Astemizole
Astemizole is a histamine H1-receptor antagonist. Astemizole competitively binds to histamine H1-receptor sites in the gastrointestinal tract, uterus, blood vessels, and bronchial muscle. This suppresses the formation of edema and pruritus caused by histamine. Astemizole is structurally similar to terfenadine and haloperidol; it has anticholinergic and antipruritic effects.
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Chemical Information
| Name | Astemizole |
|---|---|
| Iupac Chemical Name | 1-[(4-fluorophenyl)methyl]-N-[1-[2-(4-methoxyphenyl)ethyl]piperidin-4-yl]benzimidazol-2-amine |
| Synonyms | Astemizole; Hismanal; Histaminos; Paralergin; Laridal; Retolen |
| Molecular Formula | C28H31FN4O |
| Molecular Weight | 458.57 |
| Smile | COC1=CC=C(C=C1)CCN2CCC(CC2)NC3=NC4=CC=CC=C4N3CC5=CC=C(C=C5)F |
| InChiKey | GXDALQBWZGODGZ-UHFFFAOYSA-N |
| InChi | InChI=1S/C28H31FN4O/c1-34-25-12-8-21(9-13-25)14-17-32-18-15-24(16-19-32)30-28-31-26-4-2-3-5-27(26)33(28)20-22-6-10-23(29)11-7-22/h2-13,24H,14-20H2,1H3,(H,30,31) |
| CAS Number | 68844-77-9 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | 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 |
| Handling | |
| 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. |
| HS Code |
| Targets | |
|---|---|
| Mechanism | |
| Cell study | |
| Animal study | |
| Clinical study |
1: Back HM, Lee JH, Chae JW, Song B, Seo JW, Yun HY, Kwon KI. A novel HPLC-MS/MS
method for the simultaneous determination of astemizole and its major metabolite
in dog or monkey plasma and application to pharmacokinetics. J Pharm Biomed Anal.
2015 Oct 10;114:121-6. doi: 10.1016/j.jpba.2015.04.036. Epub 2015 May 21. PubMed
PMID: 26037160.
2: de Guadalupe Chávez-López M, Pérez-Carreón JI, Zuñiga-García V, Díaz-Chávez J,
Herrera LA, Caro-Sánchez CH, Acuña-Macías I, Gariglio P, Hernández-Gallegos E,
Chiliquinga AJ, Camacho J. Astemizole-based anticancer therapy for hepatocellular
carcinoma (HCC), and Eag1 channels as potential early-stage markers of HCC.
Tumour Biol. 2015 Aug;36(8):6149-58. doi: 10.1007/s13277-015-3299-0. Epub 2015
Mar 18. PubMed PMID: 25783527.
3: Kong X, Chen L, Jiao L, Jiang X, Lian F, Lu J, Zhu K, Du D, Liu J, Ding H,
Zhang N, Shen J, Zheng M, Chen K, Liu X, Jiang H, Luo C. Astemizole arrests the
proliferation of cancer cells by disrupting the EZH2-EED interaction of polycomb
repressive complex 2. J Med Chem. 2014 Nov 26;57(22):9512-21. doi:
10.1021/jm501230c. Epub 2014 Nov 12. PubMed PMID: 25369470.
4: García-Quiroz J, García-Becerra R, Santos-Martínez N, Barrera D, Ordaz-Rosado
D, Avila E, Halhali A, Villanueva O, Ibarra-Sánchez MJ, Esparza-López J,
Gamboa-Domínguez A, Camacho J, Larrea F, Díaz L. In vivo dual targeting of the
oncogenic Ether-à-go-go-1 potassium channel by calcitriol and astemizole results
in enhanced antineoplastic effects in breast tumors. BMC Cancer. 2014 Oct
3;14:745. doi: 10.1186/1471-2407-14-745. PubMed PMID: 25280486; PubMed Central
PMCID: PMC4194404.
5: de Guadalupe Chávez-López M, Hernández-Gallegos E, Vázquez-Sánchez AY,
Gariglio P, Camacho J. Antiproliferative and proapoptotic effects of astemizole
on cervical cancer cells. Int J Gynecol Cancer. 2014 Jun;24(5):824-8. doi:
10.1097/IGC.0000000000000151. PubMed PMID: 24819656.
6: Wagner E, Wittmann HJ, Elz S, Strasser A. Pharmacological profile of
astemizole-derived compounds at the histamine H1 and H4 receptor--H1/H4 receptor
selectivity. Naunyn Schmiedebergs Arch Pharmacol. 2014 Mar;387(3):235-50. doi:
10.1007/s00210-013-0926-4. Epub 2013 Nov 17. PubMed PMID: 24241585.
7: Roman G, Crandall IE, Szarek WA. Synthesis and anti-Plasmodium activity of
benzimidazole analogues structurally related to astemizole. ChemMedChem. 2013
Nov;8(11):1795-804. doi: 10.1002/cmdc.201300172. Epub 2013 Sep 10. PubMed PMID:
24022991.
8: Karapetyan YE, Sferrazza GF, Zhou M, Ottenberg G, Spicer T, Chase P, Fallahi
M, Hodder P, Weissmann C, Lasmézas CI. Unique drug screening approach for prion
diseases identifies tacrolimus and astemizole as antiprion agents. Proc Natl Acad
Sci U S A. 2013 Apr 23;110(17):7044-9. doi: 10.1073/pnas.1303510110. Epub 2013
Apr 1. PubMed PMID: 23576755; PubMed Central PMCID: PMC3637718.
9: García-Quiroz J, García-Becerra R, Barrera D, Santos N, Avila E, Ordaz-Rosado
D, Rivas-Suárez M, Halhali A, Rodríguez P, Gamboa-Domínguez A, Medina-Franco H,
Camacho J, Larrea F, Díaz L. Astemizole synergizes calcitriol antiproliferative
activity by inhibiting CYP24A1 and upregulating VDR: a novel approach for breast
cancer therapy. PLoS One. 2012;7(9):e45063. doi: 10.1371/journal.pone.0045063.
Epub 2012 Sep 12. PubMed PMID: 22984610; PubMed Central PMCID: PMC3440370.
10: García-Quiroz J, Camacho J. Astemizole: an old anti-histamine as a new
promising anti-cancer drug. Anticancer Agents Med Chem. 2011 Mar;11(3):307-14.
Review. PubMed PMID: 21443504.
11: Lee EH, Oh JH, Park HJ, Kim DG, Lee JH, Kim CY, Kwon MS, Yoon S. Simultaneous
gene expression signature of heart and peripheral blood mononuclear cells in
astemizole-treated rats. Arch Toxicol. 2010 Aug;84(8):609-18. doi:
10.1007/s00204-010-0529-5. Epub 2010 Mar 11. PubMed PMID: 20221588.
12: Rojo LE, Alzate-Morales J, Saavedra IN, Davies P, Maccioni RB. Selective
interaction of lansoprazole and astemizole with tau polymers: potential new
clinical use in diagnosis of Alzheimer's disease. J Alzheimers Dis.
2010;19(2):573-89. doi: 10.3233/JAD-2010-1262. PubMed PMID: 20110603; PubMed
Central PMCID: PMC2951486.
13: Vu K, Gelli A. Astemizole and an analogue promote fungicidal activity of
fluconazole against Cryptococcus neoformans var. grubii and Cryptococcus gattii.
Med Mycol. 2010 Mar;48(2):255-62. doi: 10.1080/13693780903081968. PubMed PMID:
19572230.
14: Li F, Hsieh Y, Kang L, Sondey C, Lachowicz J, Korfmacher WA. MALDI-tandem
mass spectrometry imaging of astemizole and its primary metabolite in rat brain
sections. Bioanalysis. 2009 May;1(2):299-307. doi: 10.4155/bio.09.27. PubMed
PMID: 21083169.
15: Musonda CC, Whitlock GA, Witty MJ, Brun R, Kaiser M. Chloroquine-astemizole
hybrids with potent in vitro and in vivo antiplasmodial activity. Bioorg Med Chem
Lett. 2009 Jan 15;19(2):481-4. doi: 10.1016/j.bmcl.2008.11.047. Epub 2008 Nov 18.
PubMed PMID: 19054674.
16: Sastry CS, Naidu PY. Spectrophotometric determination of astemizole. Talanta.
1998 Mar;45(5):795-9. PubMed PMID: 18967063.
17: Srikanth D, Shenoy RR, Rao CM. The effects of topical (gel) astemizole and
terfenadine on wound healing. Indian J Pharmacol. 2008 Aug;40(4):170-4. doi:
10.4103/0253-7613.43164. PubMed PMID: 20040951; PubMed Central PMCID: PMC2792619.
18: Guba W, Green LG, Martin RE, Roche O, Kratochwil N, Mauser H, Bissantz C,
Christ A, Stahl M. From astemizole to a novel hit series of small-molecule
somatostatin 5 receptor antagonists via GPCR affinity profiling. J Med Chem. 2007
Dec 13;50(25):6295-8. Epub 2007 Nov 19. PubMed PMID: 18020391.
19: Gómez-Varela D, Contreras-Jurado C, Furini S, García-Ferreiro R, Stühmer W,
Pardo LA. Different relevance of inactivation and F468 residue in the mechanisms
of hEag1 channel blockage by astemizole, imipramine and dofetilide. FEBS Lett.
2006 Sep 18;580(21):5059-66. Epub 2006 Aug 28. PubMed PMID: 16949586.
20: Chong CR, Chen X, Shi L, Liu JO, Sullivan DJ Jr. A clinical drug library
screen identifies astemizole as an antimalarial agent. Nat Chem Biol. 2006
Aug;2(8):415-6. Epub 2006 Jul 2. PubMed PMID: 16816845.
Chemical Structure
