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Compound Detail

CHEMBL547

ISOTRETINOIN
💊 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 CHEMBL547
Name ISOTRETINOIN
Phase Approved
Structure Type MOL
InChI Key SHGAZHPCJJPHSC-XFYACQKRSA-N
Therapeutic ✓ Yes

Known Names

13 cis-retinoic acid 13-cis-retinoic acid Absorica Absorica ld Accutane Amnesteem Claravis Isotretinoin Isotretinoina Isotretinoine Isotrex Myorisan +11 more
13
Targets
27
Activities
3
Assay Types
20
PK Parameters
20
Publications
23
Known Names
20
Indications
1
Mechanisms

Molecular Properties

300.4
MW (Da)
5.60
ALogP
1
HBA
1
HBD
37.3
PSA (Ų)
0.53
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning Natural Product
USAN Stem -retin-
USAN Year 1979

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 Brain Neoplasms Breast Neoplasms Central Nervous System Neoplasms Ganglioneuroblastoma Head and Neck Neoplasms Kidney Neoplasms Lung Neoplasms Medulloblastoma Neuroblastoma Rosacea Severe Acute Respiratory Syndrome Uterine Cervical Dysplasia Azoospermia Emphysema Glioblastoma Glioblastoma Glomerulosclerosis, Focal Segmental HIV Infections Ichthyosis

ATC Classification

D10AD04
isotretinoin
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
D10AD54
isotretinoin, combinations
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
D10BA01
isotretinoin
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 22 meas. best 7.31
Ki 4 meas. best 6.27
EC50 1 meas. best 5.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Liver
CHEMBL613642
 IC50 7.31 7.31 49.4 1
Unchecked
CHEMBL612545
 IC50 7.0 7.0 100.0 1
Olfactory receptor 51E2
CHEMBL4523454
 IC50 6.8 6.8 160.0 1
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 6.33 6.33 462.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 Ki 6.27 6.27 540.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
 IC50 6.07 6.07 848.0 1
Cellular retinoic acid-binding protein 1
CHEMBL4945
 IC50 6.05 6.05 900.0 2
Adenosine receptor A3
CHEMBL256
 Ki 5.63 5.63 2357.0 1
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 5.6 5.6 2529.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
 Ki 5.52 5.52 3019.0 1
Adenosine receptor A3
CHEMBL256
 IC50 5.38 5.38 4169.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 5.36 5.36 4400.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
 IC50 5.18 5.18 6612.0 1
Plasmodium falciparum
CHEMBL364
 IC50 5.1 4.9571 7943.3 7
Unchecked
CHEMBL612545
 Ki 4.7 4.7 20000.0 1
A549
CHEMBL392
 IC50 4.45 4.45 35800.0 1
Bile salt export pump
CHEMBL6020
 IC50 4.43 4.43 37100.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.4 4.385 39700.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 10.0 ng.hr.mL-1 Homo sapiens
AUC 3.703 ng.hr.mL-1 Homo sapiens
AUC 3033.37 ng.hr.mL-1 Homo sapiens
AUC 6003.81 ng.hr.mL-1 Homo sapiens
AUC 5082.0 ng.hr.mL-1 Homo sapiens
AUC 10010.66 ng.hr.mL-1 Homo sapiens
CL/F 17.96 L/hr Homo sapiens
Cmax 2869.13 nM Homo sapiens
Cmax 1001.86 nM Homo sapiens
Cmax 1908.2 nM Homo sapiens
Cmax 2436.43 nM Homo sapiens
Cmax 2870.0 nM Homo sapiens
Css min 352.32 ng/mL Homo sapiens
T1/2 21.0 hr Homo sapiens
T1/2 21.0 hr Homo sapiens
T1/2 15.69 hr Homo sapiens
Tmax 5.3 hr Homo sapiens
Tmax 3.2 hr Homo sapiens
Tmax 6.0 hr Homo sapiens
Tmax 4.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Liver IC50 = 49.4 nM 7.31 Induction of mitochondrial dysfunction in Sprague-Dawley rat liver mitochondria ... 24799086
Unchecked IC50 = 100.0 nM 7.0 Tested for its concentration necessary to achieve a 50% reduction in absolute ce... 7799400
Olfactory receptor 51E2 IC50 = 160.0 nM 6.8 Antagonist activity at PSGR/OR51E2 (unknown origin) expressed in human Hana3A ce... -
Mitogen-activated protein kinase 1 IC50 = 462.0 nM 6.33 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ... -
5-hydroxytryptamine receptor 2B Ki = 540.0 nM 6.27 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2B IC50 = 848.0 nM 6.07 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Cellular retinoic acid-binding protein 1 IC50 = 900.0 nM 6.05 Tested for its ability to inhibit the binding of (all-E-)-RA to cytoplasmic reti... 7799400
Cellular retinoic acid-binding protein 1 IC50 = 900.0 nM 6.05 Inhibition of binding to chick skin Cytoplasmic retinoic acid binding protein 7608895
Adenosine receptor A3 Ki = 2357.0 nM 5.63 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Mitogen-activated protein kinase 14 IC50 = 2529.0 nM 5.6 DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substra... -
Alpha-2B adrenergic receptor Ki = 3019.0 nM 5.52 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Adenosine receptor A3 IC50 = 4169.0 nM 5.38 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
NON-PROTEIN TARGET EC50 = 4400.0 nM 5.36 Antiviral activity against JC polyomavirus M1/SVEdelta infected in human SVG-A c... 19258267
Alpha-2B adrenergic receptor IC50 = 6612.0 nM 5.18 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Plasmodium falciparum IC50 = 7943.28 nM 5.1 Antiplasmodial activity against Plasmodium falciparum 7G8 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
Plasmodium falciparum IC50 = 10000.0 nM 5.0 Antiplasmodial activity against Plasmodium falciparum HB3 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum Dd2 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum GB4 after 72 hrs by SYBR g... 19734910
Plasmodium falciparum IC50 = 12589.25 nM 4.9 Antiplasmodial activity against Plasmodium falciparum D10 after 72 hrs by SYBR g... 19734910

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
16472241 10.2174/1570163043334794 Hepatotoxicity 18
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
9572893 10.1021/jm970635h NON-PROTEIN TARGET 6
20014752 10.1021/tx900326k Hepatotoxicity 3
19231037 10.1016/j.ejmech.2009.01.029 NON-PROTEIN TARGET 2
24799086 10.1002/hep.27206 Homo sapiens 2
19258267 10.1128/aac.01614-08 ADMET 2
7608895 10.1021/jm00013a006 Cellular retinoic acid-binding protein 1 2
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
6754935 10.1021/jm00353a001 Mus musculus 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
23956101 10.1093/toxsci/kft176 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2

Data from ChEMBL 36 via Core Engine