Carbanilide
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MedKoo CAT#: 571456

CAS#: 102-07-8

Description: Carbanilide, also known as diphenylurea, has many derivatives that have been used to treat a number of medical conditions. These include treatments for Alzheimer's, protozoal infections, and certain tumors.


Chemical Structure

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Carbanilide
CAS# 102-07-8

Theoretical Analysis

MedKoo Cat#: 571456
Name: Carbanilide
CAS#: 102-07-8
Chemical Formula: C13H12N2O
Exact Mass: 212.095
Molecular Weight: 212.25
Elemental Analysis: C, 73.56; H, 5.70; N, 13.20; O, 7.54

Price and Availability

Size Price Availability Quantity
25.0g USD 180.0 2 Weeks
100.0g USD 325.0 2 Weeks
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Synonym: Carbanilide; Acardite; Diphenylurea, AD 30; AD30; AD-30; BRN 0782650; BRN-0782650; BRN0782650

IUPAC/Chemical Name: 1,3-Diphenylurea

InChi Key: GWEHVDNNLFDJLR-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H12N2O/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H,(H2,14,15,16)

SMILES Code: O=C(NC1=CC=CC=C1)NC2=CC=CC=C2

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 212.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Galan JF, Germany E, Pawlowski A, Strickland L, Galinato MG. Theoretical and spectroscopic analysis of N,N'-diphenylurea and N,N'-dimethyl-N,N'-diphenylurea conformations. J Phys Chem A. 2014 Jul 17;118(28):5304-15. doi: 10.1021/jp503539m. Epub 2014 Jul 8. PubMed PMID: 24971844.

2: Chang JC, Lai CC, Chiu SH. A redox-controllable molecular switch based on weak recognition of BPX26C6 at a diphenylurea station. Molecules. 2015 Jan 22;20(2):1775-87. doi: 10.3390/molecules20021775. PubMed PMID: 25621422.

3: Ríos Martínez CH, Lagartera L, Kaiser M, Dardonville C. Antiprotozoal activity and DNA binding of N-substituted N-phenylbenzamide and 1,3-diphenylurea bisguanidines. Eur J Med Chem. 2014 Jun 23;81:481-91. doi: 10.1016/j.ejmech.2014.04.083. Epub 2014 May 9. PubMed PMID: 24865793.

4: Farokhcheh A, Alizadeh N. Photochemically induced fluorescence studies of 1,3-diethyl-1,3-diphenylurea as stabilizer and its quantitative determination. Forensic Sci Int. 2014 Jul;240:35-40. doi: 10.1016/j.forsciint.2014.04.012. Epub 2014 Apr 15. PubMed PMID: 24795294.

5: Badawi HM, Förner W. Analysis of the infrared and Raman spectra of the symmetrically substituted 1,3-diphenylurea and 1,3-diphenylacetone (dibenzyl ketone). Spectrochim Acta A Mol Biomol Spectrosc. 2012 Sep;95:435-41. doi: 10.1016/j.saa.2012.04.014. Epub 2012 Apr 23. PubMed PMID: 22580138.

6: Huang W, Lv D, Yu H, Sheng R, Kim SC, Wu P, Luo K, Li J, Hu Y. Dual-target-directed 1,3-diphenylurea derivatives: BACE 1 inhibitor and metal chelator against Alzheimer's disease. Bioorg Med Chem. 2010 Aug 1;18(15):5610-5. doi: 10.1016/j.bmc.2010.06.042. Epub 2010 Jun 17. PubMed PMID: 20620068.

7: Ettrich TJ, Seufferlein T. Regorafenib. Recent Results Cancer Res. 2014;201:185-96. doi: 10.1007/978-3-642-54490-3_10. Review. PubMed PMID: 24756792.

8: Ganis P, Avitabile G, Benedetti E, Pedone C, Goodman M. Crystal and molecular structure of n,n'-diethyl-n,n'-diphenylurea. Proc Natl Acad Sci U S A. 1970 Sep;67(1):426-33. PubMed PMID: 16591865; PubMed Central PMCID: PMC283222.

9: Siragusa M, Carra A, Salvia L, Puglia AM, De Pasquale F, Carimi F. Genetic instability in calamondin (Citrus madurensis Lour.) plants derived from somatic embryogenesis induced by diphenylurea derivatives. Plant Cell Rep. 2007 Aug;26(8):1289-96. Epub 2007 Mar 2. PubMed PMID: 17333016.

10: Hansen RS, Diness TG, Christ T, Demnitz J, Ravens U, Olesen SP, Grunnet M. Activation of human ether-a-go-go-related gene potassium channels by the diphenylurea 1,3-bis-(2-hydroxy-5-trifluoromethyl-phenyl)-urea (NS1643). Mol Pharmacol. 2006 Jan;69(1):266-77. Epub 2005 Oct 11. PubMed PMID: 16219910.

11: Burrows WJ, Leworthy DP. Metabolism of N,N'-diphenylurea by cytokinin-dependent tobacco callus: identification of the glucoside. Biochem Biophys Res Commun. 1976 Jun 21;70(4):1109-14. PubMed PMID: 942432.

12: Mok MC, Kim SG, Armstrong DJ, Mok DW. Induction of cytokinin autonomy by N,N'-diphenylurea in tissue cultures of Phaseolus lunatus L. Proc Natl Acad Sci U S A. 1979 Aug;76(8):3880-4. PubMed PMID: 16592694; PubMed Central PMCID: PMC383939.

13: Furuya Y, Itoho K, Miyagi H. Kinetic studies of the triethylenediamine-catalyzed transamidation of 1,3-diphenylurea with n-butylamine in dioxane. Bull Chem Soc Jpn. 1969 Aug;42(8):2348-51. PubMed PMID: 5346838.

14: Doi H, Barletta J, Suzuki M, Noyori R, Watanabe Y, Langstrom B. Synthesis of 11C-labelled N,N'-diphenylurea and ethyl phenylcarbamate by a rhodium-promoted carbonylation via [11C]isocyanatobenzene using phenyl azide and [11C]carbon monoxide. Org Biomol Chem. 2004 Nov 7;2(21):3063-6. Epub 2004 Sep 13. PubMed PMID: 15505707.

15: Giorgi I, Biagi G, Bianucci AM, Borghini A, Livi O, Leonardi M, Pietra D, Calderone V, Martelli A. N6-1,3-diphenylurea derivatives of 2-phenyl-9-benzyladenines and 8-azaadenines: synthesis and biological evaluation as allosteric modulators of A2A adenosine receptors. Eur J Med Chem. 2008 Aug;43(8):1639-47. Epub 2007 Oct 24. PubMed PMID: 18045744.

16: Burrows WJ. Mode of action of N,N'-diphenylurea: The isolation and identification of the cytokinins in the transfer RNA from tobacco callus grown in the presence of N,N'-diphenylurea. Planta. 1976 Jan;130(3):313-6. doi: 10.1007/BF00387838. PubMed PMID: 24424645.

17: Wu SN, Peng H, Chen BS, Wang YJ, Wu PY, Lin MW. Potent activation of large-conductance Ca2+-activated K+ channels by the diphenylurea 1,3-bis-[2-hydroxy-5-(trifluoromethyl)phenyl]urea (NS1643) in pituitary tumor (GH3) cells. Mol Pharmacol. 2008 Dec;74(6):1696-704. doi: 10.1124/mol.108.049106. Epub 2008 Sep 22. PubMed PMID: 18809671.

18: Sørensen SR, Arbeli Z, Aamand J, Ronen Z. Metabolism of diphenylurea by a Marinobacter sp. isolated from a contaminated ephemeral stream bed in the Negev Desert. FEMS Microbiol Lett. 2002 Aug 6;213(2):199-204. PubMed PMID: 12167538.

19: Mikles-Robertson F, Dave C, Porter CW. Apparent autophagocytosis of mitochondria in L1210 leukemia cells treated in vitro with 4,4'-diacetyl-diphenylurea-bis(guanylhydrazone). Cancer Res. 1980 Apr;40(4):1054-61. PubMed PMID: 6892613.

20: Elmedyb P, Olesen SP, Grunnet M. Activation of ERG2 potassium channels by the diphenylurea NS1643. Neuropharmacology. 2007 Aug;53(2):283-94. Epub 2007 May 21. PubMed PMID: 17610913.