WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H329658
CAS#: 81103-11-9
Description: Clarithromycin is an antibiotic used to treat various bacterial infections. This includes strep throat, pneumonia, skin infections, H. pylori infection, and Lyme disease, among others. Clarithromycin was developed in 1980. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. Clarithromycin prevents bacteria by acting as a protein synthesis inhibitor. It binds to 23S rRNA, a component of the 50S subunit of the bacterial ribosome, thus inhibiting the translation of peptides.
Hodoodo Cat#: H329658
Name: Clarithromycin
CAS#: 81103-11-9
Chemical Formula: C38H69NO13
Exact Mass: 747.48
Molecular Weight: 747.964
Elemental Analysis: C, 61.02; H, 9.30; N, 1.87; O, 27.81
Synonym: Clarithromycin; Abbott-56268; A-56268; brand name Biaxin.
IUPAC/Chemical Name: (3R,4S,5S,6R,7R,9R,11R,12R,13S,14R)-6-(((2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-14-ethyl-12,13-dihydroxy-4-(((2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyltetrahydro-2H-pyran-2-yl)oxy)-7-methoxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione
InChi Key: AGOYDEPGAOXOCK-KCBOHYOISA-N
InChi Code: InChI=1S/C38H69NO13/c1-15-26-38(10,45)31(42)21(4)28(40)19(2)17-37(9,47-14)33(52-35-29(41)25(39(11)12)16-20(3)48-35)22(5)30(23(6)34(44)50-26)51-27-18-36(8,46-13)32(43)24(7)49-27/h19-27,29-33,35,41-43,45H,15-18H2,1-14H3/t19-,20-,21+,22+,23-,24+,25+,26-,27+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
SMILES Code: CC[C@@H]1[C@@](C)(O)[C@H](O)[C@@H](C)C([C@H](C)C[C@@](C)(OC)[C@H](O[C@H]2[C@H](O)[C@@H](N(C)C)C[C@@H](C)O2)[C@@H](C)[C@H](O[C@H]3C[C@@](C)(OC)[C@@H](O)[C@H](C)O3)[C@@H](C)C(O1)=O)=O
Appearance: White to off-white crystalline 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: 2930.90.2900
More Info:
| Biological target: | Clarithromycin is a macrolide antibiotic and a CYP3A4 inhibitor. |
| In vitro activity: | Moreover, both hERG1 silencing and E4031 reduced the effects of Cla (clarithromycin) on LC3 conversion (Fig. 3a), AVOs (Figs. (Figs. 3b and S3b) and vacuoles (Fig. S3c) formation. These data indicate that Cla exerts its effect on CRC cell autophagy, by modulating hERG1. Reference: Cell Death Dis. 2020 Mar; 11(3): 161. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7052256/ |
| In vivo activity: | Post-SAH 50 mg/kg CAM (clarithromycin) treatment most effectively improved neurological scores and brain water content at 24 and 48 h and reduced immunoglobulin G extravasation at 24 h compared with vehicle-treated SAH mice (p < 0.01). Western blotting showed that post-SAH BBB disruption was associated with increased expressions of periostin, phosphorylated signal transducer and activator of transcription 1 and 3, matrix metalloproteinase-9, and the consequent degradation of zonula occludens-1, which were suppressed by 50 mg/kg CAM treatment (p < 0.05, respectively, versus vehicle-treated SAH mice). Reference: Neurotherapeutics. 2021 Apr 7. https://pubmed.ncbi.nlm.nih.gov/33829412/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 13.1 | 17.53 | |
| DMF | 1.0 | 1.34 | |
| Ethanol | 1.0 | 1.34 | |
| Ethanol:PBS (pH 7.2) (1:1) | 0.5 | 0.67 |
The following data is based on the product molecular weight 747.96 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. Petroni G, Bagni G, Iorio J, Duranti C, Lottini T, Stefanini M, Kragol G, Becchetti A, Arcangeli A. Clarithromycin inhibits autophagy in colorectal cancer by regulating the hERG1 potassium channel interaction with PI3K. Cell Death Dis. 2020 Mar 2;11(3):161. doi: 10.1038/s41419-020-2349-8. Erratum in: Cell Death Dis. 2020 Mar 30;11(3):209. Erratum in: Cell Death Dis. 2020 Jul 17;11(7):541. PMID: 32123164; PMCID: PMC7052256. 2. Hara K, Kondo M, Tsuji M, Takeyama K, Tamaoki J. Clarithromycin suppresses IL-13-induced goblet cell metaplasia via the TMEM16A-dependent pathway in guinea pig airway epithelial cells. Respir Investig. 2019 Jan;57(1):79-88. doi: 10.1016/j.resinv.2018.10.001. Epub 2018 Nov 2. PMID: 30393041. 3. Kanamaru H, Kawakita F, Nishikawa H, Nakano F, Asada R, Suzuki H. Clarithromycin Ameliorates Early Brain Injury After Subarachnoid Hemorrhage via Suppressing Periostin-Related Pathways in Mice. Neurotherapeutics. 2021 Apr 7. doi: 10.1007/s13311-021-01050-5. Epub ahead of print. PMID: 33829412. 4. Ezomike NE, Ezomike UO, Osim EE. Effects of Clarithromycin Administration on Gastric Acid Secretion and Cytoprotection in Wistar Rats. Niger J Physiol Sci. 2020 Jun 30;35(1):96-100. PMID: 33084612. |
| In vitro protocol: | 1. Petroni G, Bagni G, Iorio J, Duranti C, Lottini T, Stefanini M, Kragol G, Becchetti A, Arcangeli A. Clarithromycin inhibits autophagy in colorectal cancer by regulating the hERG1 potassium channel interaction with PI3K. Cell Death Dis. 2020 Mar 2;11(3):161. doi: 10.1038/s41419-020-2349-8. Erratum in: Cell Death Dis. 2020 Mar 30;11(3):209. Erratum in: Cell Death Dis. 2020 Jul 17;11(7):541. PMID: 32123164; PMCID: PMC7052256. 2. Hara K, Kondo M, Tsuji M, Takeyama K, Tamaoki J. Clarithromycin suppresses IL-13-induced goblet cell metaplasia via the TMEM16A-dependent pathway in guinea pig airway epithelial cells. Respir Investig. 2019 Jan;57(1):79-88. doi: 10.1016/j.resinv.2018.10.001. Epub 2018 Nov 2. PMID: 30393041. |
| In vivo protocol: | 1. Kanamaru H, Kawakita F, Nishikawa H, Nakano F, Asada R, Suzuki H. Clarithromycin Ameliorates Early Brain Injury After Subarachnoid Hemorrhage via Suppressing Periostin-Related Pathways in Mice. Neurotherapeutics. 2021 Apr 7. doi: 10.1007/s13311-021-01050-5. Epub ahead of print. PMID: 33829412. 2. Ezomike NE, Ezomike UO, Osim EE. Effects of Clarithromycin Administration on Gastric Acid Secretion and Cytoprotection in Wistar Rats. Niger J Physiol Sci. 2020 Jun 30;35(1):96-100. PMID: 33084612. |
1: Gorito AM, Ribeiro AR, Almeida CMR, Silva AMT. A review on the application of constructed wetlands for the removal of priority substances and contaminants of emerging concern listed in recently launched EU legislation. Environ Pollut. 2017 May 6;227:428-443. doi: 10.1016/j.envpol.2017.04.060. [Epub ahead of print] Review. PubMed PMID: 28486186.
2: Gisbert JP, McNicholl AG. Optimization strategies aimed to increase the efficacy of H. pylori eradication therapies. Helicobacter. 2017 May 2. doi: 10.1111/hel.12392. [Epub ahead of print] Review. PubMed PMID: 28464347.
3: Jung YS, Park CH, Park JH, Nam E, Lee HL. Efficacy of Helicobacter pylori eradication therapies in Korea: A systematic review and network meta-analysis. Helicobacter. 2017 Apr 19. doi: 10.1111/hel.12389. [Epub ahead of print] Review. PubMed PMID: 28425141.
4: Abad VC, Guilleminault C. New developments in the management of narcolepsy. Nat Sci Sleep. 2017 Mar 3;9:39-57. doi: 10.2147/NSS.S103467. eCollection 2017. Review. PubMed PMID: 28424564; PubMed Central PMCID: PMC5344488.
5: Wong AY, Chan EW, Anand S, Worsley AJ, Wong IC. Managing Cardiovascular Risk of Macrolides: Systematic Review and Meta-Analysis. Drug Saf. 2017 Apr 10. doi: 10.1007/s40264-017-0533-2. [Epub ahead of print] Review. PubMed PMID: 28397186.
6: Hu Y, Zhu Y, Lu NH. Primary Antibiotic Resistance of Helicobacter pylori in China. Dig Dis Sci. 2017 May;62(5):1146-1154. doi: 10.1007/s10620-017-4536-8. Epub 2017 Mar 17. Review. PubMed PMID: 28315035.
7: Zareifopoulos N, Panayiotakopoulos G. Neuropsychiatric Effects of Antimicrobial Agents. Clin Drug Investig. 2017 May;37(5):423-437. doi: 10.1007/s40261-017-0498-z. Review. PubMed PMID: 28197902.
8: Giguère S. Treatment of Infections Caused by Rhodococcus equi. Vet Clin North Am Equine Pract. 2017 Apr;33(1):67-85. doi: 10.1016/j.cveq.2016.11.002. Epub 2017 Feb 1. Review. PubMed PMID: 28161038.
9: Talebi Bezmin Abadi A. Helicobacter pylori treatment: New perspectives using current experience. J Glob Antimicrob Resist. 2017 Mar;8:123-130. doi: 10.1016/j.jgar.2016.11.008. Epub 2017 Jan 25. Review. PubMed PMID: 28131855.
10: Lee JY, Park KS. Optimal First-Line Treatment for Helicobacter pylori Infection: Recent Strategies. Gastroenterol Res Pract. 2016;2016:9086581. doi: 10.1155/2016/9086581. Epub 2016 Dec 13. Review. PubMed PMID: 28070184; PubMed Central PMCID: PMC5187483.
11: Nenoff P, Manos A, Ehrhard I, Krüger C, Paasch U, Helmbold P, Handrick W. [Non-viral sexually transmitted infections - Epidemiology, clinical manifestations, diagnostics and therapy : Part 2: Chlamydia and mycoplasma]. Hautarzt. 2017 Jan;68(1):50-58. doi: 10.1007/s00105-016-3906-z. Review. German. PubMed PMID: 27981387.
12: Vardakas KZ, Trigkidis KK, Falagas ME. Fluoroquinolones or macrolides in combination with β-lactams in adult patients hospitalized with community acquired pneumonia: a systematic review and meta-analysis. Clin Microbiol Infect. 2017 Apr;23(4):234-241. doi: 10.1016/j.cmi.2016.12.002. Epub 2016 Dec 10. Review. PubMed PMID: 27965070.
13: Zhanel GG, Hartel E, Adam H, Zelenitsky S, Zhanel MA, Golden A, Schweizer F, Gorityala B, Lagacé-Wiens PR, Walkty AJ, Gin AS, Hoban DJ, Lynch JP 3rd, Karlowsky JA. Solithromycin: A Novel Fluoroketolide for the Treatment of Community-Acquired Bacterial Pneumonia. Drugs. 2016 Dec;76(18):1737-1757. Review. PubMed PMID: 27909995.
14: Abokwidir M, Feldman SR. Rosacea Management. Skin Appendage Disord. 2016 Sep;2(1-2):26-34. Epub 2016 May 18. Review. PubMed PMID: 27843919; PubMed Central PMCID: PMC5096126.
15: Kafshdooz T, Akbarzadeh A, Majdi Seghinsara A, Pourhassan M, Nasrabadi HT, Milani M. Role of Probiotics in Managing of Helicobacter Pylori Infection: A Review. Drug Res (Stuttg). 2017 Feb;67(2):88-93. doi: 10.1055/s-0042-116441. Epub 2016 Nov 7. Review. PubMed PMID: 27824431.
16: Murad HA. Does Helicobacter pylori eradication therapy trigger or protect against Crohn's disease? Acta Gastroenterol Belg. 2016 Jul-Sep;79(3):349-354. Review. PubMed PMID: 27821031.
17: Pellicano R, Ribaldone DG, Fagoonee S, Astegiano M, Saracco GM, Mégraud F. A 2016 panorama of Helicobacter pylori infection: key messages for clinicians. Panminerva Med. 2016 Dec;58(4):304-317. Review. PubMed PMID: 27716738.
18: Vianna JS, Ramis IB, Ramos DF, VON Groll A, Silva PE. DRUG RESISTANCE IN HELICOBACTER PYLORI. Arq Gastroenterol. 2016 Oct-Dec;53(4):215-223. doi: 10.1590/S0004-28032016000400002. Review. PubMed PMID: 27706449.
19: Xin Y, Manson J, Govan L, Harbour R, Bennison J, Watson E, Wu O. Pharmacological regimens for eradication of Helicobacter pylori: an overview of systematic reviews and network meta-analysis. BMC Gastroenterol. 2016 Jul 26;16(1):80. doi: 10.1186/s12876-016-0491-7. Review. PubMed PMID: 27460211; PubMed Central PMCID: PMC4962503.
20: Pereyre S, Goret J, Bébéar C. Mycoplasma pneumoniae: Current Knowledge on Macrolide Resistance and Treatment. Front Microbiol. 2016 Jun 22;7:974. doi: 10.3389/fmicb.2016.00974. eCollection 2016. Review. PubMed PMID: 27446015; PubMed Central PMCID: PMC4916212.
