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
1. Blaner, W.S. Cellular metabolism and actions of 13-cis-retinoic acid. J. Am. Acad. Dermatol. 45(5), S129-S135 (2001).
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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Updated at
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