Home Nitriles Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-

Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-

CAS No.:
13647-35-3
Catalog Number:
AG0011WK
Molecular Formula:
C20H27NO3
Molecular Weight:
329.4333
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
100mg
98%
In Stock USA
United States
$175
- +
1g
98%
In Stock USA
United States
$483
- +
5g
98%
In Stock USA
United States
$1953
- +
Product Description
Catalog Number:
AG0011WK
Chemical Name:
Androst-2-ene-2-carbonitrile, 4,5-epoxy-3,17-dihydroxy-, (4α,5α,17β)-
CAS Number:
13647-35-3
Molecular Formula:
C20H27NO3
Molecular Weight:
329.4333
MDL Number:
MFCD00199295
IUPAC Name:
(1S,2R,6R,8S,11S,12S,15S,16S)-5,15-dihydroxy-2,16-dimethyl-7-oxapentacyclo[9.7.0.02,8.06,8.012,16]octadec-4-ene-4-carbonitrile
InChI:
InChI=1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
InChI Key:
KVJXBPDAXMEYOA-CXANFOAXSA-N
SMILES:
N#CC1=C(O)[C@@H]2[C@]3([C@@](C1)(C)[C@H]1CC[C@]4([C@H]([C@@H]1CC3)CC[C@@H]4O)C)O2
EC Number:
237-133-0
UNII:
L0FPV48Q5R
Properties
Complexity:
692  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Defined Bond Stereocenter Count:
0
Exact Mass:
329.199g/mol
Formal Charge:
0
Heavy Atom Count:
24  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
329.44g/mol
Monoisotopic Mass:
329.199g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
76.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.9  
Literature
Title Journal
Temporal changes in biological responses and uncertainty in assessing risks of endocrine-disrupting chemicals: insights from intensive time-course studies with fish. Toxicological sciences : an official journal of the Society of Toxicology 20150401
17β-trenbolone, an anabolic-androgenic steroid as well as an environmental hormone, contributes to neurodegeneration. Toxicology and applied pharmacology 20150101
Expression of LH receptor in nonpregnant mouse endometrium: LH induction of 3β-HSD and de novo synthesis of progesterone. The Journal of endocrinology 20121001
Effects of fibroblast growth factor 9 (FGF9) on steroidogenesis and gene expression and control of FGF9 mRNA in bovine granulosa cells. Endocrinology 20120901
The influence of trilostane on steroid hormone metabolism in canine adrenal glands and corpora lutea-an in vitro study. Veterinary research communications 20120301
Feline pituitary-dependent hyperadrenocorticism and insulin resistance due to a plurihormonal adenoma. Topics in companion animal medicine 20120201
Effects of nonylphenol on aldosterone release from rat zona glomerulosa cells. Chemico-biological interactions 20120105
The antidepressant-like effects of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane in mice is related to changes in neuroactive steroid and monoamine levels. Neuropharmacology 20120101
Long-term follow-up of renal function in dogs after treatment for ACTH-dependent hyperadrenocorticism. Journal of veterinary internal medicine 20120101
Pharmaceutical evaluation of compounded trilostane products. Journal of the American Animal Hospital Association 20120101
Trilostane dose versus body weight in the treatment of naturally occurring pituitary-dependent hyperadrenocorticism in dogs. Journal of veterinary internal medicine 20120101
Gh is produced by the testis of Japanese eel and stimulates proliferation of spermatogonia. Reproduction (Cambridge, England) 20111201
Transcriptional regulatory dynamics of the hypothalamic-pituitary-gonadal axis and its peripheral pathways as impacted by the 3-beta HSD inhibitor trilostane in zebrafish (Danio rerio). Ecotoxicology and environmental safety 20110901
Temporal evaluation of effects of a model 3β-hydroxysteroid dehydrogenase inhibitor on endocrine function in the fathead minnow. Environmental toxicology and chemistry 20110901
Decreased cytochrome c oxidase IV expression reduces steroidogenesis. The Journal of pharmacology and experimental therapeutics 20110801
Evaluation of twice-daily lower-dose trilostane treatment administered orally in dogs with naturally occurring hyperadrenocorticism. Journal of the American Veterinary Medical Association 20110601
Determination of the concentrations of trilostane and ketotrilostane that inhibit ex vivo canine adrenal gland synthesis of cortisol, corticosterone, and aldosterone. American journal of veterinary research 20110501
Effects of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane on luteal progesterone production in the dog. Theriogenology 20110415
Adrenocorticotropic hormone, but not trilostane, causes severe adrenal hemorrhage, vacuolization, and apoptosis in rats. Domestic animal endocrinology 20110401
Anti-ovulatory effects of RU486 and trilostane involve impaired cyclooxygenase-2 expression and mitotic activity of follicular granulosa cells in rats. Prostaglandins & other lipid mediators 20110401
The antidepressant-like effect of the 3β-hydroxysteroid dehydrogenase inhibitor trilostane involves a regulation of β-type estrogen receptors. Psychopharmacology 20110301
A comparison of factors that influence survival in dogs with adrenal-dependent hyperadrenocorticism treated with mitotane or trilostane. Journal of veterinary internal medicine 20110101
Long-term efficacy of trilostane for Cushing's syndrome due to adrenocorticotropin-independent bilateral macronodular adrenocortical hyperplasia. Internal medicine (Tokyo, Japan) 20110101
Retrospective evaluation of the effect of trilostane on insulin requirement and fructosamine concentration in eight diabetic dogs with hyperadrenocorticism. The Journal of small animal practice 20101201
Trilostane, an inhibitor of 3β-hydroxysteroid dehydrogenase, has an agonistic activity on androgen receptor in human prostate cancer cells. Cancer letters 20101128
Prochloraz-induced oocyte maturation in rainbow trout (Oncorhynchus mykiss), a molecular and functional analysis. Toxicological sciences : an official journal of the Society of Toxicology 20101101
Evaluation of the use of baseline cortisol concentration as a monitoring tool for dogs receiving trilostane as a treatment for hyperadrenocorticism. Journal of the American Veterinary Medical Association 20101001
Aldosterone, hypertension and heart failure: insights from clinical trials. Hypertension research : official journal of the Japanese Society of Hypertension 20100901
3beta-hydroxysteroid dehydrogenase is a possible pharmacological target in the treatment of castration-resistant prostate cancer. Endocrinology 20100801
The functions of key residues in the inhibitor, substrate and cofactor sites of human 3beta-hydroxysteroid dehydrogenase type 1 are validated by mutagenesis. The Journal of steroid biochemistry and molecular biology 20100601
Induction of progesterone receptor A form attenuates the induction of cytosolic phospholipase A2alpha expression by cortisol in human amnion fibroblasts. Reproduction (Cambridge, England) 20100501
Monitoring the response of canine hyperadrenocorticism to trilostane treatment by assessment of acute phase protein concentrations. The Journal of small animal practice 20100401
Hypophysectomy for a dog with coexisting Cushing's disease and diabetes mellitus. The Journal of veterinary medical science 20100301
Trilostane in dogs. The Veterinary clinics of North America. Small animal practice 20100301
Effects of trilostane on the pituitary-adrenocortical and renin-aldosterone axis in dogs with pituitary-dependent hypercortisolism. Veterinary journal (London, England : 1997) 20100101
Management of Cushing's syndrome in dogs. The Veterinary record 20091024
Trilostane exerts antidepressive effects among wild-type, but not estrogen receptor [beta] knockout mice. Neuroreport 20090805
The 3beta-hydroxysteroid dehydrogenase inhibitor trilostane shows antidepressant properties in mice. Psychoneuroendocrinology 20090601
Expression and regulation of tumor necrosis factor (TNF) and TNF-receptor family members in the macaque corpus luteum during the menstrual cycle. Molecular reproduction and development 20090401
Trilostane, FAD286, and the role of aldosterone in the central regulation of blood pressure: focus on 'Role of central nervous system aldosterone synthase and mineralocorticoid receptors in salt-induced hypertension in Dahl salt-sensitive rats'. American journal of physiology. Regulatory, integrative and comparative physiology 20090401
Structural basis for the selective inhibition of human 3beta-hydroxysteroid dehydrogenase 1 in human breast tumor MCF-7 cells. Molecular and cellular endocrinology 20090325
The effects of luteinizing hormone ablation/replacement versus steroid ablation/replacement on gene expression in the primate corpus luteum. Molecular human reproduction 20090301
Trilostane-induced inhibition of cortisol secretion results in reduced negative feedback at the hypothalamic-pituitary axis. Domestic animal endocrinology 20090101
Cushing's disease in dogs and humans. Hormone research 20090101
Urinary corticoid: creatinine ratios in dogs with pituitary-dependent hypercortisolism during trilostane treatment. Journal of veterinary internal medicine 20090101
Persistent isolated hypocortisolism following brief treatment with trilostane. Australian veterinary journal 20081201
Serum concentrations of cortisol and cortisone in healthy dogs and dogs with pituitary-dependent hyperadrenocorticism treated with trilostane. The Veterinary record 20081018
Trilostane therapy for hyperadrenocorticism in three dogs with adrenocortical metastasis. The Veterinary record 20080809
Effects of a 3beta-hydroxysteroid dehydrogenase inhibitor, trilostane, on the fathead minnow reproductive axis. Toxicological sciences : an official journal of the Society of Toxicology 20080701
Structure/function of the inhibition of human 3beta-hydroxysteroid dehydrogenase type 1 and type 2 by trilostane. The Journal of steroid biochemistry and molecular biology 20080701
Evaluation of twice-daily, low-dose trilostane treatment administered orally in dogs with naturally occurring hyperadrenocorticism. Journal of the American Veterinary Medical Association 20080501
Involvement of neurosteroids in the anxiolytic-like effects of AC-5216 in mice. Pharmacology, biochemistry, and behavior 20080401
The effect of trilostane treatment on circulating thyroid hormone concentrations in dogs with pituitary-dependent hyperadrenocorticism. The Journal of small animal practice 20080301
Aldosterone-, corticosterone- and cortisol-secreting adrenocortical carcinoma in a dog: case report. The Journal of veterinary medical science 20080301
Rapid estrogen regulation of DHEA metabolism in the male and female songbird brain. Journal of neurochemistry 20080101
Comparison of non-selective adrenocorticolysis with mitotane or trilostane for the treatment of dogs with pituitary-dependent hyperadrenocorticism. The Veterinary record 20071215
Follicle-stimulating hormone induces spermatogenesis mediated by androgen production in Japanese eel, Anguilla japonica. Biology of reproduction 20071201
The influence of di-(2-ethylhexyl) phthalate on steroidogenesis by the ovarian granulosa cells of immature female rats. The Journal of endocrinology 20070901
Rv1106c from Mycobacterium tuberculosis is a 3beta-hydroxysteroid dehydrogenase. Biochemistry 20070807
Cushing's syndrome in a guinea pig. The Veterinary record 20070623
Changes of cytosol glucocorticoid receptor and renal Na(+)-K(+)-ATPase activity after swimming training in rat. The Journal of sports medicine and physical fitness 20070601
Evidence that the preovulatory rise in intrafollicular progesterone may not be required for ovulation in cattle. The Journal of endocrinology 20070301
Hyperadrenocorticism: treating dogs. Compendium (Yardley, PA) 20070301
Histological evaluation of the adrenal glands of seven dogs with hyperadrenocorticism treated with trilostane. The Veterinary record 20070217
Medical management of pituitary-dependent hyperadrenocorticism: mitotane versus trilostane. Clinical techniques in small animal practice 20070201
Trilostane in advanced breast cancer. Expert opinion on pharmacotherapy 20061201
Effects of crude adlay hull acetone extract on corticosterone release from rat zona fasciculata-reticularis cells. Naunyn-Schmiedeberg's archives of pharmacology 20061101
Regulation of hepatic steroid receptors and enzymes by the 3beta-hydroxysteroid dehydrogenase inhibitor trilostane. The Journal of steroid biochemistry and molecular biology 20061001
Relationship between the expression of hepatic but not testicular 3beta-hydroxysteroid dehydrogenase with androstenone deposition in pig adipose tissue. Journal of animal science 20061001
Update on drugs used to treat endocrine diseases in small animals. The Veterinary clinics of North America. Small animal practice 20060901
Study of the effects of once daily doses of trilostane on cortisol concentrations and responsiveness to adrenocorticotrophic hormone in hyperadrenocorticoid dogs. The Veterinary record 20060826
Comparison of effects of 4-hydroxy tamoxifen and trilostane on oestrogen-regulated gene expression in MCF-7 cells: up-regulation of oestrogen receptor beta. The Journal of steroid biochemistry and molecular biology 20060801
Cortisol, aldosterone, cortisol precursor, androgen and endogenous ACTH concentrations in dogs with pituitary-dependant hyperadrenocorticism treated with trilostane. Domestic animal endocrinology 20060701
[Adrenocortical adenoma]. Nihon rinsho. Japanese journal of clinical medicine 20060528
In vitro effects of insulin-like growth factors and insulin on oocyte maturation and maturation-inducing steroid production in ovarian follicles of common carp, Cyprinus carpio. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20060501
Long-term efficacy of trilostane administered twice daily in dogs with pituitary-dependent hyperadrenocorticism. Journal of the American Animal Hospital Association 20060101
Dehydroepiandrosterone restoration of growth hormone gene expression in aging female rats, in vivo and in vitro: evidence for actions via estrogen receptors. Endocrinology 20051201
Canine hyperadrenocorticism: effects of trilostane on parathyroid hormone, calcium and phosphate concentrations. The Journal of small animal practice 20051101
Haptoglobin concentrations in dogs undergoing trilostane treatment for hyperadrenocorticism. Veterinary clinical pathology 20050901
Identification of key amino acids responsible for the substantially higher affinities of human type 1 3beta-hydroxysteroid dehydrogenase/isomerase (3beta-HSD1) for substrates, coenzymes, and inhibitors relative to human 3beta-HSD2. The Journal of biological chemistry 20050603
Labor induction abortion utilizing trilostane, a 3beta-hydroxysteroid dehydrogenase inhibitor. Contraception 20050501
Dynamic expression of caspase-2, -3, -8, and -9 proteins and enzyme activity, but not messenger ribonucleic acid, in the monkey corpus luteum during the menstrual cycle. The Journal of clinical endocrinology and metabolism 20050401
Reversal of caffeine-induced anxiety by neurosteroid 3-alpha-hydroxy-5-alpha-pregnane-20-one in rats. Neuropharmacology 20050401
Effect of 3beta-hydroxysteroid dehydrogenase inhibition by trilostane on blood pressure in the Dahl salt-sensitive rat. American journal of physiology. Regulatory, integrative and comparative physiology 20050201
The use of trilostane for the treatment of alopecia X in Alaskan malamutes. Journal of the American Animal Hospital Association 20050101
A comparison of the survival times of dogs treated with mitotane or trilostane for pituitary-dependent hyperadrenocorticism. Journal of veterinary internal medicine 20050101
Treatment of canine Alopecia X with trilostane. Veterinary dermatology 20041001
Effect of trilostane on serum concentrations of aldosterone, cortisol, and potassium in dogs with pituitary-dependent hyperadrenocorticism. American journal of veterinary research 20040901
ADAMTS-1/METH-1 and TIMP-3 expression in the primate corpus luteum: divergent patterns and stage-dependent regulation during the natural menstrual cycle. Molecular human reproduction 20040801
Modulation of the firing activity of female dorsal raphe nucleus serotonergic neurons by neuroactive steroids. The Journal of endocrinology 20040701
Adrenal necrosis in a dog receiving trilostane for the treatment of hyperadrenocorticism. The Journal of small animal practice 20040601
Trilostane treatment of bilateral adrenal enlargement and excessive sex steroid hormone production in a cat. The Journal of small animal practice 20040501
Serum insulin concentrations in horses with equine Cushing's syndrome: response to a cortisol inhibitor and prognostic value. Equine veterinary journal 20040401
Adrenocorticotropic hormone levels in dogs with pituitary-dependent hyperadrenocorticism following trilostane therapy. The Veterinary record 20040327
Gonadotropin and steroid regulation of matrix metalloproteinases and their endogenous tissue inhibitors in the developed corpus luteum of the rhesus monkey during the menstrual cycle. Biology of reproduction 20040101
Trilostane therapy for treatment of pituitary-dependent hyperadrenocorticism in 5 cats. Journal of veterinary internal medicine 20040101
Antisteroidogenic actions of hydrogen peroxide on rat Leydig cells. Journal of cellular biochemistry 20031215
Effects of dehydroepiandrosterone on corticosterone release in rat zona fasciculata-reticularis cells. Naunyn-Schmiedeberg's archives of pharmacology 20031201
Trilostane treatment in dogs with pituitary-dependent hyperadrenocorticism. Australian veterinary journal 20031001
The luteinizing hormone surge is preceded by an estrogen-induced increase of hypothalamic progesterone in ovariectomized and adrenalectomized rats. Neuroendocrinology 20030701
Use of trilostane for the treatment of pituitary-dependent hyperadrenocorticism in a cat. The Journal of small animal practice 20030601
Efficacy of trilostane for the treatment of equine Cushing's syndrome. Equine veterinary journal 20030601
3 beta-hydroxysteroid dehydrogenase isomerase (3beta-HSD) activity in the rat sciatic nerve: kinetic analysis and regulation by steroids. The Journal of steroid biochemistry and molecular biology 20030501
Trilostane treatment of a dog with functional adrenocortical neoplasia. The Journal of small animal practice 20030301
Characterization and regulation of the 3beta-hydroxysteroid dehydrogenase isomerase enzyme in the rat sciatic nerve. Journal of neurochemistry 20030101
Exogenous steroid substrate modifies the effect of 2,3,7,8-tetrachlorodibenzo-p-dioxin on estradiol production of human luteinized granulosa cells in vitro. Biology of reproduction 20030101
Changes in ultrasonographic appearance of adrenal glands in dogs with pituitary-dependent hyperadrenocorticism treated with trilostane. Veterinary radiology & ultrasound : the official journal of the American College of Veterinary Radiology and the International Veterinary Radiology Association 20030101
Medical treatment of hyperadrenocorticism in the dog. Australian veterinary journal 20030101
Effects of prostaglandins E2 and F2alpha (PGE2; PGF2alpha), trilostane, mifepristone, palmitic acid (PA), indomethacin (INDO), ethamoxytriphetol (MER-25), PGE2 + PA, or PGF2alpha + PA on PGE2, PGF2alpha, and progesterone secretion by bovine corpora lutea of mid-pregnancy in vitro. The Chinese journal of physiology 20021231
Non-competitive steroid inhibition of oestrogen receptor functions. International journal of cancer 20020901
Seasonal changes in plasma steroid levels in Indian major carp Labeo rohita: influence of homologous pituitary extract on steroid production and development of oocyte maturational competence. General and comparative endocrinology 20020901
Inhibition of testosterone production by propylthiouracil in rat Leydig cells. Biology of reproduction 20020801
Trilostane treatment of 78 dogs with pituitary-dependent hyperadrenocorticism. The Veterinary record 20020629
Inhibition of progesterone secretion with trilostane for mid-trimester termination of pregnancy: randomized controlled trials. Human reproduction (Oxford, England) 20020601
Results of clinical examinations, laboratory tests, and ultrasonography in dogs with pituitary-dependent hyperadrenocorticism treated with trilostane. American journal of veterinary research 20020401
Effects of fasting on corticosterone production by zona fasciculata-reticularis cells in ovariectomized rats. Journal of investigative medicine : the official publication of the American Federation for Clinical Research 20020301
[Secondary forms of hypertension. 5. Hypertension caused by Cushing syndrome and Conn's disease]. MMW Fortschritte der Medizin 20020227
Cortisol/progesterone antagonism in regulation of 15-hydroxysteroid dehydrogenase activity and mRNA levels in human chorion and placental trophoblast cells at term. The Journal of clinical endocrinology and metabolism 20020201
Effects of indomethacin, luteinizing hormone (LH), prostaglandin E2 (PGE2), trilostane, mifepristone, ethamoxytriphetol (MER-25) on secretion of prostaglandin E (PGE), prostaglandin F2alpha (PGF2alpha) and progesterone by ovine corpora lutea of pregnancy or the estrous cycle. Prostaglandins & other lipid mediators 20010301
Inhibition of human placental progesterone synthesis and aromatase activity by synthetic steroidogenic inhibitors in vitro. Fertility and sterility 19830601
Treatment of Cushing's syndrome with trilostane (WIN 24,540), an inhibitor of adrenal steroid biosynthesis. The Journal of clinical endocrinology and metabolism 19781101
Properties