Structure Database (LMSD)
Common Name
13-cis-retinoic acid,Isotretinoin
Systematic Name
Synonyms
3D model of 13-cis-retinoic acid,Isotretinoin
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Isotretinoin is a retinoid that is converted in vivo into all-trans retinoic acid and has diverse biological activities.1,2,3,4 It increases the doubling time and transcription of retinoic acid receptor β (RARβ) mRNA in Hep2, FaDu, CCL-17, SCC-9, SCC-15, and SCC-25 human oral squamous cell carcinoma cells when used at a concentration of 1 μM.2 Isotretinoin inhibits proliferation of primary human sebocytes (IC50 = 10 μM).3 It also decreases triglyceride, stearyl ester, and free fatty acid synthesis and modulates keratin expression in primary human sebocytes at a concentration of 0.1 μM. Isotretinoin (2 mg/kg per day) reduces chronic rejection damage and decreases mRNA expression of IFN-γ and IL-10 in allografts in chronic Fisher344➛Lewis transplant mice, an allograft nephropathy model.4 It also slows rod and cone recovery and prevents light-induced photoreceptor damage in an albino rat model of photoreceptor degeneration when administered at a dose of 40 mg/kg.5 Formulations containing isotretinoin have been used in the treatment of severe recalcitrant nodular acne.
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
SHGAZHPCJJPHSC-XFYACQKRSA-N
InChi (Click to copy)
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-
SMILES (Click to copy)
C1C(C)(C)C(/C=C/C(=C/C=C/C(=C\C(O)=O)/C)/C)=C(C)CC1
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
22
Rings
1
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
343.94
Topological Polar Surface Area
37.30
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
2
logP
5.60
Molar Refractivity
93.76
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Created at
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Updated at
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