MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 561817 | Name: MK-386
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

MK-386 is a potent and selective human type-1 5alpha-reductase inhibitor.

Chemical Structure

MK-386
MK-386
CAS#158493-17-5

Theoretical Analysis

MedKoo Cat#: 561817

Name: MK-386

CAS#: 158493-17-5

Chemical Formula: C28H49NO

Exact Mass: 415.3814

Molecular Weight: 415.71

Elemental Analysis: C, 80.90; H, 11.88; N, 3.37; O, 3.85

Price and Availability

Size Price Availability Quantity
1mg USD 485.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
No Data
Synonym
MK-386; MK 386; MK386;
IUPAC/Chemical Name
(4aR,4bS,6aR,7R,9aS,9bS,10S,11aR)-7-[(1R)-1,5-Dimethylhexyl]hexadecahydro-1,4a,6a,10-tetramethyl-2H-indeno[5,4-f]quinolin-2-one
InChi Key
XUTZDXHKQDPUMA-MVJJLJOTSA-N
InChi Code
InChI=1S/C28H49NO/c1-18(2)9-8-10-19(3)21-11-12-22-26-20(4)17-24-28(6,16-14-25(30)29(24)7)23(26)13-15-27(21,22)5/h18-24,26H,8-17H2,1-7H3/t19-,20+,21-,22+,23+,24-,26+,27-,28-/m1/s1
SMILES Code
O=C1N(C)[C@]2([H])C[C@H](C)[C@]([C@]3([H])CC[C@H]([C@H](C)CCCC(C)C)[C@@]3(C)CC4)([H])[C@@]4([H])[C@@]2(C)CC1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
MK 386 is a potent and selective human type 1 5α-reductase inhibitor (5αR1, IC50 = 0.9 nM).
In vitro activity:
In both cell types, the isotype 1 inhibitor MK386 completely inhibited the conversion of testosterone to 5alpha-dihydrotestosterone in concentrations higher than 10 (-9) M. MK386, but not finasteride, reduced testosterone-stimulated proliferation and slightly reduced the testosterone-induced increase in the amount of SZ95 sebocyte proteins. Reference: Horm Metab Res. 2007 Feb;39(2):141-8. https://pubmed.ncbi.nlm.nih.gov/17326010/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMSO 41.6 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 415.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Seiffert K, Seltmann H, Fritsch M, Zouboulis CC. Inhibition of 5alpha-reductase activity in SZ95 sebocytes and HaCaT keratinocytes in vitro. Horm Metab Res. 2007 Feb;39(2):141-8. doi: 10.1055/s-2007-961814. PMID: 17326010. 2. Festuccia C, Angelucci A, Gravina GL, Muzi P, Vicentini C, Bologna M. Effects of 5 alpha reductase inhibitors on androgendependent human prostatic carcinoma cells. J Cancer Res Clin Oncol. 2005 Apr;131(4):243-54. doi: 10.1007/s00432-004-0632-1. Epub 2005 Jan 14. PMID: 15650886
In vitro protocol:
1. Seiffert K, Seltmann H, Fritsch M, Zouboulis CC. Inhibition of 5alpha-reductase activity in SZ95 sebocytes and HaCaT keratinocytes in vitro. Horm Metab Res. 2007 Feb;39(2):141-8. doi: 10.1055/s-2007-961814. PMID: 17326010. 2. Festuccia C, Angelucci A, Gravina GL, Muzi P, Vicentini C, Bologna M. Effects of 5 alpha reductase inhibitors on androgendependent human prostatic carcinoma cells. J Cancer Res Clin Oncol. 2005 Apr;131(4):243-54. doi: 10.1007/s00432-004-0632-1. Epub 2005 Jan 14. PMID: 15650886
In vivo protocol:
TBD
1: Bühler P, Fischer T, Wolf P, Gierschner D, Schultze-Seemann W, Wetterauer U, Elsässer-Beile U. Comparison of gene expression in LNCaP prostate cancer cells after treatment with bicalutamide or 5-alpha-reductase inhibitors. Urol Int. 2010;84(2):203-11. doi: 10.1159/000277600. Epub 2010 Mar 4. PubMed PMID: 20215827. 2: Festuccia C, Gravina GL, Muzi P, Pomante R, Angelucci A, Vicentini C, Bologna M. Effects of dutasteride on prostate carcinoma primary cultures: a comparative study with finasteride and MK386. J Urol. 2008 Jul;180(1):367-72. doi: 10.1016/j.juro.2008.02.036. Epub 2008 May 22. PubMed PMID: 18499161. 3: Liu S, Yamauchi H. Different patterns of 5alpha-reductase expression, cellular distribution, and testosterone metabolism in human follicular dermal papilla cells. Biochem Biophys Res Commun. 2008 Apr 18;368(4):858-64. doi: 10.1016/j.bbrc.2008.01.130. Epub 2008 Feb 5. PubMed PMID: 18258185. 4: Seiffert K, Seltmann H, Fritsch M, Zouboulis CC. Inhibition of 5alpha-reductase activity in SZ95 sebocytes and HaCaT keratinocytes in vitro. Horm Metab Res. 2007 Feb;39(2):141-8. PubMed PMID: 17326010. 5: Festuccia C, Angelucci A, Gravina GL, Muzi P, Vicentini C, Bologna M. Effects of 5 alpha reductase inhibitors on androgen-dependent human prostatic carcinoma cells. J Cancer Res Clin Oncol. 2005 Apr;131(4):243-54. Epub 2005 Jan 14. PubMed PMID: 15650886. 6: Steckelbroeck S, Watzka M, Reichelt R, Hans VH, Stoffel-Wagner B, Heidrich DD, Schramm J, Bidlingmaier F, Klingmüller D. Characterization of the 5alpha-reductase-3alpha-hydroxysteroid dehydrogenase complex in the human brain. J Clin Endocrinol Metab. 2001 Mar;86(3):1324-31. PubMed PMID: 11238528. 7: Kuhlmann K, Bühler H, Ragosch V, Halis G, Weitzel HK, Hundertmark S. Kinetic studies on rabbit liver glucocorticoid 5alpha-reductase. Horm Metab Res. 2000 Jan;32(1):20-5. PubMed PMID: 10727009. 8: Steckelbroeck S, Heidrich DD, Stoffel-Wagner B, Hans VH, Schramm J, Bidlingmaier F, Klingmüller D. Characterization of aromatase cytochrome P450 activity in the human temporal lobe. J Clin Endocrinol Metab. 1999 Aug;84(8):2795-801. Erratum in: J Clin Endocrinol Metab 1999 Dec;84(12):4606. PubMed PMID: 10443682. 9: Altenburger R, Kissel T. The human keratinocyte cell line HaCaT: an in vitro cell culture model for keratinocyte testosterone metabolism. Pharm Res. 1999 May;16(5):766-71. PubMed PMID: 10350023. 10: Constanzer ML, Chavez CM, Matuszewski BK, Carlin J, Graham D. Low level determination of a novel 4-azasteroid and its carboxylic acid metabolite in human plasma and semen using high-performance liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1997 May 23;693(1):117-29. PubMed PMID: 9200525. 11: Schwartz JI, Tanaka WK, Wang DZ, Ebel DL, Geissler LA, Dallob A, Hafkin B, Gertz BJ. MK-386, an inhibitor of 5alpha-reductase type 1, reduces dihydrotestosterone concentrations in serum and sebum without affecting dihydrotestosterone concentrations in semen. J Clin Endocrinol Metab. 1997 May;82(5):1373-7. PubMed PMID: 9141518. 12: Ye F, Imamura K, Imanishi N, Rhodes L, Uno H. Effects of topical antiandrogen and 5-alpha-reductase inhibitors on sebaceous glands in male fuzzy rats. Skin Pharmacol. 1997;10(5-6):288-97. PubMed PMID: 9449168. 13: Schwartz JI, Van Hecken A, De Schepper PJ, De Lepeleire I, Lasseter KC, Shamblen EC, Winchell GA, Constanzer ML, Chavez CM, Wang DZ, Ebel DL, Justice SJ, Gertz BJ. Effect of MK-386, a novel inhibitor of type 1 5 alpha-reductase, alone and in combination with finasteride, on serum dihydrotestosterone concentrations in men. J Clin Endocrinol Metab. 1996 Aug;81(8):2942-7. PubMed PMID: 8768856. 14: Ellsworth K, Azzolina B, Baginsky W, Bull H, Chang B, Cimis G, Mitra S, Toney J, Bakshi RK, Rasmusson GR, Tolman RL, Harris GS. MK386: a potent, selective inhibitor of the human type 1 5alpha-reductase. J Steroid Biochem Mol Biol. 1996 Jul;58(4):377-84. PubMed PMID: 8903421. 15: Chen W, Zouboulis CC, Orfanos CE. The 5 alpha-reductase system and its inhibitors. Recent development and its perspective in treating androgen-dependent skin disorders. Dermatology. 1996;193(3):177-84. Review. PubMed PMID: 8944337. 16: Bakshi RK, Patel GF, Rasmusson GH, Baginsky WF, Cimis G, Ellsworth K, Chang B, Bull H, Tolman RL, Harris GS. 4,7 beta-Dimethyl-4-azacholestan-3-one (MK-386) and related 4-azasteroids as selective inhibitors of human type 1 5 alpha-reductase. J Med Chem. 1994 Nov 11;37(23):3871-4. PubMed PMID: 7966146.