Clofoctol | CAS# 37693-01-9 | antibiotic

MedKoo Cat#: 592586 | Name: Clofoctol

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Clofoctol is a drug, which belongs to the group of phenolic compounds. It is used as an effective antibacterial agent against gram positive bacteria. Its mode of action may involve the inhibition of the generation of adenosine triphosphate(ATP)required for the cell wall synthesis. Clofoctol is a bacteriostatic antibiotic. It is used in the treatment of respiratory tract and ear, nose and throat infections caused by Gram-positive bacteria. It has been marketed in France till 2005 under the trade name Octofene and in Italy as Gramplus. It is only functional against Gram-positive bacteria. It penetrates into human lung tissue. Apteeus is developing clofoctol as a potential therapy against SARS-CoV-2.

Chemical Structure

Clofoctol

CAS#37693-01-9

Theoretical Analysis

MedKoo Cat#: 592586

Name: Clofoctol

CAS#: 37693-01-9

Chemical Formula: C21H26Cl2O

Exact Mass: 364.1361

Molecular Weight: 365.34

Elemental Analysis: C, 69.04; H, 7.17; Cl, 19.41; O, 4.38

Price and Availability

Size	Price	Availability	Quantity
100mg	USD 350.00	2 Weeks
500mg	USD 750.00	2 Weeks

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Synonym

Clofoctol; NSC 758389; NSC-758389; NSC758389; Octofene;

IUPAC/Chemical Name

alpha-(2,4-Dichlorophenyl)-4-(1,1,3,3-tetramethylbutyl)-o-cresol

InChi Key

HQVZOORKDNCGCK-UHFFFAOYSA-N

InChi Code

InChI=1S/C21H26Cl2O/c1-20(2,3)13-21(4,5)16-7-9-19(24)15(11-16)10-14-6-8-17(22)12-18(14)23/h6-9,11-12,24H,10,13H2,1-5H3

SMILES Code

CC(C)(C)CC(C1=CC=C(O)C(CC2=CC=C(Cl)C=C2Cl)=C1)(C)C

Appearance

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 DMSO

Shelf Life

>3 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

2934.99.03.00

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Product Data

Product Data

Instruction

View handling instruction

Biological target:

Clofoctol is a bacteriostatic antibiotic.

In vitro activity:

The results showed that the clonogenic potential was decreased; strikingly, tumorsphere formation was completely abolished after pretreatment with 3 μM and 10 μM clofoctol, and no living cells could be collected in GSC2 and GSC5 (Figure 2, E and F, and Supplemental Figure 3, A and C). Reference: J Clin Invest. 2019 Aug 1; 129(8): 3072–3085. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6668693/

In vivo activity:

PC3 cells were implanted s.c. into athymic nude mice and the mice were treated with either vehicle or clofoctol for 37 days. Tumour volume was measured during the course of the treatment. As shown in Figure 7A, PC3 tumour growth was significantly inhibited by clofoctol. Reference: Br J Pharmacol. 2014 Oct; 171(19): 4478–4489. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4209153/

	Solvent	mg/mL	mM	comments
Solubility
	DMSO	100.0	273.72

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 365.34 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. Hu Y, Zhang M, Tian N, Li D, Wu F, Hu P, Wang Z, Wang L, Hao W, Kang J, Yin B, Zheng Z, Jiang T, Yuan J, Qiang B, Han W, Peng X. The antibiotic clofoctol suppresses glioma stem cell proliferation by activating KLF13. J Clin Invest. 2019 May 21;129(8):3072-3085. doi: 10.1172/JCI124979. PMID: 31112526; PMCID: PMC6668693. 2. Wang M, Shim JS, Li RJ, Dang Y, He Q, Das M, Liu JO. Identification of an old antibiotic clofoctol as a novel activator of unfolded protein response pathways and an inhibitor of prostate cancer. Br J Pharmacol. 2014 Oct;171(19):4478-89. doi: 10.1111/bph.12800. Epub 2014 Sep 5. PMID: 24903412; PMCID: PMC4209153.

In vitro protocol:

In vivo protocol:

1: Aherfi S, Pradines B, Devaux C, Honore S, Colson P, Scola B, Raoult D. Drug repurposing against SARS-CoV-1, SARS-CoV-2 and MERS-CoV. Future Microbiol. 2021 Nov;16:1341-1370. doi: 10.2217/fmb-2021-0019. Epub 2021 Nov 10. PMID: 34755538; PMCID: PMC8579950. 2: Lee J, Stone J, Desai P, Kosowicz JG, Liu JO, Ambinder RF. Arsenicals, the Integrated Stress Response, and Epstein-Barr Virus Lytic Gene Expression. Viruses. 2021 Apr 30;13(5):812. doi: 10.3390/v13050812. PMID: 33946406; PMCID: PMC8147158. 3: Bailly C, Vergoten G. A new horizon for the old antibacterial drug clofoctol. Drug Discov Today. 2021 May;26(5):1302-1310. doi: 10.1016/j.drudis.2021.02.004. Epub 2021 Feb 10. PMID: 33581321. 4: Lee J, Kosowicz JG, Hayward SD, Desai P, Stone J, Lee JM, Liu JO, Ambinder RF. Pharmacologic Activation of Lytic Epstein-Barr Virus Gene Expression without Virion Production. J Virol. 2019 Sep 30;93(20):e00998-19. doi: 10.1128/JVI.00998-19. PMID: 31341058; PMCID: PMC6798122. 5: Hu Y, Zhang M, Tian N, Li D, Wu F, Hu P, Wang Z, Wang L, Hao W, Kang J, Yin B, Zheng Z, Jiang T, Yuan J, Qiang B, Han W, Peng X. The antibiotic clofoctol suppresses glioma stem cell proliferation by activating KLF13. J Clin Invest. 2019 May 21;129(8):3072-3085. doi: 10.1172/JCI124979. PMID: 31112526; PMCID: PMC6668693. 6: Li T, Feng J, Xiao S, Shi W, Sullivan D, Zhang Y. Identification of FDA- Approved Drugs with Activity against Stationary Phase Bartonella henselae. Antibiotics (Basel). 2019 Apr 29;8(2):50. doi: 10.3390/antibiotics8020050. PMID: 31035691; PMCID: PMC6628006. 7: Scaglione F, Lucini V, Dugnani S, Pani A. Comparative Emergence of Resistance to Clofoctol, Erythromycin, and Amoxicillin against Community-Acquired Bacterial Respiratory Tract Pathogens in Italy. Chemotherapy. 2018;63(6):330-337. doi: 10.1159/000496931. Epub 2019 Mar 25. PMID: 30909281. 8: Fan L, He Z, Head SA, Zhou Y, Lu T, Feng X, Zhang X, Zhang M, Dang Y, Jiang X, Wang M. Clofoctol and sorafenib inhibit prostate cancer growth via synergistic induction of endoplasmic reticulum stress and UPR pathways. Cancer Manag Res. 2018 Oct 23;10:4817-4829. doi: 10.2147/CMAR.S175256. PMID: 30425575; PMCID: PMC6205540. 9: Cheng AN, Lo YK, Lin YS, Tang TK, Hsu CH, Hsu JT, Lee AY. Identification of Novel Cdc7 Kinase Inhibitors as Anti-Cancer Agents that Target the Interaction with Dbf4 by the Fragment Complementation and Drug Repositioning Approach. EBioMedicine. 2018 Oct;36:241-251. doi: 10.1016/j.ebiom.2018.09.030. Epub 2018 Oct 5. PMID: 30293817; PMCID: PMC6197782. 10: D'Angelo F, Baldelli V, Halliday N, Pantalone P, Polticelli F, Fiscarelli E, Williams P, Visca P, Leoni L, Rampioni G. Identification of FDA-Approved Drugs as Antivirulence Agents Targeting the pqs Quorum-Sensing System of Pseudomonas aeruginosa. Antimicrob Agents Chemother. 2018 Oct 24;62(11):e01296-18. doi: 10.1128/AAC.01296-18. PMID: 30201815; PMCID: PMC6201120. 11: Niu H, Yee R, Cui P, Zhang S, Tian L, Shi W, Sullivan D, Zhu B, Zhang W, Zhang Y. Identification and Ranking of Clinical Compounds with Activity Against Log-phase Growing Uropathogenic Escherichia coli. Curr Drug Discov Technol. 2020;17(2):191-196. doi: 10.2174/1570163815666180808115501. PMID: 30088449. 12: Niu H, Cui P, Shi W, Zhang S, Feng J, Wang Y, Sullivan D, Zhang W, Zhu B, Zhang Y. Identification of Anti-Persister Activity against Uropathogenic Escherichia coli from a Clinical Drug Library. Antibiotics (Basel). 2015 May 12;4(2):179-87. doi: 10.3390/antibiotics4020179. PMID: 27025620; PMCID: PMC4790332. 13: Wang M, Shim JS, Li RJ, Dang Y, He Q, Das M, Liu JO. Identification of an old antibiotic clofoctol as a novel activator of unfolded protein response pathways and an inhibitor of prostate cancer. Br J Pharmacol. 2014 Oct;171(19):4478-89. doi: 10.1111/bph.12800. Epub 2014 Sep 5. PMID: 24903412; PMCID: PMC4209153. 14: Scaglione F, Dugnani S, Lucini V, Pannacci M, Paraboni L. In vitro and in vivo pharmacokinetic/pharmacodynamic activity of clofoctol. J Chemother. 2012 Aug;24(4):201-6. doi: 10.1179/1973947812Y.0000000018. PMID: 23040683. 15: Bidat E, Bary A, Amgar A. Comparative clinical study of clofoctol versus josamycin in respiratory tract infections. J Chemother. 1989 Jul;1(4 Suppl):792-3. PMID: 16312642. 16: Danesi R, Gasperini M, Senesi S, Freer G, Angeletti CA, Del Tacca M. A pharmacokinetic study of clofoctol in human plasma and lung tissue by using a microbiological assay. Drugs Exp Clin Res. 1988;14(1):39-43. PMID: 3391105. 17: Del Tacca M, Danesi R, Senesi S, Gasperini M, Mussi A, Angeletti CA. Penetration of clofoctol into human lung. J Antimicrob Chemother. 1987 May;19(5):679-83. doi: 10.1093/jac/19.5.679. PMID: 3610901. 18: De Rose V, Bersani C, Grassi G, Piccioni PD, Merlini C, Sabato A, Gialdroni Grassi G. Influenza del clofoctolo su alcuni parametri di funzionalità fagocitaria [Effect of clofoctol on various parameters of phagocyte function]. G Ital Chemioter. 1987 Jan-Dec;34(1-3):73-6. Italian. PMID: 3504417. 19: Panattoni E, Marcucci M, Danesi R, Del Tacca M. Efficacia clinica del clofoctolo nel trattamento di infezioni odontogene [Clinical efficacy of clofoctol in treating odontogenic infections]. Minerva Stomatol. 1986 Nov;35(11):1071-4. Italian. PMID: 3543641. 20: Capuzzi P, Balla G, Mazzanti F, Tani P. Prime esperienze sull'utilizzazione del Clofoctolo [Initial experience with the use of Clofoctol]. G Stomatol Ortognatodonzia. 1986 Jul-Sep;5(3):45-7. Italian. PMID: 3478316.