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SML1221

Sigma-Aldrich

Dutasteride

≥98% (HPLC)

Synonym(s):

17β-N-[2,5-Bis(trifluoromethyl)phenyl]carbamoyl-4-aza-5α-androst-1-en-3-one, (5α,17β)-N-[2,5-Bis(trifluoromethyl)phenyl]-3-oxo-4-azaandrost-1-ene-17-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C27H30F6N2O2
CAS Number:
164656-23-9
Molecular Weight:
528.53
MDL number:
MFCD00937869
UNSPSC Code:
51111800
PubChem Substance ID:
329825728
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +18 to +24°, c = 1 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C1C=C[C@@]2(C)[C@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@@H]4C(NC5=CC(C(F)(F)F)=CC=C5C(F)(F)F)=O)([H])N1

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

InChI key

JWJOTENAMICLJG-QWBYCMEYSA-N

Gene Information

human ... SRD5A1(6715) , SRD5A2(6716) , SRD5A3(79644)

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Biochem/physiol Actions

Dutasteride is a potent dual inhibitor of 5α-reductase isoenzymes types 1 and 2 (IC50 = 6 nM 5-AR1; 7 nM 5-AR2). Dutasteride blocks testosterone conversion to dihydrotesterone, and is used clinically for treating benign prostatic hyperplasia (BPH).

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H351,H360FD

Hazard Classifications

Carc. 2 - Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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5α-Reductase Inhibition Coupled with Short Off Cycles Increases Survival in the LNCaP Xenograft Prostate Tumor Model on Intermittent Androgen Deprivation Therapy.
Pascal, L.E., et al.
The Journal of Urology, Oct 31 (2014)
Sungsin Jo et al.
Arthritis research & therapy, 22(1), 121-121 (2020-05-26)
Ankylosing spondylitis (AS) is characteristically male-predominant, and progressive spinal ankylosis affects male patients more severely; however, the hormonal effects in males with AS are poorly understood. In the present study, the regulatory effects of dutasteride, a 5-α reductase inhibitor that
Christopher Wu et al.
Expert opinion on pharmacotherapy, 14(10), 1399-1408 (2013-06-12)
Benign prostatic hyperplasia (BPH) is an age-related phenomenon associated with prostatic enlargement and bladder outlet obstruction that can cause significant lower urinary tract symptoms that greatly affect quality of life. Dutasteride is a selective inhibitor of type 1 and type
Akira Tsujimura et al.
Urology, 85(1), 274-274 (2014-12-03)
To evaluate histologic change in human prostate samples treated with dutasteride and to elucidate direct effects of dutasteride on human prostate tissue, the present study was conducted by using a xenograft model with improved severe combined immunodeficient (super-SCID) mice, although

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