Synonym
Dyphylline; Diprophylline; Lufyllin; Corphyllin; Neothylline;
IUPAC/Chemical Name
7-(2,3-dihydroxypropyl)-1,3-dimethylpurine-2,6-dione
InChi Key
KSCFJBIXMNOVSH-UHFFFAOYSA-N
InChi Code
InChI=1S/C10H14N4O4/c1-12-8-7(9(17)13(2)10(12)18)14(5-11-8)3-6(16)4-15/h5-6,15-16H,3-4H2,1-2H3
SMILES Code
CN1C2=C(C(=O)N(C1=O)C)N(C=N2)CC(CO)O
Appearance
White to off-white crystalline 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, not in water
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:
Diphylline (Diprophylline) is a potent A1/A2 adenosine receptor antagonist and cyclic nucleotide phosphodiesterase inhibitor.
In vitro activity:
This study found that a group of xanthines including caffeine, theophylline, and dyphylline can dramatically decrease ABCG2 protein in cells that have either moderate (BeWo, a placental choriocarcinoma cell line) or high (MCF-7/MX100, a breast cancer drug-resistant cell subline) levels of ABCG2 expression.
Reference: Mol Pharmacol. 2012 Mar;81(3):328-37. https://pubmed.ncbi.nlm.nih.gov/22113078/
In vivo activity:
Diprophylline significantly increased the reduced MLCK expression and myosin extent in constipation-prominent rats and significantly decreased the increased MLCK expression and myosin extent in diarrhea-prominent rats, suggesting that the change of MLCK expression may also be involved in diprophylline-induced BM on rat jejunal contractility.
Reference: Korean J Physiol Pharmacol. 2014 Feb;18(1):47-53. https://pubmed.ncbi.nlm.nih.gov/24634596/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
10.0 |
0.39 |
| DMSO |
37.0 |
145.53 |
| Ethanol |
1.0 |
3.93 |
| PBS (pH 7.2) |
1.0 |
3.93 |
| Water |
35.5 |
139.63 |
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
254.25
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.
| 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. Ding R, Shi J, Pabon K, Scotto KW. Xanthines down-regulate the drug transporter ABCG2 and reverse multidrug resistance. Mol Pharmacol. 2012 Mar;81(3):328-37. doi: 10.1124/mol.111.075556. Epub 2011 Nov 23. PMID: 22113078; PMCID: PMC3286305.
2. Kim WI, Choi KA, Do HS, Yu YG. Expression and purification of human mPGES-1 in E. coli and identification of inhibitory compounds from a drug-library. BMB Rep. 2008 Nov 30;41(11):808-13. doi: 10.5483/bmbrep.2008.41.11.808. PMID: 19017494.
3. Liu FF, Chen DP, Xiong YJ, Lv BC, Lin Y. Characteristics of diprophylline-induced bidirectional modulation on rat jejunal contractility. Korean J Physiol Pharmacol. 2014 Feb;18(1):47-53. doi: 10.4196/kjpp.2014.18.1.47. Epub 2014 Feb 13. PMID: 24634596; PMCID: PMC3951823.
In vitro protocol:
1. Ding R, Shi J, Pabon K, Scotto KW. Xanthines down-regulate the drug transporter ABCG2 and reverse multidrug resistance. Mol Pharmacol. 2012 Mar;81(3):328-37. doi: 10.1124/mol.111.075556. Epub 2011 Nov 23. PMID: 22113078; PMCID: PMC3286305.
2. Kim WI, Choi KA, Do HS, Yu YG. Expression and purification of human mPGES-1 in E. coli and identification of inhibitory compounds from a drug-library. BMB Rep. 2008 Nov 30;41(11):808-13. doi: 10.5483/bmbrep.2008.41.11.808. PMID: 19017494.
In vivo protocol:
1. Liu FF, Chen DP, Xiong YJ, Lv BC, Lin Y. Characteristics of diprophylline-induced bidirectional modulation on rat jejunal contractility. Korean J Physiol Pharmacol. 2014 Feb;18(1):47-53. doi: 10.4196/kjpp.2014.18.1.47. Epub 2014 Feb 13. PMID: 24634596; PMCID: PMC3951823.
1: Fleming WK, Herrington AM, Chandler MH. Preventing theophylline dosing errors
from conversion of dyphylline. Ann Pharmacother. 1993 Jun;27(6):792-3. PubMed
PMID: 8329808.
2: Touitou E, Shaco-Ezra N, Dayan N, Jushynski M, Rafaeloff R, Azoury R.
Dyphylline liposomes for delivery to the skin. J Pharm Sci. 1992 Feb;81(2):131-4.
PubMed PMID: 1545351.
3: Tagliaro F, Dorizzi R, Frigerio A, Marigo M. Non-extraction HPLC method for
simultaneous measurement of dyphylline and doxofylline in serum. Clin Chem. 1990
Jan;36(1):113-5. PubMed PMID: 2297899.
4: Acara M, Carr EA Jr, Terry EN. Probenecid inhibition of the renal excretion of
dyphylline in chicken, rat and man. J Pharm Pharmacol. 1987 Jul;39(7):526-30.
PubMed PMID: 2886621.
5: Kester MB, Saccar CL, Mansmann HC Jr. Microassay for the simultaneous
determination of theophylline and dyphylline in serum by high-performance liquid
chromatography. J Chromatogr. 1987 Apr 24;416(1):91-7. PubMed PMID: 3597645.
6: Tang SR. [Application of second derivative spectrometry to the determination
of bromhexine hydrochloride and spectrophotometry to the determination of
dyphylline in compound preparations]. Yao Xue Xue Bao. 1986 Oct;21(10):776-80.
Chinese. PubMed PMID: 3577779.
7: Ayres JW, Pearson EG, Riebold TW, Chang SF. Theophylline and dyphylline
pharmacokinetics in the horse. Am J Vet Res. 1985 Dec;46(12):2500-6. PubMed PMID:
4083583.
8: Straughn AB, Wood GC, Raghow G, Meyer MC. Bioavailability of dyphylline and
dyphylline-guaifenesin tablets in humans. J Pharm Sci. 1985 Mar;74(3):335-7.
PubMed PMID: 4009445.
9: Simons KJ, Plett KD, Simons FE. Dissolution studies of some regular and
sustained-release dyphylline dosage forms. Pharm Acta Helv. 1984;59(5-6):145-8.
PubMed PMID: 6739505.
10: Ackerman BL, Chhatriwalla A. Theophylline toxicity after dyphylline therapy.
Am Rev Respir Dis. 1982 Apr;125(4):484. PubMed PMID: 7073120.
11: Gupta RN, Andrew K. Theophylline and dyphylline. Can Med Assoc J. 1981 Sep
1;125(5):425. PubMed PMID: 20313615; PubMed Central PMCID: PMC1862463.
12: Lee CC, Wang LH, Majeske BL, Marbury TC. Pharmacokinetics of dyphylline
elimination by uremic patients. J Pharmacol Exp Ther. 1981 May;217(2):340-4.
PubMed PMID: 7229976.
13: Valia KH, Hartman CA, Kucharczyk N, Sofia RD. Simultaneous determination of
dyphylline and theophylline in human plasma by high-performance liquid
chromatography. J Chromatogr. 1980 Nov 14;221(1):170-5. PubMed PMID: 7451620.
14: Ng PK, Locock RA. Comparative pharmacokinetics of theophylline and dyphylline
following intravenous injection in rabbits. Res Commun Chem Pathol Pharmacol.
1979 Dec;26(3):509-24. PubMed PMID: 523786.
15: Moussa AF. A new rapid spectrophotometric method for the determination of
theophylline, dyphylline and khellin in some pharmaceutical preparations.
Pharmazie. 1978 Apr;33(4):238. PubMed PMID: 674328.
16: Moussa AF. Spectrophotometric determination of theophylline, dyphylline and
khellin in some pharmaceutical preparations. Pharmazie. 1977 Apr;32(4):242-3.
PubMed PMID: 896918.
17: Maijub AG, Stafford DT. Theophylline and dyphylline levels in serum by liquid
chromatography. J Chromatogr Sci. 1976 Nov;14(11):521-5. PubMed PMID: 977712.
18: Warembourg H, Jaillard J. [Clinical trial with Corverum (dinicotinic ester of
dyphylline) in treatment of chronic respiratory insufficiency and right
ventricular insufficiency. Apropos of 35 cases]. Lille Med. 1968 Dec;13(10):Suppl
7:1069+. French. PubMed PMID: 5720294.
19: Huang WS, Lin SJ, Wu HL, Chen SH. Simultaneous determination of theophylline
and dyphylline by micellar electrokinetic chromatography and application in drug
formulations. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Oct
5;795(2):329-35. PubMed PMID: 14522037.
20: Iturriaga H, Coello J, Maspoch S, Porcel M. Kinetic-spectrophotometric
determination of theophylline, dyphylline, and proxyphylline by use of partial
least-squares regression. Anal Bioanal Chem. 2002 Sep;374(1):33-8. Epub 2002 Jun
25. PubMed PMID: 12207237.
