Compound Detail

CHEMBL38

TRETINOIN

💊 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	CHEMBL38
Name	TRETINOIN
Phase	Approved
Structure Type	MOL
InChI Key	SHGAZHPCJJPHSC-YCNIQYBTSA-N
Therapeutic	✓ Yes

Known Names

Aberel Acticin All-trans retinoic acid All-trans-retinoic acid Altreno Atralin Avita Eudyna Kerlocal NSC-122758 Oristar rna Renova +15 more

246

Targets

840

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	1971
Availability	Prescription
Chirality	Achiral

Routes of Administration

Oral Topical

Flags

Black Box Warning Natural Product

USAN Stem	-retin-
USAN Year	1970

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
Retinoic acid receptor agonist	AGONIST	Retinoic acid receptor	✓	✓

Indications

Acne Vulgaris Hyperpigmentation Leukemia, Promyelocytic, Acute Melanosis Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Basal Cell Carcinoma, Non-Small-Cell Lung Carcinoma, Squamous Cell Leukemia Leukemia, Myeloid, Acute Myelodysplastic Syndromes Myeloproliferative Disorders Purpura, Thrombocytopenic, Idiopathic Purpura, Thrombocytopenic, Idiopathic Rosacea Skin Neoplasms Anemia Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis

ATC Classification

D10AD01

tretinoin

Level 1: DERMATOLOGICALS

Level 2: ANTI-ACNE PREPARATIONS

D10AD51

tretinoin, combinations

Level 1: DERMATOLOGICALS

Level 2: ANTI-ACNE PREPARATIONS

L01XF01

tretinoin

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning

hematological toxicity

Country: United States

Black Box Warning

teratogenicity

Country: United States

Black Box Warning

carcinogenicity

Country: United States

Activity Summary

IC50 653 meas. best 11.0

EC50 104 meas. best 9.7

Kd 54 meas. best 9.7

Ki 29 meas. best 10.4

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Trachea CHEMBL613452	IC50	11.0	11.0	0.0	1
Retinoic acid receptor gamma CHEMBL2003	Ki	10.4	9.0533	0.0	6
Retinoic acid receptor alpha CHEMBL2055	Ki	10.0	8.2525	0.1	4
F9 CHEMBL614296	IC50	10.0	10.0	0.1	1
Nuclear receptor ROR-beta CHEMBL3091268	IC50	9.82	7.1067	0.1	3
Retinoic acid receptor gamma CHEMBL2003	EC50	9.7	8.3871	0.2	21
Retinoic acid receptor gamma CHEMBL2003	Kd	9.7	8.1023	0.2	13
Retinoic acid receptor gamma CHEMBL4177	EC50	9.66	9.44	0.2	2
Retinoic acid receptor beta CHEMBL2008	Kd	9.4	8.0417	0.4	12
Retinoic acid receptor beta CHEMBL2008	Ki	9.4	8.6	0.4	5
Retinoic acid receptor RXR-alpha CHEMBL2061	Ki	9.4	7.4467	0.4	3
Cellular retinoic acid-binding protein 1 CHEMBL3208	Kd	9.4	9.4	0.4	2
Retinoic acid receptor RXR-beta CHEMBL1870	Ki	9.3	7.54	0.5	3
Retinoic acid receptor gamma CHEMBL2003	IC50	9.3	8.7533	0.5	3
Retinoic acid receptor beta CHEMBL3266	EC50	9.28	8.9667	0.5	3
Unchecked CHEMBL612545	IC50	9.2	6.4333	0.6	6
Retinoic acid receptor alpha CHEMBL2055	IC50	9.11	7.7575	0.8	4
Retinoic acid receptor beta CHEMBL2008	IC50	9.05	7.8725	0.9	4
Retinoic acid receptor beta CHEMBL2008	EC50	9.0	7.8742	1.0	24
Retinoic acid receptor alpha CHEMBL2055	EC50	9.0	7.3536	1.0	22
Retinoic acid receptor CHEMBL2363069	EC50	9.0	9.0	1.0	1
Unchecked CHEMBL612545	EC50	9.0	9.0	1.0	1
Retinoic acid receptor alpha CHEMBL2792	EC50	8.92	8.4667	1.2	3
Retinoic acid receptor RXR-gamma CHEMBL2004	Ki	8.85	7.4367	1.4	3
SK-BR-3 CHEMBL613834	IC50	8.77	8.77	1.7	1
Retinoic acid receptor RXR-gamma CHEMBL2004	EC50	8.7	6.4083	2.0	6
Cellular retinoic acid-binding protein 2 CHEMBL4172	Kd	8.7	8.7	2.0	2
Retinoic acid receptor alpha CHEMBL2055	Kd	8.64	7.8982	2.3	11
Retinoic acid receptor gamma CHEMBL4177	IC50	8.4	8.4	4.0	2
Retinoic acid receptor RXR-beta CHEMBL1870	EC50	8.35	6.2683	4.5	6
Retinoic acid receptor alpha CHEMBL2792	IC50	8.3	8.2467	5.0	3
Retinoic acid receptor beta CHEMBL3266	IC50	8.3	8.3	5.0	2
HL-60 CHEMBL383	EC50	8.3	8.3	5.0	2
Retinoic acid receptor RXR-gamma CHEMBL4402	EC50	8.22	7.12	6.0	2
T47D CHEMBL614361	IC50	8.22	7.46	6.0	2
Retinoic acid receptor RXR-alpha CHEMBL2061	Kd	8.05	7.665	9.0	2
Retinoic acid receptor beta CHEMBL3266	Kd	7.89	7.89	13.0	1
Retinoic acid receptor alpha CHEMBL2792	Kd	7.82	7.82	15.0	1
Human gammaherpesvirus 4 CHEMBL613124	IC50	7.81	7.81	15.4	1
Retinoic acid receptor gamma CHEMBL4177	Kd	7.75	7.75	18.0	1
MV4-11 CHEMBL613835	IC50	7.68	7.68	21.0	1
ATN-1 CHEMBL2366277	IC50	7.52	7.52	30.3	1
Mus musculus CHEMBL375	IC50	7.51	7.51	31.0	2
Retinoic acid receptor RXR-alpha CHEMBL2061	EC50	7.27	6.23	54.0	9
NON-PROTEIN TARGET CHEMBL3879801	IC50	7.0	5.2833	100.0	3
MC-IXC CHEMBL1075495	IC50	6.81	6.81	154.4	1
Amyloid-beta precursor protein CHEMBL2487	IC50	6.75	6.75	180.0	1
HH CHEMBL2366310	IC50	6.71	6.71	195.5	1
Nuclear receptor ROR-gamma CHEMBL1741186	IC50	6.7	6.7	199.5	1
Nuclear receptor ROR-alpha CHEMBL5868	IC50	6.7	6.7	199.5	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	1686.0	ng.hr.mL-1	Mus musculus
AUC	6472.0	ng.hr.mL-1	Mus musculus
AUC	9896.0	ng.hr.mL-1	Mus musculus
F	49.0	%	Homo sapiens
F	90.0	%	Homo sapiens
F	1.41	%	Homo sapiens
F	0.82	%	Homo sapiens
T1/2	-	hr	Rattus norvegicus
T1/2	0.75	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Trachea	IC50	=	0.01	nM	11.0	Reversal of keratinization in vitamin A-deficient hamster trachea after 10 days ...	17489579
Retinoic acid receptor gamma	Ki	=	0.04	nM	10.4	Agonistic activity towards retinoic acid receptor-gamma	9435893
Retinoic acid receptor alpha	Ki	=	0.1	nM	10.0	Binding affinity towards human Retinoic acid receptor alpha	-
F9	IC50	=	0.1	nM	10.0	Induction of terminal differentiation in mouse F9 cells assessed by measuring se...	17489579
Nuclear receptor ROR-beta	IC50	=	0.15	nM	9.82	Inhibition of ROR beta (unknown origin)-mediated transactivation	-
Retinoic acid receptor gamma	Kd	=	0.2	nM	9.7	Dissociation constant for Retinoic acid receptor gamma	16190748
Retinoic acid receptor gamma	EC50	=	0.2	nM	9.7	Activity at human RARgamma ligand binding domain expressed in COS7 cells co-tran...	19058965
Retinoic acid receptor gamma	EC50	=	0.22	nM	9.66	Transactivation of mouse Gal4-fused RARgamma-LBD expressed in COS-7 cells after ...	29288071
Retinoic acid receptor gamma	Kd	=	0.3	nM	9.52	Apparent binding constant against Retinoic acid receptor gamma in HeLa cell GAl-...	8691435
Cellular retinoic acid-binding protein 1	Kd	=	0.4	nM	9.4	Inhibition of [3H]ATRA binding to murine Cytoplasmic retinoic acid binding prote...	8809153
Cellular retinoic acid-binding protein 1	Kd	=	0.4	nM	9.4	Binding affinity for mouse Cytoplasmic retinoic acid binding protein type 1	7608895
Retinoic acid receptor RXR-alpha	Ki	=	0.4	nM	9.4	Binding affinity for retinoic acid receptor RAR alpha	12161154
Retinoic acid receptor beta	Ki	=	0.4	nM	9.4	Binding affinity towards cRAR-beta-2 receptor by displacing 1.1 nM 3[H]-9-cis-RA	-
Retinoic acid receptor beta	Kd	=	0.4	nM	9.4	Apparent binding constant for Retinoic acid receptor beta in HeLa cellGAL-4 tran...	8691435
Retinoic acid receptor gamma	EC50	=	0.5	nM	9.3	Transcriptional activation of retinoic acid receptor RAR gamma	-
Retinoic acid receptor gamma	EC50	=	0.5	nM	9.3	Transcriptional activation of Retinoic acid receptor RAR gamma	10585206
Retinoic acid receptor gamma	EC50	=	0.5	nM	9.3	Transcriptional activation for RAR gamma receptor	-
Retinoic acid receptor gamma	IC50	=	0.5	nM	9.3	Inhibition of [3H]ATRA-Hl60 binding to Retinoic acid receptor gamma	10762038
Retinoic acid receptor beta	Ki	=	0.5	nM	9.3	Binding affinity towards cRARbeta2 receptor by displacing 0.82 nM 3[H]all-trans-...	-
Retinoic acid receptor RXR-beta	Ki	=	0.5	nM	9.3	Binding affinity for retinoic acid receptor RAR beta	12161154

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	295
2849641	10.1021/np50059a019	Unchecked	18
16472241	10.2174/1570163043334794	Hepatotoxicity	18
2578190	10.1021/jm00379a021	Cricetinae gen. sp.	16
6208361	10.1021/jm00377a022	Unchecked	15
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
7799400	10.1021/jm00052a009	Mus musculus	13
22197381	10.1016/j.ejmech.2011.12.002	Albumin	12
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
16504501	10.1016/j.bmcl.2006.02.020	Mus musculus	9
19375825	10.1016/j.ejmech.2009.03.029	LNCaP	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
29439915	10.1016/j.bmc.2018.02.002	Unchecked	8
28927789	10.1016/j.bmcl.2017.09.005	IMR-32	8
28927789	10.1016/j.bmcl.2017.09.005	SK-N-AS	7
31278031	10.1016/j.bmcl.2019.06.024	HL-60	7
-	10.6019/CHEMBL4495565	SARS-CoV-2	6
16441065	10.1021/np058080d	Unchecked	6
9572893	10.1021/jm970635h	NON-PROTEIN TARGET	6
6208361	10.1021/jm00377a022	Mus musculus	6

Data from ChEMBL 36 via Core Engine