Compound Detail

CHEMBL705

ALITRETINOIN

💊 Approved Drug

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💊 Approved Drug

CC1=C(/C=C/C(C)=C\C=C\C(C)=C\C(=O)O)C(C)(C)CCC1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL705
Name	ALITRETINOIN
Phase	Approved
Structure Type	MOL
InChI Key	SHGAZHPCJJPHSC-ZVCIMWCZSA-N
Therapeutic	✓ Yes

Known Names

9-cis retinoic acid 9-cis-retinoic acid AGN 192013 AGN-192013 AGN192013 Alitretinoin Alitretinoina Alitretinoine ALRT-1057 ALRT1057 BAL-4079 LG-100057 +7 more

Targets

153

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

300.4

MW (Da)

5.60

ALogP

HBA

HBD

37.3

PSA (Å²)

0.53

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
First Approval	1999
Availability	Prescription
Chirality	Achiral

Routes of Administration

Topical

Flags

Natural Product

USAN Stem	-retin-
USAN Year	1998

Extended Properties

Molecular Formula	C20H28O2
MW	300.44
Aromatic Rings	0
Heavy Atoms	22
NP-Likeness	2.31

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Retinoid receptor agonist	AGONIST	Retinoid receptor	✓	✓

Indications

Eczema Neoplasms Sarcoma, Kaposi Hand Dermatoses Lichen Planus Lupus Erythematosus, Cutaneous Psoriasis Breast Neoplasms

ATC Classification

D11AH04

alitretinoin

Level 1: DERMATOLOGICALS

Level 2: OTHER DERMATOLOGICAL PREPARATIONS

L01XF02

alitretinoin

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

EC50 82 meas. best 9.1

Kd 42 meas. best 9.1

Ki 18 meas. best 9.3

IC50 11 meas. best 8.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Retinoic acid receptor beta CHEMBL2008	Ki	9.3	8.8033	0.5	3
Retinoic acid receptor beta CHEMBL2008	EC50	9.1	7.895	0.8	12
Retinoic acid receptor gamma CHEMBL2003	Kd	9.1	7.448	0.8	5
Retinoic acid receptor alpha CHEMBL2055	EC50	9.0	7.1857	1.0	14
Retinoic acid receptor gamma CHEMBL2003	Ki	9.0	8.35	1.0	2
Retinoic acid receptor RXR-alpha CHEMBL2061	EC50	8.82	7.4947	1.5	17
Retinoic acid receptor RXR-alpha CHEMBL2061	Kd	8.82	7.5731	1.5	13
HL-60 CHEMBL383	EC50	8.7	8.7	2.0	2
Retinoic acid receptor RXR-beta CHEMBL1870	EC50	8.59	7.2313	2.6	8
Retinoic acid receptor RXR-beta CHEMBL1870	Ki	8.42	8.2	3.8	3
Retinoic acid receptor RXR-gamma CHEMBL4402	Kd	8.4	8.4	4.0	1
Retinoic acid receptor RXR-gamma CHEMBL2004	IC50	8.4	8.4	4.0	1
Retinoic acid receptor gamma CHEMBL2003	EC50	8.4	7.71	4.0	11
Retinoic acid receptor RXR-gamma CHEMBL2004	EC50	8.37	7.2543	4.3	7
Retinoic acid receptor alpha CHEMBL2792	Kd	8.15	8.15	7.0	1
Retinoic acid receptor beta CHEMBL2008	IC50	8.15	8.15	7.0	1
Retinoic acid receptor beta CHEMBL2008	Kd	8.15	7.2925	7.0	4
Retinoic acid receptor beta CHEMBL3266	Kd	8.15	8.15	7.0	1
Retinoic acid receptor alpha CHEMBL2055	IC50	8.15	8.15	7.0	1
Retinoic acid receptor RXR-alpha CHEMBL2061	Ki	8.1	7.33	8.0	5
Unchecked CHEMBL612545	Kd	8.05	8.05	9.0	1
Retinoic acid receptor alpha CHEMBL2055	Kd	7.96	7.2675	11.0	4
Retinoic acid receptor RXR-beta CHEMBL1870	Kd	7.96	7.7467	11.0	3
Retinoic acid receptor RXR-gamma CHEMBL2004	Ki	7.96	7.8175	11.0	4
Retinoic acid receptor RXR-beta CHEMBL4047	Kd	7.92	7.87	12.0	2
Retinoic acid receptor RXR-beta CHEMBL1870	IC50	7.92	7.92	12.0	1
Unchecked CHEMBL612545	EC50	7.89	7.3933	13.0	3
Retinoic acid receptor RXR-gamma CHEMBL2004	Kd	7.85	7.755	14.0	4
Retinoic acid receptor gamma CHEMBL2003	IC50	7.77	7.77	17.0	1
Retinoic acid receptor gamma CHEMBL4177	Kd	7.77	7.77	17.0	1
Retinoic acid receptor alpha CHEMBL2055	Ki	7.65	7.65	22.3	1
Retinoic acid receptor RXR-alpha CHEMBL2061	IC50	7.54	7.52	29.0	2
Retinoic acid receptor alpha CHEMBL2792	IC50	7.51	7.51	31.0	1
Retinoic acid receptor RXR-alpha CHEMBL3084	Kd	7.5	7.5	32.0	1
Mus musculus CHEMBL375	IC50	7.24	7.24	58.0	2
Retinoic acid receptor RXR-alpha CHEMBL3084	IC50	7.09	7.09	82.0	1
Retinoic acid receptor RXR-alpha CHEMBL4431	EC50	6.96	6.94	110.0	2
Retinoic acid receptor RXR-gamma CHEMBL4402	EC50	6.91	6.91	124.0	1
Retinoic acid receptor RXR-beta CHEMBL4047	EC50	6.89	6.89	128.0	1
Retinoic acid receptor RXR-alpha CHEMBL3084	EC50	6.7	6.7	200.0	1
Nuclear receptor subfamily 4immunitygroup A member 1 CHEMBL1293229	Kd	6.09	6.09	810.0	1
Oxysterols receptor LXR-alpha CHEMBL2808	EC50	5.96	5.96	1090.0	1
Oxysterols receptor LXR-beta CHEMBL4093	EC50	5.76	5.76	1730.0	1
Nuclear receptor ROR-gamma CHEMBL1741186	EC50	4.85	4.85	14000.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
Cmax	810.0	nM	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Retinoic acid receptor beta	Ki	=	0.5	nM	9.3	Binding affinity towards cRAR-beta-2 receptor by displacing 1.1 nM 3[H]-9-cis-RA	-
Retinoic acid receptor beta	Ki	=	0.7	nM	9.15	Binding affinity towards cRAR-beta-2 receptor by displacing 0.82 nM 3[H]all-tran...	-
Retinoic acid receptor beta	EC50	=	0.8	nM	9.1	Agonist activity at human RAR-beta expressed in CHO-K1 cells by PathHunter assay	35797110
Retinoic acid receptor gamma	Kd	=	0.8	nM	9.1	Dissociation constant for Retinoic acid receptor gamma	16190748
Retinoic acid receptor alpha	EC50	=	1.0	nM	9.0	Agonist activity at human RAR-alpha expressed in CHO-K1 cells by PathHunter assa...	35797110
Retinoic acid receptor gamma	Ki	=	1.0	nM	9.0	Agonistic activity towards retinoic acid receptor-gamma	9435893
Retinoic acid receptor RXR-alpha	EC50	=	1.5	nM	8.82	Transcriptional activation in CV-1 cells expressing retinoid X receptor RXR alph...	11428923
Retinoic acid receptor RXR-alpha	Kd	=	1.5	nM	8.82	Dissociation constant for Retinoid X receptor alpha	16190748
HL-60	EC50	=	2.0	nM	8.7	Transglutaminase activity in HL-60 cdm-1 cells	7636843
HL-60	EC50	=	2.0	nM	8.7	Induction of transglutaminase (TGase) activity in HL-60 cells	8784454
Retinoic acid receptor RXR-beta	EC50	=	2.6	nM	8.59	Effective concentrations against Retinoic acid receptor RXR-beta	7650690
Retinoic acid receptor beta	EC50	=	3.0	nM	8.52	Transcriptional activation in CV-1 cells expressing retinoic acid receptor RAR b...	11428923
Retinoic acid receptor RXR-alpha	Kd	=	3.0	nM	8.52	Inhibition of binding to human Retinoic acid receptor RXR DEF domain	8809153
Retinoic acid receptor beta	EC50	=	3.3	nM	8.48	Transcriptional activation of Retinoic acid receptor RAR beta	7636843
Retinoic acid receptor beta	EC50	=	3.3	nM	8.48	Transcriptional activation for RAR beta receptor	-
Retinoic acid receptor beta	EC50	=	3.3	nM	8.48	Transcriptional activation of Retinoic acid receptor RAR beta	10585206
Retinoic acid receptor RXR-beta	Ki	=	3.8	nM	8.42	Agonistic activity towards retinoid X receptor-beta	9435893
Retinoic acid receptor RXR-gamma	IC50	=	4.0	nM	8.4	Binding affinity against retinoic Acid X gamma receptor using [3H]- -9-cis-Retin...	8308867
Retinoic acid receptor RXR-alpha	EC50	=	4.0	nM	8.4	Agonist activity at human RXR-alpha	27652492
Retinoic acid receptor gamma	EC50	=	4.0	nM	8.4	Transcriptional activation in CV-1 cells expressing retinoic acid receptor RAR g...	11428923

Literature References

PubMed	DOI	Target Context	# Activities
39258574	10.1021/acs.jmedchem.4c01231	Retinoic acid receptor RXR-alpha	6
28169169	10.1016/j.bmcl.2017.01.066	Oxysterols receptor LXR-alpha	6
24801499	10.1021/jm5004792	Retinoic acid receptor RXR-alpha	4
8809153	10.1021/jm9603126	Cellular retinoic acid-binding protein 1	3
28169169	10.1016/j.bmcl.2017.01.066	Homo sapiens	3
8709094	10.1021/jm960285j	Retinoic acid receptor RXR-gamma	3
20014752	10.1021/tx900326k	Hepatotoxicity	3
8709094	10.1021/jm960285j	Retinoic acid receptor RXR-beta	3
8709094	10.1021/jm960285j	Retinoic acid receptor beta	3
8709094	10.1021/jm960285j	Retinoic acid receptor gamma	3
8709094	10.1021/jm960285j	Retinoic acid receptor RXR-alpha	3
8709094	10.1021/jm960285j	Retinoic acid receptor alpha	3
8809153	10.1021/jm9603126	Retinoic acid receptor RXR-alpha	3
8308867	10.1021/jm00029a013	Retinoic acid receptor gamma	2
8308867	10.1021/jm00029a013	Retinoic acid receptor beta	2
8308867	10.1021/jm00029a013	Retinoic acid receptor RXR-alpha	2
7650690	10.1021/jm00017a021	Retinoic acid receptor RXR-alpha	2
8308867	10.1021/jm00029a013	Retinoic acid receptor alpha	2
-	10.1016/S0960-894X(97)00420-4	Retinoic acid receptor beta	2
8410972	10.1021/jm00070a003	Retinoic acid receptor beta	2

Data from ChEMBL 36 via Core Engine