Cyclizine

• CAS: 82-92-8
• Catalog Number: ACM82928
• Category: Main Products
• Molecular Weight: 266.40
• Molecular Formula: C18H22N2
• Synonyms: 1-benzhydryl-4-methylpiperazine
• Appearance: Solid

Case Study

Cyclizine as a Cytotoxic Agent Inducing Apoptosis in Macrophages via Extrinsic and Intrinsic Pathways

Lu, Yin-Che, et al. Environmental Toxicology 39.5 (2024): 2970-2979.

Cyclizine, an over-the-counter antihistamine used for motion sickness, induces concentration-dependent cytotoxicity and apoptosis in RAW264.7 macrophages by activating both the extrinsic (death receptor) and intrinsic (mitochondrial) apoptotic pathways, raising safety concerns regarding its overuse or misuse.
Experimental Protocol: RAW264.7 macrophages were incubated with cyclizine at 0-500μM for 24h. Cytotoxicity was measured by lactate dehydrogenase release. Apoptosis and necrosis were quantified by flow cytometry using annexin V-FITC/PI staining. Caspase-3,-8 and-9 activities were assessed with fluorogenic substrates.
Performance Evaluation: Cyclizine reduced cell viability in a concentration-dependent manner (CC50 = 331.5μM). At ≥200μM, it significantly increased apoptosis and necrosis, activated caspases-3,-8 and-9, induced mitochondrial membrane potential depolarisation, and promoted cytochrome c release. Cyclizine upregulated TNF-αR and Fas receptor expression (extrinsic pathway) and decreased Bcl2 while increasing Bad expression (intrinsic pathway). All effects were concentration-dependent.
Cyclizine triggers macrophage apoptosis through concurrent activation of the extrinsic (death receptor/caspase-8) and intrinsic (mitochondrial/cytochrome c/caspase-9) pathways, leading to caspase-3-mediated cell death. These findings highlight potential immunotoxic risks associated with cyclizine overuse.

Cyclizine as a Prophylactic Antiemetic for Postoperative Nausea and Vomiting in Day-Case Gynaecological Surgery

Johns, R. A., et al. Anaesthesia 61.11 (2006): 1053-1057.

Cyclizine, a histamine H1 receptor antagonist, acts as an effective antiemetic when administered alone or in combination with granisetron. Combined therapy significantly reduces the incidence of postoperative nausea and vomiting (PONV) compared with either agent alone, without increasing major side effects.
Study Protocol: A randomised, double-blinded trial enrolled 960 women undergoing day-case gynaecological surgery. Patients received intravenous cyclizine 50mg, granisetron 1mg, or both drugs at induction of anaesthesia. The primary outcome was the incidence of PONV (nausea or vomiting/retching) before discharge and within 24h postoperatively. Rescue antiemetic (buccal prochlorperazine) use, hospital admissions and side effects (drowsiness, dizziness, headache) were recorded.
Performance Evaluation: The incidence of PONV was 23% (73/316) in the cyclizine group, 24% (77/322) in the granisetron group and 17% (53/322) in the combination group (p=0.04). Rescue antiemetic use was 9%, 8% and 6% respectively (p=0.45). Drowsiness was reported more frequently with cyclizine (56% vs. 45% with granisetron, p=0.005), but this did not increase unplanned admissions. Hospital admission for PONV was low (<1%). No significant differences in anaesthetic technique or opioid use were observed between groups.
Cyclizine 50mg is an effective prophylactic antiemetic. When combined with granisetron, it further reduces PONV risk in high-risk women undergoing day-case surgery.

Custom Q&A

What is the molecular formula of Cyclizine?

The molecular formula of Cyclizine is C18H22N2.

What is the molecular weight of Cyclizine?

The molecular weight of Cyclizine is 266.4 g/mol.

What is the IUPAC name of Cyclizine?

The IUPAC name of Cyclizine is 1-benzhydryl-4-methylpiperazine.

What is the InChIKey of Cyclizine?

The InChIKey of Cyclizine is UVKZSORBKUEBAZ-UHFFFAOYSA-N.

What is the CAS number of Cyclizine?

The CAS number of Cyclizine is 82-92-8.

What is the European Community (EC) number of Cyclizine?

The European Community (EC) number of Cyclizine is 201-445-5.

What is the UNII of Cyclizine?

The UNII of Cyclizine is QRW9FCR9P2.

What is the XLogP3 value of Cyclizine?

The XLogP3 value of Cyclizine is 3.6.

How many hydrogen bond donor counts does Cyclizine have?

Cyclizine has no hydrogen bond donor count.

What is the ChEMBL ID of Cyclizine?

The ChEMBL ID of Cyclizine is CHEMBL648.