Meclocycline
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| Category | Antibiotics |
| Catalog number | BBF-04496 |
| CAS | 2013-58-3 |
| Molecular Weight | 476.86 |
| Molecular Formula | C22H21ClN2O8 |
| Purity | ≥98% |
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Description
Meclocycline is a tetracycline antibiotic derived from methacycline. It has a broad-spectrum antibacterial and antiprotozoan activity.
Specification
| Synonyms | GS-2989; NSC 78502; (4S,4aR,5S,5aR,12aS)-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide; 7-Chloro-6-methylene-5-oxytetracycline; [4S-(4α,4aα,5α,5aα,12aα)]-7-Chloro-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide |
| Storage | Store at -20°C under inert atmosphere |
| IUPAC Name | (4S,4aR,5S,5aR,12aR)-7-chloro-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide |
| Canonical SMILES | CN(C)C1C2C(C3C(=C)C4=C(C=CC(=C4C(=C3C(=O)C2(C(=C(C1=O)C(=O)N)O)O)O)O)Cl)O |
| InChI | InChI=1S/C22H21ClN2O8/c1-6-9-7(23)4-5-8(26)11(9)16(27)12-10(6)17(28)14-15(25(2)3)18(29)13(21(24)32)20(31)22(14,33)19(12)30/h4-5,10,14-15,17,26-28,31,33H,1H2,2-3H3,(H2,24,32)/t10-,14-,15+,17+,22+/m1/s1 |
| InChI Key | RNIADBXQDMCFEN-IWVLMIASSA-N |
Properties
| Appearance | Yellow to Dark Yellow Solid |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 837.0±65.0°C (Predicted) |
| Melting Point | >167°C (dec.) |
| Density | 1.72±0.1 g/cm3 (Predicted) |
| Solubility | Slightly soluble in DMSO, Methanol |
Reference Reading
1. 13C-NMR spectroscopy of three tetracycline antibiotics: minocycline hydrochloride, meclocycline, and rolitetracycline
L G Wayland, J A Melin, E P Mazzola J Pharm Sci . 1980 Feb;69(2):229-30. doi: 10.1002/jps.2600690236.
13C-NMR data and spectral assignments are presented for tetracycline antibiotics minocycline hydrochloride, meclocycline, and rolitetracycline.
2. Meclocycline sulfosalicylate. Topical antibiotic agent for the treatment of acne vulgaris
D D Knutson, W H Smoot, L J Swinyer Cutis . 1981 Feb;27(2):203-4, 208-10.
Meclocycline sulfosalicylate is a broad spectrum antimicrobial agent that was synthesized in 1960 and has been marketed abroad for several years. Clinical studies in the United States to date involve 351 patients. The results of a regimen using topically applied meclocycline sulfosalicylate, 1 percent, as the sole treatment are examined. Overall 82 percent of the patients treated with the active preparation experienced clinical improvement in a twice daily application regimen. Excellent of good results were obtained in 62.3 percent of patients treated with meclocycline sulfosalicylate cream as compared with 27.5 percent of those treated with the cream vehicle alone. The median percent reduction in the number of inflammatory lesions of acne among patients treated for 11 weeks was 57.1 percent. Rapid response was noted at week 5, with nearly a 50 percent median reduction in papules and pustules. The low incidence of local adverse effects was noteworthy. Only one case of contact dermatitis possibly related to treatment was reported among the patients studied.
3. Topical kanamycin: an effective therapeutic option in aerobic vaginitis
E Cammarata, G Ettore, A Raimondi, S Corsello, G Tempera, D Nicolosi, G Bonfiglio, A Cianci, P M Furneri, G Abbadessa J Chemother . 2006 Aug;18(4):409-14. doi: 10.1179/joc.2006.18.4.409.
Eighty-one patients with clinical diagnosis of aerobic vaginitis (AV) were included in the study. The patients were randomized for treatment, 45 with kanamycin (100 mg vaginal ovules for 6 days, consecutively) and 36 with meclocycline (35 mg vaginal ovules for 6 days, consecutively). The patients were examined before starting the study, 1-2 days after treatment and 30 days after the end of the study. At the first follow-up the patients showed different levels of symptom reduction. Reduction in the presence of leukocytes, vaginal mucosa burning and itching were statistically significant in the group treated with kanamycin with respect to the group treated with meclocycline. Moreover, there was also reduced isolation of Enterobacteriaeae (97%) in the group treated with kanamycin versus those treated with meclocycline (76%). At the second follow-up, vaginal homeostasis (normalization of pH and presence of lactobacilli) was more evident in the kanamycin-treated group. In conclusion, our data suggest that the topical use of kanamycin could be considered a specific antibiotic for the therapy of this new pathology.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
