TADALAFIL, (6S ,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-KKSFZXQISA-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

(6S ,12AS)-Tadalafil is an inactive enantiomer 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

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, (6S ,12AS)-

Common Name

English

ENT-TADALAFIL

Common Name

English

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

Common Name

English

(6S ,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

(-)-TRANS-TADALAFIL

Common Name

English

TADALAFIL IMPURITY B [EP IMPURITY]

Common Name

English

TADALAFIL 6S ,12AS ENANTIOMER

Common Name

English

(6S,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

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-, (6S,12AS)-

Systematic Name

English

Code System Code Type Description

CAS

629652-72-8

Created by admin on Sat Dec 16 08:39:53 GMT 2023 , Edited by admin on Sat Dec 16 08:39:53 GMT 2023

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FDA UNII

HZ6QJN0D4Z

Created by admin on Sat Dec 16 08:39:53 GMT 2023 , Edited by admin on Sat Dec 16 08:39:53 GMT 2023

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PUBCHEM

9908373

Created by admin on Sat Dec 16 08:39:53 GMT 2023 , Edited by admin on Sat Dec 16 08:39:53 GMT 2023

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EPA CompTox

DTXSID40212165

Created by admin on Sat Dec 16 08:39:53 GMT 2023 , Edited by admin on Sat Dec 16 08:39:53 GMT 2023

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SUBSTANCE RECORD


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TADALAFIL, (6S ,12AS)-