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SML1877

Sigma-Aldrich

Tadalafil

≥98% (HPLC)

Synonym(s):

(6R,12aR)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methylpyrazino[1′,2′:1,6]pyrido[3,4-b]indole-1,4-dione, ICI-351

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About This Item

Empirical Formula (Hill Notation):
C22H19N3O4
CAS Number:
171596-29-5
Molecular Weight:
389.40
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +68 to +78°, c = 1 in chloroform-d

color

white to beige

solubility

DMSO: 20 mg/mL, clear

storage temp.

−20°C

InChI

1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1

InChI key

WOXKDUGGOYFFRN-IIBYNOLFSA-N

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Biochem/physiol Actions

Tadalafil is a potent, selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) used to treat erectile dysfunction, pulmonary hypertension, and benign prostatic hyperplasia (BPH).
This β-carboline-based drug has a long elimination half-life of about 18 hours.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

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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Kazuhiko Fukumoto et al.
International journal of urology : official journal of the Japanese Urological Association, 24(3), 206-210 (2016-12-30)
To investigate the effects of tadalafil on vascular endothelial function and cardiovascular risk in patients with prostatic hyperplasia. Tadalafil 5 mg was given to 20 patients with prostatic hyperplasia for whom an α1-blocker was ineffective. Voiding symptoms and vascular endothelial
Alaa E El-Sisi et al.
Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie, 84, 861-869 (2016-10-14)
Life threatening conditions characterized by renal ischemia/reperfusion (RIR) such as kidney transplantation, partial nephrectomy, renal artery angioplasty, cardiopulmonary bypass and aortic bypass surgery, continue to be among the most frequent causes of acute renal failure. The current study investigated the
Hossein Karami et al.
Urology journal, 13(6), 2920-2926 (2016-12-09)
To compare monotherapy with tadalafil or tamsulosin and their combination therapy in men with benignprostatic hyperplasia and erectile dysfunction by comparing IPSS score, prostate volume and Qmax and someother outcomes. This randomized, single-blind, paralleled group clinical trial was done in
Luqiang Wang et al.
American journal of physiology. Endocrinology and metabolism, 315(4), E446-E453 (2018-06-20)
Cyclic GMP (cGMP) is an important intracellular regulator of endochondral bone growth and skeletal remodeling. Tadalafil, an inhibitor of the phosphodiesterase (PDE) type 5 (PDE5) that specifically hydrolyzes cGMP, is increasingly used to treat children with pulmonary arterial hypertension (PAH)
A once-daily dose of tadalafil for erectile dysfunction: compliance and efficacy.
Washington III S L and Shindel A W
Drug design, development and therapy, 4, 159-159 (2010)

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