Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H30O2 |
Molecular Weight | 302.451 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=GCKMFJBGXUYNAG-HLXURNFRSA-N
InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
DescriptionSources: http://www.drugbank.ca/drugs/DB06710Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/methyltestosterone.html
Sources: http://www.drugbank.ca/drugs/DB06710
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/pro/methyltestosterone.html
Methyltestosterone is an anabolic steroid hormone used to treat men with a testosterone deficiency. It is also used in women to treat breast cancer, breast pain, swelling due to pregnancy, and with the addition of estrogen it can treat symptoms of menopause. 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 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. Methyltestosterone is marketed under the brand names Android, Androral, Metandren, Oraviron, Testred, Virilon.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2363075 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17218080 |
1.9 µM [IC50] | ||
Target ID: CHEMBL1871 Sources: http://www.drugbank.ca/drugs/DB06710 |
0.125 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TESTRED Approved Use1. Males
Androgens are indicated for replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone:
1. Primary hypogonadism (congenital or acquired) — testicular failure due to cryptorchidism, bilateral torsions, orchitis, vanishing testis syndrome; or orchidectomy.
2. Hypogonadotropic hypogonadism (congenital or acquired) — idiopathic gonadotropin or LHRH deficiency, or pituitary hypothalamic injury from tumors, trauma, or radiation. If the above conditions occur prior to puberty, androgen replacement therapy will be needed during the adolescent years for development of secondary sexual characteristics. Prolonged androgen
treatment will be required to maintain sexual characteristics in these and other males who develop testosterone deficiency after puberty.
3. Androgens may be used to stimulate puberty in carefully selected males with clearly delayed puberty. These patients usually have a familial pattern of delayed puberty that is not secondary to a pathological disorder; puberty is expected to occur spontaneously at a relatively late date. Brief treatment with conservative doses may occasionally be justified in these patients if they do not respond to psychological support. The potential adverse effect on bone maturation should be discussed with the patient and parents prior to androgen administration. An X-ray of the hand and wrist to determine bone age should be obtained every 6 months to assess the effect of treatment on the epiphyseal centers.
2. Females
Androgens may be used secondarily in women with advancing inoperable metastatic (skeletal) mammary cancer who are 1 to 5 years postmenopausal. Primary goals of therapy in these women include ablation of the ovaries. Other methods of counteracting estrogen activity are adrenalectomy, hypophysectomy, and/or antiestrogen therapy. This treatment has also been used in premenopausal women with breast cancer who have benefitted from oophorectomy and are considered to have a hormone-responsive tumor. Launch Date1973 |
|||
Primary | TESTRED Approved Use1. Males
Androgens are indicated for replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone:
1. Primary hypogonadism (congenital or acquired) — testicular failure due to cryptorchidism, bilateral torsions, orchitis, vanishing testis syndrome; or orchidectomy.
2. Hypogonadotropic hypogonadism (congenital or acquired) — idiopathic gonadotropin or LHRH deficiency, or pituitary hypothalamic injury from tumors, trauma, or radiation. If the above conditions occur prior to puberty, androgen replacement therapy will be needed during the adolescent years for development of secondary sexual characteristics. Prolonged androgen
treatment will be required to maintain sexual characteristics in these and other males who develop testosterone deficiency after puberty.
3. Androgens may be used to stimulate puberty in carefully selected males with clearly delayed puberty. These patients usually have a familial pattern of delayed puberty that is not secondary to a pathological disorder; puberty is expected to occur spontaneously at a relatively late date. Brief treatment with conservative doses may occasionally be justified in these patients if they do not respond to psychological support. The potential adverse effect on bone maturation should be discussed with the patient and parents prior to androgen administration. An X-ray of the hand and wrist to determine bone age should be obtained every 6 months to assess the effect of treatment on the epiphyseal centers.
2. Females
Androgens may be used secondarily in women with advancing inoperable metastatic (skeletal) mammary cancer who are 1 to 5 years postmenopausal. Primary goals of therapy in these women include ablation of the ovaries. Other methods of counteracting estrogen activity are adrenalectomy, hypophysectomy, and/or antiestrogen therapy. This treatment has also been used in premenopausal women with breast cancer who have benefitted from oophorectomy and are considered to have a hormone-responsive tumor. Launch Date1973 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
95.9 ng/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHYLTESTOSTERONE serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
275.2 ng × h/mL |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHYLTESTOSTERONE serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.39 h |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
METHYLTESTOSTERONE serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
PubMed
Title | Date | PubMed |
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[Sex-difference on flutamide metabolism in rat liver microsomal cytochrome P450 1A2]. | 2002 Aug |
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Solid-state photodimerization of steroid enones. | 2002 Dec 13 |
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Activation of the growth hormone/insulin-like growth factor axis by treatment with 17 alpha-methyltestosterone and seawater rearing in the tilapia, Oreochromis mossambicus. | 2002 Jul |
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Effect on growth and reproduction of hormone immersed and masculinized fighting fish Betta splendens. | 2002 Nov 1 |
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Androgens and the development of the vagina. | 2002 Oct |
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Anabolic androgenic steroids induce age-, sex-, and dose-dependent changes in GABA(A) receptor subunit mRNAs in the mouse forebrain. | 2002 Sep |
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Mechanisms of anabolic androgenic steroid modulation of alpha(1)beta(3)gamma(2L) GABA(A) receptors. | 2002 Sep |
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Methyl-testosterone induces male-typical ventilatory behavior in response to putative steroidal pheromones in female round gobies (Neogobius melanostomus). | 2002 Sep |
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Detection of environmental androgens: a novel method based on enzyme-linked immunosorbent assay of spiggin, the stickleback (Gasterosteus aculeatus) glue protein. | 2002 Sep |
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[Cholestatic jaundice and pruritus]. | 2002 Sep 18 |
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Effects of environmental endocrine disruptors on the sex differentiation in Korean rockfish, Sebastes schlegeli. | 2003 |
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In vivo biotransformation of 17 alpha-methyltestosterone in the horse revisited: identification of 17-hydroxymethyl metabolites in equine urine by capillary gas chromatography/mass spectrometry. | 2003 |
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Neuroendocrine and behavioral effects of high-dose anabolic steroid administration in male normal volunteers. | 2003 Apr |
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Lack of estrogenic or (anti-)androgenic effects of d-phenothrin in the uterotrophic and Hershberger assays. | 2003 Apr 22 |
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Estratest and Estratest HS (esterified estrogens and methyltestosterone) therapy: a summary of safety surveillance data, January 1989 to August 2002. | 2003 Dec |
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Spermatogenetic disorders in adult rats exposed to tributyltin chloride during puberty. | 2003 Dec |
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Photoaffinity labeling identification of thyroid hormone-regulated glucocorticoid-binding peptides in rat liver endoplasmic reticulum: an oligomeric protein with high affinity for 16beta-hydroxylated stanozolol. | 2003 Dec |
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Effects of environmental salinity and 17alpha-methyltestosterone on growth and oxygen consumption in the tilapia, Oreochromis mossambicus. | 2003 Dec |
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OECD validation of the Hershberger assay in Japan: phase 2 dose response of methyltestosterone, vinclozolin, and p,p'-DDE. | 2003 Dec |
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Gonad development and vitellogenin production in zebrafish (Danio rerio) exposed to ethinylestradiol and methyltestosterone. | 2003 Dec 10 |
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Chronic administration of anabolic steroids disrupts pubertal onset and estrous cyclicity in rats. | 2003 Feb |
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Optimization and validation of conventional and micellar LC methods for the analysis of methyltestosterone in sugar-coated pills. | 2003 Feb 5 |
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Syntheses of steroid-based molecularly imprinted polymers and their molecular recognition study with spectrometric detection. | 2003 Jan 15 |
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Androgens stimulate sex change in protogynous grouper, Epinephelus coioides: spawning performance in sex-changed males. | 2003 Jul |
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UV filters with antagonistic action at androgen receptors in the MDA-kb2 cell transcriptional-activation assay. | 2003 Jul |
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Tibolone is not converted by human aromatase to 7alpha-methyl-17alpha-ethynylestradiol (7alpha-MEE): analyses with sensitive bioassays for estrogens and androgens and with LC-MSMS. | 2003 Mar |
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Effects of oxytocin on semen release response in African catfish (Clarias gariepinus). | 2003 May |
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17alpha-methyltestosterone: 28-day oral toxicity study in the rat based on the "Enhanced OECD Test Guideline 407" to detect endocrine effects. | 2003 Nov 5 |
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Study of 202 natural, synthetic, and environmental chemicals for binding to the androgen receptor. | 2003 Oct |
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Glucuronidation of anabolic androgenic steroids by recombinant human UDP-glucuronosyltransferases. | 2003 Sep |
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The role of androgens in female sexual dysfunction. | 2004 Apr |
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Hot flashes and androgens: a biological rationale for clinical practice. | 2004 Apr |
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Testosterone-stimulated weanlings as an alternative to castrated male rats in the Hershberger anti-androgen assay. | 2004 Apr |
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Aromatase modulation alters gonadal differentiation in developing zebrafish (Danio rerio). | 2004 Apr 14 |
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Effects of a model androgen (methyl testosterone) and a model anti-androgen (cyproterone acetate) on reproductive endocrine endpoints in a short-term adult mummichog (Fundulus heteroclitus) bioassay. | 2004 Apr 28 |
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Screening of free 17-alkyl-substituted anabolic steroids in human urine by liquid chromatography-electrospray ionization tandem mass spectrometry. | 2004 Feb |
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Are sex steroids involved in the sexual growth dimorphism in Eurasian perch juveniles? | 2004 Feb |
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Mechanistic basis for estrogenic effects in fathead minnow (Pimephales promelas) following exposure to the androgen 17alpha-methyltestosterone: conversion of 17alpha-methyltestosterone to 17alpha-methylestradiol. | 2004 Jan 7 |
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Evaluation of the rodent Hershberger assay using three reference endocrine disrupters (androgen and antiandrogens). | 2004 Jan-Feb |
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Reproductive disorders in pubertal and adult phase of the male rats exposed to vinclozolin during puberty. | 2004 Jul |
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Hereditary angioedema: the rewards of studying a rare disease. | 2004 Jul |
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Analysis of anabolic steroids by partial filling micellar electrokinetic capillary chromatography and electrospray mass spectrometry. | 2004 Jun 18 |
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Androgenic and estrogenic effects of the synthetic androgen 17alpha-methyltestosterone on sexual development and reproductive performance in the fathead minnow (Pimephales promelas) determined using the gonadal recrudescence assay. | 2004 Jun 24 |
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Fish full life-cycle testing for androgen methyltestosterone on medaka (Oryzias latipes). | 2004 Mar |
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Prediction of whole-body metabolic clearance of drugs through the combined use of slices from rat liver, lung, kidney, small intestine and colon. | 2004 Mar |
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Oxandrolone treatment of childhood hereditary angioedema. | 2004 Mar |
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Application of the revised EU criteria for the confirmation of anabolic steroids in meat using GC-MS. | 2004 Mar |
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Effect of the combination of methyltestosterone and esterified estrogens compared with esterified estrogens alone on apolipoprotein CIII and other apolipoproteins in very low density, low density, and high density lipoproteins in surgically postmenopausal women. | 2004 May |
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Interlaboratory comparison of four in vitro assays for assessing androgenic and antiandrogenic activity of environmental chemicals. | 2004 May |
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Effects of organotin compounds on pubertal male rats. | 2004 Oct 1 |
Patents
Sample Use Guides
Replacement therapy in androgen-deficient males is 10 to 50 mg of methylTESTOSTERone daily.
The dosage of methylTESTOSTERone for androgen therapy
in breast carcinoma in females is from 50-200 mg daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6863484
Estradiol production was significantly stimulated in explants of normal human term placenta cultured in the presence of 0.01 mM methyltestosterone.
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Classification Tree | Code System | Code | ||
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DEA NO. |
4000
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NDF-RT |
N0000000146
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WHO-VATC |
QG03EK01
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WHO-VATC |
QG03BA02
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WHO-ATC |
G03BA02
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CFR |
21 CFR 310.528
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WIKIPEDIA |
Designer-drugs-Methyltestosterone
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WHO-VATC |
QG03EA01
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LIVERTOX |
627
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NCI_THESAURUS |
C243
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WHO-ATC |
G03EA01
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NDF-RT |
N0000175824
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NDF-RT |
N0000008241
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WHO-ATC |
G03EK01
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399
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3356
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27436
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D008777
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CHEMBL1395
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V9EFU16ZIF
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DB06710
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6010
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58-18-4
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6904
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139965
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100000085467
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METHYLTESTOSTERONE
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PRIMARY | Description: Colourless or almost colourless crystals or a white or slightly yellowish white, crystalline powder; odourless. Solubility: Practically insoluble in water; freely soluble in ethanol (~750 g/l) TS; sparingly soluble in ether R. Category: Androgen. Storage: Methyltestosterone should be kept in a well-closed container, protected from light. Definition: Methyltestosterone contains not less than 97.0% and not more than 102.0% of C20H30O2, calculated with reference to the dried substance. | ||
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200-366-3
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1438001
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DTXSID1033664
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SUB08876MIG
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C648
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3365
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9701
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m7467
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PRIMARY | Merck Index | ||
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METHYLTESTOSTERONE
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V9EFU16ZIF
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)