Clemizole penicillin | CAS# 6011-39-8 (penicillin) | histamine H1- blocker

MedKoo Cat#: 413066 | Name: Clemizole penicillin

Description:

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

Clemizole, also known as AL 20, P 48, or Reactrol, is a potent inhibitor of transient receptor potential channel TRPC5. Clemizole efficiently blocks TRPC5 currents and Ca(2+) entry in the low micromolar range (IC50 = 1.0-1.3 µM). Clemizole blocks TRPC5 currents irrespectively of the mode of activation. Based on fluorometric [Ca(2+)]i measurements, clemizole exhibits a sixfold selectivity for TRPC5 over TRPC4β (IC50 = 6.4 µM). Clemizole was not only effective in blocking heterologously expressed TRPC5 homomers but also TRPC1:TRPC5 heteromers as well as native TRPC5-like currents in the U-87 glioblastoma cell line.

Chemical Structure

Clemizole penicillin

CAS#6011-39-8 (penicillin)

Theoretical Analysis

MedKoo Cat#: 413066

Name: Clemizole penicillin

CAS#: 6011-39-8 (penicillin)

Chemical Formula: C35H38ClN5O4S

Exact Mass: 659.2333

Molecular Weight: 660.23

Elemental Analysis: C, 63.67; H, 5.80; Cl, 5.37; N, 10.61; O, 9.69; S, 4.86

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

442-52-4 (free base) 1163-36-6 (HCl) 6011-39-8 (penicillin) 17162-20-8 (sulfate)

Synonym

Clemizole penicillin; NSC 46261; NSC-46261; NSC46261; AL 20, P 48, or Reactrol;

IUPAC/Chemical Name

1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzo[d]imidazole (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

InChi Key

GKPMEGXMKPQRTN-CBDIPHIASA-N

InChi Code

InChI=1S/C19H20ClN3.C16H18N2O4S/c20-16-9-7-15(8-10-16)13-23-18-6-2-1-5-17(18)21-19(23)14-22-11-3-4-12-22;1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h1-2,5-10H,3-4,11-14H2;3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t;11-,12+,14-/m.1/s1

SMILES Code

CC1(S[C@@H]2[C@@H](C(N2[C@H]1C(O)=O)=O)NC(Cc3ccccc3)=O)C.Clc4ccc(Cn(c(CN5CCCC5)n6)c7c6cccc7)cc4

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

>2 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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 660.23 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

1: Kumaş-Kulualp M, Gepdiremen A, Karataş E, Eşrefoğlu M. Clemizole hydrochloride, a potent TRPC5 calcium channel inhibitor, prevents cisplatin- induced nephrotoxicity in Spraque-Dawley rats. J Biochem Mol Toxicol. 2023 Jul;37(7):e23372. doi: 10.1002/jbt.23372. Epub 2023 Apr 26. PMID: 37102204. 2: Moog M, Baraban SC. Clemizole and trazodone are effective antiseizure treatments in a zebrafish model of STXBP1 disorder. Epilepsia Open. 2022 Sep;7(3):504-511. doi: 10.1002/epi4.12604. Epub 2022 May 17. PMID: 35451230; PMCID: PMC9436285. 3: Kobaisi F, Sulpice E, Barette C, Fayyad N, Fauvarque MO, Badran B, Fayyad- Kazan M, Fayyad-Kazan H, Gidrol X, Rachidi W. Isoconazole and Clemizole Hydrochloride Partially Reverse the Xeroderma Pigmentosum C Phenotype. Int J Mol Sci. 2021 Jul 29;22(15):8156. doi: 10.3390/ijms22158156. PMID: 34360928; PMCID: PMC8346964. 4: Dolinina J, Rippe A, Öberg CM. Clemizole and La3+ salts ameliorate angiotensin II-induced glomerular hyperpermeability in vivo. Physiol Rep. 2021 May;9(10):e14781. doi: 10.14814/phy2.14781. PMID: 34042270; PMCID: PMC8157770. 5: Griffin A, Hamling KR, Knupp K, Hong S, Lee LP, Baraban SC. Clemizole and modulators of serotonin signalling suppress seizures in Dravet syndrome. Brain. 2017 Mar 1;140(3):669-683. doi: 10.1093/brain/aww342. PMID: 28073790; PMCID: PMC6075536. 6: Jie LJ, Wu WY, Li G, Xiao GS, Zhang S, Li GR, Wang Y. Clemizole hydrochloride blocks cardiac potassium currents stably expressed in HEK 293 cells. Br J Pharmacol. 2017 Feb;174(3):254-266. doi: 10.1111/bph.13679. Epub 2017 Jan 12. PMID: 27886373; PMCID: PMC5241390. 7: Richter JM, Schaefer M, Hill K. Clemizole hydrochloride is a novel and potent inhibitor of transient receptor potential channel TRPC5. Mol Pharmacol. 2014 Nov;86(5):514-21. doi: 10.1124/mol.114.093229. Epub 2014 Aug 19. PMID: 25140002. 8: Vlahakis JZ, Vukomanovic D, Nakatsu K, Szarek WA. Selective inhibition of heme oxygenase-2 activity by analogs of 1-(4-chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole (clemizole): Exploration of the effects of substituents at the N-1 position. Bioorg Med Chem. 2013 Nov 1;21(21):6788-95. doi: 10.1016/j.bmc.2013.07.050. Epub 2013 Aug 8. PMID: 24021581. 9: Baraban SC, Dinday MT, Hortopan GA. Drug screening in Scn1a zebrafish mutant identifies clemizole as a potential Dravet syndrome treatment. Nat Commun. 2013;4:2410. doi: 10.1038/ncomms3410. PMID: 24002024; PMCID: PMC3891590. 10: Einav S, Sobol HD, Gehrig E, Glenn JS. The hepatitis C virus (HCV) NS4B RNA binding inhibitor clemizole is highly synergistic with HCV protease inhibitors. J Infect Dis. 2010 Jul 1;202(1):65-74. doi: 10.1086/653080. PMID: 20486856; PMCID: PMC3008401. 11: Martinez-Mir I, Estañ L, Rubio E, Morales-Olivas FJ. Antihistaminic and anticholinergic activities of mequitazine in comparison with clemizole. J Pharm Pharmacol. 1988 Sep;40(9):655-6. doi: 10.1111/j.2042-7158.1988.tb05331.x. PMID: 2907038. 12: Belal S, Elsayed MA, Abdel-Hamid ME, Abdine H. Utility of chloranil in assay of naphazoline, clemizole, penicillin G sodium, and piperazine. J Pharm Sci. 1981 Feb;70(2):127-30. doi: 10.1002/jps.2600700204. PMID: 6110697. 13: Atay O, Türeli F, Celebioğlu A, Yazan Z. Clemizole'un bir pomad kombinasyonunda hexachlorophene ve hydrocortisone yaninda ince tabaka kromatografisi yöntemi ile teşhis ve miktar tayini [Method for the identification and quantitative determination, by thin-layer chromatography, of clemizole in a combination ointment of hexachlorophene and hydrocortisone]. Turk Hij Tecr Biyol Derg. 1978;38(1-3):28-36. Turkish. PMID: 38545. 14: Kleinhans D. Blutspiegel-Untersuchungen zur Frage der Depotwirkung von Clemizol-Penicillin G bei antiluischer Therapie [Blood level studies on the depot effect of clemizole-penicillin G in antiluetic therapy]. Z Haut Geschlechtskr. 1971 Jun 1;46(11):359-65. German. PMID: 4397107. 15: Cardenas L, Ruipérez JA, Hermosillo JA, Kabela E, Méndez R. Sur le traitement du flutter auriculaire par mouvement circulaire (emploi d'un antihistaminique: Clemizole) [Treatment of circular movement auricular flutter (the use of an antihistaminic: clemizole)]. Arch Mal Coeur Vaiss. 1969 Mar 3;62(3):401-11. French. PMID: 4396674. 16: Mendez R, Kabela E, Pastelin G, Martínez-López M, Sánchez-Pérez S. Antiarrhythmic actions of clemizole as pharmacologic evidence for a circus movement mechanism in atrial flutter. Naunyn Schmiedebergs Arch Exp Pathol Pharmakol. 1969;262(3):325-36. doi: 10.1007/BF00538434. PMID: 4388778. 17: Jubelin J, de Lumley L, Raybaud A. Exploration des conséquences allergiques éventuelles de l'emploi de Clémizole-Pénicilline [Exploration of the possible allergic consequences of utilization of clemizole-penicillin]. Mars Med. 1968;105(2):189-92. French. PMID: 4391633. 18: Cárdenas M, Ruipérez JA, Hermosillo A, Kabela E, Méndez R. El antihistaminico clemizole en el flutter auricular por movimiento circular [The antihistaminic clemizole in auricular flutter caused by circular movement]. Arch Inst Cardiol Mex. 1967 May-Jun;37(3):380-7. Spanish. PMID: 4383385. 19: Keller H. Verblüffende Wirkung von Clemizol-Penicillin G (Antihistamin- Penicillin-G in drei Notfällen) [Astonishing effect of clemizole-penicillin G (antihistamine-penicillin G in three emergencies)]. Landarzt. 1966 Jul 10;42(19):827-8. German. PMID: 4383488. 20: Bornemann K, Schulz E, Heinecker R. Akute, nichtallergische Reaktionen nach i.m. Gabe von Clemizol-Penicillin G und Streptomycin [Acute, non-allergic reactions following i.m. administration of clemizole-penicillin G and streptomycin]. Munch Med Wochenschr. 1966 Apr 15;108(15):834-7. German. PMID: 4383676.