TRETINOIN

Search structure
Trade Names:
Synonyms:
Status: Approved (1971)
Entry Type: Small molecule
Molecule Category: Parent
ATC: D10AD01
UNII: 5688UTC01R

Structure
InChI Key SHGAZHPCJJPHSC-YCNIQYBTSA-N
Smile CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(=O)O)C(C)(C)CCC1
InChI
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+

Physicochemical Descriptors

Property Name Value
Molecular Formula C20H28O2
Molecular Weight 300.44
AlogP 5.6
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 37.3
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 22.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Retinoic acid receptor agonist DailyMed
Primary Target
Retinoic acid receptor-α
Retinoic acid receptor-β
Retinoic acid receptor-γ
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Auxiliary transport protein Fatty acid binding protein family
- - - - 100
Enzyme Hydrolase
- - - -
Enzyme Isomerase
- 820 800 820 -
Enzyme Lyase
- - - - 87-92
Enzyme Oxidoreductase
- 28700 - - 9
Enzyme Transferase
- 91000 - - -
Membrane receptor
- 180 - - -
Other cytosolic protein
- 370-600 0-0 - 100
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 1
1-563 1-9000 2-16 0-187 100-100
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 2
1-105 1-3000 0-17 0-17 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group B Nuclear hormone receptor subfamily 1 group B member 3
0-50 1-18 0-19 0-19 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group F Nuclear hormone receptor subfamily 1 group F member 1
- 200 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group F Nuclear hormone receptor subfamily 1 group F member 3
18000 200 - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group F
18000 0-25119 280 - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 1
54-1084 - 9-53 0-350 10
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 2
5-1400 - 306-1000 1-881 -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 2 Nuclear hormone receptor subfamily 2 group B Nuclear hormone receptor subfamily 2 group B member 3
2-1225 350 306-350 1-288 -
Unclassified protein
- 6700-21000 - - 72-86

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Melanosis 4 D008548 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 3 D016553 ClinicalTrials
Purpura, Thrombocytopenic, Idiopathic 3 D016553 ClinicalTrials
Carcinoma, Squamous Cell 3 D002294 ClinicalTrials
Myelodysplastic Syndromes 3 D009190 ClinicalTrials
Leukemia 3 D007938 ClinicalTrials
Rosacea 3 D012393 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 3 D002289 ClinicalTrials
Myeloproliferative Disorders 3 D009196 ClinicalTrials
Carcinoma, Basal Cell 3 D002280 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Cholangitis, Sclerosing 2 D015209 ClinicalTrials
Lymphoma 2 D008223 ClinicalTrials
Multiple Myeloma 2 D009101 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
Melanoma 2 D008545 ClinicalTrials
Keratosis, Actinic 2 D055623 ClinicalTrials
Anti-Neutrophil Cytoplasmic Antibody-Associated Vasculitis 2 D056648 ClinicalTrials
Carcinoma, Adenoid Cystic 2 D003528 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Kidney Neoplasms 2 D007680 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Lentigo 2 D007911 ClinicalTrials
Severe Acute Respiratory Syndrome 2 D045169 ClinicalTrials
Emphysema 2 D004646 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Anemia 2 D000740 ClinicalTrials
Myelodysplastic-Myeloproliferative Diseases 1 D054437 ClinicalTrials
Hematologic Neoplasms 1 D019337 ClinicalTrials
Amyotrophic Lateral Sclerosis 1 D000690 ClinicalTrials
Hypercholesterolemia 0 D006937 ClinicalTrials

Related Entries

MCS

Mixture
Mixture
Mixture

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
21.11
General disorders and administration site conditions
20.43
Injury, poisoning and procedural complications
18.91
Nervous system disorders
6.05
Blood and lymphatic system disorders
4.6
Vascular disorders
3.41
Respiratory, thoracic and mediastinal disorders
2.86
Infections and infestations
2.73
Cardiac disorders
2.46
Product issues
2.29
Gastrointestinal disorders
2.18

Cross References

Resources Reference
CAS NUMBER 302-79-4
ChEBI 15367
ChEMBL CHEMBL38
DrugBank DB00755
DrugCentral 2722
EPA CompTox DTXSID7021239
FDA SRS 5688UTC01R
Human Metabolome Database HMDB0001852
Guide to Pharmacology 2644
KEGG C00777
PDB REA
PharmGKB PA164746900
PubChem 444795
SureChEMBL SCHEMBL19091395
ZINC ZINC000012358651
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