WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 202385
CAS#: 69-05-6 (HCl)
Description: Quinacrine, aslo known as Mepacrine, is A 9-aminoacridine derivative quinacrine with potential antineoplastic and antiparasitic activities. Quinacrine may inhibit the transcription and activity of both basal and inducible nuclear factor-kappaB (NF-kappaB), which may result in the induction of tumor suppressor p53 transcription, the restoration of p53-dependent apoptotic pathways, and tumor cell apoptosis. Continuous NF-kappaB signaling, present in many tumors and in chronic inflammatory processes, promotes the expression of antiapoptotic proteins and cytokines while downregulating the expression of proapoptotic proteins, such as p53.
MedKoo Cat#: 202385
Name: Quinacrine hydrochloride
CAS#: 69-05-6 (HCl)
Chemical Formula: C23H32Cl3N3O
Exact Mass:
Molecular Weight: 472.88
Elemental Analysis: C, 58.42; H, 6.82; Cl, 22.49; N, 8.89; O, 3.38
Related CAS #: 83-89-6 (free base) 69-05-6 (HCl) 316-05-2 (mesylate) 6151-30-0 (HCl hydrate) 6598-46-5 (mesylate hydrate)
Synonym: SN 390; SN-390; SN390; ST 439; Acrichine; Acrinamine; Acriquine; AI3-04467; Quinacrine dihydrochloride; mepacrine dihydrochoride. trade name: atabrine.
IUPAC/Chemical Name: N4-(6-chloro-2-methoxyacridin-9-yl)-N1,N1-diethylpentane-1,4-diamine dihydrochloride
InChi Key: UDKVBVICMUEIKS-UHFFFAOYSA-N
InChi Code: InChI=1S/C23H30ClN3O.2ClH/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23;;/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26);2*1H
SMILES Code: CC(NC1=C(C=C(OC)C=C2)C2=NC3=CC(Cl)=CC=C31)CCCN(CC)CC.[H]Cl.[H]Cl
Appearance: Yellow solid 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 water (50mg/ mL)
Shelf Life: >5 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: | Quinacrine dihydrochloride is an antimalarial agent which suppresses NF-κB and activates p53 signaling. |
| In vitro activity: | Quinacrine (QA) demonstrates high degree of cytotoxicity against both immortalized and primary patient-derived cell lines with sub-micromolar 50% inhibitory concentration (IC50) values ranging from 1.2 µM (H2452) to 5.03 µM (H28). Further, QA also inhibited cellular migration and colony formation in MPM (malignant pleural mesothelioma) cells, demonstrated using scratch and clonogenic assays, respectively. Anti-angiogenic properties were also discovered for QA. Autophagy inhibition assay was performed, and results revealed that QA successfully inhibited autophagy process in MPM cells, which has been cited to be one of the survival pathways for MPM. Annexin V real-time apoptosis study revealed significant apoptotic induction in MPM cells following QA treatment. Western blots confirmed inhibition of autophagy and induction of apoptosis. Reference: Int J Mol Sci. 2020 Aug 31;21(17):6306. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7503636/ |
| In vivo activity: | The efficacy of quinacrine was assessed in an AML-PS (acute myeloid leukemia) mouse model. The in vivo use of quinacrine (100mg/kg three times per week for two consecutive weeks) significantly suppressed circulating blast cells at days 30/31 and increased the median survival time (MST) of the mice. Evaluation of circulating leukemic cells detected in blood samples (in percent of white blood cells (WBC)) at day 30/31 showed 72% human tumor cells in the control mice, whereas in mice treated with quinacrine, this was only 2.2% (Fig. 1a). In agreement with these data, the MST of control mice was 34 days whereas it was 46 days in quinacrine-treated mice (p < 0.0001, Fig. 1b). Reference: Leuk Res. 2017 Dec;63:41-46. https://www.sciencedirect.com/science/article/pii/S0145212617305659?via%3Dihub |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 29.0 | 61.33 | |
| Water | 27.45 | 58.05 | |
| Ethanol | 28.0 | 59.21 |
The following data is based on the product molecular weight 472.88 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. Kulkarni NS, Vaidya B, Parvathaneni V, Bhanja D, Gupta V. Repurposing Quinacrine for Treatment of Malignant Mesothelioma: In-Vitro Therapeutic and Mechanistic Evaluation. Int J Mol Sci. 2020 Aug 31;21(17):6306. doi: 10.3390/ijms21176306. PMID: 32878257; PMCID: PMC7503636. 2. Eriksson A, Chantzi E, Fryknäs M, Gullbo J, Nygren P, Gustafsson M, Höglund M, Larsson R. Towards repositioning of quinacrine for treatment of acute myeloid leukemia - Promising synergies and in vivo effects. Leuk Res. 2017 Dec;63:41-46. doi: 10.1016/j.leukres.2017.10.012. Epub 2017 Oct 28. PMID: 29100024. |
| In vitro protocol: | 1. Kulkarni NS, Vaidya B, Parvathaneni V, Bhanja D, Gupta V. Repurposing Quinacrine for Treatment of Malignant Mesothelioma: In-Vitro Therapeutic and Mechanistic Evaluation. Int J Mol Sci. 2020 Aug 31;21(17):6306. doi: 10.3390/ijms21176306. PMID: 32878257; PMCID: PMC7503636. |
| In vivo protocol: | 1. Eriksson A, Chantzi E, Fryknäs M, Gullbo J, Nygren P, Gustafsson M, Höglund M, Larsson R. Towards repositioning of quinacrine for treatment of acute myeloid leukemia - Promising synergies and in vivo effects. Leuk Res. 2017 Dec;63:41-46. doi: 10.1016/j.leukres.2017.10.012. Epub 2017 Oct 28. PMID: 29100024. |
1: Bhattacharyya S. Quinacrine sterilization (QS): the ethical issues. Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S13-21. Review. PubMed PMID: 14763181.
2: Zipper J, Kessel E. Quinacrine sterilization: a retrospective. Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S7-11. Review. PubMed PMID: 14763180.
3: Furukawa H, Takahashi M, Nakajima M, Yamada T. [Prospects of the therapeutic approaches to Creutzfeldt-Jakob disease: a clinical trial of antimalarial, quinacrine]. Nihon Rinsho. 2002 Aug;60(8):1649-57. Review. Japanese. PubMed PMID: 12187766.
4: Lippes J. Quinacrine sterilization: the imperative need for american clinical trials. Fertil Steril. 2002 Jun;77(6):1106-9. Review. PubMed PMID: 12057713.
5: Benagiano G. Non-surgical female sterilization with quinacrine: an update. Contraception. 2001 May;63(5):239-45. Review. PubMed PMID: 11448462.
Related CAS
CAS#69-05-6 ( Quinacrine HCl)
CAS#83-89-6 ( Quinacrine free).
