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    Tadalafil

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      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

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