Dutasteride

Dutasteride Properties

Melting point	242-250°C
Boiling point	620.3±55.0 °C(Predicted)
Density	1.303±0.06 g/cm3(Predicted)
storage temp.	-20°C
solubility	DMSO: soluble2mg/mL, clear
pka	13.32±0.70(Predicted)
form	powder
color	white to beige
optical activity	[α]/D +18 to +24°, c = 1 in chloroform-d
BCS Class	2/4
InChIKey	JWJOTENAMICLJG-QWBYCMEYSA-N
SMILES	N1[C@@]2([H])[C@@](C)([C@@]3([H])CC[C@@]4(C)[C@]([H])([C@]3([H])CC2)CC[C@@H]4C(NC2=CC(C(F)(F)F)=CC=C2C(F)(F)F)=O)C=CC1=O
NCI Dictionary of Cancer Terms	Avodart; dutasteride
FDA UNII	O0J6XJN02I
NCI Drug Dictionary	Avodart
ATC code	G04CB02

Pharmacokinetic data

Protein binding	>99.5%
Excreted unchanged in urine	0.1%
Volume of distribution	300-500 Litres
Biological half-life	3-5 weeks / Unchanged

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS08
Signal word	Danger
Hazard statements	H351-H360FD
Precautionary statements	P201-P202-P280-P308+P313-P405-P501
HS Code	2937290000

Dutasteride price More Price(27)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	SML1221	Dutasteride ≥98% (HPLC)	164656-23-9	10mg	$100	2024-03-01	Buy
Sigma-Aldrich	1229922	Dutasteride United States Pharmacopeia (USP) Reference Standard	164656-23-9	200mg	$607	2024-03-01	Buy
Cayman Chemical	15956	Dutasteride ≥98%	164656-23-9	5mg	$68	2024-03-01	Buy
Cayman Chemical	15956	Dutasteride ≥98%	164656-23-9	10mg	$130	2024-03-01	Buy
Sigma-Aldrich	Y0001603	Dutasteride for system suitability European Pharmacopoeia (EP) Reference Standard	164656-23-9	y0001603	$152	2024-03-01	Buy

Product number	Packaging	Price	Buy
SML1221	10mg	$100	Buy
1229922	200mg	$607	Buy
15956	5mg	$68	Buy
15956	10mg	$130	Buy
Y0001603	y0001603	$152	Buy

Dutasteride Chemical Properties,Uses,Production

Description

Dutasteride is a synthetic 4-azasteroid compound. It is a dual inhibitor of type 1 and 2 isoforms of 5α-reductase unlike finasteride, the first marketed 5α-reductase inhibitor, which only acts on type 2 isozyme. Dutasteride is a 3-fold greater inhibitor of type-2 5α-reductase than finasteride in men and has greater effect on the type-l than on type-2 isozyme. In animal models,dutasteride exhibited superior efficacy and pharmacokinetics compared to finasteride. In patients with benign prostate hyperplasia, administration of dutasteride was shown to dose-dependently decrease serum dihydrotestosterone levels with greater efficacy as compared to finasteride (95% vs 67%). Serum testosterone levels increased with both active drugs, in conjunction with dihydrotestosterone suppression but remained within normal ranges. In long term studies, in men with moderate to severe benign prostate hyperplasia, once daily dutasteride significantly reduced prostate volume, reduced the risk of acute urinary retention and surgery by 57% and improved lower urinary tract symptoms and urinary flow measurements.

Chemical Properties

Dutasteride is a white to pale yellow powder It is soluble in ethanol (44 mg/mL), methanol (64 mg/mL), and polyethylene glycol 400 (3 mg/mL), but it is insoluble in water.

Originator

GlaxoSmithKline (UK)

Uses

Dutasteride is a dual inhibitor of 5a-reductase isoenzymes type 1 and 2; structurally related to Finasteride. Dutasteride is used in the treatment of benign prostatic hyperplasia. Dutasteride is associated with a low rate of transient serum aminotransferase elevations, but has yet to be linked to instances of clinically apparent acute liver injury.

Definition

ChEBI: 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 member of (trifluoromethyl)benzenes and a delta-lactam. It derives from a hydride of a 5alpha-androstane.

brand name

Avodart (GlaxoSmithKline).

Biological Functions

Similar to finasteride, dutasteride is a competitive and mechanism-based inhibitor not only of type 2 but also of type 1 5α-reductase isoenzymes, with which stable enzyme-NADP adduct complexes are formed, inhibiting the conversion of testosterone to DHT. The suppression of both type 1 and type 2 isoforms results in greater and more consistent reduction of plasma DHT than that observed for finasteride. The more effective dual inhibition of type 1 and type 2 5α-reductase isoforms lowers circulating DHT to a greater extent than with finasteride and shows advantages in treating BPH and other disease states (e.g., prostate cancer) that are DHT-dependent.

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).

Pharmacokinetics

The maximum effect of 0.5 mg daily doses of dutasteride on the suppression of DHT is dose-dependent and is observed within 1 to 2 weeks. After 2 weeks of 0.5 mg daily dosing, median plasma DHT concentrations were reduced by 90%, and after 1 year, the median decrease in plasma DHT was 94%. The median increase in plasma testosterone was 19% but remained within the physiological range. The drug also reduced serum prostatic specific antigen by approximately 50% at 6 months and total prostate volume by 25% at 2 years. Dutasteride produced improvements in quality of life and peak urinary flow rate and reduction of acute urinary retention without the need for surgery.

Clinical Use

Dutasteride belongs to azasteriod class of compounds and function as a 5α-reductase inhibitor1 which prevents the conversion of the androgen sex hormone testosterone into the more potent metabolite dihydrotestosterone (DHT). In 2009, South Korea has been licensed dutasteride for the treatment of androgenetic alopecia and in Japan 2015.
Dutasteride is the first and only double 5α reductase inhibitor used to treat Benign prostatic hyperplasia, and it is mainly used clinically to treat prostate enlargement, male-pattern hair loss, seborrheic hair loss, and hereditary hair loss.

Side effects

The main side effects are ED, decreased libido, gynecomastia, and ejaculation disorders. Long-term use (>4 years), however, did not reveal increased onset of sexual side effects. In addition, the combination of dutasteride and tamsulosin is well-tolerated and has the added advantage of rapid symptomatic relief.

Synthesis

Dutasteride can be prepared from 3-oxo-4-androstene-17β-carboxylic acid by several ways in 6 or 8 steps. In the preparation of dutasteride, the introduction of the carbon-carbon double bond in conjugation with C-3 carbonyl carbon of azaandrosteriods is one of the most important chemical reaction.
an efficient synthesis of dutasteride: utilizing benzoyl group as novel lactamic protecting group

in vivo

dutasteride, which inhibits both 5αr1/5αr2, is efficacious in blocking prostate cancer development or progression in c57bl/6 tramp x fvb mice [2].

Metabolism

Dutasteride is metabolised by the cytochrome P450 isoenzymes CYP3A4 and CYP3A5, and most of a dose is excreted as metabolites in the faeces.

Mode of action

The human body contains type I and type II 5α reductase, with type II found mainly in the prostate, and type I found mainly in the liver and skin. 5α reductase is the main cause for continuous benign prostate enlargement; it promotes the transformation of testosterone in patients’ prostate into the more active dihydrotestosterone, thus causing prostate cells to enlarge and the prostate to swell. Dutasteride can inhibit both type I and II 5α reductase at the same time. This type of simultaneous inhibiting mechanism can rapidly and continuously reduce prostate size, dramatically improve urination, and reduce the risk fo acute urinary retention and its related prostate surgeries.

Clinical claims and research

The American FDA approved a 2-year multicenter randomized double-blind control clinical trial – the first long term clinical assessment of the combined usage of Dutasteride and α receptor blockers. Included subjects were male patients with moderate to severe prostate enlargement (ages greater than or equal to 50, prostate volume (PV) ≥30 cc, serum prostate specific antigen (PSA) levels 1.5-10ng/ml, 5ml/sec < maximum urinary flow (Qmax) ≤15ml/sec, minimum urination ≥ 125ml, international prostate symptom score (IPSS) ≥ 12). Patients were first given a placebo for 4 weeks and then were randomly given either 0.5mg/day of Dutasteride and 0.4mg/day of Tamsulosin, only 0.5mg/day of Dutasteride, or only 0.4mg/day of Tamsulosin.
Results showed: After 12-24 months, the combined usage of Dutasteride with Tamsulosin had better curative effects than did individual usage.

References

[1] schmidt lj1, murillo h, tindall dj. gene expression in prostate cancer cells treated with the dual 5 alpha-reductase inhibitor dutasteride. j androl. 2004 nov-dec;25(6):944-53.
[2] opoku-acheampong ab1, unis d, henningson jn, beck ap, lindshield bl.preventive and therapeutic efficacy of finasteride and dutasteride in tramp mice. plos one. 2013 oct 18;8(10):e77738. doi: 10.1371/journal.pone.0077738. ecollection 2013.

Dutasteride Preparation Products And Raw materials

Raw materials

Preparation Products

Dutasteride Suppliers

Global( 619)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
HEBEI Meijinnong Import And Export Trade Co.,LTD	+8617363028569	admin@mjn-cn.com	China	78	58
Sigma Audley	+86-15937194204 +86-18126314766	nova@sh-teruiop.com	China	467	58
Hong Kong Excellence Biotechnology Co., Ltd.		ada@sh-teruiop.com	China	875	58
Hebei Dangtong Import and export Co LTD	+86-13910575315 +86-13910575315	admin@hbdangtong.com	China	1000	58
Henan Bao Enluo International TradeCo.，LTD	+86-17331933971 +86-17331933971	deasea125996@gmail.com	China	2472	58
Shaanxi Haibo Biotechnology Co., Ltd	+undefined18602966907	qinhe02@xaltbio.com	China	997	58
zhuzhou dingcheng meihei comestic co.,ltd	+8618873369619	dingchengbusiness8@163.com	China	260	58
Shaanxi TNJONE Pharmaceutical Co., Ltd	+8618092446649	sarah@tnjone.com	China	1143	58
Shanghai Getian Industrial Co., LTD	+86-15373193816 +86-15373193816	mike@ge-tian.com	China	269	58
Hebei Mojin Biotechnology Co.,Ltd	+86-15028179902	angelia@hbmojin.com	China	1177	58

Supplier	Advantage
HEBEI Meijinnong Import And Export Trade Co.,LTD	58
Sigma Audley	58
Hong Kong Excellence Biotechnology Co., Ltd.	58
Hebei Dangtong Import and export Co LTD	58
Henan Bao Enluo International TradeCo.，LTD	58
Shaanxi Haibo Biotechnology Co., Ltd	58
zhuzhou dingcheng meihei comestic co.,ltd	58
Shaanxi TNJONE Pharmaceutical Co., Ltd	58
Shanghai Getian Industrial Co., LTD	58
Hebei Mojin Biotechnology Co.,Ltd	58

View Lastest Price from Dutasteride manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-11-19	Dutasteride 164656-23-9	US $32.00-80.00 / mg		99.58%	10g	TargetMol Chemicals Inc.
2024-11-18	Dutasteride 164656-23-9	US $0.00 / g	1g	More Than 99%	100kg/Month	BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
2024-11-01	Dutasteride 164656-23-9	US $150.00-0.00 / g	1ASSAYS	98%+	10kgs	Wuhan Nutra Biotechnology Co.,Ltd

Dutasteride
164656-23-9
US $32.00-80.00 / mg
99.58%
TargetMol Chemicals Inc.

Dutasteride
164656-23-9
US $0.00 / g
More Than 99%
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.

Dutasteride
164656-23-9
US $150.00-0.00 / g
98%+
Wuhan Nutra Biotechnology Co.,Ltd

Dutasteride Spectrum

Dutasteride(164656-23-9)¹HNMR

164656-23-9(Dutasteride)Related Search:

2,5-Bis(trifluoromethyl)aniline 1,4-Bis(trifluoromethyl)-benzene Diphenyl ether Finasteride PHENYL VALERATE

PHENYL RESIN METHYL 4-AZA-5ALPHA-ANDROSTA-1-EN-3-ONE-17BETA-CARBOXYLATE Dihydrodutasteride 5β-Dutasteride (5a,6a,17)-N-(1,1-Dimethylethyl)-6-hydroxy-3-oxo-4-azaandrost-1-ene-17-carboxamide

2,6-BIS(TRIFLUOROMETHYL)ANILINE 4-Aza-5a-androstan-1-ene-3-one-17b-carboxylic acid 3,4-Bis-trifluoromethyl-phenylamine Dutasteride EP Impurity I Dutasteride Related Impurity 1

Ethyl 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylate JWJOTENAMICLJG-XHGXNVPLSA-N 5,6-Dehydro-17β-dutasteride

1of4

(1S,2R,7R,10S,11S,14S,15S)-N-[2,5-bis(trifluoroMethyl)phenyl]-2,15-diMethyl-5-oxo-6-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-3-ene-14-carboxaMide (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-[2,5-Bis(trifluoroMethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-diMethyl-2-oxo-1H-Indeno[5,4-f]quinoline-7-carboxaMide (5α,17β)- (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-[2,5-Bis(trifluoroMethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-diMethyl-2-oxo-1H-indeno[5,4-f]quinoline-7-carboxaMide-13C6 6β-Hydroxy Dutasteride 4-Azaandrost-1-ene-17-carboxaMide, N-[2,5-bis(trifluoroMethyl)phenyl]-3-oxo-, (5a,17b)- Avolve Dutasteride API (4aR,4bS,6aS,7S,9aS,9bS,11aR)-N-(2,5-Bis(trifluoroMethyl)phenyl)-4a,6a-diMethyl-2-oxo-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxaMide Dutasteride for system suitability Dutasteride (200 mg) Duagen (5a,17)-N-[2,5-Bis(trifluoromethyl)phenyl]-3-oxo-4-azaandrost-1-ene-17-carboxamide GI 198745 GG-745, GI-198745, 5α,17β)-N-[2,5-Bis(trifluoromethyl)phenyl]-3-oxo-4- Aza -androst-1-ene-17-carboxamide (5alpha,17beta)-n-{2,5-bis(trifluoromethyl)phenyl}-3-oxo-4-azaandrost-l-ene-17-carboxamide DUTASTERIDE Dutasteride(Avodart) 5,6-Dehydro-17&alpha Dutasteride (GG-745) 5,6-Dehydro-17&beta Dutasteride CRS Dutasteride for system suitability CRS 1H-Indeno[5,4-f]quinoline-7-carboxamide, N-[2,5-bis(trifluoromethyl)phenyl]-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-4a,6a-dimethyl-2-oxo-, (4aR,4bS,6aS,7S,9aS,9bS,11aR)- Dutasteride USP/EP/BP Dutasteride (1.0mg/ml in DMSO) Avodart , Dutasteride Anti-Hairloss CAS 164656-23-9 99% Powder Ru58841 Finasteride Dutasteride Dutasteride for system suitability (Y0001603) Dutasteride (Y0001598) Dutasteride (1229922) Avodart Oral Dutasteride Avodart utasteride Dutasteride CAS 164656-23-9 Dutarantine DUTASTERIDE 0.25% , 0.5% PELLETS 1,(5α)-ANDROSTEN-4-AZA-3-ONE-17β- N - [2,5-BIS (TRIFLUOROMETHYL0 PHENYL] - CARBOXAMIDE Dutasteride in Methanol 164656-23-9 64656-23-9 C27H30F6N2O2 Hormone Drugs API Inhibitors Intermediates & Fine Chemicals Pharmaceuticals Steroids Steroid and Hormone Miscellaneous Biochemicals All Inhibitors 164656-23-9