Diphenylpyraline
(Synonyms: 二苯拉林； 双苯拉林) 目录号 : GC48835A histamine H1 receptor antagonist
Cas No.:147-20-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Diphenylpyraline is a first generation histamine H1 receptor antagonist (Ki = 20 nM in a radioligand binding assay using bovine cerebral cortex membranes).1,2 It also inhibits muscarinic acetylcholine receptors (Ki = 0.84 nM).2 Diphenylpyraline (1 and 3 µM) inhibits contractions induced by prostaglandin E1 in isolated guinea pig ileum.3 It inhibits ovalbumin-induced bronchoconstriction in ovalbumin-sensitized guinea pigs when administered intravenously at a dose of 20 µmol/kg.4 Diphenylpyraline (14 mg/kg) also reduces dopamine uptake in rat nucleus accumbens.1 Formulations containing diphenylpyraline have been used in the treatment of allergic rhinitis.
1.Oleson, E.B., Ferris, M.J., EspaÑa, R.A., et al.Effects of the histamine H1 receptor antagonist and benztropine analog diphenylpyraline on dopamine uptake, locomotion and rewardEur. J. Pharmacol.683(1-3)161-165(2012) 2.Kubo, N., Shirakawa, S., Kuno, T., et al.Antimuscarinic effects of antihistamines: Quantitative evaluation by receptor-binding assayJpn. J. Pharmacol.43(3)277-282(1987) 3.Nakabou, Y., Kubota, M., Takada, K., et al.A possible approach to the suppression of side effects induced by PGE1Prostaglandins Leukot. Essent. Fatty Acids52(1)17-20(1995) 4.Dulabh, R., and Vickers, M.R.The effects of H2-receptor antagonists on anaphylaxis in the guinea-pigAgents Actions8(6)559-565(1978)
| Cas No. | 147-20-6 | SDF | |
| 别名 | 二苯拉林； 双苯拉林 | ||
| Canonical SMILES | CN(CC1)CCC1OC(C2=CC=CC=C2)C3=CC=CC=C3 | ||
| 分子式 | C19H23NO | 分子量 | 281.4 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,Ethanol:PBS (pH 7.2) (1:1): 0.5 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.5537 mL | 17.7683 mL | 35.5366 mL |
| 5 mM | 0.7107 mL | 3.5537 mL | 7.1073 mL |
| 10 mM | 0.3554 mL | 1.7768 mL | 3.5537 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Diphenylpyraline (Lergobine) in the treatment of patients suffering from allergic and vasomotor rhinitis
J Int Med Res 1977;5(1):37-41.PMID:14039DOI:10.1177/030006057700500106.
In a double-blind study, Diphenylpyraline (Lergobine) was given to 63 patients whose main symptoms were stuffiness of the nose, increased secretion of mucus, snuffling, sneezing and redness of the eyes. Fifty-seven patients were given placebo for identical symptoms. Diphenylpyraline was found to have a better effect on all the symptoms than placebo. The difference was statistically significant in respect of the discharge of mucus and redness of the eyes, and when the total symptoms were considered as a whole. In atopic patients the better effect of Diphenylpyraline was highly significant.
Antimycobacterial activity of Diphenylpyraline derivatives
Eur J Med Chem 2008 Apr;43(4):872-9.PMID:17714832DOI:10.1016/j.ejmech.2007.06.012.
2-Substituted derivatives of Diphenylpyraline and their 1-phenyl and 1-phenethyl analogues have been prepared in several steps from dihydropyridine-2(1H)-thiones. The structures of all new compounds have been confirmed by NMR spectroscopy. Their activity against Mycobacterium tuberculosis H(37)Rv as well as their cytotoxicity against human cells (HEK-293) have been determined via in vitro assays. The antimycobacterial potency was in general increased by substitution in ring position 2. The most promising modifications were a 2-isopropyl derivative and a 1,2-diphenyl analogue.
Enhanced fluorimetric detection of Diphenylpyraline HCl using micelle and cyclodextrin mediated approach: Spectrofluorimetric and micellar liquid chromatographic application for either single or combined formulation with caffeine and paracetamol
Spectrochim Acta A Mol Biomol Spectrosc 2023 Apr 15;291:122317.PMID:36621026DOI:10.1016/j.saa.2023.122317.
Highly sensitive micellar spectrofluorimetric method (Method I) has been developed and validated for the determination of Diphenylpyraline HCl in pharmaceutical tablets and in plasma. Sodium dodecyl sulfate improves the intensity of fluorescence of Diphenylpyraline at 286 nm at pH 5 that allow its determination in plasma at nano-level. the mean percent recovery ± S.D was 99.719 ± 0.338 in plasma. In addition, Green cyclodextrin-modified micellar liquid chromatographic method (Method II) has been developed and validated for simultaneous determination of Diphenylpyraline, paracetamol and caffeine using cyclodextrin micellar mobile phase consisted of 30 mM Brij*35, 0.5 mM hydroxypropyl β-cyclodextrin and phosphate buffer pH 4: MeOH (95:5, %v/v) that allows their simultaneous determination with enhanced spectrofluorimetric detection of Diphenylpyraline. Method II was effectively applied for the simultaneous determination of Diphenylpyraline, paracetamol and caffeine in a ternary laboratory prepared mixture which contained all possible excipients with mean percent recoveries ± S.D of 100.176 ± 1.008, 101.166 ± 0.415 and 100.708 ± 1.836, respectively. Linearity range for Method I was 0.1-1 μg. mL-1 for Diphenylpyraline and for Method II was 0.3-50, 25-350, and 0.5-50 for caffeine, paracetamol and Diphenylpyraline, respectively. Method I was also applied in spiked human plasma with linearity range 0.2-0.5 μg. mL-1. The methods are verified to have excellent greenness.
Diphenylpyraline, a histamine H1 receptor antagonist, has psychostimulant properties
Eur J Pharmacol 2005 Jan 4;506(3):237-40.PMID:15627433DOI:10.1016/j.ejphar.2004.11.017.
Diphenylpyraline hydrochloride (DPP) is used clinically as an antihistamine drug, but its neurobiological effects are not completely understood. Voltammetry and microdialysis were used to investigate potential actions of DPP on the dopamine system. Voltammetric monitoring of dopamine signals in mouse nucleus accumbens slices showed that DPP (10 microM) markedly inhibited dopamine uptake. There was a 20-fold increase in apparent Km for dopamine uptake, while Vmax was unchanged. Microdialysis experiments demonstrated that DPP (5 mg/kg, i.p.) elevated extracellular dopamine levels (approximately 200%) in mouse nucleus accumbens. DPP (5 and 10 mg/kg) also induced locomotor activation. All of the effects of DPP were comparable with those of cocaine. Taken together, these results indicate that DPP acts as a competitive dopamine transporter inhibitor similar to cocaine.
Diphenylpyraline-responsive parkinsonism in cerebrotendinous xanthomatosis: long-term follow up of three patients
J Neurol Sci 2001 Jan 1;182(2):95-7.PMID:11137513DOI:10.1016/s0022-510x(00)00441-x.
A long-term follow-up study was made of three patients with cerebrotendinous xanthomatosis (CTX) associated with parkinsonism, two of whom were siblings. Besides typical CTX symptoms, all three patients showed severe parkinsonism. This observation has been rarely reported in CTX. The fact that the two siblings showed parkinsonism strongly suggests the genetic propensity to parkinsonism in these CTX patients. Positron emission tomography studies of the two patients revealed presynaptic dysfunction of the nigro-striatal dopaminergic system. Treatment with the reductase inhibitor hydroxymethyl glutaryl coenzyme successfully corrected the serum cholestanol level in the early stage of the disease, which, however, did not arrest the progression of clinical symptoms, particularly their parkinsonism. Clinically, levodopa had a little effect on parkinsonism, whereas an antihistamine drug, Diphenylpyraline hydrochloride (DPP) had excellent effects on all three patients throughout the long-term follow up. The mechanism of the action of DPP on parkinsonism is unclear, however, the drug seems to be a therapeutic choice for treating parkinsonism in CTX.