Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C22H19N3O4 |
| Molecular Weight | 389.404 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC3=C(NC4=C3C=CC=C4)[C@H](N1C(=O)CN(C)C2=O)C5=CC6=C(OCO6)C=C5
InChI
InChIKey=WOXKDUGGOYFFRN-HRAATJIYSA-N
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+/m0/s1
| Molecular Formula | C22H19N3O4 |
| Molecular Weight | 389.404 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
(6R,12AS)-Tadalafil is a diastereomer of "Tadalafil" which is the active ingredient in Cialis which is used to treat erectile dysfunction. Tadalafil has 4 isomers [(RR), (SS), (RS), and (SR)], of which (RR) is the name-sake isomer and potent inhibitor of phosphodiesterase-5. The (RS) diastereomer is the only other isomer with some PDE-5 inhibitory activity.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Chiral separation of two pairs of enantiomers of tadalafil by high-performance liquid chromatography. | 2007 Sep |
|
| Stereochemistry of the tadalafil diastereoisomers: a critical assessment of vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion. | 2013 Nov 14 |
|
| Doubly charged trimeric cluster ions: effective in mutual chiral recognition of tadalafil and three proton pump inhibitors. | 2017 Feb 27 |
|
| Nickel(II)-assisted enantiomeric differentiation and quantitation of tadalafil by direct electrospray ionization mass spectrometry. | 2017 Jul |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:52:57 GMT 2023
by
admin
on
Sat Dec 16 07:52:57 GMT 2023
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| Record UNII |
E319TQ0B6R
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| Record Status |
Validated (UNII)
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E319TQ0B6R
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171596-27-3
Created by
admin on Sat Dec 16 07:52:57 GMT 2023 , Edited by admin on Sat Dec 16 07:52:57 GMT 2023
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| Related Record | Type | Details | ||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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