ML: Pharmacology of testosterone replacement therapy preparations. Transl Androl Urol. 2016 Dec;5(6):834-843. doi: 10.21037/tau.2016.07.10. [Article]
  5. Dailymed [Link]
  6. Pfizer monograph [Link]
  7. Pfizer monograph [Link]
KEGG Drug
D00957
KEGG Compound
C08156
ChemSpider
390140
ChEBI
9463
ChEMBL
CHEMBL1201101
ZINC
ZINC000004097468
Wikipedia
Testosterone_cypionate
FDA label
MSDS
Clinical Trials
Phase Status Purpose Conditions Count
4 Active Not Recruiting Treatment Klinefelter's Syndrome 1
4 Recruiting Treatment Testicular Hypogonadism 1
3 Completed Treatment Cancer, Advanced 1
2 Active Not Recruiting Treatment Adenocarcinoma, Prostate / Castration-Resistant Prostate Carcinoma 1
2 Active Not Recruiting Treatment Prostate Cancer 1
2 Completed Treatment Metastatic Castration Resistant Prostate Cancer (CRPC) 1
2 Recruiting Supportive Care Prostate Cancer 1
2 Recruiting Treatment Metastatic Castration Resistant Prostate Cancer (CRPC) 1
2 Recruiting Treatment Prostate Cancer 1
2 Withdrawn Treatment Bone Metabolism 1
Manufacturers

Not Available

Packagers

Not Available

Dosage Forms
Form Route Strength
Solution Intramuscular 100 mg/1ml
Injection, solution Intramuscular 250 mg/1ml
Injection, solution Intramuscular 200 mg/1mL
Solution Intramuscular 100 mg / mL
Injection Intramuscular 100 mg/ml
Injection Intramuscular 200 mg/ml
Liquid Intramuscular 100 mg / mL
Injection Intramuscular 100 mg/1mL
Injection Intramuscular 200 mg/10mL
Injection Intramuscular 200 mg/1mL
Injection Intramuscular; Subcutaneous 200 mg/1mL
Injection, solution Intramuscular 100 mg/1mL
Powder Not applicable 1 g/1g
Solution Intramuscular 200 mg/1mL
Prices
Not Available
Patents
Not Available
State
Solid
Experimental Properties
Property Value Source
melting point (°C) 98-104ºC 'MSDS'
water solubility Insoluble 'FDA label'
Predicted Properties
Property Value Source
Water Solubility 0.000437 mg/mL ALOGPS
logP 5.1 ALOGPS
logP 6.11 ChemAxon
logS -6 ALOGPS
pKa (Strongest Acidic) 18.52 ChemAxon
pKa (Strongest Basic) -4.8 ChemAxon
Physiological Charge 0 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 43.37 Å2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 119.36 m3·mol-1 ChemAxon
Polarizability 49.84 Å3 ChemAxon
Number of Rings 5 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five No ChemAxon
Ghose Filter No ChemAxon
Veber's Rule No ChemAxon
MDDR-like Rule No ChemAxon
Predicted ADMET Features
Not Available
Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets2

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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. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Kojima H, Iida M, Katsura E, Kanetoshi A, Hori Y, Kobayashi K: Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities. Environ Health Perspect. 2003 Apr;111(4):497-502. [Article]
Kind
Protein
Organism
Humans
Pharmacological action

Unknown

General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. Takeda AN, Pinon GM, Bens M, Fagart J, Rafestin-Oblin ME, Vandewalle A: The synthetic androgen methyltrienolone (r1881) acts as a potent antagonist of the mineralocorticoid receptor. Mol Pharmacol. 2007 Feb;71(2):473-82. Epub 2006 Nov 14. [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
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. Pfizer monograph [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

Other/unknown

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

Other/unknown

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]
  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. [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]
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
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 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]
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]
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]

Drug created at January 11, 2018 23:07 / Updated at December 10, 2021 21:39