TADALAFIL, (6R ,12AS)-

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

Structure Search

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19782492 | https://www.ncbi.nlm.nih.gov/pubmed/28470986 | https://www.ncbi.nlm.nih.gov/pubmed/28197557 | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000436/WC500026314.pdf | https://www.ncbi.nlm.nih.gov/pubmed/18019566 | https://www.ncbi.nlm.nih.gov/pubmed/24116968

(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

Targets

Primary Target	Pharmacology	Condition	Potency
Phosphodiesterase 5A 30 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19782492	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Chiral separation of two pairs of enantiomers of tadalafil by high-performance liquid chromatography.	2007 Sep	18019566
The identification of (-)-trans-tadalafil, tadalafil, and sildenafil in counterfeit Cialis and the optical purity of tadalafil stereoisomers.	2010 Feb 5	19782492
Stereochemistry of the tadalafil diastereoisomers: a critical assessment of vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion.	2013 Nov 14	24116968
Doubly charged trimeric cluster ions: effective in mutual chiral recognition of tadalafil and three proton pump inhibitors.	2017 Feb 27	28197557
Nickel(II)-assisted enantiomeric differentiation and quantitation of tadalafil by direct electrospray ionization mass spectrometry.	2017 Jul	28470986

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

TADALAFIL, (6R ,12AS)-

Common Name

English

(-)-TADALAFIL 6R ,12AS DIASTEREOMER

Common Name

English

(6R ,12AS )-6-(1,3-BENZODIOXOL-5-YL)-2,3,6,7,12,12A-HEXAHYDRO-2-METHYL-PYRAZINO(1',2':1,6)PYRIDO(3,4-B )INDOLE-1,4-DIONE

Systematic Name

English

TADALAFIL 6R ,12AS DIASTEREOMER

Common Name

English

CIS-ENT-TADALAFIL

Common Name

English

TADALAFIL IMPURITY A [EP IMPURITY]

Common Name

English

TADALAFIL IMPURITY, 6R ,12AS DIASTEREOMER- [USP IMPURITY]

Common Name

English

PYRAZINO(1',2':1,6)PYRIDO(3,4-B)INDOLE-1,4-DIONE, 6-(1,3-BENZODIOXOL-5-YL)-2,3,6,7,12,12A-HEXAHYDRO-2-METHYL-, (6R,12AS)-

Systematic Name

English

12-EPI-TADALAFIL

Common Name

English

(6R,12AS)-6-(1,3-BENZODIOXOL-5-YL)-2-METHYL-2,3,6,7,12,12A-HEXAHYDROPYRAZINO(1',2':1,6)PYRIDO(3,4-B)INDOLE-1,4-DIONE

Systematic Name

English

Code System Code Type Description

PUBCHEM

9821704

Created by admin on Sat Dec 16 07:52:57 GMT 2023 , Edited by admin on Sat Dec 16 07:52:57 GMT 2023

PRIMARY

FDA UNII

E319TQ0B6R

Created by admin on Sat Dec 16 07:52:57 GMT 2023 , Edited by admin on Sat Dec 16 07:52:57 GMT 2023

PRIMARY

CAS

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

PRIMARY

SUBSTANCE RECORD


					E319TQ0B6R

TADALAFIL, (6R ,12AS)-