Tadalafil, (6R,12aS)-

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 Search

SMILES

CN1CC(=O)N2[C@@H](CC3=C(NC4=C3C=CC=C4)[C@H]2C5=CC=C6OCOC6=C5)C1=O

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

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

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 31 Target ID: CHEMBL1827 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19782492	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2596

PubMed

Title	Date	PubMed
Nickel(II)-assisted enantiomeric differentiation and quantitation of tadalafil by direct electrospray ionization mass spectrometry.	2017-07	28470986
Doubly charged trimeric cluster ions: effective in mutual chiral recognition of tadalafil and three proton pump inhibitors.	2017-02-27	28197557
Stereochemistry of the tadalafil diastereoisomers: a critical assessment of vibrational circular dichroism, electronic circular dichroism, and optical rotatory dispersion.	2013-11-14	24116968
The identification of (-)-trans-tadalafil, tadalafil, and sildenafil in counterfeit Cialis and the optical purity of tadalafil stereoisomers.	2010-02-05	19782492
Chiral separation of two pairs of enantiomers of tadalafil by high-performance liquid chromatography.	2007-09	18019566

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:44:42 GMT 2025` Edited by `admin` on `Mon Mar 31 21:44:42 GMT 2025`
Record UNII	E319TQ0B6R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Tadalafil, (6R,12aS)-

Common Name

English

(-)-TADALAFIL 6R, 12AS DIASTEREOMER

Preferred 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

(6R,12aS)-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

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

12-epi-Tadalafil

Common Name

English

Code System Code Type Description

PUBCHEM

9821704

Created by admin on Mon Mar 31 21:44:42 GMT 2025 , Edited by admin on Mon Mar 31 21:44:42 GMT 2025

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FDA UNII

E319TQ0B6R

Created by admin on Mon Mar 31 21:44:42 GMT 2025 , Edited by admin on Mon Mar 31 21:44:42 GMT 2025

PRIMARY

CAS

171596-27-3

Created by admin on Mon Mar 31 21:44:42 GMT 2025 , Edited by admin on Mon Mar 31 21:44:42 GMT 2025

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Tadalafil

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