Structure Database (LMSD)

Common Name
13-cis-retinoic acid,Isotretinoin
Systematic Name
Synonyms
LM ID
LMPR01090021
Formula
Exact Mass
Calculate m/z
300.20893
Status
Curated


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

KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
VVA0020
PubChem CID
Cayman ID
GuidePharm ID

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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