Dihydrodutasteride | CAS# 164656-22-8 | Biochemical

MedKoo Cat#: 574669 | Name: Dihydrodutasteride

Description:

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

Dihydrodutasteride is an impurity of Dutasteride.

Chemical Structure

Dihydrodutasteride

CAS#164656-22-8

Theoretical Analysis

MedKoo Cat#: 574669

Name: Dihydrodutasteride

CAS#: 164656-22-8

Chemical Formula: C27H32F6N2O2

Exact Mass: 530.2368

Molecular Weight: 530.56

Elemental Analysis: C, 61.12; H, 6.08; F, 21.49; N, 5.28; O, 6.03

Price and Availability

Size	Price	Availability	Quantity

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Dihydrodutasteride; Dihydro Dutasteride; 1,2-Dihydrodutasteride

IUPAC/Chemical Name

(4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-[2,5-Bis(trifluoromethyl)phenyl]hexadecahydro-4a,6a-dimethyl-2-oxo-1H-Indeno[5,4-f]quinoline-7-carboxamide

InChi Key

AIUHDIPAGREENV-QWBYCMEYSA-N

InChi Code

InChI=1S/C27H32F6N2O2/c1-24-11-9-17-15(4-8-21-25(17,2)12-10-22(36)35-21)16(24)6-7-19(24)23(37)34-20-13-14(26(28,29)30)3-5-18(20)27(31,32)33/h3,5,13,15-17,19,21H,4,6-12H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1

SMILES Code

O=C([C@H]1CC[C@]2([H])[C@]1(C)CC[C@]3([H])[C@@]4(C)CCC(N[C@]4([H])CC[C@]32[H])=O)NC5=CC(C(F)(F)F)=CC=C5C(F)(F)F

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

>3 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:

Dihydro Dutasteride is a metabolite of Dutasteride. Dutasteride is a potent inhibitor of both 5 alpha-reductase isozymes.

In vitro activity:

Human astrocytoma U-87 MG cell line was cultured and incubated with 10 μg/mL of LPS for 24 hours to create a neuro-inflammation model, using two different treatment approaches. The first approach included LPS treatment for 24 hours, followed by dutasteride (20 μg/mL) incubation for the next 72 hours. In the second treatment approach, the cells were co-incubated with LPS and dutasteride for 72 hours.Dutasteride significantly decreased the secretion of NO and also, the levels of TLR4, MyD88, and NF-κBp65 in both treatment approaches. Dutasteride has anti-inflammatory properties and probably analgesic effects, by mechanisms different from conventional analgesics. Reference: Iran J Allergy Asthma Immunol. 2022 Oct 26;21(5):574-583. https://pubmed.ncbi.nlm.nih.gov/36341565/

In vivo activity:

A significantly upregulated mean PSMA protein expression was observed in the groups treated with 1 mg/kg (1087% ± 374%, P < 0.001) and 10 mg/kg (685% ± 263%, P < 0.05) Dutasteride, respectively, compared to mice treated with vehicle only. Reference: Cancer Rep (Hoboken). 2021 Dec;4(6):e1418. https://pubmed.ncbi.nlm.nih.gov/34008909/

Preparing Stock Solutions

The following data is based on the product molecular weight 530.56 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.

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. Taheran L, Zali H, Sharifi K, Yazdani M, Ajoudanian M, Safari MS, Rajaei S, Dabbagh A. Inhibitory Effects of Dutasteride on TLR4: An In vitro Pain Study. Iran J Allergy Asthma Immunol. 2022 Oct 26;21(5):574-583. doi: 10.18502/ijaai.v21i5.11044. PMID: 36341565. 2. Ateeq B, Vellaichamy A, Tomlins SA, Wang R, Cao Q, Lonigro RJ, Pienta KJ, Varambally S. Role of dutasteride in pre-clinical ETS fusion-positive prostate cancer models. Prostate. 2012 Oct 1;72(14):1542-9. doi: 10.1002/pros.22509. Epub 2012 Mar 13. PMID: 22415461. 3. Kranzbühler B, Sousa R, Prause L, Burger IA, Rupp NJ, Sulser T, Salemi S, Eberli D. Impact of short-term Dutasteride treatment on prostate-specific membrane antigen expression in a mouse xenograft model. Cancer Rep (Hoboken). 2021 Dec;4(6):e1418. doi: 10.1002/cnr2.1418. Epub 2021 May 19. PMID: 34008909; PMCID: PMC8714546.

In vitro protocol:

In vivo protocol:

1. Kranzbühler B, Sousa R, Prause L, Burger IA, Rupp NJ, Sulser T, Salemi S, Eberli D. Impact of short-term Dutasteride treatment on prostate-specific membrane antigen expression in a mouse xenograft model. Cancer Rep (Hoboken). 2021 Dec;4(6):e1418. doi: 10.1002/cnr2.1418. Epub 2021 May 19. PMID: 34008909; PMCID: PMC8714546.

1. Arif T, Dorjay K, Adil M, Sami M. Dutasteride in Androgenetic Alopecia: An Update. Curr Clin Pharmacol. 2017;12(1):31-35. doi:10.2174/1574884712666170310111125