Synonym
Laurocapram; Azone; N 0252; N-0252; N-Lauryl caprolactam; Tranzone;
IUPAC/Chemical Name
2H-Azepin-2-one, 1-dodecylhexahydro-
InChi Key
AXTGDCSMTYGJND-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-13-16-19-17-14-11-12-15-18(19)20/h2-17H2,1H3
SMILES Code
O=C1N(CCCCCCCCCCCC)CCCCC1
Purity
>97% (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
Biological target:
Laurocapram is a absorption enhancer and has been one of the most effective for substances of both lipophilic and hydrophilic nature.
In vitro activity:
Pre-exposure to laurocapram enhanced penetration of SLS (sodium lauryl sulfate) compared to all other treatments (p < 0.05). Since subsequent pre-exposure of skin to laurocapram increased SLS penetration, the chances of an elevated skin irritation reaction at the exposed site may therefore be possible. Pre-exposure of the skin with SLS did not increase the SLS flux values significantly, compared to the laurocapram pretreated skin.
Reference: Acta Derm Venereol. 1996 May;76(3):182-5. https://pubmed.ncbi.nlm.nih.gov/8800295/
In vivo activity:
In vivo anti-inflammatory tests in mice showed that ear edema could be inhibited by CXB (celecoxib) associated with 5.0% DMSO (53.0%) or 10.0% AZ (40.0%).
Reference: Curr Drug Deliv. 2017;14(7):992-1004. https://pubmed.ncbi.nlm.nih.gov/28124617/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
100.0 |
355.26 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
281.48
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.
| 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 |
Formulation protocol:
1. López-Castellano A, Cortell-Ivars C, López-Carballo G, Herráez-Domínguez M. The influence of Span20 on stratum corneum lipids in langmuir monolayers: comparison with Azone. Int J Pharm. 2000 Aug 10;203(1-2):245-53. doi: 10.1016/s0378-5173(00)00463-4. PMID: 10967446.
2. Szolar-Platzer C, Patil S, Maibach HI. Effect of topical laurocapram (Azone) on the in vitro percutaneous permeation of sodium lauryl sulfate using human skin. Acta Derm Venereol. 1996 May;76(3):182-5. doi: 10.2340/000155557682185. PMID: 8800295.
3. Senna TD, Mata Dos Santos HA, Kibwila DM, Leitao AC, Santos Pyrrho AD, de Padula M, Rosas EC, Padua TA, Lara MG, Riemma Pierre MB. In Vitro and In Vivo Evaluation of DMSO and Azone as Penetration Enhancers for Cutaneous Application of Celecoxib. Curr Drug Deliv. 2017;14(7):992-1004. doi: 10.2174/1567201814666170125120331. PMID: 28124617.
4. Meng-Lund E, Jacobsen J, Jin L, Janfelt C, Holm R, Müllertz A, Nicolazzo JA. Azone® decreases the buccal mucosal permeation of diazepam in a concentration-dependent manner via a reservoir effect. J Pharm Sci. 2014 Apr;103(4):1133-41. doi: 10.1002/jps.23877. Epub 2014 Feb 15. PMID: 24532052.
In vitro protocol:
1. López-Castellano A, Cortell-Ivars C, López-Carballo G, Herráez-Domínguez M. The influence of Span20 on stratum corneum lipids in langmuir monolayers: comparison with Azone. Int J Pharm. 2000 Aug 10;203(1-2):245-53. doi: 10.1016/s0378-5173(00)00463-4. PMID: 10967446.
2. Szolar-Platzer C, Patil S, Maibach HI. Effect of topical laurocapram (Azone) on the in vitro percutaneous permeation of sodium lauryl sulfate using human skin. Acta Derm Venereol. 1996 May;76(3):182-5. doi: 10.2340/000155557682185. PMID: 8800295.
In vivo protocol:
1. Senna TD, Mata Dos Santos HA, Kibwila DM, Leitao AC, Santos Pyrrho AD, de Padula M, Rosas EC, Padua TA, Lara MG, Riemma Pierre MB. In Vitro and In Vivo Evaluation of DMSO and Azone as Penetration Enhancers for Cutaneous Application of Celecoxib. Curr Drug Deliv. 2017;14(7):992-1004. doi: 10.2174/1567201814666170125120331. PMID: 28124617.
2. Meng-Lund E, Jacobsen J, Jin L, Janfelt C, Holm R, Müllertz A, Nicolazzo JA. Azone® decreases the buccal mucosal permeation of diazepam in a concentration-dependent manner via a reservoir effect. J Pharm Sci. 2014 Apr;103(4):1133-41. doi: 10.1002/jps.23877. Epub 2014 Feb 15. PMID: 24532052.
1: López-Cervantes M, Márquez-Mejía E, Cázares-Delgadillo J, Quintanar-Guerrero D, Ganem-Quintanar A, Angeles-Anguiano E. Chemical enhancers for the absorption of substances through the skin: Laurocapram and its derivatives. Drug Dev Ind Pharm. 2006 Mar;32(3):267-86. Review. PubMed PMID: 16556532.
2: Demierre MF, Vachon L, Ho V, Sutton L, Cato A, Leyland-Jones B. Phase 1/2 pilot study of methotrexate-laurocapram topical gel for the treatment of patients with early-stage mycosis fungoides. Arch Dermatol. 2003 May;139(5):624-8. PubMed PMID: 12756099.
3: Gao JQ, Hu QH, Liang WQ. The synergistic effect of laurocapram pretreatment and iontophoresis on the percutaneous permeation of non-steroidal anti-inflammatory drugs in vitro. Pharmazie. 2000 Jun;55(6):467. PubMed PMID: 10907261.
4: Szolar-Platzer C, Patil S, Maibach HI. Effect of topical laurocapram (Azone) on the in vitro percutaneous permeation of sodium lauryl sulfate using human skin. Acta Derm Venereol. 1996 May;76(3):182-5. PubMed PMID: 8800295.
5: Singh J, Satyanarayana S, Singh S. Effect of PEG 400, ethanol and laurocapram (Azone) on the transport of testosterone through rat skin. Pharmazie. 1992 Dec;47(12):948-9. PubMed PMID: 1293619.
6: Ogiso T, Iwaki M, Bechako K, Tsutsumi Y. Enhancement of percutaneous absorption by laurocapram. J Pharm Sci. 1992 Aug;81(8):762-7. Erratum in: J Pharm Sci 1992 Dec;81(12):1233. PubMed PMID: 1328599.
7: Priborský J, Takayama K, Obata Y, Príborská Z, Nagai T. Influence of limonene and laurocapram on percutaneous absorption of nonsteroidal anti-inflammatory drugs. Arzneimittelforschung. 1992 Feb;42(2):116-9. PubMed PMID: 1610418.
8: Sugibayashi K, Nakayama S, Seki T, Hosoya K, Morimoto Y. Mechanism of skin penetration-enhancing effect by laurocapram. J Pharm Sci. 1992 Jan;81(1):58-64. PubMed PMID: 1619571.
9: Zhou JX, Dai ZQ, Yu YG, Xu JY, Yuan XJ, Shen XL. [Influence of laurocapram on ultrastructures of mouse skin and sarcoma 180 membrane]. Zhongguo Yao Li Xue Bao. 1989 Sep;10(5):447-9. Chinese. PubMed PMID: 2618734.
10: van Hoogdalem EJ, de Best MA, de Boer AG, Breimer DD. Variable effects of laurocapram (Azone) on rectal cefoxitin absorption in rats. J Pharm Sci. 1989 Aug;78(8):691-2. PubMed PMID: 2778677.
11: Príborský J, Takayama K, Nagai T, Waitzová D, Elis J, Makino Y, Suzuki Y. Comparison of penetration-enhancing ability of laurocapram, N-methyl-2-pyrrolidone and dodecyl-L-pyroglutamate. Pharm Weekbl Sci. 1988 Oct 14;10(5):189-92. PubMed PMID: 3060835.
