Related CAS #
914-00-1 (free base); 41672-87-1 (trolamine); 3963-95-9 (HCl)
Synonym
Globociclina, Londomycin, Megamycine, Methacycline hydrochloride; Methacycline HCl, Metadomus, Metilenbiotic, Optimycin; Physiomycine, Rindex, Rondomycin
IUPAC/Chemical Name
2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, monohydrochloride, (4S,4aR,5S,5aR,12aS)-
InChi Key
VZQARNDJLLWXGL-CCHMMTNSSA-N
InChi Code
InChI=1S/C22H22N2O8.ClH/c1-7-8-5-4-6-9(25)11(8)16(26)12-10(7)17(27)14-15(24(2)3)18(28)13(21(23)31)20(30)22(14,32)19(12)29;/h4-6,10,14-15,17,25,27-29,32H,1H2,2-3H3,(H2,23,31);1H/t10-,14-,15+,17+,22+;/m1./s1
SMILES Code
O=C(C(C1=O)=C(O)[C@@H](N(C)C)[C@]2([H])[C@@H](O)[C@]3([H])C(C4=C(C(C3=C(O)[C@@]21O)=O)C(O)=CC=C4)=C)N.[H]Cl
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
Biological target:
Methacycline hydrochloride is a tetracycline antibiotic and can inhibits bacterial protein synthesis.
In vitro activity:
This study presents the screening of a small library of tetracycline congeners in order to identify the most effective compound in preventing ataxin-3 aggregation. Methacycline was identified as the most effective compound. The treatment with methacycline induced a significant improvement in motility and locomotion of the transgenic C. elegans without changing its lifespan.
Reference: Biochim Biophys Acta Gen Subj. 2019 Feb;1863(2):279-290. https://pubmed.ncbi.nlm.nih.gov/30420336/
In vivo activity:
In vivo, 100 mg/kg intraperitoneal methacycline delivered daily beginning 10 days after intratracheal bleomycin improved survival at Day 17 (P < 0.01) in mice. Bleomycin-induced canonical EMT markers, Snail1, Twist1, collagen I, as well as fibronectin protein and mRNA, were attenuated by methacycline (Day 17).
Reference: Am J Respir Cell Mol Biol. 2014 Jan;50(1):51-60. https://pubmed.ncbi.nlm.nih.gov/23944988/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMF |
10.0 |
20.88 |
|
| DMSO |
19.3 |
40.37 |
|
| PBS (pH 7.2) |
1.0 |
2.09 |
|
| Water |
5.8 |
12.18 |
|
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
478.88
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. Amigoni L, Airoldi C, Natalello A, Romeo M, Diomede L, Tortora P, Regonesi ME. Methacycline displays a strong efficacy in reducing toxicity in a SCA3 Caenorhabditis elegans model. Biochim Biophys Acta Gen Subj. 2019 Feb;1863(2):279-290. doi: 10.1016/j.bbagen.2018.10.008. Epub 2018 Oct 27. PMID: 30420336.
2. Dong C, Lu N, Liu Y. Binding of methacycline to human serum albumin at subdomain IIA using multispectroscopic and molecular modeling methods. Luminescence. 2013 Nov-Dec;28(6):933-41. doi: 10.1002/bio.2462. Epub 2012 Dec 12. PMID: 23233363.
3. Xi Y, Tan K, Brumwell AN, Chen SC, Kim YH, Kim TJ, Wei Y, Chapman HA. Inhibition of epithelial-to-mesenchymal transition and pulmonary fibrosis by methacycline. Am J Respir Cell Mol Biol. 2014 Jan;50(1):51-60. doi: 10.1165/rcmb.2013-0099OC. PMID: 23944988; PMCID: PMC3930932.
In vitro protocol:
1. Amigoni L, Airoldi C, Natalello A, Romeo M, Diomede L, Tortora P, Regonesi ME. Methacycline displays a strong efficacy in reducing toxicity in a SCA3 Caenorhabditis elegans model. Biochim Biophys Acta Gen Subj. 2019 Feb;1863(2):279-290. doi: 10.1016/j.bbagen.2018.10.008. Epub 2018 Oct 27. PMID: 30420336.
2. Dong C, Lu N, Liu Y. Binding of methacycline to human serum albumin at subdomain IIA using multispectroscopic and molecular modeling methods. Luminescence. 2013 Nov-Dec;28(6):933-41. doi: 10.1002/bio.2462. Epub 2012 Dec 12. PMID: 23233363.
In vivo protocol:
1. Xi Y, Tan K, Brumwell AN, Chen SC, Kim YH, Kim TJ, Wei Y, Chapman HA. Inhibition of epithelial-to-mesenchymal transition and pulmonary fibrosis by methacycline. Am J Respir Cell Mol Biol. 2014 Jan;50(1):51-60. doi: 10.1165/rcmb.2013-0099OC. PMID: 23944988; PMCID: PMC3930932.
1: Rauthan M, Pilon M. A chemical screen to identify inducers of the mitochondrial unfolded protein response in C. elegans. Worm. 2015 Oct 2;4(4):e1096490. doi: 10.1080/21624054.2015.1096490. eCollection 2015 Oct-Dec. PubMed PMID: 27123370; PubMed Central PMCID: PMC4826155.
2: Sun XX, Aboul-Enein HY. Quantitative analysis of methacycline hydrochloride by direct potentiometry using the internal solid contact sensor. Anal Sci. 2007 Feb;23(2):231-3. PubMed PMID: 17297239.
3: Podhorniak LV, Leake S, Schenck FJ. Stability of tetracycline antibiotics in raw milk under laboratory storage conditions. J Food Prot. 1999 May;62(5):547-8. PubMed PMID: 10340680.
4: Saha U, Sen AK, Das TK, Bhowal SK. Spectrophotometric determination of tetracyclines in pharmaceutical preparations, with uranyl acetate. Talanta. 1990 Dec;37(12):1193-6. PubMed PMID: 18965095.
5: Saha U. Colorimetric determination of tetracycline derivatives in pharmaceutical preparations. J Assoc Off Anal Chem. 1989 Mar-Apr;72(2):242-4. PubMed PMID: 2708271.
6: Hügel HE, Schinko H, Bischof HP. [Drug induced esophageal ulcers]. Z Gastroenterol. 1982 Oct;20(10):599-603. German. PubMed PMID: 7157902.
7: Berezovskaia LN, Grakovskaia LK, Nesterova LIa. [Comparative evaluation of methacycline hydrochloride capsules and tablets according to their dissolubility and rate of solution]. Antibiotiki. 1979 Aug;24(8):604-8. Russian. PubMed PMID: 485108.
8: Miyazaki S, Nakano M, Arita T. A comparison of bioavailability of free bases and hydrochloride salts of chlortetracycline, demethylchlortetracycline, and methacycline. Chem Pharm Bull (Tokyo). 1975 Sep;23(9):2151-5. PubMed PMID: 810254.
9: Miyazaki S, Nakano M, Arita T. A comparison of solubility characteristics of free bases and hydrochloride salts of tetracycline antibiotics in hydrochloric acid solutions. Chem Pharm Bull (Tokyo). 1975 Jun;23(6):1197-204. PubMed PMID: 241499.
10: Kahán IL, Hammer H. The parenteral application of a new metacycline preparation, tri-metacycline. Arzneimittelforschung. 1975 Feb;25(2):234-7. PubMed PMID: 804312.
11: Malone DN, Gold JC, Grant IW. A comparative study of ampicillin, tetracycline hydrochloride, and methacycline hydrochloride in acute exacerbations of chronic bronchitis. Lancet. 1968 Sep 14;2(7568):594-6. PubMed PMID: 4175157.
12: Bush AM. An evaluation of methacycline hydrochloride (6 methylene oxytetracycline). N Z Med J. 1967 Apr;66(416):240-3. PubMed PMID: 4165256.
13: Weitman J. [Clinical study of methacycline hydrochloride in 85 cases of acute medico-surgical infections of various etiologies]. Rev Med Chil. 1966 Sep;94(9):569-71. Spanish. PubMed PMID: 5991499.
14: Ekmekci A, Kuyumciyan K, Agbaba O, Pinhas R, Alothman I, Prifti J. [Clinical results with a new antibiotic, methacycline hydrochloride (Rondomycin)]. Turk Tip Cemiy Mecm. 1966 Jul;32(7):435-42. Turkish. PubMed PMID: 5929088.
