Dutasteride

CAT: 0804-HY-13613-04Size: 50 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-13613-04Size:50 mg

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Description

Dutasteride (GG745) is a potent inhibitor of both 5α-reductase isozymes. Dutasteride may possess off-target effects on the androgen receptor (AR) due to its structural similarity to DHT[1].

CAS Number

164656-23-9

Product Name Alternative

GG 745; GI 198745

UNSPSC

12352005

Hazard Statement

H302, H315, H319, H335

Target

5 alpha Reductase; Apoptosis

Type

Reference compound

Related Pathways

Apoptosis; Metabolic Enzyme/Protease

Applications

Cancer-programmed cell death

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/Dutasteride.html

Purity

99.75

Solubility

DMSO : 33.33 mg/mL (ultrasonic)

Smiles

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

Molecular Formula

C27H30F6N2O2

Molecular Weight

528.53

Precautions

H302, H315, H319, H335

References & Citations

[1]Lazier CB, et al. Dutasteride, the dual 5alpha-reductase inhibitor, inhibits androgen action and promotes cell death in the LNCaP prostate cancer cell line. Prostate. 2004 Feb 1;58 (2) :130-44.|[2]Biancolella M, et al. Effects of dutasteride on the expression of genes related to androgen metabolism and related pathway in human prostate cancer cell lines. Invest New Drugs. 2007 Oct;25 (5) :491-7.|[3]Bramson HN, et al. Unique preclinical characteristics of GG745, a potent dual inhibitor of 5AR. J Pharmacol Exp Ther. 1997 Sep;282 (3) :1496-502.|[4]Andriole GL, et al. Clinical usefulness of serum prostate specific antigen for the detection of prostate cancer is preserved in men receiving the dual 5alpha-reductase inhibitor dutasteride. J Urol. 2006 May;175 (5) :1657-62.|[5]Margiotta-Casaluci L, et al. Mode of action of human pharmaceuticals in fish: the effects of the 5-alpha-reductase inhibitor, dutasteride, on reproduction as a case study. Aquat Toxicol. 2013 Mar 15;128-129:113-23.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Reference compound1

Clinical Information

Launched

Chemical Information

Dutasteride

Dutasteride is an aza-steroid that is inasteride in which the tert-butyl group is replaced by a 2,5-bis(trifluoromethyl)phenyl group. A synthetic 4-azasteroid, dutasteride is a selective inhibitor of both the type 1 and type 2 isoforms of steroid 5alpha-reductase, an intracellular enzyme that converts testosterone to 5alpha-dihydrotestosterone. Dutasteride is used for the treatment of symptomatic benign prostatic hyperplasia in men with an enlarged prostate gland. It has a role as an EC 1.3.1.22 [3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+))] inhibitor and an antihyperplasia drug. It is an aza-steroid, a delta-lactam and a member of (trifluoromethyl)benzenes. It derives from a hydride of a 5alpha-androstane.

CAS Number	164656-23-9
PubChem CID	6918296
IUPAC Name	(1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-[2,5-bis(trifluoromethyl)phenyl]-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
Molecular Formula	C27H30F6N2O2
Molecular Weight	528.5
XLogP	5.4
Topological Polar Surface Area	58.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Heavy Atom Count	37
Formal Charge	0
Complexity	964

SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)NC4=C(C=CC(=C4)C(F)(F)F)C(F)(F)F)CC[C@@H]5[C@@]3(C=CC(=O)N5)C

InChI

InChI=1S/C27H30F6N2O2/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/h3,5,10,12-13,15-17,19,21H,4,6-9,11H2,1-2H3,(H,34,37)(H,35,36)/t15-,16-,17-,19+,21+,24-,25+/m0/s1

InChIKey

JWJOTENAMICLJG-QWBYCMEYSA-N

Chemical Structure

2D Structure

CAS: 164656-23-9

CID: 6918296

Formula: C27H30F6N2O2

MW: 528.5

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	528.5
XLogP3	5.4
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	2
Exact Mass	528.22114718
Monoisotopic Mass	528.22114718
Topological Polar Surface Area	58.2 Å²
Heavy Atom Count	37
Formal Charge	0
Complexity	964
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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