A prodrug form of diclofenac
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Diclofenac amide

Item No. 21969

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1-(2,6-dichlorophenyl)-1,3-dihydro-2H-indol-2-one
CAS Number
15362-40-0
Synonyms
  • Diclofenac Lactam
  • 1-(2,6-Dichlorophenyl)oxindole
  • NSC 621845
Molecular Formula
C14H9Cl2NO
Formula Weight
278.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: >50 mg/mlDMSO: >40 mg/mlEthanol: >35 mg/mlPBS (pH 7.2): >9 mg/ml
SMILES
ClC1=C(N2C(CC3=C2C=CC=C3)=O)C(Cl)=CC=C1
InChi Code
InChI=1S/C14H9Cl2NO/c15-10-5-3-6-11(16)14(10)17-12-7-2-1-4-9(12)8-13(17)18/h1-7H,8H2
InChi Key
JCICIFOYVSPMHG-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 mg

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    100 mg

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    500 mg

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    1 g

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    Product Description

    Diclofenac amide is a prodrug form of the non-steroidal anti-inflammatory drug (NSAID) diclofenac (Item Nos. 70680 | 22983).1 It decreases paw thickness in a rat model of carrageenan-induced paw edema when administered at a dose of 100 μmol/kg and decreases acetic acid-induced writhing in mice at 100 μmol/kg.2 Diclofenac amide has reduced ulcerogenicity in rats compared to diclofenac. It is also a degradation product of diclofenac resulting from photo-transformation or spontaneous cyclization in strongly acidic pH conditions.3,4 Diclofenac amide has been used as a synthetic intermediate in the synthesis of compounds with anticancer activity as well as compounds with COX-1, COX-2, and/or 5-lipoxygenase (5-LO) inhibitory activity.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Santos, J., Moreira, V., Campos, M.L., et al. Pharmacological evaluation and preliminary pharmacokinetics studies of a new diclofenac prodrug without gastric ulceration effect. Int. J. Mol. Sci. 13(11), 15305-15320 (2012).

    2. Chung, M.C., dos Santos, J.L., Oliveira, E.V., et al. Synthesis, ex vivo and in vitro hydrolysis study of an indoline derivative designed as an anti-inflammatory with reduced gastric ulceration properties. Molecules 14(9), 3187-3197 (2009).

    3. Epold, I., Dulova, N., and Trapido, M. Degradation of diclofenac in aqueous solution by homogeneous and heterogeneous photolysis. J. Environ. Eng. Ecol. Sci. 1(3), 1-8 (2012).

    4. Mertz, N., Larsen, S.W., Kristensen, J., et al. Long-acting diclofenac ester prodrugs for joint injection: Kinetics, mechanism of degradation, and in vitro release from prodrug suspension. J. Pharm. Sci. 105(10), 3079-3087 (2016).

    5. Kaur, M., and Singh, P. Targeting tyrosine kinase: Development of acridone – pyrrole – oxindole hybrids against human breast cancer. Bioorg. Med. Chem. Lett. 29(1), 32-35 (2018).

    6. Shaveta, Singh, A., Kaur, M., et al. Rational design, synthesis and evaluation of chromone-indole and chromone-pyrazole based conjugates: Identification of a lead for anti-inflammatory drug. Eur. J. Med. Chem. 77, 185-192 (2014).