Repositioning Candidate Details
| Candidate ID: | R0354 |
| Source ID: | DB00982 |
| Source Type: | approved |
| Compound Type: | small molecule |
| Compound Name: | Isotretinoin |
| Synonyms: | (7E,9E,11E,13Z)-retinoic acid; 13-cis-retinoic acid; 13-cis-Vitamin A acid; 13-RA; cis-RA; Isotretinoin; Neovitamin A acid |
| Molecular Formula: | C20H28O2 |
| SMILES: | C\C(\C=C\C1=C(C)CCCC1(C)C)=C/C=C/C(/C)=C\C(O)=O |
| Structure: |
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| DrugBank Description: | Isotretinoin is a retinoid derivative of vitamin A used in the treatment of severe recalcitrant acne. It was most widely marketed under the brand name Accutane, which has since been discontinued. Isotretinoin is associated with major risks in pregnancy and is therefore only available under the iPLEDGE program in the United States. The first isotretinoin-containing product was FDA approved on 7 May 1982. |
| CAS Number: | 4759-48-2 |
| Molecular Weight: | 300.4351 |
| DrugBank Indication: | Isotretinoin is indicated to treat severe recalcitrant nodular acne and patients ≥12 years enrolled in the iPLEDGE program. |
| DrugBank Pharmacology: | The pharmacodynamics of isotretinoin are poorly understood. |
| DrugBank MoA: | Isotretinoin produces its effects through altering progress through the cell cycle, cell differentiation, survival, and apoptosis. These actions reduce sebum production, preventing the blockage of pores, and growth of acne causing bacteria. Isotretinoin and 4-oxo-isotretinoin both significantly reduce the production of sebum. Isotretinoin has little to no affinity for retinol binding proteins (RBPs) and retinoic acid nuclear receptors (RARs). Tretinoin and 4-oxo-tretinion bind to the RAR-γ receptor, which is suspected to be part of the action of acne treatment by isotretinoin. Isotretinoin induces apoptosis in sebocytes, leading to a decrease in sebum production. Isotretinoin also reduces the formation of comedones by reducing hyperkeratinization through an unknown mechanism. Isotretinoin does not directly kill bacteria but it does reduce the size of sebum ducts and makes the microenvironment less hospitable to acne causing bacteria. It may also increase immune mechanisms and alter chemotaxis of monocytes to reduce inflammation. There is preliminary evidence suggesting isotretinoin may interact with FoxO1, which may explain a substantial number of isotretinoin's unexplained actions. |
| Targets: | Retinoic acid receptor alpha other/unknown; Retinoic acid receptor gamma |
| Inclusion Criteria: | Therapeutic strategy associated |
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