A retinoid
Related Products
Active Metabolite(s)
343884-oxo Isotretinoin
Metabolite(s)
230915,6-epoxy-13-cis Retinoic Acid
Technical Support & Resources

Visit our FAQ

Contact Us

Toll Free Phone (USA and Canada Only): (888) 526-5351
Direct Phone: (734) 975-3888

Request Technical Support

Technical Support Request

To streamline the process attach the appropriate questionnaire to your inquiry.

Download IHC QuestionnaireDownload WB Questionnaire

View Our Privacy Statement for details on how we use and protect your data. In addition, this site is protected by hCaptcha and its Privacy Policy and Terms of Service apply.

Isotretinoin

Item No. 21648

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
13-cis-retinoic acid
CAS Number
4759-48-2
Synonyms
  • AGN 190013
  • 13(Z)-Retinoic Acid
  • 13-cis-Vitamin A Acid
Molecular Formula
C20H28O2
Formula Weight
300.4
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMF:PBS (pH 7.2) (1:4): 0.2 mg/mlDMSO: 1 mg/ml
λmax
242, 356 nm
SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C\C(O)=O)C(C)(C)CCC1
InChi Code
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-
InChi Key
SHGAZHPCJJPHSC-XFYACQKRSA-N
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
Recommended Products

Certificates of Analysis & Batch Specific Data

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data packs, and GC-MS data.

Download most recent Certificate of Analysis for this product

    50 mg

    $36

    Add

    100 mg

    $63

    Add

    1 g

    $219

    Add

    5 g

    $402

    Add
    Cayman Chemical
    Visit Our Cancer Resource Center
    Find Tools & Resources to Study the Hallmarks of Cancer
    • Cancer cell signaling & regulation
    • Cancer metabolism
    • Tumor microenvironment
    EXPLORE NOW
    Product Description

    Isotretinoin is a retinoid that is converted in vivo into all-trans retinoic acid (Item No. 11017) 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.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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

    2. Giannini, F., Maestro, R., Vukosavljevic, T., et al. All-trans, 13-cis and 9-cis retinoic acids induce a fully reversible growth inhibition in HNSCC cell lines: Implications for in vivo retinoic acid use. Int. J. Cancer. 70(2), 194-200 (1997).

    3. Zouboulis, C.C., Korge, B., Akamatsu, H., et al. Effects of 13-cis-retinoic acid, all-trans-retinoic acid, and acitretin on the proliferation, lipid synthesis and keratin expression of cultured human sebocytes in vitro. J. Invest. Dermatol. 96(5), 792-797 (1991).

    4. Adams, J., Kiss, E., Arroyo, A.B., et al. 13-cis retinoic acid inhibits development and progression of chronic allograft nephropathy. Am. J. Pathol. 167(1), 285-298 (2005).

    5. Sieving, P.A., Chaudhry, P., Kondo, M., et al. Inhibition of the visual cycle in vivo by 13-cis retinoic acid protects from light damage and provides a mechanism for night blindness in isotretinoin therapy. Proc. Natl. Acad. Sci. USA 98(4), 1835-1840 (2001).