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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H19N3O4
Molecular Weight 389.404
Optical Activity ( + )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Tadalafil, (6S,12aR)-

SMILES

CN1CC(=O)N2[C@H](CC3=C(NC4=CC=CC=C34)[C@@H]2C5=CC=C6OCOC6=C5)C1=O

InChI

InChIKey=WOXKDUGGOYFFRN-IERDGZPVSA-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+/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H19N3O4
Molecular Weight 389.404
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

(6S ,12AR)-Tadalafil is an inactive 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

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
MGY23Z94HY
Record Status Validated (UNII)
Record Version