Tadalafil

SKU: T0455

Category: API's & Intermediates

Synonyms: GF196960 , (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; 171596-29-5
CAS-Number: C₂₂H₁₉N₃O₄
Molecular Formula: 389.40
Molecular Weight

Product Data
Handling
Safety Information
Details

Specifications

Purity: ≥98%
Identity: 1H-NMR
Appearance: White to beige powder

Properties

Density: ~1.5 g/cm3 (Predicted)
Refractive Index: n20D 1.76 (Predicted)
Optical Activity: a20/D +56.3°, c = 0.5 in chloroform, a20/D +71°, c = 1 in chloroform (lit.)
UV / Vis: 221, 284, 292 nm (lit.)
Boiling Point: ~679.1° C at 760 mmHg (Predicted)
Melting Point: 276-279° C (lit.)
Solvents: DMSO (20 mg/ml), DMF (25 mg/ml)

Shipping: AMBIENT
Use / Stability: Stable for at least 2 years after receipt when stored at -20°C.
Handling Advice: Protect from light and moisture.
Long Term Storage: -20°C
Short Term Storage: -20°C

Transportation: Not dangerous goods
Signal word: Warning
GHS Symbol: GHS07
Precautionary statements: P305 + P351 + P338
Hazard statements: H315-H319-H335

Description: Tadalafil is a potent long-acting and selective inhibitor of the cGMP specific phosphodiesterase 5 (PDE5, IC50 = 1.2 nM). It is selective for PDE5 over PDE1-4 and 7-10 (IC50s = 9.2-280 ?M), however, it does also inhibit PDE11 (IC50 = 11 nM). In vivo, tadalafil (10 mg/kg) decreases production of the proinflammatory cytokines TNF-α, IL-1β, and IL-6 and improves renal function in a rat model of ischemia/reperfusion injury. Formulations containing tadalafil have been used to treat erectile dysfunction, pulmonary arterial hypertension, benign prostatic hyperplasia (BPH) and lower urinary tract dysfunction. Also delays tumor growth in a mouse model via inhibition of MDSC-mediated immunosuppression.
InChi: 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
References: (1) A. Daugan, et al., J. Med. Chem. 46, 4533 (2003) , (2) G.L. Card, et al., Structure 12, 2233 (2004) , (3) P. Serafini, et al., J. Exp. Med. 203, 2691 (2006) , (4) J. Kuan & G. Brock, Expert Opin. Investig. Drugs 11, 1605 (2002) (Review) , (5) R.A. Kloner, et al., Am. J. Cardiol. 92, 37M (2003) (Review) , (6) S.A. Arif & H. Poon, Clin. Ther. 33, 993 (2011) (Review)
InChi Key: WOXKDUGGOYFFRN-IIBYNOLFSA-N
Smiles: [H][C@@]12N(C(CN(C)C2=O)=O)[C@H](C3=CC=C(OCO4)C4=C3)C5=C(C(C=CC=C6)=C6N5)C1

Tadalafil is a potent long-acting and selective inhibitor of the cGMP specific phosphodiesterase 5 (PDE5, IC50 = 1.2 nM). It is selective for PDE5 over PDE1-4 and 7-10 (IC50s = 9.2-280 ?M), however, it does also inhibit PDE11 (IC50 = 11 nM). In vivo, tadalafil (10 mg/kg) decreases production of the proinflammatory cytokines TNF-α, IL-1β, and IL-6 and improves renal function in a rat model of ischemia/reperfusion injury. Formulations containing tadalafil have been used to treat erectile dysfunction, pulmonary arterial hypertension, benign prostatic hyperplasia (BPH) and lower urinary tract dysfunction. Also delays tumor growth in a mouse model via inhibition of MDSC-mediated immunosuppression.

Artikelnummer: T0455 Kategorie: API's & Intermediates

Zusätzliche Information

Zusätzliche Information

Synonyms	GF196960, (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
Purity	≥98%
Appearance	White to beige powder
CAS-Number	171596-29-5
Molecular Formula	C22H19N3O4
Molecular Weight	389.40
Identity	1H-NMR
Solvents	DMSO (20 mg/ml), DMF (25 mg/ml)
Melting Point	276-279° C (lit.)
Boiling Point	~679.1° C at 760 mmHg (Predicted)
UV / Vis	221, 284, 292 nm (lit.)
Optical Activity	a20/D +56.3°, c = 0.5 in chloroform, a20/D +71°, c = 1 in chloroform (lit.)
Refractive Index	n20D 1.76 (Predicted)
Density	~1.5 g/cm3 (Predicted)
Smiles	[H][C@@]12N(C(CN(C)C2=O)=O)[C@H](C3=CC=C(OCO4)C4=C3)C5=C(C(C=CC=C6)=C6N5)C1
InChi Key	WOXKDUGGOYFFRN-IIBYNOLFSA-N
Shipping	AMBIENT
Short Term Storage	-20°C
Long Term Storage	-20°C
Handling Advice	Protect from light and moisture.
Use / Stability	Stable for at least 2 years after receipt when stored at -20°C.
Hazard statements	H315-H319-H335
Precautionary statements	P305 + P351 + P338
GHS Symbol	GHS07
Signal word	Warning
Transportation	Not dangerous goods
References	(1) A. Daugan, et al., J. Med. Chem. 46, 4533 (2003), (2) G.L. Card, et al., Structure 12, 2233 (2004), (3) P. Serafini, et al., J. Exp. Med. 203, 2691 (2006), (4) J. Kuan & G. Brock, Expert Opin. Investig. Drugs 11, 1605 (2002) (Review), (5) R.A. Kloner, et al., Am. J. Cardiol. 92, 37M (2003) (Review), (6) S.A. Arif & H. Poon, Clin. Ther. 33, 993 (2011) (Review)
InChi	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
Quantity	500 mg, Bulk